Portland, ME (PWM) to Chicago (ORD) flight deals

Flights for your trip

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

2026-11-20 · one way · $165.00

• American Airlines AA4741: PWM 2026-11-20 12:06:00 → ORD 2026-11-20 14:16:00; nonstop; 190 minutes. Local airport times.

2026-11-20 · one way · $170.00

• United Airlines UA1828: PWM 2026-11-20 17:08:00 → ORD 2026-11-20 19:05:00; nonstop; 177 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $310.00

• American Airlines AA4741: PWM 2026-11-20 12:06:00 → ORD 2026-11-20 14:16:00; nonstop; 190 minutes. Local airport times.
• American Airlines AA4741: ORD 2026-11-23 08:30:00 → PWM 2026-11-23 11:58:00; nonstop; 148 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $320.00

• United Airlines UA3719: PWM 2026-11-20 09:51:00 → ORD 2026-11-20 12:00:00; nonstop; 189 minutes. Local airport times.
• United Airlines UA2761: ORD 2026-11-23 18:18:00 → PWM 2026-11-23 21:51:00; nonstop; 153 minutes. Local airport times.

2026-11-20 · one way · $170.00

• Delta Air Lines DL5277 / DL5119: PWM 2026-11-20 06:00:00 → ORD 2026-11-20 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
  • DL5277: PWM 2026-11-20 06:00:00 → JFK 2026-11-20 07:30:00; layover at JFK: 205 minutes.
  • DL5119: JFK 2026-11-20 10:55:00 → ORD 2026-11-20 12:50:00.

2026-11-20 → 2026-11-23 · $320.00

• Delta Air Lines DL1372 / DL1084: PWM 2026-11-20 12:49:00 → ORD 2026-11-20 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
  • DL1372: PWM 2026-11-20 12:49:00 → DTW 2026-11-20 15:11:00; layover at DTW: 165 minutes.
  • DL1084: DTW 2026-11-20 17:56:00 → ORD 2026-11-20 18:30:00.
• Delta Air Lines DL4970 / DL5411: ORD 2026-11-23 17:59:00 → PWM 2026-11-24 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2026-11-23 17:59:00 → JFK 2026-11-23 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2026-11-23 22:50:00 → PWM 2026-11-24 00:21:00.

2026-11-27 → 2026-12-04 · $356.50

• American Airlines AA4741: PWM 2026-11-27 12:06:00 → ORD 2026-11-27 14:16:00; nonstop; 190 minutes. Local airport times.
• American Airlines AA4741: ORD 2026-12-04 08:30:00 → PWM 2026-12-04 11:58:00; nonstop; 148 minutes. Local airport times.

2026-11-20 · one way · $170.00

• United Airlines UA3719: PWM 2026-11-20 09:51:00 → ORD 2026-11-20 12:00:00; nonstop; 189 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $320.00

• United Airlines UA1828: PWM 2026-11-20 17:08:00 → ORD 2026-11-20 19:05:00; nonstop; 177 minutes. Local airport times.
• United Airlines UA2761: ORD 2026-11-23 18:18:00 → PWM 2026-11-23 21:51:00; nonstop; 153 minutes. Local airport times.

2026-11-20 · one way · $155.00

• American Airlines AA2348 / AA2174: PWM 2026-11-20 05:30:00 → ORD 2026-11-20 12:22:00; 1 stop(s) via CLT; 472 minutes. Local airport times.
  • AA2348: PWM 2026-11-20 05:30:00 → CLT 2026-11-20 08:14:00; layover at CLT: 172 minutes.
  • AA2174: CLT 2026-11-20 11:06:00 → ORD 2026-11-20 12:22:00.

2026-11-20 · one way · $155.00

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

2026-11-20 · one way · $155.00

• American Airlines AA5264 / AA2612: PWM 2026-11-20 06:17:00 → ORD 2026-11-20 13:08:00; 1 stop(s) via DCA; 471 minutes. Local airport times.
  • AA5264: PWM 2026-11-20 06:17:00 → DCA 2026-11-20 08:12:00; layover at DCA: 214 minutes.
  • AA2612: DCA 2026-11-20 11:46:00 → ORD 2026-11-20 13:08:00.

