Portland (PWM) to Chicago (ORD) · Dec 9, 2026 · return Dec 23, 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

2026-12-09 → 2026-12-23 · Axel-exclusive $348.75

• American Airlines AA4741: PWM 2026-12-09 12:15:00 → ORD 2026-12-09 14:30:00; nonstop; 195 minutes. Local airport times.
• American Airlines AA4741: ORD 2026-12-23 08:30:00 → PWM 2026-12-23 11:58:00; nonstop; 148 minutes. Local airport times.

2026-12-09 → 2026-12-23 · Axel-exclusive $337.50

• United Airlines UA3504 / UA1525: PWM 2026-12-09 06:00:00 → ORD 2026-12-09 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
  • UA3504: PWM 2026-12-09 06:00:00 → EWR 2026-12-09 07:43:00; layover at EWR: 129 minutes.
  • UA1525: EWR 2026-12-09 09:52:00 → ORD 2026-12-09 11:42:00.
• United Airlines UA2776 / UA4604: ORD 2026-12-23 05:55:00 → PWM 2026-12-23 13:38:00; 1 stop(s) via EWR; 403 minutes. Local airport times.
  • UA2776: ORD 2026-12-23 05:55:00 → EWR 2026-12-23 09:02:00; layover at EWR: 193 minutes.
  • UA4604: EWR 2026-12-23 12:15:00 → PWM 2026-12-23 13:38:00.

2026-12-09 → 2026-12-23 · Axel-exclusive $360.00

• Delta Air Lines DL5277 / DL5119: PWM 2026-12-09 06:00:00 → ORD 2026-12-09 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
  • DL5277: PWM 2026-12-09 06:00:00 → JFK 2026-12-09 07:30:00; layover at JFK: 205 minutes.
  • DL5119: JFK 2026-12-09 10:55:00 → ORD 2026-12-09 12:50:00.
• Delta Air Lines DL4970 / DL5411: ORD 2026-12-23 17:59:00 → PWM 2026-12-24 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2026-12-23 17:59:00 → JFK 2026-12-23 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2026-12-23 22:50:00 → PWM 2026-12-24 00:21:00.

2026-12-09 → 2026-12-23 · Axel-exclusive $336.25

• American Airlines AA4741: PWM 2026-12-09 12:06:00 → ORD 2026-12-09 14:16:00; nonstop; 190 minutes. Local airport times.
• American Airlines AA2840 / AA6049: ORD 2026-12-23 15:19:00 → PWM 2026-12-23 22:56:00; 1 stop(s) via PHL; 397 minutes. Local airport times.
  • AA2840: ORD 2026-12-23 15:19:00 → PHL 2026-12-23 18:30:00; layover at PHL: 175 minutes.
  • AA6049: PHL 2026-12-23 21:25:00 → PWM 2026-12-23 22:56:00.

2026-12-09 → 2026-12-23 · Axel-exclusive $338.75

• American Airlines AA2348 / AA2174: PWM 2026-12-09 05:30:00 → ORD 2026-12-09 12:22:00; 1 stop(s) via CLT; 472 minutes. Local airport times.
  • AA2348: PWM 2026-12-09 05:30:00 → CLT 2026-12-09 08:14:00; layover at CLT: 172 minutes.
  • AA2174: CLT 2026-12-09 11:06:00 → ORD 2026-12-09 12:22:00.
• American Airlines AA4741: ORD 2026-12-23 08:30:00 → PWM 2026-12-23 11:58:00; nonstop; 148 minutes. Local airport times.

2026-12-09 → 2026-12-23 · Axel-exclusive $347.50

• United Airlines UA3719: PWM 2026-12-09 09:51:00 → ORD 2026-12-09 12:00:00; nonstop; 189 minutes. Local airport times.
• United Airlines UA2776 / UA4604: ORD 2026-12-23 05:55:00 → PWM 2026-12-23 13:38:00; 1 stop(s) via EWR; 403 minutes. Local airport times.
  • UA2776: ORD 2026-12-23 05:55:00 → EWR 2026-12-23 09:02:00; layover at EWR: 193 minutes.
  • UA4604: EWR 2026-12-23 12:15:00 → PWM 2026-12-23 13:38:00.

2026-12-09 → 2026-12-23 · Axel-exclusive $360.00

• Delta Air Lines DL1372 / DL1084: PWM 2026-12-09 12:49:00 → ORD 2026-12-09 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
  • DL1372: PWM 2026-12-09 12:49:00 → DTW 2026-12-09 15:11:00; layover at DTW: 165 minutes.
  • DL1084: DTW 2026-12-09 17:56:00 → ORD 2026-12-09 18:30:00.
• Delta Air Lines DL4970 / DL5411: ORD 2026-12-23 17:59:00 → PWM 2026-12-24 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2026-12-23 17:59:00 → JFK 2026-12-23 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2026-12-23 22:50:00 → PWM 2026-12-24 00:21:00.

Explore this route

• All dates for this route
• Dec 8, 2026 · Return options
• Dec 10, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PWM) to Chicago (ORD) · Dec 9, 2026 · return Dec 23, 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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