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Portland → Chicago

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PWM → ORD1 adulteconomy

25 flight options · 3 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

United Airlines
9:51 amPWM
3h 9m
Nonstop
12:00 pmORD
United Airlines
6:18 pmORD
2h 33m
Nonstop
9:51 pmPWM

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

American Airlines
12:15 pmPWM
3h 15m
Nonstop
2:30 pmORD
American Airlines
8:45 amORD
5h 47m
DCA · 1h 53m
3:32 pmPWM

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

American Airlines
6:17 amPWM
7h 51m
DCA · 3h 34m
1:08 pmORD
American Airlines
8:30 amORD
2h 28m
Nonstop
11:58 amPWM

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

American Airlines
6:47 pmPWM
5h 43m
PHL · 1h 22m
11:30 pmORD
American Airlines
8:30 amORD
2h 28m
Nonstop
11:58 amPWM

Round-trip total · 1 adult · Taxes included

Show 8 more flights

Fri, Nov 20 – Mon, Nov 23

United Airlines
6:00 amPWM
6h 42m
EWR · 2h 9m
11:42 amORD
United Airlines
6:18 pmORD
2h 33m
Nonstop
9:51 pmPWM

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Delta Air Lines
6:00 amPWM
7h 50m
JFK · 3h 25m
12:50 pmORD
Delta Air Lines
5:59 pmORD
5h 22m
JFK · 1h 31m
12:21 am+1PWM

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

American Airlines
6:47 pmPWM
5h 43m
PHL · 1h 22m
11:30 pmORD
American Airlines
8:30 amORD
2h 28m
Nonstop
11:58 amPWM

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

United Airlines
6:00 amPWM
6h 42m
EWR · 2h 9m
11:42 amORD
United Airlines
1:00 pmORD
5h 12m
IAD · 1h 22m
7:12 pmPWM

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

American Airlines
12:15 pmPWM
3h 15m
Nonstop
2:30 pmORD
American Airlines
8:45 amORD
5h 47m
DCA · 1h 53m
3:32 pmPWM

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Delta Air Lines
6:00 amPWM
7h 50m
JFK · 3h 25m
12:50 pmORD
Delta Air Lines
5:59 pmORD
5h 22m
JFK · 1h 31m
12:21 am+1PWM

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

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

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

American Airlines
12:06 pmPWM
3h 10m
Nonstop
2:16 pmORD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

United Airlines
5:08 pmPWM
2h 57m
Nonstop
7:05 pmORD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
6:00 amPWM
7h 50m
JFK · 3h 25m
12:50 pmORD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

United Airlines
9:51 amPWM
3h 9m
Nonstop
12:00 pmORD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

American Airlines
5:30 amPWM
7h 52m
CLT · 2h 52m
12:22 pmORD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

American Airlines
6:47 pmPWM
5h 43m
PHL · 1h 22m
11:30 pmORD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

American Airlines
6:17 amPWM
7h 51m
DCA · 3h 34m
1:08 pmORD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

United Airlines
6:00 amPWM
6h 42m
EWR · 2h 9m
11:42 amORD

One-way total · 1 adult · Taxes included

Show 1 more flights

Fri, Nov 20 · One way

Delta Air Lines
12:49 pmPWM
6h 41m
DTW · 2h 45m
6:30 pmORD

One-way total · 1 adult · Taxes included

Make this trip yours

PWM ⇄ ORD

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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More dates