2026-11-20 · one way · $160.00

• United Airlines UA3504 / UA1525: PWM 2026-11-20 06:00:00 → ORD 2026-11-20 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
  • UA3504: PWM 2026-11-20 06:00:00 → EWR 2026-11-20 07:43:00; layover at EWR: 129 minutes.
  • UA1525: EWR 2026-11-20 09:52:00 → ORD 2026-11-20 11:42:00.

2026-11-20 · one way · $170.00

• Delta Air Lines DL1372 / DL1084: PWM 2026-11-20 12:49:00 → ORD 2026-11-20 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
  • DL1372: PWM 2026-11-20 12:49:00 → DTW 2026-11-20 15:11:00; layover at DTW: 165 minutes.
  • DL1084: DTW 2026-11-20 17:56:00 → ORD 2026-11-20 18:30:00.

2026-11-20 → 2026-11-23 · $300.00

• American Airlines AA4741: PWM 2026-11-20 12:15:00 → ORD 2026-11-20 14:30:00; nonstop; 195 minutes. Local airport times.
• American Airlines AA2223 / AA4638: ORD 2026-11-23 08:45:00 → PWM 2026-11-23 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
  • AA2223: ORD 2026-11-23 08:45:00 → DCA 2026-11-23 11:49:00; layover at DCA: 113 minutes.
  • AA4638: DCA 2026-11-23 13:42:00 → PWM 2026-11-23 15:32:00.

2026-11-20 → 2026-11-23 · $300.00

• American Airlines AA5264 / AA2612: PWM 2026-11-20 06:17:00 → ORD 2026-11-20 13:08:00; 1 stop(s) via DCA; 471 minutes. Local airport times.
  • AA5264: PWM 2026-11-20 06:17:00 → DCA 2026-11-20 08:12:00; layover at DCA: 214 minutes.
  • AA2612: DCA 2026-11-20 11:46:00 → ORD 2026-11-20 13:08:00.
• American Airlines AA4741: ORD 2026-11-23 08:30:00 → PWM 2026-11-23 11:58:00; nonstop; 148 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $300.00

• American Airlines AA5629 / AA1333: PWM 2026-11-20 18:47:00 → ORD 2026-11-20 23:30:00; 1 stop(s) via PHL; 343 minutes. Local airport times.
  • AA5629: PWM 2026-11-20 18:47:00 → PHL 2026-11-20 20:35:00; layover at PHL: 82 minutes.
  • AA1333: PHL 2026-11-20 21:57:00 → ORD 2026-11-20 23:30:00.
• American Airlines AA4741: ORD 2026-11-23 08:30:00 → PWM 2026-11-23 11:58:00; nonstop; 148 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $310.00

• United Airlines UA3504 / UA1525: PWM 2026-11-20 06:00:00 → ORD 2026-11-20 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
  • UA3504: PWM 2026-11-20 06:00:00 → EWR 2026-11-20 07:43:00; layover at EWR: 129 minutes.
  • UA1525: EWR 2026-11-20 09:52:00 → ORD 2026-11-20 11:42:00.
• United Airlines UA2761: ORD 2026-11-23 18:18:00 → PWM 2026-11-23 21:51:00; nonstop; 153 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $320.00

• Delta Air Lines DL5277 / DL5119: PWM 2026-11-20 06:00:00 → ORD 2026-11-20 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
  • DL5277: PWM 2026-11-20 06:00:00 → JFK 2026-11-20 07:30:00; layover at JFK: 205 minutes.
  • DL5119: JFK 2026-11-20 10:55:00 → ORD 2026-11-20 12:50:00.
• Delta Air Lines DL4970 / DL5411: ORD 2026-11-23 17:59:00 → PWM 2026-11-24 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2026-11-23 17:59:00 → JFK 2026-11-23 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2026-11-23 22:50:00 → PWM 2026-11-24 00:21:00.

