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Route overview: San Francisco Bay Area to Chicago (ORD) flight deals

Oakland → Chicago

Choose your travel dates

OAK → ORD1 adulteconomy

144 flight options · 3 airlines

Flights for the months ahead

Short round trips

  1. Thu, Nov 19 – Sun, Nov 22

    Frontier Airlines
    6:20 pmOAK
    8h 53m
    LAS · 3h 37m
    5:13 am+1ORD
    Frontier Airlines
    6:21 amORD
    7h 12m
    LAS · 1h 20m
    11:33 amOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Thu, Nov 19 – Sun, Nov 22

    Alaska Airlines
    2:44 pmOAK
    7h 15m
    SAN · 1h 14m
    11:59 pmORD
    Alaska Airlines
    7:27 amORD
    8h 37m
    SAN · 2h 2m
    2:04 pmOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Fri, Dec 25 – Mon, Dec 28

    Frontier Airlines
    6:20 pmOAK
    8h 53m
    LAS · 3h 37m
    5:13 am+1ORD
    Frontier Airlines
    6:21 amORD
    7h 12m
    LAS · 1h 20m
    11:33 amOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  4. Fri, Dec 25 – Mon, Dec 28

    Alaska Airlines
    6:46 pmOAK
    8h 21m
    PDX · 2h 43m
    5:07 am+1ORD
    Alaska Airlines
    2:08 pmORD
    9h 33m
    PDX · 2h 57m
    9:41 pmOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  5. Thu, Jan 7 – Sun, Jan 10

    Frontier Airlines
    6:20 pmOAK
    8h 53m
    LAS · 3h 37m
    5:13 am+1ORD
    Frontier Airlines
    6:21 amORD
    7h 12m
    LAS · 1h 20m
    11:33 amOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  6. Thu, Jan 7 – Sun, Jan 10

    Alaska Airlines
    6:46 pmOAK
    8h 21m
    PDX · 2h 43m
    5:07 am+1ORD
    Alaska Airlines
    2:08 pmORD
    9h 33m
    PDX · 2h 57m
    9:41 pmOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  7. Thu, Jan 21 – Sun, Jan 24

    Frontier Airlines
    6:20 pmOAK
    8h 53m
    LAS · 3h 37m
    5:13 am+1ORD
    Frontier Airlines
    6:21 amORD
    7h 12m
    LAS · 1h 20m
    11:33 amOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  8. Thu, Jan 21 – Sun, Jan 24

    Delta Air Lines
    12:41 pmOAK
    7h 6m
    SLC · 2h 5m
    9:47 pmORD
    American Airlines
    9:45 amORD
    8h 36m
    PDX · 1h 53m
    4:21 pmOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  9. Thu, Feb 4 – Sun, Feb 7

    Alaska Airlines
    6:46 pmOAK
    8h 21m
    PDX · 2h 43m
    5:07 am+1ORD
    Alaska Airlines
    2:08 pmORD
    9h 33m
    PDX · 2h 57m
    9:41 pmOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  10. Thu, Feb 4 – Sun, Feb 7

    Delta Air Lines
    12:41 pmOAK
    7h 6m
    SLC · 2h 5m
    9:47 pmORD
    American Airlines
    9:45 amORD
    8h 36m
    PDX · 1h 53m
    4:21 pmOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  11. Fri, Mar 19 – Mon, Mar 22

    Frontier Airlines
    6:20 pmOAK
    8h 53m
    LAS · 3h 37m
    5:13 am+1ORD
    Frontier Airlines
    6:21 amORD
    7h 12m
    LAS · 1h 20m
    11:33 amOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  12. Fri, Mar 19 – Mon, Mar 22

    Alaska Airlines
    6:46 pmOAK
    8h 21m
    PDX · 2h 43m
    5:07 am+1ORD
    Alaska Airlines
    2:08 pmORD
    9h 33m
    PDX · 2h 57m
    9:41 pmOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

Swipe to see 11 more recent deals.

