Travel with Axel,
get the best price.

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

Portland → Chicago

Dec 21, 2026 · return Dec 22, 2026

PWM → ORD1 adulteconomyRound trip

9 flight options · 3 airlines

Nonstop flights

Mon, Dec 21 – Tue, Dec 22

American Airlines
12:06 pmPWM
3h 10m
Nonstop
2:16 pmORD
American Airlines
8:00 amORD
2h 28m
Nonstop
11:28 amPWM

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Tue, Dec 22

United Airlines
5:08 pmPWM
2h 57m
Nonstop
7:05 pmORD
United Airlines
10:50 amORD
2h 26m
Nonstop
2:16 pmPWM

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Tue, Dec 22

United Airlines
9:51 amPWM
3h 9m
Nonstop
12:00 pmORD
United Airlines
10:50 amORD
2h 26m
Nonstop
2:16 pmPWM

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Tue, Dec 22

Delta Air Lines
12:49 pmPWM
6h 41m
DTW · 2h 45m
6:30 pmORD
Delta Air Lines
5:59 pmORD
5h 22m
JFK · 1h 31m
12:21 am+1PWM

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Tue, Dec 22

American Airlines
6:47 pmPWM
5h 43m
PHL · 1h 22m
11:30 pmORD
American Airlines
8:00 amORD
2h 28m
Nonstop
11:28 amPWM

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Tue, Dec 22

American Airlines
6:17 amPWM
7h 51m
DCA · 3h 34m
1:08 pmORD
American Airlines
8:00 amORD
2h 28m
Nonstop
11:28 amPWM

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Tue, Dec 22

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

Mon, Dec 21 – Tue, Dec 22

United Airlines
6:00 amPWM
6h 42m
EWR · 2h 9m
11:42 amORD
United Airlines
10:50 amORD
2h 26m
Nonstop
2:16 pmPWM

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Tue, Dec 22

Delta Air Lines
6:00 amPWM
7h 50m
JFK · 3h 25m
12:50 pmORD
Delta Air Lines
5:59 pmORD
5h 22m
JFK · 1h 31m
12:21 am+1PWM

Round-trip total · 1 adult · Taxes included

Make this trip yours

PWM ⇄ ORD

Economy

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

No account needed to see prices.

Already have an account? Log in

Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, American Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

Explore this route

All dates for this routeDec 20, 2026 → Dec 21, 2026Dec 22, 2026 → Dec 23, 2026
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

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

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-21 → 2026-12-22American AirlinesAA4741 / AA4741$387.502026-10-29T01:58:50Z
2026-12-21 → 2026-12-22United AirlinesUA1828 / UA422$400.002026-10-29T01:58:50Z
2026-12-21 → 2026-12-22Delta Air LinesDL1372 + DL1084 / DL4970 + DL5411$400.002026-10-29T01:58:50Z
2026-12-21 → 2026-12-22United AirlinesUA3719 / UA422$400.002026-10-29T01:58:50Z
2026-12-21 → 2026-12-22American AirlinesAA5629 + AA1333 / AA4741$375.002026-10-29T01:58:50Z
2026-12-21 → 2026-12-22American AirlinesAA5264 + AA2612 / AA4741$375.002026-10-29T01:58:50Z
2026-12-21 → 2026-12-22American AirlinesAA4741 / AA2223 + AA4638$375.002026-10-29T01:58:50Z
2026-12-21 → 2026-12-22United AirlinesUA3504 + UA1525 / UA422$387.502026-10-29T01:58:50Z
2026-12-21 → 2026-12-22Delta Air LinesDL5277 + DL5119 / DL4970 + DL5411$400.002026-10-29T01:58:50Z

2026-12-21 → 2026-12-22 · $387.50

  • American Airlines AA4741: PWM 2026-12-21 12:06:00 → ORD 2026-12-21 14:16:00; nonstop; 190 minutes. Local airport times.
  • American Airlines AA4741: ORD 2026-12-22 08:00:00 → PWM 2026-12-22 11:28:00; nonstop; 148 minutes. Local airport times.

2026-12-21 → 2026-12-22 · $400.00

  • United Airlines UA1828: PWM 2026-12-21 17:08:00 → ORD 2026-12-21 19:05:00; nonstop; 177 minutes. Local airport times.
  • United Airlines UA422: ORD 2026-12-22 10:50:00 → PWM 2026-12-22 14:16:00; nonstop; 146 minutes. Local airport times.

