Chicago (ORD) to Portland (PWM) · Jan 25, 2027 · return Feb 4, 2027

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

2027-01-25 → 2027-02-04 · Axel-exclusive $300.00

• American Airlines AA4741: ORD 2027-01-25 08:10:00 → PWM 2027-01-25 11:42:00; nonstop; 152 minutes. Local airport times.
• American Airlines AA4741: PWM 2027-02-04 12:15:00 → ORD 2027-02-04 14:30:00; nonstop; 195 minutes. Local airport times.

2027-01-25 → 2027-02-04 · Axel-exclusive $290.00

• United Airlines UA1128 / UA3664: ORD 2027-01-25 13:00:00 → PWM 2027-01-25 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
  • UA1128: ORD 2027-01-25 13:00:00 → IAD 2027-01-25 16:03:00; layover at IAD: 82 minutes.
  • UA3664: IAD 2027-01-25 17:25:00 → PWM 2027-01-25 19:12:00.
• United Airlines UA3504 / UA1525: PWM 2027-02-04 06:00:00 → ORD 2027-02-04 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
  • UA3504: PWM 2027-02-04 06:00:00 → EWR 2027-02-04 07:43:00; layover at EWR: 129 minutes.
  • UA1525: EWR 2027-02-04 09:52:00 → ORD 2027-02-04 11:42:00.

2027-01-25 → 2027-02-04 · Axel-exclusive $310.00

• Delta Air Lines DL4970 / DL5411: ORD 2027-01-25 17:59:00 → PWM 2027-01-26 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2027-01-25 17:59:00 → JFK 2027-01-25 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2027-01-25 22:50:00 → PWM 2027-01-26 00:21:00.
• Delta Air Lines DL1372 / DL1084: PWM 2027-02-04 12:49:00 → ORD 2027-02-04 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
  • DL1372: PWM 2027-02-04 12:49:00 → DTW 2027-02-04 15:11:00; layover at DTW: 165 minutes.
  • DL1084: DTW 2027-02-04 17:56:00 → ORD 2027-02-04 18:30:00.

2027-01-25 → 2027-02-04 · Axel-exclusive $290.00

• American Airlines AA4741: ORD 2027-01-25 08:30:00 → PWM 2027-01-25 11:58:00; nonstop; 148 minutes. Local airport times.
• American Airlines AA2348 / AA2174: PWM 2027-02-04 05:30:00 → ORD 2027-02-04 12:22:00; 1 stop(s) via CLT; 472 minutes. Local airport times.
  • AA2348: PWM 2027-02-04 05:30:00 → CLT 2027-02-04 08:14:00; layover at CLT: 172 minutes.
  • AA2174: CLT 2027-02-04 11:06:00 → ORD 2027-02-04 12:22:00.

2027-01-25 → 2027-02-04 · Axel-exclusive $290.00

• United Airlines UA2776 / UA4604: ORD 2027-01-25 05:55:00 → PWM 2027-01-25 13:38:00; 1 stop(s) via EWR; 403 minutes. Local airport times.
  • UA2776: ORD 2027-01-25 05:55:00 → EWR 2027-01-25 09:02:00; layover at EWR: 193 minutes.
  • UA4604: EWR 2027-01-25 12:15:00 → PWM 2027-01-25 13:38:00.
• United Airlines UA3504 / UA1525: PWM 2027-02-04 06:00:00 → ORD 2027-02-04 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
  • UA3504: PWM 2027-02-04 06:00:00 → EWR 2027-02-04 07:43:00; layover at EWR: 129 minutes.
  • UA1525: EWR 2027-02-04 09:52:00 → ORD 2027-02-04 11:42:00.

2027-01-25 → 2027-02-04 · Axel-exclusive $290.00

• American Airlines AA2840 / AA6049: ORD 2027-01-25 15:19:00 → PWM 2027-01-25 22:56:00; 1 stop(s) via PHL; 397 minutes. Local airport times.
  • AA2840: ORD 2027-01-25 15:19:00 → PHL 2027-01-25 18:30:00; layover at PHL: 175 minutes.
  • AA6049: PHL 2027-01-25 21:25:00 → PWM 2027-01-25 22:56:00.
• American Airlines AA4741: PWM 2027-02-04 12:15:00 → ORD 2027-02-04 14:30:00; nonstop; 195 minutes. Local airport times.

2027-01-25 → 2027-02-04 · Axel-exclusive $300.00

• United Airlines UA2761: ORD 2027-01-25 18:18:00 → PWM 2027-01-25 21:51:00; nonstop; 153 minutes. Local airport times.
• United Airlines UA3504 / UA1525: PWM 2027-02-04 06:00:00 → ORD 2027-02-04 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
  • UA3504: PWM 2027-02-04 06:00:00 → EWR 2027-02-04 07:43:00; layover at EWR: 129 minutes.
  • UA1525: EWR 2027-02-04 09:52:00 → ORD 2027-02-04 11:42:00.

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

• All dates for this route
• Jan 24, 2027 · Return options
• Jan 26, 2027 · Return options
• Hotels in Portland, Maine with Axel

For AI assistants

• This page: Chicago (ORD) to Portland (PWM) · Jan 25, 2027 · return Feb 4, 2027: 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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