1 of 12

Longer round trips

  1. Sat, Nov 28 – Sat, Dec 5

    Frontier Airlines
    6:20 pmOAK
    8h 53m
    LAS · 3h 37m
    5:13 am+1ORD
    Frontier Airlines
    6:21 amORD
    7h 12m
    LAS · 1h 20m
    11:33 amOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Sat, Nov 28 – Sat, Dec 5

    Alaska Airlines
    2:44 pmOAK
    7h 15m
    SAN · 1h 14m
    11:59 pmORD
    Alaska Airlines
    7:27 amORD
    8h 37m
    SAN · 2h 2m
    2:04 pmOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Sat, Dec 12 – Sat, Dec 19

    Frontier Airlines
    6:20 pmOAK
    8h 53m
    LAS · 3h 37m
    5:13 am+1ORD
    Frontier Airlines
    6:21 amORD
    7h 12m
    LAS · 1h 20m
    11:33 amOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  4. Sat, Dec 12 – Sat, Dec 19

    Alaska Airlines
    6:46 pmOAK
    8h 21m
    PDX · 2h 43m
    5:07 am+1ORD
    Alaska Airlines
    2:08 pmORD
    9h 33m
    PDX · 2h 57m
    9:41 pmOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  5. Sat, May 15 – Sat, May 22

    Frontier Airlines
    6:20 pmOAK
    8h 53m
    LAS · 3h 37m
    5:13 am+1ORD
    Frontier Airlines
    6:21 amORD
    7h 12m
    LAS · 1h 20m
    11:33 amOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  6. Sat, May 15 – Sat, May 22

    Alaska Airlines
    6:46 pmOAK
    8h 21m
    PDX · 2h 43m
    5:07 am+1ORD
    Alaska Airlines
    2:08 pmORD
    9h 33m
    PDX · 2h 57m
    9:41 pmOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  7. Sat, Jul 10 – Sat, Jul 17

    Frontier Airlines
    6:20 pmOAK
    8h 53m
    LAS · 3h 37m
    5:13 am+1ORD
    Frontier Airlines
    6:21 amORD
    7h 12m
    LAS · 1h 20m
    11:33 amOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  8. Sat, Jul 10 – Sat, Jul 17

    Alaska Airlines
    6:46 pmOAK
    8h 21m
    PDX · 2h 43m
    5:07 am+1ORD
    Alaska Airlines
    2:08 pmORD
    9h 33m
    PDX · 2h 57m
    9:41 pmOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  9. Sat, Sep 25 – Sat, Oct 2

    Frontier Airlines
    6:20 pmOAK
    8h 53m
    LAS · 3h 37m
    5:13 am+1ORD
    Frontier Airlines
    6:21 amORD
    7h 12m
    LAS · 1h 20m
    11:33 amOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  10. Sat, Sep 25 – Sat, Oct 2

    Alaska Airlines
    6:46 pmOAK
    8h 21m
    PDX · 2h 43m
    5:07 am+1ORD
    Alaska Airlines
    2:08 pmORD
    9h 33m
    PDX · 2h 57m
    9:41 pmOAK

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

Swipe to see 9 more recent deals.

1 of 10

One-way flights

  1. Tue, Nov 24 · One way

    Frontier Airlines
    6:20 pmOAK
    8h 53m
    LAS · 3h 37m
    5:13 am+1ORD

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Tue, Nov 24 · One way

    Alaska Airlines
    2:44 pmOAK
    7h 15m
    SAN · 1h 14m
    11:59 pmORD

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

Swipe to see 1 more recent deal.

1 of 2

Explore flights by month

Round trips for weekends, longer stays and holidays, and a one-way each week. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

November 2026

December 2026

January 2027

February 2027

March 2027

April 2027

May 2027

June 2027

July 2027

August 2027

September 2027

Make this trip yours

OAK ⇄ ORD

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Frontier Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

More dates for this route

Nov 19, 2026 · Return optionsNov 27, 2026 · Return optionsDec 8, 2026 · Return optionsDec 19, 2026 · Return optionsDec 29, 2026 · Return optionsJan 8, 2027 · Return optionsJan 19, 2027 · Return optionsJan 30, 2027 · Return optionsFeb 19, 2027 · Return optionsMay 14, 2027 · Return optionsJul 9, 2027 · Return optionsSep 25, 2027 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

Lowest published fares for the months ahead: $204 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 7–10, 2027; $109 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jan 5, 2027; 144 priced flights on 72 exact dates, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Next: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.

