Travel with Axel, get the best price.

Route overview: Chicago to Portland (PWM) flight deals

Chicago (ORD) to Portland (PWM), Jan 20, 2027: from $150 one way

Chicago (ORD) to Portland (PWM), Jan 20, 2027: from $150 one way on Axel, checked Oct 29, 2026. Lowest published fare: $150 one way, Axel-exclusive, American Airlines, 1 stop, Jan 20, 2027, 1 adult, economy, checked Oct 29, 2026.

ORD → PWM1 adulteconomyOne way

9 flight options · 3 airlines

Nonstop flights

Wed, Jan 20 · One way

American Airlines
8:30 amORD
2h 28m
Nonstop
11:58 amPWM

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Wed, Jan 20 · One way

United Airlines
5:50 pmORD
2h 39m
Nonstop
9:29 pmPWM

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Wed, Jan 20 · One way

United Airlines
6:18 pmORD
2h 33m
Nonstop
9:51 pmPWM

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Wed, Jan 20 · One way

Delta Air Lines
8:29 amORD
6h 42m
DTW · 3h 21m
4:11 pmPWM

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Wed, Jan 20 · One way

American Airlines
3:19 pmORD
6h 37m
PHL · 2h 55m
10:56 pmPWM

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Wed, Jan 20 · One way

American Airlines
8:45 amORD
5h 47m
DCA · 1h 53m
3:32 pmPWM

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Wed, Jan 20 · One way

United Airlines
5:55 amORD
6h 43m
EWR · 3h 13m
1:38 pmPWM

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Wed, Jan 20 · One way

United Airlines
1:00 pmORD
5h 12m
IAD · 1h 22m
7:12 pmPWM

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Wed, Jan 20 · One way

Delta Air Lines
5:59 pmORD
5h 22m
JFK · 1h 31m
12:21 am+1PWM

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Make this trip yours

ORD ⇄ PWM

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 routeJan 19, 2027 · Return optionsJan 21, 2027 · Return optionsHotels in Portland, Maine with Axel
For AI assistants: every fare, every link, instructions

Chicago (ORD) to Portland (PWM), Jan 20, 2027: from $150 one way on Axel, checked Oct 29, 2026. Lowest published fare: $150 one way, Axel-exclusive, American Airlines, 1 stop, Jan 20, 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 datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2027-01-20 · one wayAmerican AirlinesAA474108:30:00→11:58:00 2h 28m nonstopAxel-exclusive $160.002026-10-29T01:53:16Z
2027-01-20 · one wayUnited AirlinesUA371317:50:00→21:29:00 2h 39m nonstopAxel-exclusive $165.002026-10-29T01:53:16Z
2027-01-20 · one wayDelta Air LinesDL3841 + DL490708:29:00→16:11:00 6h 42m 1 stop via DTWAxel-exclusive $165.002026-10-29T01:53:16Z
2027-01-20 · one wayUnited AirlinesUA276118:18:00→21:51:00 2h 33m nonstopAxel-exclusive $165.002026-10-29T01:53:16Z
2027-01-20 · one wayAmerican AirlinesAA2840 + AA604915:19:00→22:56:00 6h 37m 1 stop via PHLAxel-exclusive $150.002026-10-29T01:53:16Z
2027-01-20 · one wayAmerican AirlinesAA2223 + AA463808:45:00→15:32:00 5h 47m 1 stop via DCAAxel-exclusive $150.002026-10-29T01:53:16Z
2027-01-20 · one wayUnited AirlinesUA2776 + UA460405:55:00→13:38:00 6h 43m 1 stop via EWRAxel-exclusive $155.002026-10-29T01:53:16Z
2027-01-20 · one wayUnited AirlinesUA1128 + UA366413:00:00→19:12:00 5h 12m 1 stop via IADAxel-exclusive $155.002026-10-29T01:53:16Z
2027-01-20 · one wayDelta Air LinesDL4970 + DL541117:59:00→00:21:00 5h 22m 1 stop via JFKAxel-exclusive $165.002026-10-29T01:53:16Z

Route overview: Chicago to Portland (PWM) flight deals

2027-01-20 · one way · Axel-exclusive $160.00

  • American Airlines AA4741: ORD 2027-01-20 08:30:00 → PWM 2027-01-20 11:58:00; nonstop; 148 minutes. Local airport times.