Nov 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)
2026-11-20 · one wayAmerican AirlinesAA4741$165.002026-10-29T01:58:50Z
2026-11-20 · one wayUnited AirlinesUA1828$170.002026-10-29T01:58:50Z
2026-11-20 → 2026-11-23American AirlinesAA4741 / AA4741$310.002026-10-29T01:58:50Z
2026-11-20 → 2026-11-23United AirlinesUA3719 / UA2761$320.002026-10-29T01:58:50Z
2026-11-20 · one wayDelta Air LinesDL5277 + DL5119$170.002026-10-29T01:58:50Z
2026-11-20 → 2026-11-23Delta Air LinesDL1372 + DL1084 / DL4970 + DL5411$320.002026-10-29T01:58:50Z
2026-11-27 → 2026-12-04American AirlinesAA4741 / AA4741$356.502026-10-29T01:58:50Z
2026-11-20 · one wayUnited AirlinesUA3719$170.002026-10-29T01:58:50Z
2026-11-20 → 2026-11-23United AirlinesUA1828 / UA2761$320.002026-10-29T01:58:50Z
2026-11-20 · one wayAmerican AirlinesAA2348 + AA2174$155.002026-10-29T01:58:50Z
2026-11-20 · one wayAmerican AirlinesAA5629 + AA1333$155.002026-10-29T01:58:50Z
2026-11-20 · one wayAmerican AirlinesAA5264 + AA2612$155.002026-10-29T01:58:50Z
2026-11-20 · one wayUnited AirlinesUA3504 + UA1525$160.002026-10-29T01:58:50Z
2026-11-20 · one wayDelta Air LinesDL1372 + DL1084$170.002026-10-29T01:58:50Z
2026-11-20 → 2026-11-23American AirlinesAA4741 / AA2223 + AA4638$300.002026-10-29T01:58:50Z
2026-11-20 → 2026-11-23American AirlinesAA5264 + AA2612 / AA4741$300.002026-10-29T01:58:50Z
2026-11-20 → 2026-11-23American AirlinesAA5629 + AA1333 / AA4741$300.002026-10-29T01:58:50Z
2026-11-20 → 2026-11-23United AirlinesUA3504 + UA1525 / UA2761$310.002026-10-29T01:58:50Z
2026-11-20 → 2026-11-23Delta Air LinesDL5277 + DL5119 / DL4970 + DL5411$320.002026-10-29T01:58:50Z
2026-11-27 → 2026-12-04American AirlinesAA5629 + AA1333 / AA4741$343.502026-10-29T01:58:50Z
2026-11-27 → 2026-12-04United AirlinesUA3504 + UA1525 / UA1128 + UA3664$345.002026-10-29T01:58:50Z
2026-11-27 → 2026-12-04American AirlinesAA4741 / AA2223 + AA4638$346.502026-10-29T01:58:50Z
2026-11-27 → 2026-12-04United AirlinesUA1828 / UA1128 + UA3664$358.002026-10-29T01:58:50Z
2026-11-27 → 2026-12-04Delta Air LinesDL5277 + DL5119 / DL4970 + DL5411$368.002026-10-29T01:58:50Z
2026-11-27 → 2026-12-04Delta Air LinesDL1372 + DL1084 / DL4970 + DL5411$368.002026-10-29T01:58:50Z

2026-11-20 · one way · $165.00

  • American Airlines AA4741: PWM 2026-11-20 12:06:00 → ORD 2026-11-20 14:16:00; nonstop; 190 minutes. Local airport times.

2026-11-20 · one way · $170.00

  • United Airlines UA1828: PWM 2026-11-20 17:08:00 → ORD 2026-11-20 19:05:00; nonstop; 177 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $310.00

  • American Airlines AA4741: PWM 2026-11-20 12:06:00 → ORD 2026-11-20 14:16:00; nonstop; 190 minutes. Local airport times.
  • American Airlines AA4741: ORD 2026-11-23 08:30:00 → PWM 2026-11-23 11:58:00; nonstop; 148 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $320.00

  • United Airlines UA3719: PWM 2026-11-20 09:51:00 → ORD 2026-11-20 12:00:00; nonstop; 189 minutes. Local airport times.
  • United Airlines UA2761: ORD 2026-11-23 18:18:00 → PWM 2026-11-23 21:51:00; nonstop; 153 minutes. Local airport times.

2026-11-20 · one way · $170.00

  • Delta Air Lines DL5277 / DL5119: PWM 2026-11-20 06:00:00 → ORD 2026-11-20 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
    • DL5277: PWM 2026-11-20 06:00:00 → JFK 2026-11-20 07:30:00; layover at JFK: 205 minutes.
    • DL5119: JFK 2026-11-20 10:55:00 → ORD 2026-11-20 12:50:00.

2026-11-20 → 2026-11-23 · $320.00

  • Delta Air Lines DL1372 / DL1084: PWM 2026-11-20 12:49:00 → ORD 2026-11-20 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
    • DL1372: PWM 2026-11-20 12:49:00 → DTW 2026-11-20 15:11:00; layover at DTW: 165 minutes.
    • DL1084: DTW 2026-11-20 17:56:00 → ORD 2026-11-20 18:30:00.
  • Delta Air Lines DL4970 / DL5411: ORD 2026-11-23 17:59:00 → PWM 2026-11-24 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
    • DL4970: ORD 2026-11-23 17:59:00 → JFK 2026-11-23 21:19:00; layover at JFK: 91 minutes.
    • DL5411: JFK 2026-11-23 22:50:00 → PWM 2026-11-24 00:21:00.

2026-11-27 → 2026-12-04 · $356.50

  • American Airlines AA4741: PWM 2026-11-27 12:06:00 → ORD 2026-11-27 14:16:00; nonstop; 190 minutes. Local airport times.
  • American Airlines AA4741: ORD 2026-12-04 08:30:00 → PWM 2026-12-04 11:58:00; nonstop; 148 minutes. Local airport times.