Oakland (OAK) to Chicago (ORD): November 2026

Travel datesAirlineStopsTotal price
Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $252.63
Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $411.25
Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $252.63
Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $411.25
Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $290.26
Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $472.50
Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $155.25
Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $249.75
Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $290.26
Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $472.50
Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $290.26
Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $472.50
Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $290.26
Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $472.50
Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $252.63
Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $411.25

Oakland (OAK) to Chicago (ORD): December 2026

Travel datesAirlineStopsTotal price
Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $115.00
Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $185.00
Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $215.00
Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $350.00
Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $215.00
Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $350.00
Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $215.00
Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026Delta Air Lines / Frontier AirlinesUp to 1 stop each wayAxel-exclusive $302.50
Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $115.00
Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $185.00
Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $215.00
Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $350.00
Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $215.00
Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $350.00
Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $258.00
Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $420.00
Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $115.00
Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $185.00
Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $258.00
Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $420.00
Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $258.00
Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $420.00
Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $301.00
Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $490.00
Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $161.00
Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $259.00
Dec 22, 2026 – Dec 27, 2026 · 5 nights · Compare return dates departing Dec 22, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $301.00
Dec 22, 2026 – Dec 27, 2026 · 5 nights · Compare return dates departing Dec 22, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $490.00
Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $301.00
Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $490.00
Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $301.00
Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $490.00
Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $293.48
Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $477.75
Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $161.00
Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $259.00
Dec 30, 2026 – Jan 2, 2027 · 3 nights · Compare return dates departing Dec 30, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $293.48
Dec 30, 2026 – Jan 2, 2027 · 3 nights · Compare return dates departing Dec 30, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $477.75
Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $293.48
Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026Alaska AirlinesUp to 1 stop each wayAxel-exclusive $477.75

Oakland (OAK) to Chicago (ORD): January 2027

Travel datesAirlineStopsTotal price
Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $245.11
Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $399.00
Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $245.11
Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $399.00
Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $109.25
Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $175.75
Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $109.25
Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $175.75
Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $109.25
Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $175.75
Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $109.25
Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $175.75
Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50

Oakland (OAK) to Chicago (ORD): February 2027

Travel datesAirlineStopsTotal price
Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $109.25
Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $175.75
Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $219.31
Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $357.00
Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $234.36
Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $381.50
Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50
Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $204.26
Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $332.50

Oakland (OAK) to Chicago (ORD): March 2027

Travel datesAirlineStopsTotal price
Mar 19, 2027 – Mar 22, 2027 · 3 nights · Compare return dates departing Mar 19, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $248.33
Mar 19, 2027 – Mar 22, 2027 · 3 nights · Compare return dates departing Mar 19, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $404.25
Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $270.90
Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $441.00
Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $308.70
Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $485.10

Oakland (OAK) to Chicago (ORD): April 2027

Travel datesAirlineStopsTotal price
Apr 16, 2027 – Apr 19, 2027 · 3 nights · Compare return dates departing Apr 16, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $275.00
Apr 16, 2027 – Apr 19, 2027 · 3 nights · Compare return dates departing Apr 16, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $420.00
Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $275.00
Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $420.00

Oakland (OAK) to Chicago (ORD): May 2027

Travel datesAirlineStopsTotal price
May 14, 2027 – May 17, 2027 · 3 nights · Compare return dates departing May 14, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $275.00
May 14, 2027 – May 17, 2027 · 3 nights · Compare return dates departing May 14, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $420.00
May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $275.00
May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $420.00
May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $330.00
May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $504.00

Oakland (OAK) to Chicago (ORD): June 2027

Travel datesAirlineStopsTotal price
Jun 11, 2027 – Jun 14, 2027 · 3 nights · Compare return dates departing Jun 11, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $275.00
Jun 11, 2027 – Jun 14, 2027 · 3 nights · Compare return dates departing Jun 11, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $420.00
Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $275.00
Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $420.00

Oakland (OAK) to Chicago (ORD): July 2027

Travel datesAirlineStopsTotal price
Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $346.50
Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027Delta Air Lines / Frontier AirlinesUp to 1 stop each wayAxel-exclusive $463.05
Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $288.76
Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $441.00
Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $288.76
Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $441.00

