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Portland → Chicago

Dec 2, 2026 · return Dec 6, 2026

PDX → ORD1 adulteconomyRound trip

11 flight options · 4 airlines

Nonstop flights

Wed, Dec 2 – Sun, Dec 6

Alaska Airlines
7:01 amPDX
4h 8m
Nonstop
1:09 pmORD
Alaska Airlines
2:08 pmORD
4h 57m
Nonstop
5:05 pmPDX

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Sun, Dec 6

American Airlines
11:09 pmPDX
3h 58m
Nonstop
5:07 am+1ORD
American Airlines
9:22 pmORD
4h 47m
Nonstop
12:09 am+1PDX

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Sun, Dec 6

United Airlines
11:30 pmPDX
3h 49m
Nonstop
5:19 am+1ORD
United Airlines
8:59 amORD
4h 43m
Nonstop
11:42 amPDX

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Sun, Dec 6

American Airlines
1:22 pmPDX
4h 22m
Nonstop
7:44 pmORD
American Airlines
9:22 pmORD
4h 47m
Nonstop
12:09 am+1PDX

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Sun, Dec 6

United Airlines
2:26 pmPDX
4h 2m
Nonstop
8:28 pmORD
United Airlines
8:59 amORD
4h 43m
Nonstop
11:42 amPDX

Round-trip total · 1 adult · Taxes included

One-stop flights

Wed, Dec 2 – Sun, Dec 6

Delta Air Lines
9:59 amPDX
6h 7m
SLC · 1h 2m
6:06 pmORD
United Airlines
8:59 amORD
4h 43m
Nonstop
11:42 amPDX

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Sun, Dec 6

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

Wed, Dec 2 – Sun, Dec 6

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

Wed, Dec 2 – Sun, Dec 6

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

Wed, Dec 2 – Sun, Dec 6

United Airlines
3:44 pmPDX
7h 15m
SFO · 1h 5m
12:59 am+1ORD
United Airlines
8:59 amORD
4h 43m
Nonstop
11:42 amPDX

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Sun, Dec 6

United Airlines
5:00 amPDX
6h 35m
DEN · 1h 27m
1:35 pmORD
United Airlines
8:59 amORD
4h 43m
Nonstop
11:42 amPDX

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 24, 2026 → Nov 29, 2026Dec 22, 2026 → Dec 27, 2026Dec 30, 2026 → Jan 2, 2027Jan 15, 2027 → Jan 18, 2027Oct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Jan 22, 2027 → Jan 25, 2027Oct 30, 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 → 2026-12-06Alaska AirlinesAS324 / AS325$360.002026-10-29T01:55:18Z
2026-12-02 → 2026-12-06American AirlinesAA519 / AA562$370.002026-10-29T01:55:18Z
2026-12-02 → 2026-12-06United AirlinesUA2094 / UA751$390.002026-10-29T01:55:18Z
2026-12-02 → 2026-12-06Delta Air Lines / United AirlinesDL1203 + DL2377 / UA751$385.002026-10-29T01:55:18Z
2026-12-02 → 2026-12-06American AirlinesAA562 / AA562$370.002026-10-29T01:55:18Z
2026-12-02 → 2026-12-06United AirlinesUA2822 / UA751$390.002026-10-29T01:55:18Z
2026-12-02 → 2026-12-06American AirlinesAA2496 + AA2221 / AA562$355.002026-10-29T01:55:18Z
2026-12-02 → 2026-12-06Alaska AirlinesAS3355 + AA3186 / AS325$355.002026-10-29T01:55:18Z
2026-12-02 → 2026-12-06Alaska AirlinesAS324 / AS407 + AS2239$355.002026-10-29T01:55:18Z
2026-12-02 → 2026-12-06United AirlinesUA1292 + UA1958 / UA751$375.002026-10-29T01:55:18Z
2026-12-02 → 2026-12-06United AirlinesUA459 + UA2329 / UA751$375.002026-10-29T01:55:18Z

2026-12-02 → 2026-12-06 · $360.00

  • Alaska Airlines AS324: PDX 2026-12-02 07:01:00 → ORD 2026-12-02 13:09:00; nonstop; 248 minutes. Local airport times.
  • Alaska Airlines AS325: ORD 2026-12-06 14:08:00 → PDX 2026-12-06 17:05:00; nonstop; 297 minutes. Local airport times.

2026-12-02 → 2026-12-06 · $370.00

  • American Airlines AA519: PDX 2026-12-02 23:09:00 → ORD 2026-12-03 05:07:00; nonstop; 238 minutes. Local airport times.
  • American Airlines AA562: ORD 2026-12-06 21:22:00 → PDX 2026-12-07 00:09:00; nonstop; 287 minutes. Local airport times.

