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

Portland (PWM) to Chicago (ORD), Jan 24–30, 2027: from $300 round trip

Portland (PWM) to Chicago (ORD), Jan 24–30, 2027: from $300 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $300 round trip, Axel-exclusive, American Airlines, 1 stop, Jan 24–30, 2027, 1 adult, economy, checked Oct 29, 2026.

PWM → ORD1 adulteconomyRound trip

7 flight options · 3 airlines

Nonstop flights

Sun, Jan 24 – Sat, Jan 30

American Airlines
12:15 pmPWM
3h 15m
Nonstop
2:30 pmORD
American Airlines
8:10 amORD
2h 32m
Nonstop
11:42 amPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Sun, Jan 24 – Sat, Jan 30

United Airlines
6:00 amPWM
6h 42m
EWR · 2h 9m
11:42 amORD
United Airlines
1:00 pmORD
5h 12m
IAD · 1h 22m
7:12 pmPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Jan 24 – Sat, Jan 30

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

Availability is checked when you select these flights.

Sun, Jan 24 – Sat, Jan 30

American Airlines
5:30 amPWM
7h 52m
CLT · 2h 52m
12:22 pmORD
American Airlines
8:10 amORD
2h 32m
Nonstop
11:42 amPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Jan 24 – Sat, Jan 30

American Airlines
12:06 pmPWM
3h 10m
Nonstop
2:16 pmORD
American Airlines
3:19 pmORD
6h 37m
PHL · 2h 55m
10:56 pmPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Jan 24 – Sat, Jan 30

United Airlines
9:51 amPWM
3h 9m
Nonstop
12:00 pmORD
United Airlines
1:00 pmORD
5h 12m
IAD · 1h 22m
7:12 pmPWM

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Jan 24 – Sat, Jan 30

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

Availability is checked when you select these flights.

Hotels for these nights (Jan 24–30, 2027 · 6 nights · 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 routeJan 23, 2027 · Return optionsJan 25, 2027 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

Portland (PWM) to Chicago (ORD), Jan 24–30, 2027: from $300 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $300 round trip, Axel-exclusive, American Airlines, 1 stop, Jan 24–30, 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 datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2027-01-24 → 2027-01-30American AirlinesAA4741 / AA474112:15:00→14:30:00 3h 15m nonstop · 08:10:00→11:42:00 2h 32m nonstopAxel-exclusive $310.002026-10-29T01:58:50Z
2027-01-24 → 2027-01-30United AirlinesUA3504 + UA1525 / UA1128 + UA366406:00:00→11:42:00 6h 42m 1 stop via EWR · 13:00:00→19:12:00 5h 12m 1 stop via IADAxel-exclusive $300.002026-10-29T01:58:50Z
2027-01-24 → 2027-01-30Delta Air LinesDL1372 + DL1084 / DL4970 + DL541112:49:00→18:30:00 6h 41m 1 stop via DTW · 17:59:00→00:21:00 5h 22m 1 stop via JFKAxel-exclusive $320.002026-10-29T01:58:50Z
2027-01-24 → 2027-01-30American AirlinesAA2348 + AA2174 / AA474105:30:00→12:22:00 7h 52m 1 stop via CLT · 08:10:00→11:42:00 2h 32m nonstopAxel-exclusive $300.002026-10-29T01:58:50Z
2027-01-24 → 2027-01-30American AirlinesAA4741 / AA2840 + AA604912:06:00→14:16:00 3h 10m nonstop · 15:19:00→22:56:00 6h 37m 1 stop via PHLAxel-exclusive $300.002026-10-29T01:58:50Z
2027-01-24 → 2027-01-30United AirlinesUA3719 / UA1128 + UA366409:51:00→12:00:00 3h 09m nonstop · 13:00:00→19:12:00 5h 12m 1 stop via IADAxel-exclusive $310.002026-10-29T01:58:50Z
2027-01-24 → 2027-01-30Delta Air LinesDL5277 + DL5119 / DL4970 + DL541106:00:00→12:50:00 7h 50m 1 stop via JFK · 17:59:00→00:21:00 5h 22m 1 stop via JFKAxel-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

2027-01-24 → 2027-01-30 · Axel-exclusive $310.00

  • American Airlines AA4741: PWM 2027-01-24 12:15:00 → ORD 2027-01-24 14:30:00; nonstop; 195 minutes. Local airport times.
  • American Airlines AA4741: ORD 2027-01-30 08:10:00 → PWM 2027-01-30 11:42:00; nonstop; 152 minutes. Local airport times.

