Travel with Axel,
get the best price.

Portland → Chicago

Jan 21, 2027 · return Feb 4, 2027

PDX → ORD1 adulteconomyRound trip

10 flight options · 4 airlines

Nonstop flights

Thu, Jan 21 – Thu, Feb 4

Alaska Airlines
7:00 amPDX
4h 8m
Nonstop
1:08 pmORD
Alaska Airlines
2:08 pmORD
4h 57m
Nonstop
5:05 pmPDX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

American Airlines
1:22 pmPDX
4h 22m
Nonstop
7:44 pmORD
American Airlines
9:44 amORD
4h 42m
Nonstop
12:26 pmPDX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

United Airlines
10:43 amPDX
4h 6m
Nonstop
4:49 pmORD
United Airlines
7:45 pmORD
4h 42m
Nonstop
10:27 pmPDX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

United Airlines
2:26 pmPDX
4h 2m
Nonstop
8:28 pmORD
United Airlines
7:45 pmORD
4h 42m
Nonstop
10:27 pmPDX

Round-trip total · 1 adult · Taxes included

One-stop flights

Thu, Jan 21 – Thu, Feb 4

Delta Air Lines
9:59 amPDX
6h 7m
SLC · 1h 2m
6:06 pmORD
United Airlines
7:45 pmORD
4h 42m
Nonstop
10:27 pmPDX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Alaska Airlines
7:01 amPDX
4h 8m
Nonstop
1:09 pmORD
Alaska Airlines
3:19 pmORD
7h 31m
SEA · 1h 43m
8:50 pmPDX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

American Airlines
1:30 pmPDX
4h 14m
Nonstop
7:44 pmORD
American Airlines
8:10 amORD
7h 38m
SLC · 1h 36m
1:48 pmPDX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

United Airlines
3:44 pmPDX
7h 15m
SFO · 1h 5m
12:59 am+1ORD
United Airlines
7:45 pmORD
4h 42m
Nonstop
10:27 pmPDX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

United Airlines
5:00 amPDX
6h 35m
DEN · 1h 27m
1:35 pmORD
United Airlines
7:45 pmORD
4h 42m
Nonstop
10:27 pmPDX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

United Airlines
10:47 amPDX
4h 6m
Nonstop
4:53 pmORD
United Airlines
8:58 amORD
7h 43m
YVR · 1h 40m
2:41 pmPDX

Round-trip total · 1 adult · Taxes included

Make this trip yours

PDX ⇄ ORD

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, Alaska 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)
2027-01-21 → 2027-02-04Alaska AirlinesAS324 / AS325$342.002026-10-29T01:55:18Z
2027-01-21 → 2027-02-04American AirlinesAA562 / AA561$351.502026-10-29T01:55:18Z
2027-01-21 → 2027-02-04United AirlinesUA1923 / UA1786$370.502026-10-29T01:55:18Z
2027-01-21 → 2027-02-04Delta Air Lines / United AirlinesDL1203 + DL2377 / UA1786$365.752026-10-29T01:55:18Z
2027-01-21 → 2027-02-04United AirlinesUA2822 / UA1786$370.502026-10-29T01:55:18Z
2027-01-21 → 2027-02-04Alaska AirlinesAS324 / AS407 + AS2239$337.252026-10-29T01:55:18Z
2027-01-21 → 2027-02-04American AirlinesAA562 / AA3186 + AS3430$337.252026-10-29T01:55:18Z
2027-01-21 → 2027-02-04United AirlinesUA1292 + UA1958 / UA1786$356.252026-10-29T01:55:18Z
2027-01-21 → 2027-02-04United AirlinesUA459 + UA2329 / UA1786$356.252026-10-29T01:55:18Z
2027-01-21 → 2027-02-04United AirlinesUA1923 / UA1498 + AC8652$356.252026-10-29T01:55:18Z

2027-01-21 → 2027-02-04 · $342.00

  • Alaska Airlines AS324: PDX 2027-01-21 07:00:00 → ORD 2027-01-21 13:08:00; nonstop; 248 minutes. Local airport times.
  • Alaska Airlines AS325: ORD 2027-02-04 14:08:00 → PDX 2027-02-04 17:05:00; nonstop; 297 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $351.50

