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Portland → Chicago

Dec 21, 2026 · return Dec 28, 2026

PDX → ORD1 adulteconomyRound trip

11 flight options · 4 airlines

Nonstop flights

Mon, Dec 21 – Mon, Dec 28

Alaska Airlines
7:00 amPDX
4h 10m
Nonstop
1:10 pmORD
Alaska Airlines
2:08 pmORD
4h 50m
Nonstop
4:58 pmPDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

American Airlines
1:46 pmPDX
4h 14m
Nonstop
8:00 pmORD
American Airlines
9:22 pmORD
4h 47m
Nonstop
12:09 am+1PDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

United Airlines
2:26 pmPDX
4h 2m
Nonstop
8:28 pmORD
United Airlines
12:40 pmORD
4h 39m
Nonstop
3:19 pmPDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

American Airlines
11:21 pmPDX
3h 54m
Nonstop
5:15 am+1ORD
American Airlines
9:22 pmORD
4h 47m
Nonstop
12:09 am+1PDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

United Airlines
11:50 pmPDX
4h 9m
Nonstop
5:59 am+1ORD
United Airlines
12:40 pmORD
4h 39m
Nonstop
3:19 pmPDX

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Mon, Dec 28

Delta Air Lines
9:59 amPDX
6h 7m
SLC · 1h 2m
6:06 pmORD
United Airlines
12:40 pmORD
4h 39m
Nonstop
3:19 pmPDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

American Airlines
2:36 pmPDX
7h 23m
DFW · 1h 2m
11:59 pmORD
American Airlines
9:22 pmORD
4h 47m
Nonstop
12:09 am+1PDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

Alaska Airlines
7:16 amPDX
6h 44m
SLC · 1h 18m
4:00 pmORD
Alaska Airlines
2:08 pmORD
4h 50m
Nonstop
4:58 pmPDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

Alaska Airlines
7:00 amPDX
4h 8m
Nonstop
1:08 pmORD
Alaska Airlines
3:19 pmORD
7h 31m
SEA · 1h 43m
8:50 pmPDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

United Airlines
3:44 pmPDX
7h 15m
SFO · 1h 5m
12:59 am+1ORD
United Airlines
12:40 pmORD
4h 39m
Nonstop
3:19 pmPDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

United Airlines
5:00 amPDX
6h 35m
DEN · 1h 27m
1:35 pmORD
United Airlines
12:40 pmORD
4h 39m
Nonstop
3:19 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.

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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)
2026-12-21 → 2026-12-28Alaska AirlinesAS324 / AS325$468.002026-10-29T01:55:18Z
2026-12-21 → 2026-12-28American AirlinesAA563 / AA562$481.002026-10-29T01:55:18Z
2026-12-21 → 2026-12-28United AirlinesUA2822 / UA2182$507.002026-10-29T01:55:18Z
2026-12-21 → 2026-12-28Delta Air Lines / United AirlinesDL1203 + DL2377 / UA2182$500.252026-10-29T01:55:18Z
2026-12-21 → 2026-12-28American AirlinesAA3329 / AA562$481.002026-10-29T01:55:18Z
2026-12-21 → 2026-12-28United AirlinesUA2094 / UA2182$507.002026-10-29T01:55:18Z
2026-12-21 → 2026-12-28American AirlinesAA2496 + AA2221 / AA562$460.752026-10-29T01:55:18Z
2026-12-21 → 2026-12-28Alaska AirlinesAS3355 + AA3186 / AS325$461.252026-10-29T01:55:18Z
2026-12-21 → 2026-12-28Alaska AirlinesAS324 / AS407 + AS2239$461.752026-10-29T01:55:18Z
2026-12-21 → 2026-12-28United AirlinesUA1292 + UA1958 / UA2182$486.752026-10-29T01:55:18Z
2026-12-21 → 2026-12-28United AirlinesUA459 + UA2329 / UA2182$486.752026-10-29T01:55:18Z

2026-12-21 → 2026-12-28 · $468.00

  • Alaska Airlines AS324: PDX 2026-12-21 07:00:00 → ORD 2026-12-21 13:10:00; nonstop; 250 minutes. Local airport times.
  • Alaska Airlines AS325: ORD 2026-12-28 14:08:00 → PDX 2026-12-28 16:58:00; nonstop; 290 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $481.00

  • American Airlines AA563: PDX 2026-12-21 13:46:00 → ORD 2026-12-21 20:00:00; nonstop; 254 minutes. Local airport times.
  • American Airlines AA562: ORD 2026-12-28 21:22:00 → PDX 2026-12-29 00:09:00; nonstop; 287 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $507.00

