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Chicago → Portland

Dec 21, 2026 · return Dec 23, 2026

ORD → PWM1 adulteconomyRound trip

9 flight options · 3 airlines

Nonstop flights

Mon, Dec 21 – Wed, Dec 23

American Airlines
8:30 amORD
2h 28m
Nonstop
11:58 amPWM
American Airlines
12:06 pmPWM
3h 10m
Nonstop
2:16 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Wed, Dec 23

United Airlines
6:18 pmORD
2h 33m
Nonstop
9:51 pmPWM
United Airlines
5:08 pmPWM
2h 57m
Nonstop
7:05 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Wed, Dec 23

United Airlines
10:50 amORD
2h 26m
Nonstop
2:16 pmPWM
United Airlines
5:08 pmPWM
2h 57m
Nonstop
7:05 pmORD

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Wed, Dec 23

Delta Air Lines
5:59 pmORD
5h 22m
JFK · 1h 31m
12:21 am+1PWM
Delta Air Lines
12:49 pmPWM
6h 41m
DTW · 2h 45m
6:30 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Wed, Dec 23

American Airlines
8:00 amORD
2h 28m
Nonstop
11:28 amPWM
American Airlines
6:47 pmPWM
5h 43m
PHL · 1h 22m
11:30 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Wed, Dec 23

American Airlines
3:19 pmORD
6h 37m
PHL · 2h 55m
10:56 pmPWM
American Airlines
12:06 pmPWM
3h 10m
Nonstop
2:16 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Wed, Dec 23

American Airlines
8:45 amORD
5h 47m
DCA · 1h 53m
3:32 pmPWM
American Airlines
12:06 pmPWM
3h 10m
Nonstop
2:16 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Wed, Dec 23

United Airlines
5:55 amORD
6h 43m
EWR · 3h 13m
1:38 pmPWM
United Airlines
5:08 pmPWM
2h 57m
Nonstop
7:05 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Wed, Dec 23

United Airlines
1:00 pmORD
5h 12m
IAD · 1h 22m
7:12 pmPWM
United Airlines
5:08 pmPWM
2h 57m
Nonstop
7:05 pmORD

Round-trip total · 1 adult · Taxes included

Make this trip yours

ORD ⇄ PWM

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)
2026-12-21 → 2026-12-23American AirlinesAA4741 / AA4741$375.002026-10-29T01:53:16Z
2026-12-21 → 2026-12-23United AirlinesUA2761 / UA1828$387.502026-10-29T01:53:16Z
2026-12-21 → 2026-12-23Delta Air LinesDL4970 + DL5411 / DL1372 + DL1084$387.502026-10-29T01:53:16Z
2026-12-21 → 2026-12-23United AirlinesUA422 / UA1828$387.502026-10-29T01:53:16Z
2026-12-21 → 2026-12-23American AirlinesAA4741 / AA5629 + AA1333$362.502026-10-29T01:53:16Z
2026-12-21 → 2026-12-23American AirlinesAA2840 + AA6049 / AA4741$362.502026-10-29T01:53:16Z
2026-12-21 → 2026-12-23American AirlinesAA2223 + AA4638 / AA4741$362.502026-10-29T01:53:16Z
2026-12-21 → 2026-12-23United AirlinesUA2776 + UA4604 / UA1828$375.002026-10-29T01:53:16Z
2026-12-21 → 2026-12-23United AirlinesUA1128 + UA3664 / UA1828$375.002026-10-29T01:53:16Z

2026-12-21 → 2026-12-23 · $375.00

  • American Airlines AA4741: ORD 2026-12-21 08:30:00 → PWM 2026-12-21 11:58:00; nonstop; 148 minutes. Local airport times.
  • American Airlines AA4741: PWM 2026-12-23 12:06:00 → ORD 2026-12-23 14:16:00; nonstop; 190 minutes. Local airport times.

2026-12-21 → 2026-12-23 · $387.50

  • United Airlines UA2761: ORD 2026-12-21 18:18:00 → PWM 2026-12-21 21:51:00; nonstop; 153 minutes. Local airport times.
  • United Airlines UA1828: PWM 2026-12-23 17:08:00 → ORD 2026-12-23 19:05:00; nonstop; 177 minutes. Local airport times.