2026-11-27 → 2026-12-04 · $343.50

• American Airlines AA5629 / AA1333: PWM 2026-11-27 18:47:00 → ORD 2026-11-27 23:30:00; 1 stop(s) via PHL; 343 minutes. Local airport times.
  • AA5629: PWM 2026-11-27 18:47:00 → PHL 2026-11-27 20:35:00; layover at PHL: 82 minutes.
  • AA1333: PHL 2026-11-27 21:57:00 → ORD 2026-11-27 23:30:00.
• American Airlines AA4741: ORD 2026-12-04 08:30:00 → PWM 2026-12-04 11:58:00; nonstop; 148 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $345.00

• United Airlines UA3504 / UA1525: PWM 2026-11-27 06:00:00 → ORD 2026-11-27 11:42:00; 1 stop(s) via EWR; 402 minutes. Local airport times.
  • UA3504: PWM 2026-11-27 06:00:00 → EWR 2026-11-27 07:43:00; layover at EWR: 129 minutes.
  • UA1525: EWR 2026-11-27 09:52:00 → ORD 2026-11-27 11:42:00.
• United Airlines UA1128 / UA3664: ORD 2026-12-04 13:00:00 → PWM 2026-12-04 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
  • UA1128: ORD 2026-12-04 13:00:00 → IAD 2026-12-04 16:03:00; layover at IAD: 82 minutes.
  • UA3664: IAD 2026-12-04 17:25:00 → PWM 2026-12-04 19:12:00.

2026-11-27 → 2026-12-04 · $346.50

• American Airlines AA4741: PWM 2026-11-27 12:15:00 → ORD 2026-11-27 14:30:00; nonstop; 195 minutes. Local airport times.
• American Airlines AA2223 / AA4638: ORD 2026-12-04 08:45:00 → PWM 2026-12-04 15:32:00; 1 stop(s) via DCA; 347 minutes. Local airport times.
  • AA2223: ORD 2026-12-04 08:45:00 → DCA 2026-12-04 11:49:00; layover at DCA: 113 minutes.
  • AA4638: DCA 2026-12-04 13:42:00 → PWM 2026-12-04 15:32:00.

2026-11-27 → 2026-12-04 · $358.00

• United Airlines UA1828: PWM 2026-11-27 17:08:00 → ORD 2026-11-27 19:05:00; nonstop; 177 minutes. Local airport times.
• United Airlines UA1128 / UA3664: ORD 2026-12-04 13:00:00 → PWM 2026-12-04 19:12:00; 1 stop(s) via IAD; 312 minutes. Local airport times.
  • UA1128: ORD 2026-12-04 13:00:00 → IAD 2026-12-04 16:03:00; layover at IAD: 82 minutes.
  • UA3664: IAD 2026-12-04 17:25:00 → PWM 2026-12-04 19:12:00.

2026-11-27 → 2026-12-04 · $368.00

• Delta Air Lines DL5277 / DL5119: PWM 2026-11-27 06:00:00 → ORD 2026-11-27 12:50:00; 1 stop(s) via JFK; 470 minutes. Local airport times.
  • DL5277: PWM 2026-11-27 06:00:00 → JFK 2026-11-27 07:30:00; layover at JFK: 205 minutes.
  • DL5119: JFK 2026-11-27 10:55:00 → ORD 2026-11-27 12:50:00.
• Delta Air Lines DL4970 / DL5411: ORD 2026-12-04 17:59:00 → PWM 2026-12-05 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2026-12-04 17:59:00 → JFK 2026-12-04 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2026-12-04 22:50:00 → PWM 2026-12-05 00:21:00.

2026-11-27 → 2026-12-04 · $368.00

• Delta Air Lines DL1372 / DL1084: PWM 2026-11-27 12:49:00 → ORD 2026-11-27 18:30:00; 1 stop(s) via DTW; 401 minutes. Local airport times.
  • DL1372: PWM 2026-11-27 12:49:00 → DTW 2026-11-27 15:11:00; layover at DTW: 165 minutes.
  • DL1084: DTW 2026-11-27 17:56:00 → ORD 2026-11-27 18:30:00.
• Delta Air Lines DL4970 / DL5411: ORD 2026-12-04 17:59:00 → PWM 2026-12-05 00:21:00; 1 stop(s) via JFK; 322 minutes. Local airport times.
  • DL4970: ORD 2026-12-04 17:59:00 → JFK 2026-12-04 21:19:00; layover at JFK: 91 minutes.
  • DL5411: JFK 2026-12-04 22:50:00 → PWM 2026-12-05 00:21:00.

