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Portland → Chicago

Dec 13, 2026 · return Dec 23, 2026

PDX → ORD1 adulteconomyRound trip

11 flight options · 4 airlines

Nonstop flights

Sun, Dec 13 – Wed, Dec 23

Alaska Airlines
7:00 amPDX
4h 8m
Nonstop
1:08 pmORD
Alaska Airlines
2:07 pmORD
4h 43m
Nonstop
4:50 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Wed, Dec 23

American Airlines
11:21 pmPDX
3h 54m
Nonstop
5:15 am+1ORD
American Airlines
5:05 pmORD
4h 42m
Nonstop
7:47 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Wed, Dec 23

United Airlines
11:30 pmPDX
3h 49m
Nonstop
5:19 am+1ORD
United Airlines
12:49 pmORD
4h 34m
Nonstop
3:23 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Wed, Dec 23

American Airlines
1:22 pmPDX
4h 22m
Nonstop
7:44 pmORD
American Airlines
5:05 pmORD
4h 42m
Nonstop
7:47 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Wed, Dec 23

United Airlines
2:34 pmPDX
4h 6m
Nonstop
8:40 pmORD
United Airlines
12:49 pmORD
4h 34m
Nonstop
3:23 pmPDX

Round-trip total · 1 adult · Taxes included

One-stop flights

Sun, Dec 13 – Wed, Dec 23

Delta Air Lines
9:59 amPDX
6h 7m
SLC · 1h 2m
6:06 pmORD
United Airlines
12:49 pmORD
4h 34m
Nonstop
3:23 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Wed, Dec 23

Alaska Airlines
7:00 amPDX
4h 10m
Nonstop
1:10 pmORD
Alaska Airlines
3:19 pmORD
7h 31m
SEA · 1h 43m
8:50 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Wed, Dec 23

Alaska Airlines
10:30 amPDX
7h 37m
GEG · 2h 32m
8:07 pmORD
Alaska Airlines
2:07 pmORD
4h 43m
Nonstop
4:50 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Wed, Dec 23

Alaska Airlines
7:16 amPDX
6h 44m
SLC · 1h 18m
4:00 pmORD
Alaska Airlines
2:07 pmORD
4h 43m
Nonstop
4:50 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Wed, Dec 23

United Airlines
5:00 amPDX
6h 35m
DEN · 1h 27m
1:35 pmORD
United Airlines
12:49 pmORD
4h 34m
Nonstop
3:23 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Wed, Dec 23

United Airlines
3:44 pmPDX
7h 15m
SFO · 1h 5m
12:59 am+1ORD
United Airlines
12:49 pmORD
4h 34m
Nonstop
3:23 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)
2026-12-13 → 2026-12-23Alaska AirlinesAS324 / AS325$423.002026-10-29T01:55:18Z
2026-12-13 → 2026-12-23American AirlinesAA3329 / AA428$434.752026-10-29T01:55:18Z
2026-12-13 → 2026-12-23United AirlinesUA2094 / UA2182$458.252026-10-29T01:55:18Z
2026-12-13 → 2026-12-23Delta Air Lines / United AirlinesDL1203 + DL2377 / UA2182$453.252026-10-29T01:55:18Z
2026-12-13 → 2026-12-23American AirlinesAA562 / AA428$434.752026-10-29T01:55:18Z
2026-12-13 → 2026-12-23United AirlinesUA2266 / UA2182$458.252026-10-29T01:55:18Z
2026-12-13 → 2026-12-23Alaska AirlinesAS324 / AS407 + AS2239$416.252026-10-29T01:55:18Z
2026-12-13 → 2026-12-23Alaska AirlinesAS250 + AA677 / AS325$418.002026-10-29T01:55:18Z
2026-12-13 → 2026-12-23Alaska AirlinesAS3355 + AA3186 / AS325$418.002026-10-29T01:55:18Z
2026-12-13 → 2026-12-23United AirlinesUA459 + UA2329 / UA2182$443.252026-10-29T01:55:18Z
2026-12-13 → 2026-12-23United AirlinesUA1292 + UA1958 / UA2182$443.252026-10-29T01:55:18Z

2026-12-13 → 2026-12-23 · $423.00

  • Alaska Airlines AS324: PDX 2026-12-13 07:00:00 → ORD 2026-12-13 13:08:00; nonstop; 248 minutes. Local airport times.
  • Alaska Airlines AS325: ORD 2026-12-23 14:07:00 → PDX 2026-12-23 16:50:00; nonstop; 283 minutes. Local airport times.

2026-12-13 → 2026-12-23 · $434.75

  • American Airlines AA3329: PDX 2026-12-13 23:21:00 → ORD 2026-12-14 05:15:00; nonstop; 234 minutes. Local airport times.
  • American Airlines AA428: ORD 2026-12-23 17:05:00 → PDX 2026-12-23 19:47:00; nonstop; 282 minutes. Local airport times.