2027-01-24 → 2027-01-30 · Axel-exclusive $300.00

  • United Airlines UA3504 / UA1525: PWM 2027-01-24 06:00:00 → ORD 2027-01-24 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
    • UA3504: PWM 2027-01-24 06:00:00 → EWR 2027-01-24 07:43:00; layover at EWR: 129 minutes.
    • UA1525: EWR 2027-01-24 09:52:00 → ORD 2027-01-24 11:42:00.
  • United Airlines UA1128 / UA3664: ORD 2027-01-30 13:00:00 → PWM 2027-01-30 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
    • UA1128: ORD 2027-01-30 13:00:00 → IAD 2027-01-30 16:03:00; layover at IAD: 82 minutes.
    • UA3664: IAD 2027-01-30 17:25:00 → PWM 2027-01-30 19:12:00.

2027-01-24 → 2027-01-30 · Axel-exclusive $320.00

  • Delta Air Lines DL1372 / DL1084: PWM 2027-01-24 12:49:00 → ORD 2027-01-24 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
    • DL1372: PWM 2027-01-24 12:49:00 → DTW 2027-01-24 15:11:00; layover at DTW: 165 minutes.
    • DL1084: DTW 2027-01-24 17:56:00 → ORD 2027-01-24 18:30:00.
  • Delta Air Lines DL4970 / DL5411: ORD 2027-01-30 17:59:00 → PWM 2027-01-31 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
    • DL4970: ORD 2027-01-30 17:59:00 → JFK 2027-01-30 21:19:00; layover at JFK: 91 minutes.
    • DL5411: JFK 2027-01-30 22:50:00 → PWM 2027-01-31 00:21:00.

2027-01-24 → 2027-01-30 · Axel-exclusive $300.00

  • American Airlines AA2348 / AA2174: PWM 2027-01-24 05:30:00 → ORD 2027-01-24 12:22:00; 1 stop(s) via CLT; 472 minutes. Local airport times.
    • AA2348: PWM 2027-01-24 05:30:00 → CLT 2027-01-24 08:14:00; layover at CLT: 172 minutes.
    • AA2174: CLT 2027-01-24 11:06:00 → ORD 2027-01-24 12:22:00.
  • American Airlines AA4741: ORD 2027-01-30 08:10:00 → PWM 2027-01-30 11:42:00; nonstop; 152 minutes. Local airport times.

2027-01-24 → 2027-01-30 · Axel-exclusive $300.00

  • American Airlines AA4741: PWM 2027-01-24 12:06:00 → ORD 2027-01-24 14:16:00; nonstop; 190 minutes. Local airport times.
  • American Airlines AA2840 / AA6049: ORD 2027-01-30 15:19:00 → PWM 2027-01-30 22:56:00; 1 stop(s) via PHL; 397 minutes. Local airport times.
    • AA2840: ORD 2027-01-30 15:19:00 → PHL 2027-01-30 18:30:00; layover at PHL: 175 minutes.
    • AA6049: PHL 2027-01-30 21:25:00 → PWM 2027-01-30 22:56:00.

2027-01-24 → 2027-01-30 · Axel-exclusive $310.00

  • United Airlines UA3719: PWM 2027-01-24 09:51:00 → ORD 2027-01-24 12:00:00; nonstop; 189 minutes. Local airport times.
  • United Airlines UA1128 / UA3664: ORD 2027-01-30 13:00:00 → PWM 2027-01-30 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
    • UA1128: ORD 2027-01-30 13:00:00 → IAD 2027-01-30 16:03:00; layover at IAD: 82 minutes.
    • UA3664: IAD 2027-01-30 17:25:00 → PWM 2027-01-30 19:12:00.

2027-01-24 → 2027-01-30 · Axel-exclusive $320.00

  • Delta Air Lines DL5277 / DL5119: PWM 2027-01-24 06:00:00 → ORD 2027-01-24 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
    • DL5277: PWM 2027-01-24 06:00:00 → JFK 2027-01-24 07:30:00; layover at JFK: 205 minutes.
    • DL5119: JFK 2027-01-24 10:55:00 → ORD 2027-01-24 12:50:00.
  • Delta Air Lines DL4970 / DL5411: ORD 2027-01-30 17:59:00 → PWM 2027-01-31 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
    • DL4970: ORD 2027-01-30 17:59:00 → JFK 2027-01-30 21:19:00; layover at JFK: 91 minutes.
    • DL5411: JFK 2027-01-30 22:50:00 → PWM 2027-01-31 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: Portland (PWM) to Chicago (ORD) · Jan 24, 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 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.