Travel with Axel,
get the best price.

Chicago → Oakland

Dec 2, 2026 · return Dec 16, 2026

MDW → OAK1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Wed, Dec 2 – Wed, Dec 16

Southwest Airlines
9:25 pmMDW
4h 55m
Nonstop
12:20 am+1OAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Wed, Dec 16

Southwest Airlines
10:00 amMDW
4h 40m
Nonstop
12:40 pmOAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Wed, Dec 2 – Wed, Dec 16

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 50m
10:50 amOAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Wed, Dec 16

Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Wed, Dec 16

Southwest Airlines
10:00 amMDW
4h 45m
Nonstop
12:45 pmOAK
Southwest Airlines
8:30 amOAK
6h 50m
LGB · 1h 35m
5:20 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Wed, Dec 16

Southwest Airlines
5:50 amMDW
6h 55m
LAS · 1h 25m
10:45 amOAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Wed, Dec 16

Southwest Airlines
8:50 amMDW
8h 25m
DAL · 2h 15m
3:15 pmOAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Wed, Dec 16

Southwest Airlines
3:45 pmMDW
7h 30m
LAX · 1h 50m
9:15 pmOAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ OAK

Economy

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

No account needed to see prices.

Already have an account? Log in

Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest 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.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. 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

All dates for this routeNov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-02 → 2026-12-16Southwest AirlinesWN2990 / WN2871$338.002026-10-29T01:29:13Z
2026-12-02 → 2026-12-16Southwest AirlinesWN3174 / WN2871$338.002026-10-29T01:29:13Z
2026-12-02 → 2026-12-16Southwest AirlinesWN2995 + WN681 / WN2871$328.002026-10-29T01:29:13Z
2026-12-02 → 2026-12-16Southwest AirlinesWN4415 + WN1144 / WN2871$328.002026-10-29T01:29:13Z
2026-12-02 → 2026-12-16Southwest AirlinesWN3174 / WN3217 + WN801$328.002026-10-29T01:29:13Z
2026-12-02 → 2026-12-16Southwest AirlinesWN2691 + WN1936 / WN2871$328.002026-10-29T01:29:13Z
2026-12-02 → 2026-12-16Southwest AirlinesWN1191 + WN1924 / WN2871$328.002026-10-29T01:29:13Z
2026-12-02 → 2026-12-16Southwest AirlinesWN2952 + WN1901 / WN2871$328.002026-10-29T01:29:13Z

2026-12-02 → 2026-12-16 · $338.00

  • Southwest Airlines WN2990: MDW 2026-12-02 21:25:00 → OAK 2026-12-03 00:20:00; nonstop; 295 minutes. Local airport times.
  • Southwest Airlines WN2871: OAK 2026-12-16 06:30:00 → MDW 2026-12-16 12:30:00; nonstop; 240 minutes. Local airport times.

2026-12-02 → 2026-12-16 · $338.00

  • Southwest Airlines WN3174: MDW 2026-12-02 10:00:00 → OAK 2026-12-02 12:40:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN2871: OAK 2026-12-16 06:30:00 → MDW 2026-12-16 12:30:00; nonstop; 240 minutes. Local airport times.

2026-12-02 → 2026-12-16 · $328.00

  • Southwest Airlines WN2995 / WN681: MDW 2026-12-02 05:05:00 → OAK 2026-12-02 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-12-02 05:05:00 → PHX 2026-12-02 07:55:00; layover at PHX: 110 minutes.
    • WN681: PHX 2026-12-02 09:45:00 → OAK 2026-12-02 10:50:00.
  • Southwest Airlines WN2871: OAK 2026-12-16 06:30:00 → MDW 2026-12-16 12:30:00; nonstop; 240 minutes. Local airport times.

2026-12-02 → 2026-12-16 · $328.00

  • Southwest Airlines WN4415 / WN1144: MDW 2026-12-02 15:15:00 → OAK 2026-12-02 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2026-12-02 15:15:00 → SAN 2026-12-02 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2026-12-02 20:05:00 → OAK 2026-12-02 21:35:00.
  • Southwest Airlines WN2871: OAK 2026-12-16 06:30:00 → MDW 2026-12-16 12:30:00; nonstop; 240 minutes. Local airport times.

2026-12-02 → 2026-12-16 · $328.00

  • Southwest Airlines WN3174: MDW 2026-12-02 10:00:00 → OAK 2026-12-02 12:45:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN3217 / WN801: OAK 2026-12-16 08:30:00 → MDW 2026-12-16 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
    • WN3217: OAK 2026-12-16 08:30:00 → LGB 2026-12-16 10:00:00; layover at LGB: 95 minutes.
    • WN801: LGB 2026-12-16 11:35:00 → MDW 2026-12-16 17:20:00.

2026-12-02 → 2026-12-16 · $328.00

  • Southwest Airlines WN2691 / WN1936: MDW 2026-12-02 05:50:00 → OAK 2026-12-02 10:45:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN2691: MDW 2026-12-02 05:50:00 → LAS 2026-12-02 07:45:00; layover at LAS: 85 minutes.
    • WN1936: LAS 2026-12-02 09:10:00 → OAK 2026-12-02 10:45:00.
  • Southwest Airlines WN2871: OAK 2026-12-16 06:30:00 → MDW 2026-12-16 12:30:00; nonstop; 240 minutes. Local airport times.

2026-12-02 → 2026-12-16 · $328.00

  • Southwest Airlines WN1191 / WN1924: MDW 2026-12-02 08:50:00 → OAK 2026-12-02 15:15:00; 1 stop(s) via DAL; 505 minutes. Local airport times.
    • WN1191: MDW 2026-12-02 08:50:00 → DAL 2026-12-02 11:20:00; layover at DAL: 135 minutes.
    • WN1924: DAL 2026-12-02 13:35:00 → OAK 2026-12-02 15:15:00.
  • Southwest Airlines WN2871: OAK 2026-12-16 06:30:00 → MDW 2026-12-16 12:30:00; nonstop; 240 minutes. Local airport times.

2026-12-02 → 2026-12-16 · $328.00

  • Southwest Airlines WN2952 / WN1901: MDW 2026-12-02 15:45:00 → OAK 2026-12-02 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-12-02 15:45:00 → LAX 2026-12-02 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-12-02 20:00:00 → OAK 2026-12-02 21:15:00.
  • Southwest Airlines WN2871: OAK 2026-12-16 06:30:00 → MDW 2026-12-16 12:30:00; nonstop; 240 minutes. Local airport times.

More dates for this route