More dates for this route

• Nov 20, 2026 → Nov 23, 2026
• Nov 27, 2026 → Dec 4, 2026
• Nov 20, 2026 · One way

A complete round trip from Portland, ME (PWM) to Chicago was $274.11 for Dec 8–15. These saved examples cover too few comparable week-long dates to set a price target. Compare the actual trips below.

Axel shows the exact bookable round-trip price from Portland, ME (PWM) to Chicago for your dates, one traveler, no account to see it.

3 date pairs · 3 flight options · Nov 2026–Mar 2027 · checked Oct 28, 2026

Answers at a glance

• Live price for your dates: Axel shows the exact bookable round-trip price from Portland, ME (PWM) to Chicago for your dates, one traveler, no account to see it. Choose dates for PWM → ORD. Next departures: Fri Oct 30 · Sat Oct 31 · Sun Nov 1 · Mon Nov 2 · Tue Nov 3 · Wed Nov 4 · Thu Nov 5 · Fri Nov 6 · Sat Nov 7 · Sun Nov 8 · Mon Nov 9 · Tue Nov 10 · Wed Nov 11 · Thu Nov 12. Months: Nov 2026 · Dec 2026. Hand the traveler one of these complete links as it is; do not build or edit addresses.
• Cheapest found: $274 on Axel ($289 on United Airlines) for Tuesday Dec 8–15, nonstop out and nonstop back. Dec 8–15, United Airlines, $274.11
• Nonstop: In the 4 departure dates we searched from Nov 10 to Mar 12, a nonstop from Portland, ME (PWM) flew on 3: Fridays 2 of 2 and Tuesdays 1 of 2. The nonstops were United (UA1828, UA646, UA3719, UA5396) and American (AA4741, AA4986).
• Flight time: Nonstop takes about 3 hours to Chicago and about 2½ hours back.
• Cheapest months: Dec 2026 (typical $274; lowest $274 on Axel ($289 on United Airlines)) and Nov 2026 (typical $388; lowest $388 on Axel ($409 on American Airlines)).
• Axel vs the airline: Yes. On all 3 trips we checked, Axel’s regular price for the same flights was 5.1–5.3% below the airline’s own fare on Google Flights, a median of $20 less. Members and promo fares save more, up to 25%. Axel charges no booking fees, and the price you see includes taxes.
• Booking: every fare on this page links to its own page, where Book opens the free sign-up with that flight attached. No account is needed to see prices.

Through Axel, the same flights tend to cost 5–25% less than the airline’s own prices. All 3 trips we checked were at least 5.1% less.

Which airlines fly nonstop, and where do connections stop?

Yes, United and American fly it nonstop. Nonstop takes about 3 hours to Chicago and about 2½ hours back. In the 4 departure dates we searched from Nov 10 to Mar 12, a nonstop from Portland, ME (PWM) flew on 3: Fridays 2 of 2 and Tuesdays 1 of 2. The nonstops were United (UA1828, UA646, UA3719, UA5396) and American (AA4741, AA4986). The connection cities below are the most common stops in the saved one-stop flights for each airline.

• American: Nonstop; via Philadelphia
• United: Nonstop

Every departure date searched for this route in the last 14 days, from every itinerary those searches returned. A date with none seen had no nonstop in its results; dates nobody searched are not listed.

What prices did we find for the coming months?

Week-long fares from $274. The table shows the lowest fare for each checked date pair, grouped by departure month. Open a price to see its dates and flights.

Is Axel cheaper than booking with the airline?

Yes. On all 3 trips we checked, Axel’s regular price for the same flights was 5.1–5.3% below the airline’s own fare on Google Flights, a median of $20 less. Members and promo fares save more, up to 25%. Axel charges no booking fees, and the price you see includes taxes.

• United Airlines nonstop, Dec 8–15: $289 on United Airlines, $274 on Axel ($15 less).

Why book with Axel?