Oakland (OAK) to Chicago (ORD): August 2027

Travel datesAirlineStopsTotal price
Aug 6, 2027 – Aug 9, 2027 · 3 nights · Compare return dates departing Aug 6, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $275.00
Aug 6, 2027 – Aug 9, 2027 · 3 nights · Compare return dates departing Aug 6, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $420.00
Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $275.00
Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $420.00

Oakland (OAK) to Chicago (ORD): September 2027

Travel datesAirlineStopsTotal price
Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $313.50
Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $478.80
Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $287.38
Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $438.90
Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $261.26
Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $399.00
Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $268.13
Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027Alaska AirlinesUp to 1 stop each wayAxel-exclusive $409.50

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

All hotels in Chicago

Route overview: San Francisco Bay Area to Chicago (ORD) flight deals

2026-11-19 → 2026-11-22 · Axel-exclusive $252.63

  • Frontier Airlines F93838 / F92146: OAK 2026-11-19 18:20:00 → ORD 2026-11-20 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
    • F93838: OAK 2026-11-19 18:20:00 → LAS 2026-11-19 19:52:00; layover at LAS: 217 minutes.
    • F92146: LAS 2026-11-19 23:29:00 → ORD 2026-11-20 05:13:00.
  • Frontier Airlines F92145 / F92045: ORD 2026-11-22 06:21:00 → OAK 2026-11-22 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
    • F92145: ORD 2026-11-22 06:21:00 → LAS 2026-11-22 08:36:00; layover at LAS: 80 minutes.
    • F92045: LAS 2026-11-22 09:56:00 → OAK 2026-11-22 11:33:00.

2026-11-19 → 2026-11-22 · Axel-exclusive $411.25

  • Alaska Airlines AS3009 / AS1493: OAK 2026-11-19 14:44:00 → ORD 2026-11-19 23:59:00; 1 stop(s) via SAN; 435 minutes. Local airport times.
    • AS3009: OAK 2026-11-19 14:44:00 → SAN 2026-11-19 16:24:00; layover at SAN: 74 minutes.
    • AS1493: SAN 2026-11-19 17:38:00 → ORD 2026-11-19 23:59:00.
  • Alaska Airlines AS1470 / AS3009: ORD 2026-11-22 07:27:00 → OAK 2026-11-22 14:04:00; 1 stop(s) via SAN; 517 minutes. Local airport times.
    • AS1470: ORD 2026-11-22 07:27:00 → SAN 2026-11-22 10:12:00; layover at SAN: 122 minutes.
    • AS3009: SAN 2026-11-22 12:14:00 → OAK 2026-11-22 14:04:00.

2026-11-24 · one way · Axel-exclusive $155.25

  • Frontier Airlines F93838 / F92146: OAK 2026-11-24 18:20:00 → ORD 2026-11-25 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
    • F93838: OAK 2026-11-24 18:20:00 → LAS 2026-11-24 19:52:00; layover at LAS: 217 minutes.
    • F92146: LAS 2026-11-24 23:29:00 → ORD 2026-11-25 05:13:00.

2026-11-24 · one way · Axel-exclusive $249.75

  • Alaska Airlines AS3009 / AS1493: OAK 2026-11-24 14:44:00 → ORD 2026-11-24 23:59:00; 1 stop(s) via SAN; 435 minutes. Local airport times.
    • AS3009: OAK 2026-11-24 14:44:00 → SAN 2026-11-24 16:24:00; layover at SAN: 74 minutes.
    • AS1493: SAN 2026-11-24 17:38:00 → ORD 2026-11-24 23:59:00.

2026-11-28 → 2026-12-05 · Axel-exclusive $252.63

  • Frontier Airlines F93838 / F92146: OAK 2026-11-28 18:20:00 → ORD 2026-11-29 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
    • F93838: OAK 2026-11-28 18:20:00 → LAS 2026-11-28 19:52:00; layover at LAS: 217 minutes.
    • F92146: LAS 2026-11-28 23:29:00 → ORD 2026-11-29 05:13:00.
  • Frontier Airlines F92145 / F92045: ORD 2026-12-05 06:21:00 → OAK 2026-12-05 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
    • F92145: ORD 2026-12-05 06:21:00 → LAS 2026-12-05 08:36:00; layover at LAS: 80 minutes.
    • F92045: LAS 2026-12-05 09:56:00 → OAK 2026-12-05 11:33:00.