  • American Airlines AA562: PDX 2027-01-21 13:22:00 → ORD 2027-01-21 19:44:00; nonstop; 262 minutes. Local airport times.
  • American Airlines AA561: ORD 2027-02-04 09:44:00 → PDX 2027-02-04 12:26:00; nonstop; 282 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $370.50

  • United Airlines UA1923: PDX 2027-01-21 10:43:00 → ORD 2027-01-21 16:49:00; nonstop; 246 minutes. Local airport times.
  • United Airlines UA1786: ORD 2027-02-04 19:45:00 → PDX 2027-02-04 22:27:00; nonstop; 282 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $365.75

  • Delta Air Lines DL1203 / DL2377: PDX 2027-01-21 09:59:00 → ORD 2027-01-21 18:06:00; 1 stop(s) via SLC; 367 minutes. Local airport times.
    • DL1203: PDX 2027-01-21 09:59:00 → SLC 2027-01-21 12:53:00; layover at SLC: 62 minutes.
    • DL2377: SLC 2027-01-21 13:55:00 → ORD 2027-01-21 18:06:00.
  • United Airlines UA1786: ORD 2027-02-04 19:45:00 → PDX 2027-02-04 22:27:00; nonstop; 282 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $370.50

  • United Airlines UA2822: PDX 2027-01-21 14:26:00 → ORD 2027-01-21 20:28:00; nonstop; 242 minutes. Local airport times.
  • United Airlines UA1786: ORD 2027-02-04 19:45:00 → PDX 2027-02-04 22:27:00; nonstop; 282 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $337.25

  • Alaska Airlines AS324: PDX 2027-01-21 07:01:00 → ORD 2027-01-21 13:09:00; nonstop; 248 minutes. Local airport times.
  • Alaska Airlines AS407 / AS2239: ORD 2027-02-04 15:19:00 → PDX 2027-02-04 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
    • AS407: ORD 2027-02-04 15:19:00 → SEA 2027-02-04 18:11:00; layover at SEA: 103 minutes.
    • AS2239: SEA 2027-02-04 19:54:00 → PDX 2027-02-04 20:50:00.

2027-01-21 → 2027-02-04 · $337.25

  • American Airlines AA562: PDX 2027-01-21 13:30:00 → ORD 2027-01-21 19:44:00; nonstop; 254 minutes. Local airport times.
  • American Airlines AA3186 / AS3430: ORD 2027-02-04 08:10:00 → PDX 2027-02-04 13:48:00; 1 stop(s) via SLC; 458 minutes. Local airport times.
    • AA3186: ORD 2027-02-04 08:10:00 → SLC 2027-02-04 10:56:00; layover at SLC: 96 minutes.
    • AS3430: SLC 2027-02-04 12:32:00 → PDX 2027-02-04 13:48:00.

2027-01-21 → 2027-02-04 · $356.25

  • United Airlines UA1292 / UA1958: PDX 2027-01-21 15:44:00 → ORD 2027-01-22 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
    • UA1292: PDX 2027-01-21 15:44:00 → SFO 2027-01-21 17:37:00; layover at SFO: 65 minutes.
    • UA1958: SFO 2027-01-21 18:42:00 → ORD 2027-01-22 00:59:00.
  • United Airlines UA1786: ORD 2027-02-04 19:45:00 → PDX 2027-02-04 22:27:00; nonstop; 282 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $356.25

  • United Airlines UA459 / UA2329: PDX 2027-01-21 05:00:00 → ORD 2027-01-21 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
    • UA459: PDX 2027-01-21 05:00:00 → DEN 2027-01-21 08:28:00; layover at DEN: 87 minutes.
    • UA2329: DEN 2027-01-21 09:55:00 → ORD 2027-01-21 13:35:00.
  • United Airlines UA1786: ORD 2027-02-04 19:45:00 → PDX 2027-02-04 22:27:00; nonstop; 282 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $356.25

  • United Airlines UA1923: PDX 2027-01-21 10:47:00 → ORD 2027-01-21 16:53:00; nonstop; 246 minutes. Local airport times.
  • United Airlines UA1498 / AC8652: ORD 2027-02-04 08:58:00 → PDX 2027-02-04 14:41:00; 1 stop(s) via YVR; 463 minutes. Local airport times.
    • UA1498: ORD 2027-02-04 08:58:00 → YVR 2027-02-04 12:45:00; layover at YVR: 100 minutes.
    • AC8652: YVR 2027-02-04 14:25:00 → PDX 2027-02-04 14:41:00.

More dates for this route