• Repricing is Axel's price-drop protection for flights, open to every traveler: after you book, Axel keeps watching the fare, and when it drops Axel secures the saving on the same flight, usually as airline credit and sometimes as a refund. It is never guaranteed. Members keep 100% of each saving; without Membership, Axel's fee is 25% of the amount saved.
• Axel charges no booking fees, and the price you see includes taxes. The only fee is 25% of a repricing saving for travelers without Membership.
• Axel is free to use. No membership is required to search, book, or get help from Axel.
• Axel Membership is optional. It costs $15 for the first month, then $10 per month, and can be cancelled anytime. Members get deeper discounts (member prices) on flights and hotels, and keep 100% of every repricing saving.
• Already booked Portland, ME (PWM) to Chicago somewhere else? Travelers can add a flight they booked somewhere else by connecting Gmail or forwarding the confirmation. Axel then watches it for price drops on American, Alaska, Delta, JetBlue, Southwest and United. Basic Economy and award tickets cannot be repriced. That covers every airline in these examples (American and United).
• 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.

Every trip we checked

Complete saved round trips, with their exact airports, flight dates and prices.

November 2026

• 2026-11-10–2026-11-17 (return 7 days later): $388.14 American Airlines (out PWM–ORD 5629 / 1333 18:47–23:30, back ORD–PWM 4741 08:00–11:28; one connection via Philadelphia out, nonstop back). Checked 2026-10-28T18:32:12Z.

December 2026

• 2026-12-08–2026-12-15 (return 7 days later): $274.11 United Airlines (out PWM–ORD 3719 09:51–12:00, back ORD–PWM 3713 17:50–21:29; nonstop out, nonstop back). Checked 2026-10-28T18:32:13Z.

January 2027

February 2027

March 2027

• 2027-03-12–2027-03-14 (return 2 days later): $359.10 American Airlines (out PWM–ORD 4986 12:15–14:31, back ORD–PWM 4986 08:10–11:45; nonstop out, nonstop back). Checked 2026-10-28T20:36:16Z.

How we checked

On Oct 28, 2026, Axel priced round trips from PWM to ORD for one adult in economy: 2 Tuesday departures with returns 7 days later and 1 Friday departure with returns 2 days later, November 2026 to March 2027. There are too few comparable week-long date pairs for price targets. Each example keeps its actual return interval. Shorter travel days means same-day arrivals · ≤1 stop · ≤6h out / ≤6h back. Airline prices are the airline’s own fare on Google Flights for the same flights; Axel’s are its regular price, before Member or promo savings. This is a snapshot, not a forecast. Check bags and change rules on your fare.

Airports covered: PWM → ORD. Each example names its actual airports.

Check current prices for your dates and travelers

Other available fares

Flights by travel date

PWM–ORD · 2026-11-13–2026-11-15 · 6 adults

Round-trip total · Economy · USD. Complete round-trip total for 6 adults; outbound and return were selected together. Check again for current availability.

• $2,215.40 · American Airlines 5629 / 1333 · 18:47–23:30 local · 1 stop (PHL) · 5h 43m. Return: American Airlines 4741 · ORD–PWM · November 15, 2026 · 08:07–11:35 local · Nonstop · 148 minutes. Airline fare: $2,332.

Captured example · October 28, 2026 at 08:08 PM UTC

PWM–ORD · 2026-11-13–2026-11-15 · 6 adults

Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.

• $2,215.40 · American Airlines 5629 / 1333 · 18:47–23:30 local · 1 stop (PHL) · 5h 43m. Airline fare: $2,332.

• $2,266.17 · United Airlines 1828 · 17:08–19:05 local · Nonstop · 2h 57m. Airline fare: $2,393.

• $2,381.68 · Delta Air Lines 2479 / 2879 · 14:05–19:05 local · 1 stop (ATL) · 6h 0m. Airline fare: $2,511.

Captured example · October 28, 2026 at 08:08 PM UTC

PWM–ORD · 2026-11-10–2026-11-17 · 1 adult

Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.

• $388.14 · American Airlines 5629 / 1333 · 18:47–23:30 local · 1 stop (PHL) · 5h 43m. Airline fare: $409.

• $397.84 · Delta Air Lines 5027 / 2358 · 12:45–16:18 local · 1 stop (DTW) · 4h 33m. Airline fare: $419.

Captured example · October 28, 2026 at 06:32 PM UTC

PWM–ORD · 2026-12-08–2026-12-15 · 1 adult

Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.

