Portland (PWM) to Chicago (ORD) · Nov 21, 2026 · return Nov 27, 2026

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: Portland, ME (PWM) to Chicago (ORD) flight deals

2026-11-21 → 2026-11-27 · Axel-exclusive $356.50

• American Airlines AA4741: PWM 2026-11-21 12:06:00 → ORD 2026-11-21 14:16:00; nonstop; 190 minutes. Local airport times.
• American Airlines AA4741: ORD 2026-11-27 08:30:00 → PWM 2026-11-27 11:58:00; nonstop; 148 minutes. Local airport times.

2026-11-21 → 2026-11-27 · Axel-exclusive $345.00

• United Airlines UA3504 / UA1525: PWM 2026-11-21 06:00:00 → ORD 2026-11-21 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
  • UA3504: PWM 2026-11-21 06:00:00 → EWR 2026-11-21 07:43:00; layover at EWR: 129 minutes.
  • UA1525: EWR 2026-11-21 09:52:00 → ORD 2026-11-21 11:42:00.
• United Airlines UA2776 / UA4604: ORD 2026-11-27 05:55:00 → PWM 2026-11-27 13:38:00; 1 stop(s) via EWR; 403 minutes. Local airport times.
  • UA2776: ORD 2026-11-27 05:55:00 → EWR 2026-11-27 09:02:00; layover at EWR: 193 minutes.
  • UA4604: EWR 2026-11-27 12:15:00 → PWM 2026-11-27 13:38:00.

2026-11-21 → 2026-11-27 · Axel-exclusive $368.00

• Delta Air Lines DL5277 / DL5119: PWM 2026-11-21 06:00:00 → ORD 2026-11-21 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
  • DL5277: PWM 2026-11-21 06:00:00 → JFK 2026-11-21 07:30:00; layover at JFK: 205 minutes.
  • DL5119: JFK 2026-11-21 10:55:00 → ORD 2026-11-21 12:50:00.
• Delta Air Lines DL4970 / DL5411: ORD 2026-11-27 17:59:00 → PWM 2026-11-28 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2026-11-27 17:59:00 → JFK 2026-11-27 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2026-11-27 22:50:00 → PWM 2026-11-28 00:21:00.

2026-11-21 → 2026-11-27 · Axel-exclusive $343.50

• American Airlines AA4741: PWM 2026-11-21 12:15:00 → ORD 2026-11-21 14:30:00; nonstop; 195 minutes. Local airport times.
• American Airlines AA2223 / AA4638: ORD 2026-11-27 08:45:00 → PWM 2026-11-27 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
  • AA2223: ORD 2026-11-27 08:45:00 → DCA 2026-11-27 11:49:00; layover at DCA: 113 minutes.
  • AA4638: DCA 2026-11-27 13:42:00 → PWM 2026-11-27 15:32:00.

2026-11-21 → 2026-11-27 · Axel-exclusive $346.50

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

2026-11-21 → 2026-11-27 · Axel-exclusive $346.50

• American Airlines AA5264 / AA2612: PWM 2026-11-21 06:17:00 → ORD 2026-11-21 13:08:00; 1 stop(s) via DCA; 471 minutes. Local airport times.
  • AA5264: PWM 2026-11-21 06:17:00 → DCA 2026-11-21 08:12:00; layover at DCA: 214 minutes.
  • AA2612: DCA 2026-11-21 11:46:00 → ORD 2026-11-21 13:08:00.
• American Airlines AA4741: ORD 2026-11-27 08:30:00 → PWM 2026-11-27 11:58:00; nonstop; 148 minutes. Local airport times.

2026-11-21 → 2026-11-27 · Axel-exclusive $355.00

• United Airlines UA1828: PWM 2026-11-21 17:08:00 → ORD 2026-11-21 19:05:00; nonstop; 177 minutes. Local airport times.
• United Airlines UA2776 / UA4604: ORD 2026-11-27 05:55:00 → PWM 2026-11-27 13:38:00; 1 stop(s) via EWR; 403 minutes. Local airport times.
  • UA2776: ORD 2026-11-27 05:55:00 → EWR 2026-11-27 09:02:00; layover at EWR: 193 minutes.
  • UA4604: EWR 2026-11-27 12:15:00 → PWM 2026-11-27 13:38:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

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For AI assistants

• This page: Portland (PWM) to Chicago (ORD) · Nov 21, 2026 · return Nov 27, 2026: 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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