Chicago (ORD) to Portland (PWM), Nov 29, 2026 – Dec 13, 2026: from $339 round trip

Lowest published fare: $339 round trip, Axel-exclusive, American Airlines, 1 stop, Nov 29, 2026 – Dec 13, 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.

Route overview: Chicago to Portland (PWM) flight deals

2026-11-29 → 2026-12-13 · Axel-exclusive $352.50

• American Airlines AA4741: ORD 2026-11-29 08:07:00 → PWM 2026-11-29 11:35:00; nonstop; 148 minutes. Local airport times.
• American Airlines AA4741: PWM 2026-12-13 12:15:00 → ORD 2026-12-13 14:30:00; nonstop; 195 minutes. Local airport times.

2026-11-29 → 2026-12-13 · Axel-exclusive $364.25

• United Airlines UA2761: ORD 2026-11-29 18:18:00 → PWM 2026-11-29 21:51:00; nonstop; 153 minutes. Local airport times.
• United Airlines UA3719: PWM 2026-12-13 09:51:00 → ORD 2026-12-13 12:00:00; nonstop; 189 minutes. Local airport times.

2026-11-29 → 2026-12-13 · Axel-exclusive $364.25

• Delta Air Lines DL4970 / DL5411: ORD 2026-11-29 17:59:00 → PWM 2026-11-30 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2026-11-29 17:59:00 → JFK 2026-11-29 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2026-11-29 22:50:00 → PWM 2026-11-30 00:21:00.
• Delta Air Lines DL1372 / DL1084: PWM 2026-12-13 12:49:00 → ORD 2026-12-13 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
  • DL1372: PWM 2026-12-13 12:49:00 → DTW 2026-12-13 15:11:00; layover at DTW: 165 minutes.
  • DL1084: DTW 2026-12-13 17:56:00 → ORD 2026-12-13 18:30:00.

2026-11-29 → 2026-12-13 · Axel-exclusive $364.25

• United Airlines UA3713: ORD 2026-11-29 17:50:00 → PWM 2026-11-29 21:29:00; nonstop; 159 minutes. Local airport times.
• United Airlines UA3719: PWM 2026-12-13 09:51:00 → ORD 2026-12-13 12:00:00; nonstop; 189 minutes. Local airport times.

2026-11-29 → 2026-12-13 · Axel-exclusive $339.00

• American Airlines AA2223 / AA4638: ORD 2026-11-29 08:45:00 → PWM 2026-11-29 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
  • AA2223: ORD 2026-11-29 08:45:00 → DCA 2026-11-29 11:49:00; layover at DCA: 113 minutes.
  • AA4638: DCA 2026-11-29 13:42:00 → PWM 2026-11-29 15:32:00.
• American Airlines AA4741: PWM 2026-12-13 12:15:00 → ORD 2026-12-13 14:30:00; nonstop; 195 minutes. Local airport times.

2026-11-29 → 2026-12-13 · Axel-exclusive $339.00

• American Airlines AA2840 / AA6049: ORD 2026-11-29 15:19:00 → PWM 2026-11-29 22:56:00; 1 stop(s) via PHL; 397 minutes. Local airport times.
  • AA2840: ORD 2026-11-29 15:19:00 → PHL 2026-11-29 18:30:00; layover at PHL: 175 minutes.
  • AA6049: PHL 2026-11-29 21:25:00 → PWM 2026-11-29 22:56:00.
• American Airlines AA4741: PWM 2026-12-13 12:15:00 → ORD 2026-12-13 14:30:00; nonstop; 195 minutes. Local airport times.

2026-11-29 → 2026-12-13 · Axel-exclusive $342.50

• American Airlines AA4741: ORD 2026-11-29 08:10:00 → PWM 2026-11-29 11:42:00; nonstop; 152 minutes. Local airport times.
• American Airlines AA2348 / AA2174: PWM 2026-12-13 05:30:00 → ORD 2026-12-13 12:22:00; 1 stop(s) via CLT; 472 minutes. Local airport times.
  • AA2348: PWM 2026-12-13 05:30:00 → CLT 2026-12-13 08:14:00; layover at CLT: 172 minutes.
  • AA2174: CLT 2026-12-13 11:06:00 → ORD 2026-12-13 12:22:00.

2026-11-29 → 2026-12-13 · Axel-exclusive $350.75

• United Airlines UA1128 / UA3664: ORD 2026-11-29 13:00:00 → PWM 2026-11-29 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
  • UA1128: ORD 2026-11-29 13:00:00 → IAD 2026-11-29 16:03:00; layover at IAD: 82 minutes.
  • UA3664: IAD 2026-11-29 17:25:00 → PWM 2026-11-29 19:12:00.
• United Airlines UA3719: PWM 2026-12-13 09:51:00 → ORD 2026-12-13 12:00:00; nonstop; 189 minutes. Local airport times.

2026-11-29 → 2026-12-13 · Axel-exclusive $350.75

• United Airlines UA2776 / UA4604: ORD 2026-11-29 05:55:00 → PWM 2026-11-29 13:38:00; 1 stop(s) via EWR; 403 minutes. Local airport times.
  • UA2776: ORD 2026-11-29 05:55:00 → EWR 2026-11-29 09:02:00; layover at EWR: 193 minutes.
  • UA4604: EWR 2026-11-29 12:15:00 → PWM 2026-11-29 13:38:00.
• United Airlines UA3719: PWM 2026-12-13 09:51:00 → ORD 2026-12-13 12:00:00; nonstop; 189 minutes. Local airport times.

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
• Nov 28, 2026 · Return options
• Nov 30, 2026 · Return options
• Hotels in Portland, Maine with Axel

For AI assistants

• This page: Chicago (ORD) to Portland (PWM) · Nov 29, 2026 · return Dec 13, 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 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.

Feedback (optional): Missing info · Axel issue