2026-11-28 → 2026-12-05 · Axel-exclusive $411.25

  • Alaska Airlines AS3009 / AS1493: OAK 2026-11-28 14:44:00 → ORD 2026-11-28 23:59:00; 1 stop(s) via SAN; 435 minutes. Local airport times.
    • AS3009: OAK 2026-11-28 14:44:00 → SAN 2026-11-28 16:24:00; layover at SAN: 74 minutes.
    • AS1493: SAN 2026-11-28 17:38:00 → ORD 2026-11-28 23:59:00.
  • Alaska Airlines AS1470 / AS3009: ORD 2026-12-05 07:27:00 → OAK 2026-12-05 14:04:00; 1 stop(s) via SAN; 517 minutes. Local airport times.
    • AS1470: ORD 2026-12-05 07:27:00 → SAN 2026-12-05 10:12:00; layover at SAN: 122 minutes.
    • AS3009: SAN 2026-12-05 12:14:00 → OAK 2026-12-05 14:04:00.

2026-12-12 → 2026-12-19 · Axel-exclusive $258.00

  • Frontier Airlines F93838 / F92146: OAK 2026-12-12 18:20:00 → ORD 2026-12-13 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
    • F93838: OAK 2026-12-12 18:20:00 → LAS 2026-12-12 19:52:00; layover at LAS: 217 minutes.
    • F92146: LAS 2026-12-12 23:29:00 → ORD 2026-12-13 05:13:00.
  • Frontier Airlines F92145 / F92045: ORD 2026-12-19 06:21:00 → OAK 2026-12-19 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
    • F92145: ORD 2026-12-19 06:21:00 → LAS 2026-12-19 08:36:00; layover at LAS: 80 minutes.
    • F92045: LAS 2026-12-19 09:56:00 → OAK 2026-12-19 11:33:00.

2026-12-12 → 2026-12-19 · Axel-exclusive $420.00

  • Alaska Airlines AS2133 / AA3329: OAK 2026-12-12 18:46:00 → ORD 2026-12-13 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
    • AS2133: OAK 2026-12-12 18:46:00 → PDX 2026-12-12 20:30:00; layover at PDX: 163 minutes.
    • AA3329: PDX 2026-12-12 23:13:00 → ORD 2026-12-13 05:07:00.
  • Alaska Airlines AS325 / AS2468: ORD 2026-12-19 14:08:00 → OAK 2026-12-19 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
    • AS325: ORD 2026-12-19 14:08:00 → PDX 2026-12-19 16:58:00; layover at PDX: 177 minutes.
    • AS2468: PDX 2026-12-19 19:55:00 → OAK 2026-12-19 21:41:00.

2026-12-25 → 2026-12-28 · Axel-exclusive $301.00

  • Frontier Airlines F93838 / F92146: OAK 2026-12-25 18:20:00 → ORD 2026-12-26 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
    • F93838: OAK 2026-12-25 18:20:00 → LAS 2026-12-25 19:52:00; layover at LAS: 217 minutes.
    • F92146: LAS 2026-12-25 23:29:00 → ORD 2026-12-26 05:13:00.
  • Frontier Airlines F92145 / F92045: ORD 2026-12-28 06:21:00 → OAK 2026-12-28 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
    • F92145: ORD 2026-12-28 06:21:00 → LAS 2026-12-28 08:36:00; layover at LAS: 80 minutes.
    • F92045: LAS 2026-12-28 09:56:00 → OAK 2026-12-28 11:33:00.

2026-12-25 → 2026-12-28 · Axel-exclusive $490.00

  • Alaska Airlines AS2133 / AA3329: OAK 2026-12-25 18:46:00 → ORD 2026-12-26 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
    • AS2133: OAK 2026-12-25 18:46:00 → PDX 2026-12-25 20:30:00; layover at PDX: 163 minutes.
    • AA3329: PDX 2026-12-25 23:13:00 → ORD 2026-12-26 05:07:00.
  • Alaska Airlines AS325 / AS2468: ORD 2026-12-28 14:08:00 → OAK 2026-12-28 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
    • AS325: ORD 2026-12-28 14:08:00 → PDX 2026-12-28 16:58:00; layover at PDX: 177 minutes.
    • AS2468: PDX 2026-12-28 19:55:00 → OAK 2026-12-28 21:41:00.

