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Portland → Chicago

Dec 21, 2026 · return Dec 24, 2026

PDX → ORD1 adulteconomyRound trip

10 flight options · 4 airlines

Nonstop flights

Mon, Dec 21 – Thu, Dec 24

Alaska Airlines
7:00 amPDX
4h 10m
Nonstop
1:10 pmORD
Alaska Airlines
2:08 pmORD
4h 57m
Nonstop
5:05 pmPDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

American Airlines
11:31 pmPDX
3h 54m
Nonstop
5:25 am+1ORD
American Airlines
9:44 amORD
4h 42m
Nonstop
12:26 pmPDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

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

Mon, Dec 21 – Thu, Dec 24

United Airlines
11:50 pmPDX
4h 9m
Nonstop
5:59 am+1ORD
United Airlines
7:45 pmORD
4h 42m
Nonstop
10:27 pmPDX

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Thu, Dec 24

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

Mon, Dec 21 – Thu, Dec 24

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 – Thu, Dec 24

Alaska Airlines
7:16 amPDX
6h 44m
SLC · 1h 18m
4:00 pmORD
Alaska Airlines
2:08 pmORD
4h 57m
Nonstop
5:05 pmPDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

American Airlines
11:21 pmPDX
3h 54m
Nonstop
5:15 am+1ORD
American Airlines
8:10 amORD
7h 38m
SLC · 1h 36m
1:48 pmPDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

United Airlines
11:30 pmPDX
3h 49m
Nonstop
5:19 am+1ORD
United Airlines
8:58 amORD
7h 43m
YVR · 1h 40m
2:41 pmPDX

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

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

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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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 → 2026-12-24Alaska AirlinesAS324 / AS325$486.002026-10-29T01:55:18Z
2026-12-21 → 2026-12-24American AirlinesAA3329 / AA561$499.502026-10-29T01:55:18Z
2026-12-21 → 2026-12-24United AirlinesUA2822 / UA1786$526.502026-10-29T01:55:18Z
2026-12-21 → 2026-12-24Delta Air Lines / United AirlinesDL1203 + DL2377 / UA1786$519.752026-10-29T01:55:18Z
2026-12-21 → 2026-12-24United AirlinesUA2094 / UA1786$526.502026-10-29T01:55:18Z
2026-12-21 → 2026-12-24Alaska AirlinesAS324 / AS407 + AS2239$479.252026-10-29T01:55:18Z
2026-12-21 → 2026-12-24Alaska AirlinesAS3355 + AA3186 / AS325$479.252026-10-29T01:55:18Z
2026-12-21 → 2026-12-24American AirlinesAA3329 / AA3186 + AS3430$479.252026-10-29T01:55:18Z
2026-12-21 → 2026-12-24United AirlinesUA2094 / UA1498 + AC8652$506.252026-10-29T01:55:18Z
2026-12-21 → 2026-12-24United AirlinesUA1292 + UA1958 / UA1786$506.252026-10-29T01:55:18Z

2026-12-21 → 2026-12-24 · $486.00

  • 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 2026-12-24 14:08:00 → PDX 2026-12-24 17:05:00; nonstop; 297 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $499.50

  • American Airlines AA3329: PDX 2026-12-21 23:31:00 → ORD 2026-12-22 05:25:00; nonstop; 234 minutes. Local airport times.
  • American Airlines AA561: ORD 2026-12-24 09:44:00 → PDX 2026-12-24 12:26:00; nonstop; 282 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $526.50

  • 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 UA1786: ORD 2026-12-24 19:45:00 → PDX 2026-12-24 22:27:00; nonstop; 282 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $519.75

  • 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 UA1786: ORD 2026-12-24 19:45:00 → PDX 2026-12-24 22:27:00; nonstop; 282 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $526.50

  • 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 UA1786: ORD 2026-12-24 19:45:00 → PDX 2026-12-24 22:27:00; nonstop; 282 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $479.25

  • 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 2026-12-24 15:19:00 → PDX 2026-12-24 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
    • AS407: ORD 2026-12-24 15:19:00 → SEA 2026-12-24 18:11:00; layover at SEA: 103 minutes.
    • AS2239: SEA 2026-12-24 19:54:00 → PDX 2026-12-24 20:50:00.

2026-12-21 → 2026-12-24 · $479.25

  • 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 2026-12-24 14:08:00 → PDX 2026-12-24 17:05:00; nonstop; 297 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $479.25

  • 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 AA3186 / AS3430: ORD 2026-12-24 08:10:00 → PDX 2026-12-24 13:48:00; 1 stop(s) via SLC; 458 minutes. Local airport times.
    • AA3186: ORD 2026-12-24 08:10:00 → SLC 2026-12-24 10:56:00; layover at SLC: 96 minutes.
    • AS3430: SLC 2026-12-24 12:32:00 → PDX 2026-12-24 13:48:00.

2026-12-21 → 2026-12-24 · $506.25

  • United Airlines UA2094: PDX 2026-12-21 23:30:00 → ORD 2026-12-22 05:19:00; nonstop; 229 minutes. Local airport times.
  • United Airlines UA1498 / AC8652: ORD 2026-12-24 08:58:00 → PDX 2026-12-24 14:41:00; 1 stop(s) via YVR; 463 minutes. Local airport times.
    • UA1498: ORD 2026-12-24 08:58:00 → YVR 2026-12-24 12:45:00; layover at YVR: 100 minutes.
    • AC8652: YVR 2026-12-24 14:25:00 → PDX 2026-12-24 14:41:00.

2026-12-21 → 2026-12-24 · $506.25

  • 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 UA1786: ORD 2026-12-24 19:45:00 → PDX 2026-12-24 22:27:00; nonstop; 282 minutes. Local airport times.

More dates for this route