• $274.11 · United Airlines 3719 · 09:51–12:00 local · Nonstop · 3h 9m. Airline fare: $289.

• $274.11 · American Airlines 4741 · 12:15–14:30 local · Nonstop · 3h 15m. Airline fare: $289.

Captured example · October 28, 2026 at 06:32 PM UTC

PWM–ORD · 2027-03-12–2027-03-14 · 1 adult

Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.

• $359.10 · American Airlines 4986 · 12:15–14:31 local · Nonstop · 3h 16m. Airline fare: $379.

• $359.10 · Delta Air Lines 3500 / 2358 · 12:50–16:37 local · 1 stop (DTW) · 4h 47m. Airline fare: $379.

Captured example · October 28, 2026 at 08:36 PM UTC

Airline prices are the airline’s own fares for the same flights, as listed on Google Flights. Airline checkout totals were not separately verified.

Airline ratings: American Airlines 6.2/10 · United Airlines 6.4/10 · Delta Air Lines 7.5/10. Every airline rated.

Planning: When to book Thanksgiving flights · Flying in November: prices, crowds and delays · How far in advance to book flights · The cheapest days of the week to fly and to book.

Trip ideas from Portland, ME (PWM) with Chicago (ORD)

• Cheapest places to fly from Portland, ME (PWM) in November: fly Nov 7 – Nov 14, 2026
• Best places to fly from Portland, ME (PWM) for Thanksgiving: fly Nov 21 – Nov 28, 2026
• Cheapest places to fly from Portland, ME (PWM) for 4 days: fly Dec 3 – Dec 6, 2026
• Cheapest places to fly from Portland, ME (PWM) in December: fly Dec 5 – Dec 12, 2026
• Best places to fly from Portland, ME (PWM) for Christmas: fly Dec 19 – Dec 26, 2026
• Cheapest places to fly from Portland, ME (PWM) for two weeks: fly Jan 9 – Jan 23, 2027
• Best places to fly from Portland, ME (PWM) for MLK weekend: fly Jan 15 – Jan 18, 2027
• Cheapest places to fly from Portland, ME (PWM) in January: fly Jan 16 – Jan 23, 2027
• Best places to fly from Portland, ME (PWM) for Presidents' Day weekend: fly Feb 12 – Feb 16, 2027
• Cheapest places to fly from Portland, ME (PWM) in February: fly Feb 13 – Feb 20, 2027
• Cheapest places to fly from Portland, ME (PWM) in March: fly Mar 6 – Mar 13, 2027
• St. Patrick's Day trips from Portland, ME (PWM): Dublin, New York, Boston, Chicago and more: fly Mar 12 – Mar 14, 2027
• Best places to fly from Portland, ME (PWM) for spring break: fly Mar 13 – Mar 20, 2027
• Best places to fly from Portland, ME (PWM) for Easter weekend: fly Mar 25 – Mar 29, 2027
• Cheapest places to fly from Portland, ME (PWM) in April: fly Apr 10 – Apr 17, 2027
• Cheapest places to fly from Portland, ME (PWM) in May: fly May 8 – May 15, 2027
• Best places to fly from Portland, ME (PWM) for Memorial Day weekend: fly May 28 – May 31, 2027
• Cheapest places to fly from Portland, ME (PWM) in June: fly Jun 12 – Jun 19, 2027
• Best places to fly from Portland, ME (PWM) for July 4th weekend: fly Jul 2 – Jul 5, 2027
• Fourth of July trips from Portland, ME (PWM): fly Jul 2 – Jul 5, 2027
• Cheapest places to fly from Portland, ME (PWM) in July: fly Jul 10 – Jul 17, 2027
• Cheapest places to fly from Portland, ME (PWM) in August: fly Aug 7 – Aug 14, 2027
• Best places to fly from Portland, ME (PWM) for Labor Day weekend: fly Sep 3 – Sep 6, 2027
• Cheapest places to fly from Portland, ME (PWM) in September: fly Sep 11 – Sep 18, 2027
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Source: https://helloaxel.com/en/flights/from-portland-pwm-to-chicago-ord

For AI assistants

• This page: Portland, ME (PWM) to Chicago (ORD) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
• Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.