2026-11-20 · one way · $170.00

  • United Airlines UA3719: PWM 2026-11-20 09:51:00 → ORD 2026-11-20 12:00:00; nonstop; 189 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $320.00

  • United Airlines UA1828: PWM 2026-11-20 17:08:00 → ORD 2026-11-20 19:05:00; nonstop; 177 minutes. Local airport times.
  • United Airlines UA2761: ORD 2026-11-23 18:18:00 → PWM 2026-11-23 21:51:00; nonstop; 153 minutes. Local airport times.

2026-11-20 · one way · $155.00

  • American Airlines AA2348 / AA2174: PWM 2026-11-20 05:30:00 → ORD 2026-11-20 12:22:00; 1 stop(s) via CLT; 472 minutes. Local airport times.
    • AA2348: PWM 2026-11-20 05:30:00 → CLT 2026-11-20 08:14:00; layover at CLT: 172 minutes.
    • AA2174: CLT 2026-11-20 11:06:00 → ORD 2026-11-20 12:22:00.

2026-11-20 · one way · $155.00

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

2026-11-20 · one way · $155.00

  • American Airlines AA5264 / AA2612: PWM 2026-11-20 06:17:00 → ORD 2026-11-20 13:08:00; 1 stop(s) via DCA; 471 minutes. Local airport times.
    • AA5264: PWM 2026-11-20 06:17:00 → DCA 2026-11-20 08:12:00; layover at DCA: 214 minutes.
    • AA2612: DCA 2026-11-20 11:46:00 → ORD 2026-11-20 13:08:00.

2026-11-20 · one way · $160.00

  • United Airlines UA3504 / UA1525: PWM 2026-11-20 06:00:00 → ORD 2026-11-20 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
    • UA3504: PWM 2026-11-20 06:00:00 → EWR 2026-11-20 07:43:00; layover at EWR: 129 minutes.
    • UA1525: EWR 2026-11-20 09:52:00 → ORD 2026-11-20 11:42:00.

2026-11-20 · one way · $170.00

  • Delta Air Lines DL1372 / DL1084: PWM 2026-11-20 12:49:00 → ORD 2026-11-20 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
    • DL1372: PWM 2026-11-20 12:49:00 → DTW 2026-11-20 15:11:00; layover at DTW: 165 minutes.
    • DL1084: DTW 2026-11-20 17:56:00 → ORD 2026-11-20 18:30:00.

2026-11-20 → 2026-11-23 · $300.00

  • American Airlines AA4741: PWM 2026-11-20 12:15:00 → ORD 2026-11-20 14:30:00; nonstop; 195 minutes. Local airport times.
  • American Airlines AA2223 / AA4638: ORD 2026-11-23 08:45:00 → PWM 2026-11-23 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
    • AA2223: ORD 2026-11-23 08:45:00 → DCA 2026-11-23 11:49:00; layover at DCA: 113 minutes.
    • AA4638: DCA 2026-11-23 13:42:00 → PWM 2026-11-23 15:32:00.

2026-11-20 → 2026-11-23 · $300.00

  • American Airlines AA5264 / AA2612: PWM 2026-11-20 06:17:00 → ORD 2026-11-20 13:08:00; 1 stop(s) via DCA; 471 minutes. Local airport times.
    • AA5264: PWM 2026-11-20 06:17:00 → DCA 2026-11-20 08:12:00; layover at DCA: 214 minutes.
    • AA2612: DCA 2026-11-20 11:46:00 → ORD 2026-11-20 13:08:00.
  • American Airlines AA4741: ORD 2026-11-23 08:30:00 → PWM 2026-11-23 11:58:00; nonstop; 148 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $300.00

  • American Airlines AA5629 / AA1333: PWM 2026-11-20 18:47:00 → ORD 2026-11-20 23:30:00; 1 stop(s) via PHL; 343 minutes. Local airport times.
    • AA5629: PWM 2026-11-20 18:47:00 → PHL 2026-11-20 20:35:00; layover at PHL: 82 minutes.
    • AA1333: PHL 2026-11-20 21:57:00 → ORD 2026-11-20 23:30:00.
  • American Airlines AA4741: ORD 2026-11-23 08:30:00 → PWM 2026-11-23 11:58:00; nonstop; 148 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $310.00

  • United Airlines UA3504 / UA1525: PWM 2026-11-20 06:00:00 → ORD 2026-11-20 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
    • UA3504: PWM 2026-11-20 06:00:00 → EWR 2026-11-20 07:43:00; layover at EWR: 129 minutes.
    • UA1525: EWR 2026-11-20 09:52:00 → ORD 2026-11-20 11:42:00.
  • United Airlines UA2761: ORD 2026-11-23 18:18:00 → PWM 2026-11-23 21:51:00; nonstop; 153 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $320.00

  • Delta Air Lines DL5277 / DL5119: PWM 2026-11-20 06:00:00 → ORD 2026-11-20 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
    • DL5277: PWM 2026-11-20 06:00:00 → JFK 2026-11-20 07:30:00; layover at JFK: 205 minutes.
    • DL5119: JFK 2026-11-20 10:55:00 → ORD 2026-11-20 12:50:00.
  • Delta Air Lines DL4970 / DL5411: ORD 2026-11-23 17:59:00 → PWM 2026-11-24 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
    • DL4970: ORD 2026-11-23 17:59:00 → JFK 2026-11-23 21:19:00; layover at JFK: 91 minutes.
    • DL5411: JFK 2026-11-23 22:50:00 → PWM 2026-11-24 00:21:00.