2026-12-21 → 2026-12-23 · $387.50

  • Delta Air Lines DL4970 / DL5411: ORD 2026-12-21 17:59:00 → PWM 2026-12-22 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
    • DL4970: ORD 2026-12-21 17:59:00 → JFK 2026-12-21 21:19:00; layover at JFK: 91 minutes.
    • DL5411: JFK 2026-12-21 22:50:00 → PWM 2026-12-22 00:21:00.
  • Delta Air Lines DL1372 / DL1084: PWM 2026-12-23 12:49:00 → ORD 2026-12-23 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
    • DL1372: PWM 2026-12-23 12:49:00 → DTW 2026-12-23 15:11:00; layover at DTW: 165 minutes.
    • DL1084: DTW 2026-12-23 17:56:00 → ORD 2026-12-23 18:30:00.

2026-12-21 → 2026-12-23 · $387.50

  • United Airlines UA422: ORD 2026-12-21 10:50:00 → PWM 2026-12-21 14:16:00; nonstop; 146 minutes. Local airport times.
  • United Airlines UA1828: PWM 2026-12-23 17:08:00 → ORD 2026-12-23 19:05:00; nonstop; 177 minutes. Local airport times.

2026-12-21 → 2026-12-23 · $362.50

  • American Airlines AA4741: ORD 2026-12-21 08:00:00 → PWM 2026-12-21 11:28:00; nonstop; 148 minutes. Local airport times.
  • American Airlines AA5629 / AA1333: PWM 2026-12-23 18:47:00 → ORD 2026-12-23 23:30:00; 1 stop(s) via PHL; 343 minutes. Local airport times.
    • AA5629: PWM 2026-12-23 18:47:00 → PHL 2026-12-23 20:35:00; layover at PHL: 82 minutes.
    • AA1333: PHL 2026-12-23 21:57:00 → ORD 2026-12-23 23:30:00.

2026-12-21 → 2026-12-23 · $362.50

  • American Airlines AA2840 / AA6049: ORD 2026-12-21 15:19:00 → PWM 2026-12-21 22:56:00; 1 stop(s) via PHL; 397 minutes. Local airport times.
    • AA2840: ORD 2026-12-21 15:19:00 → PHL 2026-12-21 18:30:00; layover at PHL: 175 minutes.
    • AA6049: PHL 2026-12-21 21:25:00 → PWM 2026-12-21 22:56:00.
  • American Airlines AA4741: PWM 2026-12-23 12:06:00 → ORD 2026-12-23 14:16:00; nonstop; 190 minutes. Local airport times.

2026-12-21 → 2026-12-23 · $362.50

  • American Airlines AA2223 / AA4638: ORD 2026-12-21 08:45:00 → PWM 2026-12-21 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
    • AA2223: ORD 2026-12-21 08:45:00 → DCA 2026-12-21 11:49:00; layover at DCA: 113 minutes.
    • AA4638: DCA 2026-12-21 13:42:00 → PWM 2026-12-21 15:32:00.
  • American Airlines AA4741: PWM 2026-12-23 12:06:00 → ORD 2026-12-23 14:16:00; nonstop; 190 minutes. Local airport times.

2026-12-21 → 2026-12-23 · $375.00

  • United Airlines UA2776 / UA4604: ORD 2026-12-21 05:55:00 → PWM 2026-12-21 13:38:00; 1 stop(s) via EWR; 403 minutes. Local airport times.
    • UA2776: ORD 2026-12-21 05:55:00 → EWR 2026-12-21 09:02:00; layover at EWR: 193 minutes.
    • UA4604: EWR 2026-12-21 12:15:00 → PWM 2026-12-21 13:38:00.
  • United Airlines UA1828: PWM 2026-12-23 17:08:00 → ORD 2026-12-23 19:05:00; nonstop; 177 minutes. Local airport times.

2026-12-21 → 2026-12-23 · $375.00

  • United Airlines UA1128 / UA3664: ORD 2026-12-21 13:00:00 → PWM 2026-12-21 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
    • UA1128: ORD 2026-12-21 13:00:00 → IAD 2026-12-21 16:03:00; layover at IAD: 82 minutes.
    • UA3664: IAD 2026-12-21 17:25:00 → PWM 2026-12-21 19:12:00.
  • United Airlines UA1828: PWM 2026-12-23 17:08:00 → ORD 2026-12-23 19:05:00; nonstop; 177 minutes. Local airport times.

More dates for this route