2026-12-13 → 2026-12-23 · $458.25

  • United Airlines UA2094: PDX 2026-12-13 23:30:00 → ORD 2026-12-14 05:19:00; nonstop; 229 minutes. Local airport times.
  • United Airlines UA2182: ORD 2026-12-23 12:49:00 → PDX 2026-12-23 15:23:00; nonstop; 274 minutes. Local airport times.

2026-12-13 → 2026-12-23 · $453.25

  • Delta Air Lines DL1203 / DL2377: PDX 2026-12-13 09:59:00 → ORD 2026-12-13 18:06:00; 1 stop(s) via SLC; 367 minutes. Local airport times.
    • DL1203: PDX 2026-12-13 09:59:00 → SLC 2026-12-13 12:53:00; layover at SLC: 62 minutes.
    • DL2377: SLC 2026-12-13 13:55:00 → ORD 2026-12-13 18:06:00.
  • United Airlines UA2182: ORD 2026-12-23 12:49:00 → PDX 2026-12-23 15:23:00; nonstop; 274 minutes. Local airport times.

2026-12-13 → 2026-12-23 · $434.75

  • American Airlines AA562: PDX 2026-12-13 13:22:00 → ORD 2026-12-13 19:44:00; nonstop; 262 minutes. Local airport times.
  • American Airlines AA428: ORD 2026-12-23 17:05:00 → PDX 2026-12-23 19:47:00; nonstop; 282 minutes. Local airport times.

2026-12-13 → 2026-12-23 · $458.25

  • United Airlines UA2266: PDX 2026-12-13 14:34:00 → ORD 2026-12-13 20:40:00; nonstop; 246 minutes. Local airport times.
  • United Airlines UA2182: ORD 2026-12-23 12:49:00 → PDX 2026-12-23 15:23:00; nonstop; 274 minutes. Local airport times.

2026-12-13 → 2026-12-23 · $416.25

  • Alaska Airlines AS324: PDX 2026-12-13 07:00:00 → ORD 2026-12-13 13:10:00; nonstop; 250 minutes. Local airport times.
  • Alaska Airlines AS407 / AS2239: ORD 2026-12-23 15:19:00 → PDX 2026-12-23 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
    • AS407: ORD 2026-12-23 15:19:00 → SEA 2026-12-23 18:11:00; layover at SEA: 103 minutes.
    • AS2239: SEA 2026-12-23 19:54:00 → PDX 2026-12-23 20:50:00.

2026-12-13 → 2026-12-23 · $418.00

  • Alaska Airlines AS250 / AA677: PDX 2026-12-13 10:30:00 → ORD 2026-12-13 20:07:00; 1 stop(s) via GEG; 457 minutes. Local airport times.
    • AS250: PDX 2026-12-13 10:30:00 → GEG 2026-12-13 11:41:00; layover at GEG: 152 minutes.
    • AA677: GEG 2026-12-13 14:13:00 → ORD 2026-12-13 20:07:00.
  • Alaska Airlines AS325: ORD 2026-12-23 14:07:00 → PDX 2026-12-23 16:50:00; nonstop; 283 minutes. Local airport times.

2026-12-13 → 2026-12-23 · $418.00

  • Alaska Airlines AS3355 / AA3186: PDX 2026-12-13 07:16:00 → ORD 2026-12-13 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
    • AS3355: PDX 2026-12-13 07:16:00 → SLC 2026-12-13 10:19:00; layover at SLC: 78 minutes.
    • AA3186: SLC 2026-12-13 11:37:00 → ORD 2026-12-13 16:00:00.
  • Alaska Airlines AS325: ORD 2026-12-23 14:07:00 → PDX 2026-12-23 16:50:00; nonstop; 283 minutes. Local airport times.

2026-12-13 → 2026-12-23 · $443.25

  • United Airlines UA459 / UA2329: PDX 2026-12-13 05:00:00 → ORD 2026-12-13 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
    • UA459: PDX 2026-12-13 05:00:00 → DEN 2026-12-13 08:28:00; layover at DEN: 87 minutes.
    • UA2329: DEN 2026-12-13 09:55:00 → ORD 2026-12-13 13:35:00.
  • United Airlines UA2182: ORD 2026-12-23 12:49:00 → PDX 2026-12-23 15:23:00; nonstop; 274 minutes. Local airport times.

2026-12-13 → 2026-12-23 · $443.25

  • United Airlines UA1292 / UA1958: PDX 2026-12-13 15:44:00 → ORD 2026-12-14 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
    • UA1292: PDX 2026-12-13 15:44:00 → SFO 2026-12-13 17:37:00; layover at SFO: 65 minutes.
    • UA1958: SFO 2026-12-13 18:42:00 → ORD 2026-12-14 00:59:00.
  • United Airlines UA2182: ORD 2026-12-23 12:49:00 → PDX 2026-12-23 15:23:00; nonstop; 274 minutes. Local airport times.

More dates for this route