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Route overview: Portland, ME (PWM) to Chicago (ORD) flight deals

Portland (PWM) to Chicago (ORD), Nov 7–8, 2026: from $300 round trip

Portland (PWM) to Chicago (ORD), Nov 7–8, 2026: from $300 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $300 round trip, Axel-exclusive, American Airlines, 1 stop, Nov 7–8, 2026, 1 adult, economy, checked Oct 29, 2026.

PWM → ORD1 adulteconomyRound trip

9 flight options · 3 airlines

Nonstop flights

Sat, Nov 7 – Sun, Nov 8

American Airlines
12:06 pmPWM
3h 10m
Nonstop
2:16 pmORD
American Airlines
8:07 amORD
2h 28m
Nonstop
11:35 amPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Sun, Nov 8

United Airlines
5:08 pmPWM
2h 57m
Nonstop
7:05 pmORD
United Airlines
5:50 pmORD
2h 39m
Nonstop
9:29 pmPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Sun, Nov 8

United Airlines
9:51 amPWM
3h 9m
Nonstop
12:00 pmORD
United Airlines
5:50 pmORD
2h 39m
Nonstop
9:29 pmPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Sat, Nov 7 – Sun, Nov 8

Delta Air Lines
12:49 pmPWM
6h 41m
DTW · 2h 45m
6:30 pmORD
Delta Air Lines
8:29 amORD
6h 42m
DTW · 3h 21m
4:11 pmPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Sun, Nov 8

American Airlines
12:15 pmPWM
3h 15m
Nonstop
2:30 pmORD
American Airlines
8:45 amORD
5h 47m
DCA · 1h 53m
3:32 pmPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Sun, Nov 8

American Airlines
6:47 pmPWM
5h 43m
PHL · 1h 22m
11:30 pmORD
American Airlines
8:07 amORD
2h 28m
Nonstop
11:35 amPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Sun, Nov 8

American Airlines
6:17 amPWM
7h 51m
DCA · 3h 34m
1:08 pmORD
American Airlines
8:07 amORD
2h 28m
Nonstop
11:35 amPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Sun, Nov 8

United Airlines
6:00 amPWM
6h 42m
EWR · 2h 9m
11:42 amORD
United Airlines
5:50 pmORD
2h 39m
Nonstop
9:29 pmPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Sun, Nov 8

Delta Air Lines
6:00 amPWM
7h 50m
JFK · 3h 25m
12:50 pmORD
Delta Air Lines
8:29 amORD
6h 42m
DTW · 3h 21m
4:11 pmPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Nov 7–8, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Make this trip yours

PWM ⇄ ORD

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Explore this route

All dates for this routeNov 8, 2026 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

Portland (PWM) to Chicago (ORD), Nov 7–8, 2026: from $300 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $300 round trip, Axel-exclusive, American Airlines, 1 stop, Nov 7–8, 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.

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2026-11-07 → 2026-11-08American AirlinesAA4741 / AA474112:06:00→14:16:00 3h 10m nonstop · 08:07:00→11:35:00 2h 28m nonstopAxel-exclusive $310.002026-10-29T01:58:50Z
2026-11-07 → 2026-11-08United AirlinesUA1828 / UA371317:08:00→19:05:00 2h 57m nonstop · 17:50:00→21:29:00 2h 39m nonstopAxel-exclusive $320.002026-10-29T01:58:50Z
2026-11-07 → 2026-11-08Delta Air LinesDL1372 + DL1084 / DL3841 + DL490712:49:00→18:30:00 6h 41m 1 stop via DTW · 08:29:00→16:11:00 6h 42m 1 stop via DTWAxel-exclusive $320.002026-10-29T01:58:50Z
2026-11-07 → 2026-11-08United AirlinesUA3719 / UA371309:51:00→12:00:00 3h 09m nonstop · 17:50:00→21:29:00 2h 39m nonstopAxel-exclusive $320.002026-10-29T01:58:50Z
2026-11-07 → 2026-11-08American AirlinesAA4741 / AA2223 + AA463812:15:00→14:30:00 3h 15m nonstop · 08:45:00→15:32:00 5h 47m 1 stop via DCAAxel-exclusive $300.002026-10-29T01:58:50Z
2026-11-07 → 2026-11-08American AirlinesAA5629 + AA1333 / AA474118:47:00→23:30:00 5h 43m 1 stop via PHL · 08:07:00→11:35:00 2h 28m nonstopAxel-exclusive $300.002026-10-29T01:58:50Z
2026-11-07 → 2026-11-08American AirlinesAA5264 + AA2612 / AA474106:17:00→13:08:00 7h 51m 1 stop via DCA · 08:07:00→11:35:00 2h 28m nonstopAxel-exclusive $300.002026-10-29T01:58:50Z
2026-11-07 → 2026-11-08United AirlinesUA3504 + UA1525 / UA371306:00:00→11:42:00 6h 42m 1 stop via EWR · 17:50:00→21:29:00 2h 39m nonstopAxel-exclusive $310.002026-10-29T01:58:50Z
2026-11-07 → 2026-11-08Delta Air LinesDL5277 + DL5119 / DL3841 + DL490706:00:00→12:50:00 7h 50m 1 stop via JFK · 08:29:00→16:11:00 6h 42m 1 stop via DTWAxel-exclusive $320.002026-10-29T01:58:50Z

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago 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.