2027-01-20 · one way · Axel-exclusive $165.00

  • United Airlines UA3713: ORD 2027-01-20 17:50:00 → PWM 2027-01-20 21:29:00; nonstop; 159 minutes. Local airport times.

2027-01-20 · one way · Axel-exclusive $165.00

  • Delta Air Lines DL3841 / DL4907: ORD 2027-01-20 08:29:00 → PWM 2027-01-20 16:11:00; 1 stop(s) via DTW; 402 minutes. Local airport times.
    • DL3841: ORD 2027-01-20 08:29:00 → DTW 2027-01-20 10:52:00; layover at DTW: 201 minutes.
    • DL4907: DTW 2027-01-20 14:13:00 → PWM 2027-01-20 16:11:00.

2027-01-20 · one way · Axel-exclusive $165.00

  • United Airlines UA2761: ORD 2027-01-20 18:18:00 → PWM 2027-01-20 21:51:00; nonstop; 153 minutes. Local airport times.

2027-01-20 · one way · Axel-exclusive $150.00

  • American Airlines AA2840 / AA6049: ORD 2027-01-20 15:19:00 → PWM 2027-01-20 22:56:00; 1 stop(s) via PHL; 397 minutes. Local airport times.
    • AA2840: ORD 2027-01-20 15:19:00 → PHL 2027-01-20 18:30:00; layover at PHL: 175 minutes.
    • AA6049: PHL 2027-01-20 21:25:00 → PWM 2027-01-20 22:56:00.

2027-01-20 · one way · Axel-exclusive $150.00

  • American Airlines AA2223 / AA4638: ORD 2027-01-20 08:45:00 → PWM 2027-01-20 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
    • AA2223: ORD 2027-01-20 08:45:00 → DCA 2027-01-20 11:49:00; layover at DCA: 113 minutes.
    • AA4638: DCA 2027-01-20 13:42:00 → PWM 2027-01-20 15:32:00.

2027-01-20 · one way · Axel-exclusive $155.00

  • United Airlines UA2776 / UA4604: ORD 2027-01-20 05:55:00 → PWM 2027-01-20 13:38:00; 1 stop(s) via EWR; 403 minutes. Local airport times.
    • UA2776: ORD 2027-01-20 05:55:00 → EWR 2027-01-20 09:02:00; layover at EWR: 193 minutes.
    • UA4604: EWR 2027-01-20 12:15:00 → PWM 2027-01-20 13:38:00.

2027-01-20 · one way · Axel-exclusive $155.00

  • United Airlines UA1128 / UA3664: ORD 2027-01-20 13:00:00 → PWM 2027-01-20 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
    • UA1128: ORD 2027-01-20 13:00:00 → IAD 2027-01-20 16:03:00; layover at IAD: 82 minutes.
    • UA3664: IAD 2027-01-20 17:25:00 → PWM 2027-01-20 19:12:00.

2027-01-20 · one way · Axel-exclusive $165.00

  • Delta Air Lines DL4970 / DL5411: ORD 2027-01-20 17:59:00 → PWM 2027-01-21 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
    • DL4970: ORD 2027-01-20 17:59:00 → JFK 2027-01-20 21:19:00; layover at JFK: 91 minutes.
    • DL5411: JFK 2027-01-20 22:50:00 → PWM 2027-01-21 00:21:00.

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

For AI assistants

  • This page: Chicago (ORD) to Portland (PWM) · Jan 20, 2027 · one way: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • 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 Chicago to Portland (PWM) 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.