2026-11-27 → 2026-12-04 · $343.50

  • American Airlines AA5629 / AA1333: PWM 2026-11-27 18:47:00 → ORD 2026-11-27 23:30:00; 1 stop(s) via PHL; 343 minutes. Local airport times.
    • AA5629: PWM 2026-11-27 18:47:00 → PHL 2026-11-27 20:35:00; layover at PHL: 82 minutes.
    • AA1333: PHL 2026-11-27 21:57:00 → ORD 2026-11-27 23:30:00.
  • American Airlines AA4741: ORD 2026-12-04 08:30:00 → PWM 2026-12-04 11:58:00; nonstop; 148 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $345.00

  • United Airlines UA3504 / UA1525: PWM 2026-11-27 06:00:00 → ORD 2026-11-27 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
    • UA3504: PWM 2026-11-27 06:00:00 → EWR 2026-11-27 07:43:00; layover at EWR: 129 minutes.
    • UA1525: EWR 2026-11-27 09:52:00 → ORD 2026-11-27 11:42:00.
  • United Airlines UA1128 / UA3664: ORD 2026-12-04 13:00:00 → PWM 2026-12-04 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
    • UA1128: ORD 2026-12-04 13:00:00 → IAD 2026-12-04 16:03:00; layover at IAD: 82 minutes.
    • UA3664: IAD 2026-12-04 17:25:00 → PWM 2026-12-04 19:12:00.

2026-11-27 → 2026-12-04 · $346.50

  • American Airlines AA4741: PWM 2026-11-27 12:15:00 → ORD 2026-11-27 14:30:00; nonstop; 195 minutes. Local airport times.
  • American Airlines AA2223 / AA4638: ORD 2026-12-04 08:45:00 → PWM 2026-12-04 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
    • AA2223: ORD 2026-12-04 08:45:00 → DCA 2026-12-04 11:49:00; layover at DCA: 113 minutes.
    • AA4638: DCA 2026-12-04 13:42:00 → PWM 2026-12-04 15:32:00.

2026-11-27 → 2026-12-04 · $358.00

  • United Airlines UA1828: PWM 2026-11-27 17:08:00 → ORD 2026-11-27 19:05:00; nonstop; 177 minutes. Local airport times.
  • United Airlines UA1128 / UA3664: ORD 2026-12-04 13:00:00 → PWM 2026-12-04 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
    • UA1128: ORD 2026-12-04 13:00:00 → IAD 2026-12-04 16:03:00; layover at IAD: 82 minutes.
    • UA3664: IAD 2026-12-04 17:25:00 → PWM 2026-12-04 19:12:00.

2026-11-27 → 2026-12-04 · $368.00

  • Delta Air Lines DL5277 / DL5119: PWM 2026-11-27 06:00:00 → ORD 2026-11-27 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
    • DL5277: PWM 2026-11-27 06:00:00 → JFK 2026-11-27 07:30:00; layover at JFK: 205 minutes.
    • DL5119: JFK 2026-11-27 10:55:00 → ORD 2026-11-27 12:50:00.
  • Delta Air Lines DL4970 / DL5411: ORD 2026-12-04 17:59:00 → PWM 2026-12-05 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
    • DL4970: ORD 2026-12-04 17:59:00 → JFK 2026-12-04 21:19:00; layover at JFK: 91 minutes.
    • DL5411: JFK 2026-12-04 22:50:00 → PWM 2026-12-05 00:21:00.

2026-11-27 → 2026-12-04 · $368.00

  • Delta Air Lines DL1372 / DL1084: PWM 2026-11-27 12:49:00 → ORD 2026-11-27 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
    • DL1372: PWM 2026-11-27 12:49:00 → DTW 2026-11-27 15:11:00; layover at DTW: 165 minutes.
    • DL1084: DTW 2026-11-27 17:56:00 → ORD 2026-11-27 18:30:00.
  • Delta Air Lines DL4970 / DL5411: ORD 2026-12-04 17:59:00 → PWM 2026-12-05 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
    • DL4970: ORD 2026-12-04 17:59:00 → JFK 2026-12-04 21:19:00; layover at JFK: 91 minutes.
    • DL5411: JFK 2026-12-04 22:50:00 → PWM 2026-12-05 00:21:00.

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