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Route overview: Chicago to Portland (PWM) flight deals

Chicago → Portland

Jan 21, 2027 · return Feb 4, 2027

ORD → PWM1 adulteconomyRound trip

7 flight options · 3 airlines

Nonstop flights

Thu, Jan 21 – Thu, Feb 4

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

One-stop flights

Thu, Jan 21 – Thu, Feb 4

United Airlines
5:55 amORD
6h 43m
EWR · 3h 13m
1:38 pmPWM
United Airlines
6:00 amPWM
6h 42m
EWR · 2h 9m
11:42 amORD

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

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

Thu, Jan 21 – Thu, Feb 4

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

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

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

Thu, Jan 21 – Thu, Feb 4

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

Thu, Jan 21 – Thu, Feb 4

United Airlines
10:50 amORD
2h 26m
Nonstop
2:16 pmPWM
United Airlines
6:00 amPWM
6h 42m
EWR · 2h 9m
11:42 amORD

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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Explore this route

All dates for this routeJan 20, 2027 → Feb 3, 2027Jan 22, 2027 → Feb 5, 2027
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.

Live price for these dates: opening any fare on this page checks it live and shows the current bookable total for 1 adult. Check live prices for Chicago (ORD) to Portland (PWM), Jan 21, 2027 · return Feb 4, 2027

Route overview: Chicago to Portland (PWM) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-01-21 → 2027-02-04American AirlinesAA4741 / AA4741$300.002026-10-29T01:53:16Z
2027-01-21 → 2027-02-04United AirlinesUA2776 + UA4604 / UA3504 + UA1525$290.002026-10-29T01:53:16Z
2027-01-21 → 2027-02-04Delta Air LinesDL4970 + DL5411 / DL1372 + DL1084$310.002026-10-29T01:53:16Z
2027-01-21 → 2027-02-04United AirlinesUA1128 + UA3664 / UA3504 + UA1525$290.002026-10-29T01:53:16Z
2027-01-21 → 2027-02-04American AirlinesAA2840 + AA6049 / AA4741$290.002026-10-29T01:53:16Z
2027-01-21 → 2027-02-04American AirlinesAA4741 / AA5629 + AA1333$290.002026-10-29T01:53:16Z
2027-01-21 → 2027-02-04United AirlinesUA422 / UA3504 + UA1525$300.002026-10-29T01:53:16Z

2027-01-21 → 2027-02-04 · $300.00

  • American Airlines AA4741: ORD 2027-01-21 08:30:00 → PWM 2027-01-21 11:58:00; nonstop; 148 minutes. Local airport times.
  • American Airlines AA4741: PWM 2027-02-04 12:06:00 → ORD 2027-02-04 14:16:00; nonstop; 190 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $290.00

  • United Airlines UA2776 / UA4604: ORD 2027-01-21 05:55:00 → PWM 2027-01-21 13:38:00; 1 stop(s) via EWR; 403 minutes. Local airport times.
    • UA2776: ORD 2027-01-21 05:55:00 → EWR 2027-01-21 09:02:00; layover at EWR: 193 minutes.
    • UA4604: EWR 2027-01-21 12:15:00 → PWM 2027-01-21 13:38:00.
  • United Airlines UA3504 / UA1525: PWM 2027-02-04 06:00:00 → ORD 2027-02-04 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
    • UA3504: PWM 2027-02-04 06:00:00 → EWR 2027-02-04 07:43:00; layover at EWR: 129 minutes.
    • UA1525: EWR 2027-02-04 09:52:00 → ORD 2027-02-04 11:42:00.

2027-01-21 → 2027-02-04 · $310.00

  • Delta Air Lines DL4970 / DL5411: ORD 2027-01-21 17:59:00 → PWM 2027-01-22 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
    • DL4970: ORD 2027-01-21 17:59:00 → JFK 2027-01-21 21:19:00; layover at JFK: 91 minutes.
    • DL5411: JFK 2027-01-21 22:50:00 → PWM 2027-01-22 00:21:00.
  • Delta Air Lines DL1372 / DL1084: PWM 2027-02-04 12:49:00 → ORD 2027-02-04 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
    • DL1372: PWM 2027-02-04 12:49:00 → DTW 2027-02-04 15:11:00; layover at DTW: 165 minutes.
    • DL1084: DTW 2027-02-04 17:56:00 → ORD 2027-02-04 18:30:00.

2027-01-21 → 2027-02-04 · $290.00

  • United Airlines UA1128 / UA3664: ORD 2027-01-21 13:00:00 → PWM 2027-01-21 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
    • UA1128: ORD 2027-01-21 13:00:00 → IAD 2027-01-21 16:03:00; layover at IAD: 82 minutes.
    • UA3664: IAD 2027-01-21 17:25:00 → PWM 2027-01-21 19:12:00.
  • United Airlines UA3504 / UA1525: PWM 2027-02-04 06:00:00 → ORD 2027-02-04 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
    • UA3504: PWM 2027-02-04 06:00:00 → EWR 2027-02-04 07:43:00; layover at EWR: 129 minutes.
    • UA1525: EWR 2027-02-04 09:52:00 → ORD 2027-02-04 11:42:00.

2027-01-21 → 2027-02-04 · $290.00

  • American Airlines AA2840 / AA6049: ORD 2027-01-21 15:19:00 → PWM 2027-01-21 22:56:00; 1 stop(s) via PHL; 397 minutes. Local airport times.
    • AA2840: ORD 2027-01-21 15:19:00 → PHL 2027-01-21 18:30:00; layover at PHL: 175 minutes.
    • AA6049: PHL 2027-01-21 21:25:00 → PWM 2027-01-21 22:56:00.
  • American Airlines AA4741: PWM 2027-02-04 12:06:00 → ORD 2027-02-04 14:16:00; nonstop; 190 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $290.00

  • American Airlines AA4741: ORD 2027-01-21 08:00:00 → PWM 2027-01-21 11:28:00; nonstop; 148 minutes. Local airport times.
  • American Airlines AA5629 / AA1333: PWM 2027-02-04 18:47:00 → ORD 2027-02-04 23:30:00; 1 stop(s) via PHL; 343 minutes. Local airport times.
    • AA5629: PWM 2027-02-04 18:47:00 → PHL 2027-02-04 20:35:00; layover at PHL: 82 minutes.
    • AA1333: PHL 2027-02-04 21:57:00 → ORD 2027-02-04 23:30:00.

2027-01-21 → 2027-02-04 · $300.00

  • United Airlines UA422: ORD 2027-01-21 10:50:00 → PWM 2027-01-21 14:16:00; nonstop; 146 minutes. Local airport times.
  • United Airlines UA3504 / UA1525: PWM 2027-02-04 06:00:00 → ORD 2027-02-04 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
    • UA3504: PWM 2027-02-04 06:00:00 → EWR 2027-02-04 07:43:00; layover at EWR: 129 minutes.
    • UA1525: EWR 2027-02-04 09:52:00 → ORD 2027-02-04 11:42:00.

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For AI assistants

  • This page: Chicago (ORD) to Portland (PWM) · Jan 21, 2027 · return Feb 4, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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