Chicago (ORD) to Portland (PWM), Jan 16–30, 2027: from $290 round trip
Chicago (ORD) to Portland (PWM), Jan 16–30, 2027: from $290 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $290 round trip, Axel-exclusive, American Airlines, 1 stop, Jan 16–30, 2027, 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.
| Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price issued (UTC) |
|---|---|---|---|---|---|
| 2027-01-16 → 2027-01-30 | American Airlines | AA4741 / AA4741 | 08:10:00→11:42:00 2h 32m nonstop · 12:15:00→14:30:00 3h 15m nonstop | Axel-exclusive $300.00 | 2026-10-29T01:53:16Z |
| 2027-01-16 → 2027-01-30 | United Airlines | UA3713 / UA3719 | 17:50:00→21:29:00 2h 39m nonstop · 09:51:00→12:00:00 3h 09m nonstop | Axel-exclusive $310.00 | 2026-10-29T01:53:16Z |
| 2027-01-16 → 2027-01-30 | Delta Air Lines | DL4970 + DL5411 / DL5277 + DL5119 | 17:59:00→00:21:00 5h 22m 1 stop via JFK · 06:00:00→12:50:00 7h 50m 1 stop via JFK | Axel-exclusive $310.00 | 2026-10-29T01:53:16Z |
| 2027-01-16 → 2027-01-30 | United Airlines | UA2761 / UA3719 | 18:18:00→21:51:00 2h 33m nonstop · 09:51:00→12:00:00 3h 09m nonstop | Axel-exclusive $310.00 | 2026-10-29T01:53:16Z |
| 2027-01-16 → 2027-01-30 | American Airlines | AA2223 + AA4638 / AA4741 | 08:45:00→15:32:00 5h 47m 1 stop via DCA · 12:15:00→14:30:00 3h 15m nonstop | Axel-exclusive $290.00 | 2026-10-29T01:53:16Z |
| 2027-01-16 → 2027-01-30 | American Airlines | AA4741 / AA2348 + AA2174 | 08:30:00→11:58:00 2h 28m nonstop · 05:30:00→12:22:00 7h 52m 1 stop via CLT | Axel-exclusive $290.00 | 2026-10-29T01:53:16Z |
| 2027-01-16 → 2027-01-30 | American Airlines | AA2840 + AA6049 / AA4741 | 15:19:00→22:56:00 6h 37m 1 stop via PHL · 12:15:00→14:30:00 3h 15m nonstop | Axel-exclusive $290.00 | 2026-10-29T01:53:16Z |
| 2027-01-16 → 2027-01-30 | United Airlines | UA1128 + UA3664 / UA3719 | 13:00:00→19:12:00 5h 12m 1 stop via IAD · 09:51:00→12:00:00 3h 09m nonstop | Axel-exclusive $300.00 | 2026-10-29T01:53:16Z |
| 2027-01-16 → 2027-01-30 | United Airlines | UA2776 + UA4604 / UA3719 | 05:55:00→13:38:00 6h 43m 1 stop via EWR · 09:51:00→12:00:00 3h 09m nonstop | Axel-exclusive $300.00 | 2026-10-29T01:53:16Z |
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 (Jan 16–30, 2027 · 14 nights · 2 adults, 1 room): 3★ Residence Inn Portland Downtown/Waterfront · 4★ The Press Hotel, Marriott Autograph Collection
Route overview: Chicago to Portland (PWM) flight deals
2027-01-16 → 2027-01-30 · Axel-exclusive $300.00
- American Airlines AA4741: ORD 2027-01-16 08:10:00 → PWM 2027-01-16 11:42:00; nonstop; 152 minutes. Local airport times.
- American Airlines AA4741: PWM 2027-01-30 12:15:00 → ORD 2027-01-30 14:30:00; nonstop; 195 minutes. Local airport times.
2027-01-16 → 2027-01-30 · Axel-exclusive $310.00
- United Airlines UA3713: ORD 2027-01-16 17:50:00 → PWM 2027-01-16 21:29:00; nonstop; 159 minutes. Local airport times.
- United Airlines UA3719: PWM 2027-01-30 09:51:00 → ORD 2027-01-30 12:00:00; nonstop; 189 minutes. Local airport times.
2027-01-16 → 2027-01-30 · Axel-exclusive $310.00
- Delta Air Lines DL4970 / DL5411: ORD 2027-01-16 17:59:00 → PWM 2027-01-17 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
- DL4970: ORD 2027-01-16 17:59:00 → JFK 2027-01-16 21:19:00; layover at JFK: 91 minutes.