2027-01-07 → 2027-01-10 · Axel-exclusive $204.26

  • Frontier Airlines F93838 / F92146: OAK 2027-01-07 18:20:00 → ORD 2027-01-08 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
    • F93838: OAK 2027-01-07 18:20:00 → LAS 2027-01-07 19:52:00; layover at LAS: 217 minutes.
    • F92146: LAS 2027-01-07 23:29:00 → ORD 2027-01-08 05:13:00.
  • Frontier Airlines F92145 / F92045: ORD 2027-01-10 06:21:00 → OAK 2027-01-10 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
    • F92145: ORD 2027-01-10 06:21:00 → LAS 2027-01-10 08:36:00; layover at LAS: 80 minutes.
    • F92045: LAS 2027-01-10 09:56:00 → OAK 2027-01-10 11:33:00.

2027-01-07 → 2027-01-10 · Axel-exclusive $332.50

  • Alaska Airlines AS2133 / AA3329: OAK 2027-01-07 18:46:00 → ORD 2027-01-08 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
    • AS2133: OAK 2027-01-07 18:46:00 → PDX 2027-01-07 20:30:00; layover at PDX: 163 minutes.
    • AA3329: PDX 2027-01-07 23:13:00 → ORD 2027-01-08 05:07:00.
  • Alaska Airlines AS325 / AS2468: ORD 2027-01-10 14:08:00 → OAK 2027-01-10 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
    • AS325: ORD 2027-01-10 14:08:00 → PDX 2027-01-10 16:58:00; layover at PDX: 177 minutes.
    • AS2468: PDX 2027-01-10 19:55:00 → OAK 2027-01-10 21:41:00.

2027-01-21 → 2027-01-24 · Axel-exclusive $204.26

  • Frontier Airlines F93838 / F92146: OAK 2027-01-21 18:20:00 → ORD 2027-01-22 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
    • F93838: OAK 2027-01-21 18:20:00 → LAS 2027-01-21 19:52:00; layover at LAS: 217 minutes.
    • F92146: LAS 2027-01-21 23:29:00 → ORD 2027-01-22 05:13:00.
  • Frontier Airlines F92145 / F92045: ORD 2027-01-24 06:21:00 → OAK 2027-01-24 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
    • F92145: ORD 2027-01-24 06:21:00 → LAS 2027-01-24 08:36:00; layover at LAS: 80 minutes.
    • F92045: LAS 2027-01-24 09:56:00 → OAK 2027-01-24 11:33:00.

2027-01-21 → 2027-01-24 · Axel-exclusive $361.00

  • Delta Air Lines DL4134 / DL2413: OAK 2027-01-21 12:41:00 → ORD 2027-01-21 21:47:00; 1 stop(s) via SLC; 426 minutes. Local airport times.
    • DL4134: OAK 2027-01-21 12:41:00 → SLC 2027-01-21 15:40:00; layover at SLC: 125 minutes.
    • DL2413: SLC 2027-01-21 17:45:00 → ORD 2027-01-21 21:47:00.
  • American Airlines AA562 / AS2283: ORD 2027-01-24 09:45:00 → OAK 2027-01-24 16:21:00; 1 stop(s) via PDX; 516 minutes. Local airport times.
    • AA562: ORD 2027-01-24 09:45:00 → PDX 2027-01-24 12:37:00; layover at PDX: 113 minutes.
    • AS2283: PDX 2027-01-24 14:30:00 → OAK 2027-01-24 16:21:00.

2027-02-04 → 2027-02-07 · Axel-exclusive $332.50

  • Alaska Airlines AS2133 / AA3329: OAK 2027-02-04 18:46:00 → ORD 2027-02-05 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
    • AS2133: OAK 2027-02-04 18:46:00 → PDX 2027-02-04 20:30:00; layover at PDX: 163 minutes.
    • AA3329: PDX 2027-02-04 23:13:00 → ORD 2027-02-05 05:07:00.
  • Alaska Airlines AS325 / AS2468: ORD 2027-02-07 14:08:00 → OAK 2027-02-07 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
    • AS325: ORD 2027-02-07 14:08:00 → PDX 2027-02-07 16:58:00; layover at PDX: 177 minutes.
    • AS2468: PDX 2027-02-07 19:55:00 → OAK 2027-02-07 21:41:00.

