Portland (PWM) to Chicago (ORD), Jan 6–20, 2027: from $300 round trip

Portland (PWM) to Chicago (ORD), Jan 6–20, 2027: from $300 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $300 round trip, Axel-exclusive, United Airlines, 1 stop, Jan 6–20, 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.

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.

• Hotels in Chicago for these nights (Jan 6–20, 2027 · 14 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

All hotels in Chicago

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

2027-01-06 → 2027-01-20 · Axel-exclusive $310.00

• American Airlines AA4741: PWM 2027-01-06 12:15:00 → ORD 2027-01-06 14:30:00; nonstop; 195 minutes. Local airport times.
• American Airlines AA4741: ORD 2027-01-20 08:30:00 → PWM 2027-01-20 11:58:00; nonstop; 148 minutes. Local airport times.

2027-01-06 → 2027-01-20 · Axel-exclusive $300.00

• United Airlines UA3504 / UA1525: PWM 2027-01-06 06:00:00 → ORD 2027-01-06 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
  • UA3504: PWM 2027-01-06 06:00:00 → EWR 2027-01-06 07:43:00; layover at EWR: 129 minutes.
  • UA1525: EWR 2027-01-06 09:52:00 → ORD 2027-01-06 11:42:00.
• 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.

2027-01-06 → 2027-01-20 · Axel-exclusive $320.00

• Delta Air Lines DL5277 / DL5119: PWM 2027-01-06 06:00:00 → ORD 2027-01-06 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
  • DL5277: PWM 2027-01-06 06:00:00 → JFK 2027-01-06 07:30:00; layover at JFK: 205 minutes.
  • DL5119: JFK 2027-01-06 10:55:00 → ORD 2027-01-06 12:50:00.
• 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.

2027-01-06 → 2027-01-20 · Axel-exclusive $300.00

• American Airlines AA4741: PWM 2027-01-06 12:06:00 → ORD 2027-01-06 14:16:00; nonstop; 190 minutes. Local airport times.
• 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.

2027-01-06 → 2027-01-20 · Axel-exclusive $300.00

• American Airlines AA2348 / AA2174: PWM 2027-01-06 05:30:00 → ORD 2027-01-06 12:22:00; 1 stop(s) via CLT; 472 minutes. Local airport times.
  • AA2348: PWM 2027-01-06 05:30:00 → CLT 2027-01-06 08:14:00; layover at CLT: 172 minutes.
  • AA2174: CLT 2027-01-06 11:06:00 → ORD 2027-01-06 12:22:00.
• American Airlines AA4741: ORD 2027-01-20 08:30:00 → PWM 2027-01-20 11:58:00; nonstop; 148 minutes. Local airport times.

2027-01-06 → 2027-01-20 · Axel-exclusive $310.00

• United Airlines UA3719: PWM 2027-01-06 09:51:00 → ORD 2027-01-06 12:00:00; nonstop; 189 minutes. Local airport times.
• 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.

2027-01-06 → 2027-01-20 · Axel-exclusive $320.00

• Delta Air Lines DL1372 / DL1084: PWM 2027-01-06 12:49:00 → ORD 2027-01-06 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
  • DL1372: PWM 2027-01-06 12:49:00 → DTW 2027-01-06 15:11:00; layover at DTW: 165 minutes.
  • DL1084: DTW 2027-01-06 17:56:00 → ORD 2027-01-06 18:30:00.
• 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

• All dates for this route
• Jan 5, 2027 · Return options
• Jan 7, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PWM) to Chicago (ORD) · Jan 6, 2027 · return Jan 20, 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.
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• 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.

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