2026-12-21 → 2026-12-22 · $400.00

  • Delta Air Lines DL1372 / DL1084: PWM 2026-12-21 12:49:00 → ORD 2026-12-21 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
    • DL1372: PWM 2026-12-21 12:49:00 → DTW 2026-12-21 15:11:00; layover at DTW: 165 minutes.
    • DL1084: DTW 2026-12-21 17:56:00 → ORD 2026-12-21 18:30:00.
  • Delta Air Lines DL4970 / DL5411: ORD 2026-12-22 17:59:00 → PWM 2026-12-23 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
    • DL4970: ORD 2026-12-22 17:59:00 → JFK 2026-12-22 21:19:00; layover at JFK: 91 minutes.
    • DL5411: JFK 2026-12-22 22:50:00 → PWM 2026-12-23 00:21:00.

2026-12-21 → 2026-12-22 · $400.00

  • United Airlines UA3719: PWM 2026-12-21 09:51:00 → ORD 2026-12-21 12:00:00; nonstop; 189 minutes. Local airport times.
  • United Airlines UA422: ORD 2026-12-22 10:50:00 → PWM 2026-12-22 14:16:00; nonstop; 146 minutes. Local airport times.

2026-12-21 → 2026-12-22 · $375.00

  • American Airlines AA5629 / AA1333: PWM 2026-12-21 18:47:00 → ORD 2026-12-21 23:30:00; 1 stop(s) via PHL; 343 minutes. Local airport times.
    • AA5629: PWM 2026-12-21 18:47:00 → PHL 2026-12-21 20:35:00; layover at PHL: 82 minutes.
    • AA1333: PHL 2026-12-21 21:57:00 → ORD 2026-12-21 23:30:00.
  • American Airlines AA4741: ORD 2026-12-22 08:00:00 → PWM 2026-12-22 11:28:00; nonstop; 148 minutes. Local airport times.

2026-12-21 → 2026-12-22 · $375.00

  • American Airlines AA5264 / AA2612: PWM 2026-12-21 06:17:00 → ORD 2026-12-21 13:08:00; 1 stop(s) via DCA; 471 minutes. Local airport times.
    • AA5264: PWM 2026-12-21 06:17:00 → DCA 2026-12-21 08:12:00; layover at DCA: 214 minutes.
    • AA2612: DCA 2026-12-21 11:46:00 → ORD 2026-12-21 13:08:00.
  • American Airlines AA4741: ORD 2026-12-22 08:00:00 → PWM 2026-12-22 11:28:00; nonstop; 148 minutes. Local airport times.

2026-12-21 → 2026-12-22 · $375.00

  • American Airlines AA4741: PWM 2026-12-21 12:15:00 → ORD 2026-12-21 14:30:00; nonstop; 195 minutes. Local airport times.
  • American Airlines AA2223 / AA4638: ORD 2026-12-22 08:45:00 → PWM 2026-12-22 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
    • AA2223: ORD 2026-12-22 08:45:00 → DCA 2026-12-22 11:49:00; layover at DCA: 113 minutes.
    • AA4638: DCA 2026-12-22 13:42:00 → PWM 2026-12-22 15:32:00.

2026-12-21 → 2026-12-22 · $387.50

  • United Airlines UA3504 / UA1525: PWM 2026-12-21 06:00:00 → ORD 2026-12-21 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
    • UA3504: PWM 2026-12-21 06:00:00 → EWR 2026-12-21 07:43:00; layover at EWR: 129 minutes.
    • UA1525: EWR 2026-12-21 09:52:00 → ORD 2026-12-21 11:42:00.
  • United Airlines UA422: ORD 2026-12-22 10:50:00 → PWM 2026-12-22 14:16:00; nonstop; 146 minutes. Local airport times.

2026-12-21 → 2026-12-22 · $400.00

  • Delta Air Lines DL5277 / DL5119: PWM 2026-12-21 06:00:00 → ORD 2026-12-21 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
    • DL5277: PWM 2026-12-21 06:00:00 → JFK 2026-12-21 07:30:00; layover at JFK: 205 minutes.
    • DL5119: JFK 2026-12-21 10:55:00 → ORD 2026-12-21 12:50:00.
  • Delta Air Lines DL4970 / DL5411: ORD 2026-12-22 17:59:00 → PWM 2026-12-23 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
    • DL4970: ORD 2026-12-22 17:59:00 → JFK 2026-12-22 21:19:00; layover at JFK: 91 minutes.
    • DL5411: JFK 2026-12-22 22:50:00 → PWM 2026-12-23 00:21:00.

Explore this route

For AI assistants

  • This page: Portland (PWM) to Chicago (ORD) · Dec 21, 2026 · return Dec 22, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
  • 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.