Portland (PWM) to Chicago (ORD) · Dec 19, 2026 · return Dec 29, 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

2026-12-19 → 2026-12-29 · Axel-exclusive $387.50

• American Airlines AA4741: PWM 2026-12-19 12:15:00 → ORD 2026-12-19 14:30:00; nonstop; 195 minutes. Local airport times.
• American Airlines AA4741: ORD 2026-12-29 08:10:00 → PWM 2026-12-29 11:42:00; nonstop; 152 minutes. Local airport times.

2026-12-19 → 2026-12-29 · Axel-exclusive $400.00

• United Airlines UA3719: PWM 2026-12-19 09:51:00 → ORD 2026-12-19 12:00:00; nonstop; 189 minutes. Local airport times.
• United Airlines UA3713: ORD 2026-12-29 17:50:00 → PWM 2026-12-29 21:29:00; nonstop; 159 minutes. Local airport times.

2026-12-19 → 2026-12-29 · Axel-exclusive $400.00

• Delta Air Lines DL1372 / DL1084: PWM 2026-12-19 12:49:00 → ORD 2026-12-19 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
  • DL1372: PWM 2026-12-19 12:49:00 → DTW 2026-12-19 15:11:00; layover at DTW: 165 minutes.
  • DL1084: DTW 2026-12-19 17:56:00 → ORD 2026-12-19 18:30:00.
• Delta Air Lines DL4970 / DL5411: ORD 2026-12-29 17:59:00 → PWM 2026-12-30 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2026-12-29 17:59:00 → JFK 2026-12-29 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2026-12-29 22:50:00 → PWM 2026-12-30 00:21:00.

2026-12-19 → 2026-12-29 · Axel-exclusive $400.00

• United Airlines UA1828: PWM 2026-12-19 17:08:00 → ORD 2026-12-19 19:05:00; nonstop; 177 minutes. Local airport times.
• United Airlines UA3713: ORD 2026-12-29 17:50:00 → PWM 2026-12-29 21:29:00; nonstop; 159 minutes. Local airport times.

2026-12-19 → 2026-12-29 · Axel-exclusive $375.00

• American Airlines AA4741: PWM 2026-12-19 12:06:00 → ORD 2026-12-19 14:16:00; nonstop; 190 minutes. Local airport times.
• American Airlines AA2840 / AA6049: ORD 2026-12-29 15:19:00 → PWM 2026-12-29 22:56:00; 1 stop(s) via PHL; 397 minutes. Local airport times.
  • AA2840: ORD 2026-12-29 15:19:00 → PHL 2026-12-29 18:30:00; layover at PHL: 175 minutes.
  • AA6049: PHL 2026-12-29 21:25:00 → PWM 2026-12-29 22:56:00.

2026-12-19 → 2026-12-29 · Axel-exclusive $375.00

• American Airlines AA5264 / AA2612: PWM 2026-12-19 06:17:00 → ORD 2026-12-19 13:08:00; 1 stop(s) via DCA; 471 minutes. Local airport times.
  • AA5264: PWM 2026-12-19 06:17:00 → DCA 2026-12-19 08:12:00; layover at DCA: 214 minutes.
  • AA2612: DCA 2026-12-19 11:46:00 → ORD 2026-12-19 13:08:00.
• American Airlines AA4741: ORD 2026-12-29 08:10:00 → PWM 2026-12-29 11:42:00; nonstop; 152 minutes. Local airport times.

2026-12-19 → 2026-12-29 · Axel-exclusive $375.00

• American Airlines AA2348 / AA2174: PWM 2026-12-19 05:30:00 → ORD 2026-12-19 12:22:00; 1 stop(s) via CLT; 472 minutes. Local airport times.
  • AA2348: PWM 2026-12-19 05:30:00 → CLT 2026-12-19 08:14:00; layover at CLT: 172 minutes.
  • AA2174: CLT 2026-12-19 11:06:00 → ORD 2026-12-19 12:22:00.
• American Airlines AA4741: ORD 2026-12-29 08:10:00 → PWM 2026-12-29 11:42:00; nonstop; 152 minutes. Local airport times.

2026-12-19 → 2026-12-29 · Axel-exclusive $387.50

• United Airlines UA3504 / UA1525: PWM 2026-12-19 06:00:00 → ORD 2026-12-19 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
  • UA3504: PWM 2026-12-19 06:00:00 → EWR 2026-12-19 07:43:00; layover at EWR: 129 minutes.
  • UA1525: EWR 2026-12-19 09:52:00 → ORD 2026-12-19 11:42:00.
• United Airlines UA3713: ORD 2026-12-29 17:50:00 → PWM 2026-12-29 21:29:00; nonstop; 159 minutes. Local airport times.

2026-12-19 → 2026-12-29 · Axel-exclusive $400.00

• Delta Air Lines DL5277 / DL5119: PWM 2026-12-19 06:00:00 → ORD 2026-12-19 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
  • DL5277: PWM 2026-12-19 06:00:00 → JFK 2026-12-19 07:30:00; layover at JFK: 205 minutes.
  • DL5119: JFK 2026-12-19 10:55:00 → ORD 2026-12-19 12:50:00.
• Delta Air Lines DL4970 / DL5411: ORD 2026-12-29 17:59:00 → PWM 2026-12-30 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2026-12-29 17:59:00 → JFK 2026-12-29 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2026-12-29 22:50:00 → PWM 2026-12-30 00:21:00.

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.

Explore this route

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For AI assistants

• This page: Portland (PWM) to Chicago (ORD) · Dec 19, 2026 · return Dec 29, 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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