  • United Airlines UA2822: PDX 2026-12-21 14:26:00 → ORD 2026-12-21 20:28:00; nonstop; 242 minutes. Local airport times.
  • United Airlines UA2182: ORD 2026-12-28 12:40:00 → PDX 2026-12-28 15:19:00; nonstop; 279 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $500.25

  • Delta Air Lines DL1203 / DL2377: PDX 2026-12-21 09:59:00 → ORD 2026-12-21 18:06:00; 1 stop(s) via SLC; 367 minutes. Local airport times.
    • DL1203: PDX 2026-12-21 09:59:00 → SLC 2026-12-21 12:53:00; layover at SLC: 62 minutes.
    • DL2377: SLC 2026-12-21 13:55:00 → ORD 2026-12-21 18:06:00.
  • United Airlines UA2182: ORD 2026-12-28 12:40:00 → PDX 2026-12-28 15:19:00; nonstop; 279 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $481.00

  • American Airlines AA3329: PDX 2026-12-21 23:21:00 → ORD 2026-12-22 05:15:00; nonstop; 234 minutes. Local airport times.
  • American Airlines AA562: ORD 2026-12-28 21:22:00 → PDX 2026-12-29 00:09:00; nonstop; 287 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $507.00

  • United Airlines UA2094: PDX 2026-12-21 23:50:00 → ORD 2026-12-22 05:59:00; nonstop; 249 minutes. Local airport times.
  • United Airlines UA2182: ORD 2026-12-28 12:40:00 → PDX 2026-12-28 15:19:00; nonstop; 279 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $460.75

  • American Airlines AA2496 / AA2221: PDX 2026-12-21 14:36:00 → ORD 2026-12-21 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
    • AA2496: PDX 2026-12-21 14:36:00 → DFW 2026-12-21 20:28:00; layover at DFW: 62 minutes.
    • AA2221: DFW 2026-12-21 21:30:00 → ORD 2026-12-21 23:59:00.
  • American Airlines AA562: ORD 2026-12-28 21:22:00 → PDX 2026-12-29 00:09:00; nonstop; 287 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $461.25

  • Alaska Airlines AS3355 / AA3186: PDX 2026-12-21 07:16:00 → ORD 2026-12-21 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
    • AS3355: PDX 2026-12-21 07:16:00 → SLC 2026-12-21 10:19:00; layover at SLC: 78 minutes.
    • AA3186: SLC 2026-12-21 11:37:00 → ORD 2026-12-21 16:00:00.
  • Alaska Airlines AS325: ORD 2026-12-28 14:08:00 → PDX 2026-12-28 16:58:00; nonstop; 290 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $461.75

  • Alaska Airlines AS324: PDX 2026-12-21 07:00:00 → ORD 2026-12-21 13:08:00; nonstop; 248 minutes. Local airport times.
  • Alaska Airlines AS407 / AS2239: ORD 2026-12-28 15:19:00 → PDX 2026-12-28 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
    • AS407: ORD 2026-12-28 15:19:00 → SEA 2026-12-28 18:11:00; layover at SEA: 103 minutes.
    • AS2239: SEA 2026-12-28 19:54:00 → PDX 2026-12-28 20:50:00.

2026-12-21 → 2026-12-28 · $486.75

  • United Airlines UA1292 / UA1958: PDX 2026-12-21 15:44:00 → ORD 2026-12-22 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
    • UA1292: PDX 2026-12-21 15:44:00 → SFO 2026-12-21 17:37:00; layover at SFO: 65 minutes.
    • UA1958: SFO 2026-12-21 18:42:00 → ORD 2026-12-22 00:59:00.
  • United Airlines UA2182: ORD 2026-12-28 12:40:00 → PDX 2026-12-28 15:19:00; nonstop; 279 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $486.75

  • United Airlines UA459 / UA2329: PDX 2026-12-21 05:00:00 → ORD 2026-12-21 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
    • UA459: PDX 2026-12-21 05:00:00 → DEN 2026-12-21 08:28:00; layover at DEN: 87 minutes.
    • UA2329: DEN 2026-12-21 09:55:00 → ORD 2026-12-21 13:35:00.
  • United Airlines UA2182: ORD 2026-12-28 12:40:00 → PDX 2026-12-28 15:19:00; nonstop; 279 minutes. Local airport times.

More dates for this route