2026-12-02 → 2026-12-06 · $390.00

  • United Airlines UA2094: PDX 2026-12-02 23:30:00 → ORD 2026-12-03 05:19:00; nonstop; 229 minutes. Local airport times.
  • United Airlines UA751: ORD 2026-12-06 08:59:00 → PDX 2026-12-06 11:42:00; nonstop; 283 minutes. Local airport times.

2026-12-02 → 2026-12-06 · $385.00

  • Delta Air Lines DL1203 / DL2377: PDX 2026-12-02 09:59:00 → ORD 2026-12-02 18:06:00; 1 stop(s) via SLC; 367 minutes. Local airport times.
    • DL1203: PDX 2026-12-02 09:59:00 → SLC 2026-12-02 12:53:00; layover at SLC: 62 minutes.
    • DL2377: SLC 2026-12-02 13:55:00 → ORD 2026-12-02 18:06:00.
  • United Airlines UA751: ORD 2026-12-06 08:59:00 → PDX 2026-12-06 11:42:00; nonstop; 283 minutes. Local airport times.

2026-12-02 → 2026-12-06 · $370.00

  • American Airlines AA562: PDX 2026-12-02 13:22:00 → ORD 2026-12-02 19:44:00; nonstop; 262 minutes. Local airport times.
  • American Airlines AA562: ORD 2026-12-06 21:22:00 → PDX 2026-12-07 00:09:00; nonstop; 287 minutes. Local airport times.

2026-12-02 → 2026-12-06 · $390.00

  • United Airlines UA2822: PDX 2026-12-02 14:26:00 → ORD 2026-12-02 20:28:00; nonstop; 242 minutes. Local airport times.
  • United Airlines UA751: ORD 2026-12-06 08:59:00 → PDX 2026-12-06 11:42:00; nonstop; 283 minutes. Local airport times.

2026-12-02 → 2026-12-06 · $355.00

  • American Airlines AA2496 / AA2221: PDX 2026-12-02 14:36:00 → ORD 2026-12-02 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
    • AA2496: PDX 2026-12-02 14:36:00 → DFW 2026-12-02 20:28:00; layover at DFW: 62 minutes.
    • AA2221: DFW 2026-12-02 21:30:00 → ORD 2026-12-02 23:59:00.
  • American Airlines AA562: ORD 2026-12-06 21:22:00 → PDX 2026-12-07 00:09:00; nonstop; 287 minutes. Local airport times.

2026-12-02 → 2026-12-06 · $355.00

  • Alaska Airlines AS3355 / AA3186: PDX 2026-12-02 07:16:00 → ORD 2026-12-02 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
    • AS3355: PDX 2026-12-02 07:16:00 → SLC 2026-12-02 10:19:00; layover at SLC: 78 minutes.
    • AA3186: SLC 2026-12-02 11:37:00 → ORD 2026-12-02 16:00:00.
  • Alaska Airlines AS325: ORD 2026-12-06 14:08:00 → PDX 2026-12-06 17:05:00; nonstop; 297 minutes. Local airport times.

2026-12-02 → 2026-12-06 · $355.00

  • Alaska Airlines AS324: PDX 2026-12-02 07:00:00 → ORD 2026-12-02 13:08:00; nonstop; 248 minutes. Local airport times.
  • Alaska Airlines AS407 / AS2239: ORD 2026-12-06 15:19:00 → PDX 2026-12-06 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
    • AS407: ORD 2026-12-06 15:19:00 → SEA 2026-12-06 18:11:00; layover at SEA: 103 minutes.
    • AS2239: SEA 2026-12-06 19:54:00 → PDX 2026-12-06 20:50:00.

2026-12-02 → 2026-12-06 · $375.00

  • United Airlines UA1292 / UA1958: PDX 2026-12-02 15:44:00 → ORD 2026-12-03 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
    • UA1292: PDX 2026-12-02 15:44:00 → SFO 2026-12-02 17:37:00; layover at SFO: 65 minutes.
    • UA1958: SFO 2026-12-02 18:42:00 → ORD 2026-12-03 00:59:00.
  • United Airlines UA751: ORD 2026-12-06 08:59:00 → PDX 2026-12-06 11:42:00; nonstop; 283 minutes. Local airport times.

2026-12-02 → 2026-12-06 · $375.00

  • United Airlines UA459 / UA2329: PDX 2026-12-02 05:00:00 → ORD 2026-12-02 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
    • UA459: PDX 2026-12-02 05:00:00 → DEN 2026-12-02 08:28:00; layover at DEN: 87 minutes.
    • UA2329: DEN 2026-12-02 09:55:00 → ORD 2026-12-02 13:35:00.
  • United Airlines UA751: ORD 2026-12-06 08:59:00 → PDX 2026-12-06 11:42:00; nonstop; 283 minutes. Local airport times.

More dates for this route