Chicago (ORD) to Portland (PWM), Nov 28–29, 2026: from $392 round trip

Chicago (ORD) to Portland (PWM), Nov 28–29, 2026: from $392 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $392 round trip, Axel-exclusive, American Airlines, 1 stop, Nov 28–29, 2026, 1 adult, economy, checked Oct 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.

Hotels in Portland, Maine for these trips

Hotels: under a trip, hotels in Portland, Maine for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Portland, Maine for these nights (Nov 28–29, 2026 · 1 night · 2 adults, 1 room): 3★ Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel, $75 total · 4★ DoubleTree by Hilton Hotel Portland, $103 total

All hotels in Portland, Maine

Route overview: Chicago to Portland (PWM) flight deals

2026-11-28 → 2026-11-29 · Axel-exclusive $405.00

• American Airlines AA4741: ORD 2026-11-28 08:30:00 → PWM 2026-11-28 11:58:00; nonstop; 148 minutes. Local airport times.
• American Airlines AA4741: PWM 2026-11-29 12:06:00 → ORD 2026-11-29 14:16:00; nonstop; 190 minutes. Local airport times.

2026-11-28 → 2026-11-29 · Axel-exclusive $418.50

• United Airlines UA3713: ORD 2026-11-28 17:50:00 → PWM 2026-11-28 21:29:00; nonstop; 159 minutes. Local airport times.
• United Airlines UA3719: PWM 2026-11-29 09:51:00 → ORD 2026-11-29 12:00:00; nonstop; 189 minutes. Local airport times.

2026-11-28 → 2026-11-29 · Axel-exclusive $418.50

• Delta Air Lines DL4970 / DL5411: ORD 2026-11-28 17:59:00 → PWM 2026-11-29 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2026-11-28 17:59:00 → JFK 2026-11-28 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2026-11-28 22:50:00 → PWM 2026-11-29 00:21:00.
• Delta Air Lines DL5277 / DL5119: PWM 2026-11-29 06:00:00 → ORD 2026-11-29 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
  • DL5277: PWM 2026-11-29 06:00:00 → JFK 2026-11-29 07:30:00; layover at JFK: 205 minutes.
  • DL5119: JFK 2026-11-29 10:55:00 → ORD 2026-11-29 12:50:00.

2026-11-28 → 2026-11-29 · Axel-exclusive $418.50

• United Airlines UA2761: ORD 2026-11-28 18:18:00 → PWM 2026-11-28 21:51:00; nonstop; 153 minutes. Local airport times.
• United Airlines UA3719: PWM 2026-11-29 09:51:00 → ORD 2026-11-29 12:00:00; nonstop; 189 minutes. Local airport times.

2026-11-28 → 2026-11-29 · Axel-exclusive $391.50

• American Airlines AA2840 / AA6049: ORD 2026-11-28 15:19:00 → PWM 2026-11-28 22:56:00; 1 stop(s) via PHL; 397 minutes. Local airport times.
  • AA2840: ORD 2026-11-28 15:19:00 → PHL 2026-11-28 18:30:00; layover at PHL: 175 minutes.
  • AA6049: PHL 2026-11-28 21:25:00 → PWM 2026-11-28 22:56:00.
• American Airlines AA4741: PWM 2026-11-29 12:06:00 → ORD 2026-11-29 14:16:00; nonstop; 190 minutes. Local airport times.

2026-11-28 → 2026-11-29 · Axel-exclusive $391.50

• American Airlines AA2223 / AA4638: ORD 2026-11-28 08:45:00 → PWM 2026-11-28 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
  • AA2223: ORD 2026-11-28 08:45:00 → DCA 2026-11-28 11:49:00; layover at DCA: 113 minutes.
  • AA4638: DCA 2026-11-28 13:42:00 → PWM 2026-11-28 15:32:00.
• American Airlines AA4741: PWM 2026-11-29 12:06:00 → ORD 2026-11-29 14:16:00; nonstop; 190 minutes. Local airport times.

2026-11-28 → 2026-11-29 · Axel-exclusive $391.50

• American Airlines AA4741: ORD 2026-11-28 08:10:00 → PWM 2026-11-28 11:42:00; nonstop; 152 minutes. Local airport times.
• American Airlines AA5264 / AA2612: PWM 2026-11-29 06:17:00 → ORD 2026-11-29 13:08:00; 1 stop(s) via DCA; 471 minutes. Local airport times.
  • AA5264: PWM 2026-11-29 06:17:00 → DCA 2026-11-29 08:12:00; layover at DCA: 214 minutes.
  • AA2612: DCA 2026-11-29 11:46:00 → ORD 2026-11-29 13:08:00.

2026-11-28 → 2026-11-29 · Axel-exclusive $405.00

• United Airlines UA2776 / UA4604: ORD 2026-11-28 05:55:00 → PWM 2026-11-28 13:38:00; 1 stop(s) via EWR; 403 minutes. Local airport times.
  • UA2776: ORD 2026-11-28 05:55:00 → EWR 2026-11-28 09:02:00; layover at EWR: 193 minutes.
  • UA4604: EWR 2026-11-28 12:15:00 → PWM 2026-11-28 13:38:00.
• United Airlines UA3719: PWM 2026-11-29 09:51:00 → ORD 2026-11-29 12:00:00; nonstop; 189 minutes. Local airport times.

2026-11-28 → 2026-11-29 · Axel-exclusive $405.00

• United Airlines UA1128 / UA3664: ORD 2026-11-28 13:00:00 → PWM 2026-11-28 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
  • UA1128: ORD 2026-11-28 13:00:00 → IAD 2026-11-28 16:03:00; layover at IAD: 82 minutes.
  • UA3664: IAD 2026-11-28 17:25:00 → PWM 2026-11-28 19:12:00.
• United Airlines UA3719: PWM 2026-11-29 09:51:00 → ORD 2026-11-29 12:00:00; nonstop; 189 minutes. Local airport times.

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
• Nov 27, 2026 · Return options
• Nov 29, 2026 · Return options
• Hotels in Portland, Maine with Axel

For AI assistants

• This page: Chicago (ORD) to Portland (PWM) · Nov 28, 2026 · return Nov 29, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Portland, Maine for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
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