Chicago (ORD) to Portland (PWM) · Jan 21, 2027 · one way

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

2027-01-21 · one way · Axel-exclusive $160.00

• American Airlines AA4741: ORD 2027-01-21 08:10:00 → PWM 2027-01-21 11:42:00; nonstop; 152 minutes. Local airport times.

2027-01-21 · one way · Axel-exclusive $165.00

• United Airlines UA3713: ORD 2027-01-21 17:50:00 → PWM 2027-01-21 21:29:00; nonstop; 159 minutes. Local airport times.

2027-01-21 · one way · Axel-exclusive $165.00

• 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.

2027-01-21 · one way · Axel-exclusive $165.00

• United Airlines UA2761: ORD 2027-01-21 18:18:00 → PWM 2027-01-21 21:51:00; nonstop; 153 minutes. Local airport times.

2027-01-21 · one way · Axel-exclusive $150.00

• 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.

2027-01-21 · one way · Axel-exclusive $150.00

• American Airlines AA2223 / AA4638: ORD 2027-01-21 08:45:00 → PWM 2027-01-21 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
  • AA2223: ORD 2027-01-21 08:45:00 → DCA 2027-01-21 11:49:00; layover at DCA: 113 minutes.
  • AA4638: DCA 2027-01-21 13:42:00 → PWM 2027-01-21 15:32:00.

2027-01-21 · one way · Axel-exclusive $155.00

• 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.

2027-01-21 · one way · Axel-exclusive $155.00

• 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.

2027-01-21 · one way · Axel-exclusive $165.00

• Delta Air Lines DL3841 / DL4907: ORD 2027-01-21 08:29:00 → PWM 2027-01-21 16:11:00; 1 stop(s) via DTW; 402 minutes. Local airport times.
  • DL3841: ORD 2027-01-21 08:29:00 → DTW 2027-01-21 10:52:00; layover at DTW: 201 minutes.
  • DL4907: DTW 2027-01-21 14:13:00 → PWM 2027-01-21 16:11:00.

Explore this route

• All dates for this route
• Jan 20, 2027 · Return options
• Jan 22, 2027 · Return options
• Hotels in Portland, Maine with Axel

For AI assistants

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