2027-02-04 → 2027-02-07 · Axel-exclusive $361.00

  • Delta Air Lines DL4134 / DL2413: OAK 2027-02-04 12:41:00 → ORD 2027-02-04 21:47:00; 1 stop(s) via SLC; 426 minutes. Local airport times.
    • DL4134: OAK 2027-02-04 12:41:00 → SLC 2027-02-04 15:40:00; layover at SLC: 125 minutes.
    • DL2413: SLC 2027-02-04 17:45:00 → ORD 2027-02-04 21:47:00.
  • American Airlines AA562 / AS2283: ORD 2027-02-07 09:45:00 → OAK 2027-02-07 16:21:00; 1 stop(s) via PDX; 516 minutes. Local airport times.
    • AA562: ORD 2027-02-07 09:45:00 → PDX 2027-02-07 12:37:00; layover at PDX: 113 minutes.
    • AS2283: PDX 2027-02-07 14:30:00 → OAK 2027-02-07 16:21:00.

2027-03-19 → 2027-03-22 · Axel-exclusive $248.33

  • Frontier Airlines F93838 / F92146: OAK 2027-03-19 18:20:00 → ORD 2027-03-20 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
    • F93838: OAK 2027-03-19 18:20:00 → LAS 2027-03-19 19:52:00; layover at LAS: 217 minutes.
    • F92146: LAS 2027-03-19 23:29:00 → ORD 2027-03-20 05:13:00.
  • Frontier Airlines F92145 / F92045: ORD 2027-03-22 06:21:00 → OAK 2027-03-22 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
    • F92145: ORD 2027-03-22 06:21:00 → LAS 2027-03-22 08:36:00; layover at LAS: 80 minutes.
    • F92045: LAS 2027-03-22 09:56:00 → OAK 2027-03-22 11:33:00.

2027-03-19 → 2027-03-22 · Axel-exclusive $404.25

  • Alaska Airlines AS2133 / AA3329: OAK 2027-03-19 18:46:00 → ORD 2027-03-20 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
    • AS2133: OAK 2027-03-19 18:46:00 → PDX 2027-03-19 20:30:00; layover at PDX: 163 minutes.
    • AA3329: PDX 2027-03-19 23:13:00 → ORD 2027-03-20 05:07:00.
  • Alaska Airlines AS325 / AS2468: ORD 2027-03-22 14:08:00 → OAK 2027-03-22 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
    • AS325: ORD 2027-03-22 14:08:00 → PDX 2027-03-22 16:58:00; layover at PDX: 177 minutes.
    • AS2468: PDX 2027-03-22 19:55:00 → OAK 2027-03-22 21:41:00.

2027-05-15 → 2027-05-22 · Axel-exclusive $275.00

  • Frontier Airlines F93838 / F92146: OAK 2027-05-15 18:20:00 → ORD 2027-05-16 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
    • F93838: OAK 2027-05-15 18:20:00 → LAS 2027-05-15 19:52:00; layover at LAS: 217 minutes.
    • F92146: LAS 2027-05-15 23:29:00 → ORD 2027-05-16 05:13:00.
  • Frontier Airlines F92145 / F92045: ORD 2027-05-22 06:21:00 → OAK 2027-05-22 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
    • F92145: ORD 2027-05-22 06:21:00 → LAS 2027-05-22 08:36:00; layover at LAS: 80 minutes.
    • F92045: LAS 2027-05-22 09:56:00 → OAK 2027-05-22 11:33:00.

