Chicago (ORD) to Portland (PWM), Nov 9–12, 2026: from $290 round trip

Chicago (ORD) to Portland (PWM), Nov 9–12, 2026: from $290 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $290 round trip, Axel-exclusive, United Airlines, 1 stop, Nov 9–12, 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 9–12, 2026 · 3 nights · 2 adults, 1 room): 3★ Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel, $225 total · 4★ DoubleTree by Hilton Hotel Portland, $218 total

All hotels in Portland, Maine

Route overview: Chicago to Portland (PWM) flight deals

2026-11-09 → 2026-11-12 · Axel-exclusive $300.00

• American Airlines AA4741: ORD 2026-11-09 08:07:00 → PWM 2026-11-09 11:35:00; nonstop; 148 minutes. Local airport times.
• American Airlines AA4741: PWM 2026-11-12 12:06:00 → ORD 2026-11-12 14:16:00; nonstop; 190 minutes. Local airport times.

2026-11-09 → 2026-11-12 · Axel-exclusive $290.00

• United Airlines UA1128 / UA3664: ORD 2026-11-09 13:00:00 → PWM 2026-11-09 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
  • UA1128: ORD 2026-11-09 13:00:00 → IAD 2026-11-09 16:03:00; layover at IAD: 82 minutes.
  • UA3664: IAD 2026-11-09 17:25:00 → PWM 2026-11-09 19:12:00.
• United Airlines UA3504 / UA1525: PWM 2026-11-12 06:00:00 → ORD 2026-11-12 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
  • UA3504: PWM 2026-11-12 06:00:00 → EWR 2026-11-12 07:43:00; layover at EWR: 129 minutes.
  • UA1525: EWR 2026-11-12 09:52:00 → ORD 2026-11-12 11:42:00.

2026-11-09 → 2026-11-12 · Axel-exclusive $310.00

• Delta Air Lines DL3841 / DL4907: ORD 2026-11-09 08:29:00 → PWM 2026-11-09 16:11:00; 1 stop(s) via DTW; 402 minutes. Local airport times.
  • DL3841: ORD 2026-11-09 08:29:00 → DTW 2026-11-09 10:52:00; layover at DTW: 201 minutes.
  • DL4907: DTW 2026-11-09 14:13:00 → PWM 2026-11-09 16:11:00.
• Delta Air Lines DL5277 / DL5119: PWM 2026-11-12 06:00:00 → ORD 2026-11-12 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
  • DL5277: PWM 2026-11-12 06:00:00 → JFK 2026-11-12 07:30:00; layover at JFK: 205 minutes.
  • DL5119: JFK 2026-11-12 10:55:00 → ORD 2026-11-12 12:50:00.

2026-11-09 → 2026-11-12 · Axel-exclusive $290.00

• United Airlines UA2776 / UA4604: ORD 2026-11-09 05:55:00 → PWM 2026-11-09 13:38:00; 1 stop(s) via EWR; 403 minutes. Local airport times.
  • UA2776: ORD 2026-11-09 05:55:00 → EWR 2026-11-09 09:02:00; layover at EWR: 193 minutes.
  • UA4604: EWR 2026-11-09 12:15:00 → PWM 2026-11-09 13:38:00.
• United Airlines UA3504 / UA1525: PWM 2026-11-12 06:00:00 → ORD 2026-11-12 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
  • UA3504: PWM 2026-11-12 06:00:00 → EWR 2026-11-12 07:43:00; layover at EWR: 129 minutes.
  • UA1525: EWR 2026-11-12 09:52:00 → ORD 2026-11-12 11:42:00.

2026-11-09 → 2026-11-12 · Axel-exclusive $290.00

• American Airlines AA4741: ORD 2026-11-09 08:00:00 → PWM 2026-11-09 11:28:00; nonstop; 148 minutes. Local airport times.
• American Airlines AA5264 / AA2612: PWM 2026-11-12 06:17:00 → ORD 2026-11-12 13:08:00; 1 stop(s) via DCA; 471 minutes. Local airport times.
  • AA5264: PWM 2026-11-12 06:17:00 → DCA 2026-11-12 08:12:00; layover at DCA: 214 minutes.
  • AA2612: DCA 2026-11-12 11:46:00 → ORD 2026-11-12 13:08:00.

2026-11-09 → 2026-11-12 · Axel-exclusive $300.00

• United Airlines UA2761: ORD 2026-11-09 18:18:00 → PWM 2026-11-09 21:51:00; nonstop; 153 minutes. Local airport times.
• United Airlines UA3504 / UA1525: PWM 2026-11-12 06:00:00 → ORD 2026-11-12 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
  • UA3504: PWM 2026-11-12 06:00:00 → EWR 2026-11-12 07:43:00; layover at EWR: 129 minutes.
  • UA1525: EWR 2026-11-12 09:52:00 → ORD 2026-11-12 11:42:00.

2026-11-09 → 2026-11-12 · Axel-exclusive $310.00

• Delta Air Lines DL4970 / DL5411: ORD 2026-11-09 17:59:00 → PWM 2026-11-10 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2026-11-09 17:59:00 → JFK 2026-11-09 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2026-11-09 22:50:00 → PWM 2026-11-10 00:21:00.
• Delta Air Lines DL5277 / DL5119: PWM 2026-11-12 06:00:00 → ORD 2026-11-12 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
  • DL5277: PWM 2026-11-12 06:00:00 → JFK 2026-11-12 07:30:00; layover at JFK: 205 minutes.
  • DL5119: JFK 2026-11-12 10:55:00 → ORD 2026-11-12 12:50:00.

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
• Nov 8, 2026 · Return options
• Nov 10, 2026 · Return options
• Hotels in Portland, Maine with Axel

For AI assistants

• This page: Chicago (ORD) to Portland (PWM) · Nov 9, 2026 · return Nov 12, 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.
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