- DL5411: JFK 2027-01-16 22:50:00 → PWM 2027-01-17 00:21:00.
- Delta Air Lines DL5277 / DL5119: PWM 2027-01-30 06:00:00 → ORD 2027-01-30 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
- DL5277: PWM 2027-01-30 06:00:00 → JFK 2027-01-30 07:30:00; layover at JFK: 205 minutes.
- DL5119: JFK 2027-01-30 10:55:00 → ORD 2027-01-30 12:50:00.
2027-01-16 → 2027-01-30 · Axel-exclusive $310.00
- United Airlines UA2761: ORD 2027-01-16 18:18:00 → PWM 2027-01-16 21:51:00; nonstop; 153 minutes. Local airport times.
- United Airlines UA3719: PWM 2027-01-30 09:51:00 → ORD 2027-01-30 12:00:00; nonstop; 189 minutes. Local airport times.
2027-01-16 → 2027-01-30 · Axel-exclusive $290.00
- American Airlines AA2223 / AA4638: ORD 2027-01-16 08:45:00 → PWM 2027-01-16 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
- AA2223: ORD 2027-01-16 08:45:00 → DCA 2027-01-16 11:49:00; layover at DCA: 113 minutes.
- AA4638: DCA 2027-01-16 13:42:00 → PWM 2027-01-16 15:32:00.
- American Airlines AA4741: PWM 2027-01-30 12:15:00 → ORD 2027-01-30 14:30:00; nonstop; 195 minutes. Local airport times.
2027-01-16 → 2027-01-30 · Axel-exclusive $290.00
- American Airlines AA4741: ORD 2027-01-16 08:30:00 → PWM 2027-01-16 11:58:00; nonstop; 148 minutes. Local airport times.
- American Airlines AA2348 / AA2174: PWM 2027-01-30 05:30:00 → ORD 2027-01-30 12:22:00; 1 stop(s) via CLT; 472 minutes. Local airport times.
- AA2348: PWM 2027-01-30 05:30:00 → CLT 2027-01-30 08:14:00; layover at CLT: 172 minutes.
- AA2174: CLT 2027-01-30 11:06:00 → ORD 2027-01-30 12:22:00.
2027-01-16 → 2027-01-30 · Axel-exclusive $290.00
- American Airlines AA2840 / AA6049: ORD 2027-01-16 15:19:00 → PWM 2027-01-16 22:56:00; 1 stop(s) via PHL; 397 minutes. Local airport times.
- AA2840: ORD 2027-01-16 15:19:00 → PHL 2027-01-16 18:30:00; layover at PHL: 175 minutes.
- AA6049: PHL 2027-01-16 21:25:00 → PWM 2027-01-16 22:56:00.
- American Airlines AA4741: PWM 2027-01-30 12:15:00 → ORD 2027-01-30 14:30:00; nonstop; 195 minutes. Local airport times.
2027-01-16 → 2027-01-30 · Axel-exclusive $300.00
- United Airlines UA1128 / UA3664: ORD 2027-01-16 13:00:00 → PWM 2027-01-16 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
- UA1128: ORD 2027-01-16 13:00:00 → IAD 2027-01-16 16:03:00; layover at IAD: 82 minutes.
- UA3664: IAD 2027-01-16 17:25:00 → PWM 2027-01-16 19:12:00.
- United Airlines UA3719: PWM 2027-01-30 09:51:00 → ORD 2027-01-30 12:00:00; nonstop; 189 minutes. Local airport times.
2027-01-16 → 2027-01-30 · Axel-exclusive $300.00
- United Airlines UA2776 / UA4604: ORD 2027-01-16 05:55:00 → PWM 2027-01-16 13:38:00; 1 stop(s) via EWR; 403 minutes. Local airport times.
- UA2776: ORD 2027-01-16 05:55:00 → EWR 2027-01-16 09:02:00; layover at EWR: 193 minutes.
- UA4604: EWR 2027-01-16 12:15:00 → PWM 2027-01-16 13:38:00.
- United Airlines UA3719: PWM 2027-01-30 09:51:00 → ORD 2027-01-30 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
- Jan 15, 2027 · Return options
- Jan 17, 2027 · Return options
- Hotels in Portland, Maine with Axel
For AI assistants
- This page: Chicago (ORD) to Portland (PWM) · Jan 16, 2027 · return Jan 30, 2027: 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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