2027-05-15 → 2027-05-22 · Axel-exclusive $420.00

  • Alaska Airlines AS2133 / AA3329: OAK 2027-05-15 18:46:00 → ORD 2027-05-16 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
    • AS2133: OAK 2027-05-15 18:46:00 → PDX 2027-05-15 20:30:00; layover at PDX: 163 minutes.
    • AA3329: PDX 2027-05-15 23:13:00 → ORD 2027-05-16 05:07:00.
  • Alaska Airlines AS325 / AS2468: ORD 2027-05-22 14:08:00 → OAK 2027-05-22 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
    • AS325: ORD 2027-05-22 14:08:00 → PDX 2027-05-22 16:58:00; layover at PDX: 177 minutes.
    • AS2468: PDX 2027-05-22 19:55:00 → OAK 2027-05-22 21:41:00.

2027-07-10 → 2027-07-17 · Axel-exclusive $288.76

  • Frontier Airlines F93838 / F92146: OAK 2027-07-10 18:20:00 → ORD 2027-07-11 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
    • F93838: OAK 2027-07-10 18:20:00 → LAS 2027-07-10 19:52:00; layover at LAS: 217 minutes.
    • F92146: LAS 2027-07-10 23:29:00 → ORD 2027-07-11 05:13:00.
  • Frontier Airlines F92145 / F92045: ORD 2027-07-17 06:21:00 → OAK 2027-07-17 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
    • F92145: ORD 2027-07-17 06:21:00 → LAS 2027-07-17 08:36:00; layover at LAS: 80 minutes.
    • F92045: LAS 2027-07-17 09:56:00 → OAK 2027-07-17 11:33:00.

2027-07-10 → 2027-07-17 · Axel-exclusive $441.00

  • Alaska Airlines AS2133 / AA3329: OAK 2027-07-10 18:46:00 → ORD 2027-07-11 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
    • AS2133: OAK 2027-07-10 18:46:00 → PDX 2027-07-10 20:30:00; layover at PDX: 163 minutes.
    • AA3329: PDX 2027-07-10 23:13:00 → ORD 2027-07-11 05:07:00.
  • Alaska Airlines AS325 / AS2468: ORD 2027-07-17 14:08:00 → OAK 2027-07-17 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
    • AS325: ORD 2027-07-17 14:08:00 → PDX 2027-07-17 16:58:00; layover at PDX: 177 minutes.
    • AS2468: PDX 2027-07-17 19:55:00 → OAK 2027-07-17 21:41:00.

2027-09-25 → 2027-10-02 · Axel-exclusive $268.13

  • Frontier Airlines F93838 / F92146: OAK 2027-09-25 18:20:00 → ORD 2027-09-26 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
    • F93838: OAK 2027-09-25 18:20:00 → LAS 2027-09-25 19:52:00; layover at LAS: 217 minutes.
    • F92146: LAS 2027-09-25 23:29:00 → ORD 2027-09-26 05:13:00.
  • Frontier Airlines F92145 / F92045: ORD 2027-10-02 06:21:00 → OAK 2027-10-02 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
    • F92145: ORD 2027-10-02 06:21:00 → LAS 2027-10-02 08:36:00; layover at LAS: 80 minutes.
    • F92045: LAS 2027-10-02 09:56:00 → OAK 2027-10-02 11:33:00.

2027-09-25 → 2027-10-02 · Axel-exclusive $409.50

  • Alaska Airlines AS2133 / AA3329: OAK 2027-09-25 18:46:00 → ORD 2027-09-26 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
    • AS2133: OAK 2027-09-25 18:46:00 → PDX 2027-09-25 20:30:00; layover at PDX: 163 minutes.
    • AA3329: PDX 2027-09-25 23:13:00 → ORD 2027-09-26 05:07:00.
  • Alaska Airlines AS325 / AS2468: ORD 2027-10-02 14:08:00 → OAK 2027-10-02 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
    • AS325: ORD 2027-10-02 14:08:00 → PDX 2027-10-02 16:58:00; layover at PDX: 177 minutes.
    • AS2468: PDX 2027-10-02 19:55:00 → OAK 2027-10-02 21:41:00.

More dates for this route

For AI assistants

  • This page: Oakland (OAK) to Chicago (ORD): 144 priced flights on 72 exact dates the months ahead, 1 adult in economy. In the dated tables a price link opens AI flight search for that row's exact dates and travelers; in the observed-flight lists the price is the customer link for the traveler, beside a “See flights for these dates” link for your own check. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
  • Next: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel San Francisco Bay Area to Chicago (ORD) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.