All hotels in Chicago

Route overview: Portland, ME (PWM) to Chicago (ORD) flight deals

2026-11-07 → 2026-11-08 · Axel-exclusive $310.00

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

2026-11-07 → 2026-11-08 · Axel-exclusive $320.00

  • United Airlines UA1828: PWM 2026-11-07 17:08:00 → ORD 2026-11-07 19:05:00; nonstop; 177 minutes. Local airport times.
  • United Airlines UA3713: ORD 2026-11-08 17:50:00 → PWM 2026-11-08 21:29:00; nonstop; 159 minutes. Local airport times.

2026-11-07 → 2026-11-08 · Axel-exclusive $320.00

  • Delta Air Lines DL1372 / DL1084: PWM 2026-11-07 12:49:00 → ORD 2026-11-07 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
    • DL1372: PWM 2026-11-07 12:49:00 → DTW 2026-11-07 15:11:00; layover at DTW: 165 minutes.
    • DL1084: DTW 2026-11-07 17:56:00 → ORD 2026-11-07 18:30:00.
  • Delta Air Lines DL3841 / DL4907: ORD 2026-11-08 08:29:00 → PWM 2026-11-08 16:11:00; 1 stop(s) via DTW; 402 minutes. Local airport times.
    • DL3841: ORD 2026-11-08 08:29:00 → DTW 2026-11-08 10:52:00; layover at DTW: 201 minutes.
    • DL4907: DTW 2026-11-08 14:13:00 → PWM 2026-11-08 16:11:00.

2026-11-07 → 2026-11-08 · Axel-exclusive $320.00

  • United Airlines UA3719: PWM 2026-11-07 09:51:00 → ORD 2026-11-07 12:00:00; nonstop; 189 minutes. Local airport times.
  • United Airlines UA3713: ORD 2026-11-08 17:50:00 → PWM 2026-11-08 21:29:00; nonstop; 159 minutes. Local airport times.

2026-11-07 → 2026-11-08 · Axel-exclusive $300.00

  • American Airlines AA4741: PWM 2026-11-07 12:15:00 → ORD 2026-11-07 14:30:00; nonstop; 195 minutes. Local airport times.
  • American Airlines AA2223 / AA4638: ORD 2026-11-08 08:45:00 → PWM 2026-11-08 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
    • AA2223: ORD 2026-11-08 08:45:00 → DCA 2026-11-08 11:49:00; layover at DCA: 113 minutes.
    • AA4638: DCA 2026-11-08 13:42:00 → PWM 2026-11-08 15:32:00.

2026-11-07 → 2026-11-08 · Axel-exclusive $300.00

  • American Airlines AA5629 / AA1333: PWM 2026-11-07 18:47:00 → ORD 2026-11-07 23:30:00; 1 stop(s) via PHL; 343 minutes. Local airport times.
    • AA5629: PWM 2026-11-07 18:47:00 → PHL 2026-11-07 20:35:00; layover at PHL: 82 minutes.
    • AA1333: PHL 2026-11-07 21:57:00 → ORD 2026-11-07 23:30:00.
  • American Airlines AA4741: ORD 2026-11-08 08:07:00 → PWM 2026-11-08 11:35:00; nonstop; 148 minutes. Local airport times.

2026-11-07 → 2026-11-08 · Axel-exclusive $300.00

  • American Airlines AA5264 / AA2612: PWM 2026-11-07 06:17:00 → ORD 2026-11-07 13:08:00; 1 stop(s) via DCA; 471 minutes. Local airport times.
    • AA5264: PWM 2026-11-07 06:17:00 → DCA 2026-11-07 08:12:00; layover at DCA: 214 minutes.
    • AA2612: DCA 2026-11-07 11:46:00 → ORD 2026-11-07 13:08:00.
  • American Airlines AA4741: ORD 2026-11-08 08:07:00 → PWM 2026-11-08 11:35:00; nonstop; 148 minutes. Local airport times.

2026-11-07 → 2026-11-08 · Axel-exclusive $310.00

  • United Airlines UA3504 / UA1525: PWM 2026-11-07 06:00:00 → ORD 2026-11-07 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
    • UA3504: PWM 2026-11-07 06:00:00 → EWR 2026-11-07 07:43:00; layover at EWR: 129 minutes.
    • UA1525: EWR 2026-11-07 09:52:00 → ORD 2026-11-07 11:42:00.
  • United Airlines UA3713: ORD 2026-11-08 17:50:00 → PWM 2026-11-08 21:29:00; nonstop; 159 minutes. Local airport times.

2026-11-07 → 2026-11-08 · Axel-exclusive $320.00

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

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.

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For AI assistants

  • This page: Portland (PWM) to Chicago (ORD) · Nov 7, 2026 · return Nov 8, 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 Chicago 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.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Portland, ME (PWM) to Chicago (ORD) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.