Chicago (ORD) to Portland (PWM) · Dec 5, 2026 · return Dec 15, 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: Chicago to Portland (PWM) flight deals

2026-12-05 → 2026-12-15 · Axel-exclusive $300.00

• American Airlines AA4741: ORD 2026-12-05 08:10:00 → PWM 2026-12-05 11:42:00; nonstop; 152 minutes. Local airport times.
• American Airlines AA4741: PWM 2026-12-15 12:15:00 → ORD 2026-12-15 14:30:00; nonstop; 195 minutes. Local airport times.

2026-12-05 → 2026-12-15 · Axel-exclusive $310.00

• United Airlines UA2761: ORD 2026-12-05 18:18:00 → PWM 2026-12-05 21:51:00; nonstop; 153 minutes. Local airport times.
• United Airlines UA3719: PWM 2026-12-15 09:51:00 → ORD 2026-12-15 12:00:00; nonstop; 189 minutes. Local airport times.

2026-12-05 → 2026-12-15 · Axel-exclusive $310.00

• Delta Air Lines DL4970 / DL5411: ORD 2026-12-05 17:59:00 → PWM 2026-12-06 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2026-12-05 17:59:00 → JFK 2026-12-05 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2026-12-05 22:50:00 → PWM 2026-12-06 00:21:00.
• Delta Air Lines DL1372 / DL1084: PWM 2026-12-15 12:49:00 → ORD 2026-12-15 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
  • DL1372: PWM 2026-12-15 12:49:00 → DTW 2026-12-15 15:11:00; layover at DTW: 165 minutes.
  • DL1084: DTW 2026-12-15 17:56:00 → ORD 2026-12-15 18:30:00.

2026-12-05 → 2026-12-15 · Axel-exclusive $310.00

• United Airlines UA3713: ORD 2026-12-05 17:50:00 → PWM 2026-12-05 21:29:00; nonstop; 159 minutes. Local airport times.
• United Airlines UA3719: PWM 2026-12-15 09:51:00 → ORD 2026-12-15 12:00:00; nonstop; 189 minutes. Local airport times.

2026-12-05 → 2026-12-15 · Axel-exclusive $290.00

• American Airlines AA2840 / AA6049: ORD 2026-12-05 15:19:00 → PWM 2026-12-05 22:56:00; 1 stop(s) via PHL; 397 minutes. Local airport times.
  • AA2840: ORD 2026-12-05 15:19:00 → PHL 2026-12-05 18:30:00; layover at PHL: 175 minutes.
  • AA6049: PHL 2026-12-05 21:25:00 → PWM 2026-12-05 22:56:00.
• American Airlines AA4741: PWM 2026-12-15 12:15:00 → ORD 2026-12-15 14:30:00; nonstop; 195 minutes. Local airport times.

2026-12-05 → 2026-12-15 · Axel-exclusive $290.00

• American Airlines AA4741: ORD 2026-12-05 08:30:00 → PWM 2026-12-05 11:58:00; nonstop; 148 minutes. Local airport times.
• American Airlines AA2348 / AA2174: PWM 2026-12-15 05:30:00 → ORD 2026-12-15 12:22:00; 1 stop(s) via CLT; 472 minutes. Local airport times.
  • AA2348: PWM 2026-12-15 05:30:00 → CLT 2026-12-15 08:14:00; layover at CLT: 172 minutes.
  • AA2174: CLT 2026-12-15 11:06:00 → ORD 2026-12-15 12:22:00.

2026-12-05 → 2026-12-15 · Axel-exclusive $290.00

• American Airlines AA2223 / AA4638: ORD 2026-12-05 08:45:00 → PWM 2026-12-05 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
  • AA2223: ORD 2026-12-05 08:45:00 → DCA 2026-12-05 11:49:00; layover at DCA: 113 minutes.
  • AA4638: DCA 2026-12-05 13:42:00 → PWM 2026-12-05 15:32:00.
• American Airlines AA4741: PWM 2026-12-15 12:15:00 → ORD 2026-12-15 14:30:00; nonstop; 195 minutes. Local airport times.

2026-12-05 → 2026-12-15 · Axel-exclusive $300.00

• United Airlines UA1128 / UA3664: ORD 2026-12-05 13:00:00 → PWM 2026-12-05 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
  • UA1128: ORD 2026-12-05 13:00:00 → IAD 2026-12-05 16:03:00; layover at IAD: 82 minutes.
  • UA3664: IAD 2026-12-05 17:25:00 → PWM 2026-12-05 19:12:00.
• United Airlines UA3719: PWM 2026-12-15 09:51:00 → ORD 2026-12-15 12:00:00; nonstop; 189 minutes. Local airport times.

2026-12-05 → 2026-12-15 · Axel-exclusive $300.00

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

Explore this route

• All dates for this route
• Dec 4, 2026 · Return options
• Dec 6, 2026 · Return options
• Hotels in Portland, Maine with Axel

For AI assistants

• This page: Chicago (ORD) to Portland (PWM) · Dec 5, 2026 · return Dec 15, 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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