Cheap Flights from Chicago, IL to Portland, ME from $282
On Cheapflightsplus.com you will find 6 direct and 487 connecting flights from Chicago to Portland. You can compare airfare deals from 9 airlines and multiple travel sites from $282, book and save on cheap plane tickets and last minute offers. Also check out CHI-PWM flight schedule to find best flight time, convenient departure and arrival airports.
Flight Information
Below we will explain in detail what the flights cost on the destination from Chicago to Portland depends on and how to choose the most interesting flight option for you.
Distance between Chicago and Portland is 1425 miles. Time difference between the cities is 1h. Airplanes depart 05:00 to 21:36 from 7 Chicago airports and arrive 05:00 to 21:36 to 1 Portland airport. Average flight time is 2h 29m.
- The fastest flight 2h 10m
- Average flight time 2h 29m
- The earliest flight 05:00
- The latest flight 21:36
- Distance 886 ml
Best Flights from Chicago to Portland Today
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $583 | 11:05 Chicago O'Hare International | 14:33 Portland Portland Intl Jetport | 2h 28m | United Airlines | UA763 |
| from $675 | 19:10 Chicago O'Hare International | 22:45 Portland Portland Intl Jetport | 2h 35m | American Airlines | AA4403 |
| from $705 | 13:40 Chicago Midway | 16:50 Portland Portland Intl Jetport | 2h 10m | Southwest Airlines | WN447 |
| from $282 | 06:40 Chicago O'Hare International | 23:04 Portland Portland Intl Jetport | 15h 24m layover 11h 27m - New York | Frontier Airlines | F91044 B6308 |
| from $294 | 13:35 Chicago O'Hare International | 23:04 Portland Portland Intl Jetport | 8h 29m layover 4h 31m - New York | JetBlue | B6906 B6308 |
| from $428 | 19:43 Chicago O'Hare International | 09:06+2 дня Portland Portland Intl Jetport | 36h 23m layover 7h 12m - Miami 21h 56m - Orlando | Spirit Airlines | NK1226 NK2212 MX738 |
| from $444 | 06:40 Chicago O'Hare International | 23:51 Portland Portland Intl Jetport | 16h 11m layover 9h 45m - New York 1h 1m - Washington D.C. | Frontier Airlines | F91044 AA4675 AA2978 |
The cheapest months to travel to Portland are july (from 142 $), august (from 145 $), october (from 148 $).
The most expensive months are september (from 148 $), october (from 148 $), august (from 145 $).
What is the lowest airfare Chicago to Portland?
The cheapest plane ticket found by our users is $282. This airfare is for economy class on one-way F91044 flight by Frontier Airlines for October 15, 2025 which leaves O'Hare International in Chicago at 06:40 am and arrives at Portland Portland Intl Jetport at 23:04.
Flight Schedule Chicago (Illinois) to Portland (Maine)
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Popular Airlines on the Route
The flight Chicago — Portland is served by 9 regular airlines and 6 low-cost airlines. Most of the flights on this route are operated by United Airlines - 165 departures per week at the price of from $ 374 . And the most expensive tickets are offered by American Airlines airline - from $ 2526.
Direct flights
There are 6 nonstop flights on the route. The fastest direct flight is WN447 by Southwest Airlines takes 2h 10m and the cheapest is F91044 by Frontier Airlines for $583.
- AA - American Airlinesfrom $675Find
- WN - Southwest Airlinesfrom $705Find
- UA - United Airlinesfrom $583Find
Connecting Flights
There are 487 flights with layovers on the route. The fastest connecting flight is DL2039 by Delta Air Lines Inc. takes 3h 50m and the cheapest is F91044 by Frontier Airlines for $282.
- UA - United Airlinesfrom $374Find
- AA - American Airlinesfrom $365Find
- F9 - Frontier Airlinesfrom $282Find
- B6 - JetBluefrom $294Find
- PD - Porter Airlinesfrom $1272Find
- SY - Sun Country Airlinesfrom $761Find
- WN - Southwest Airlinesfrom $552Find
- DL - Delta Air Lines Inc.from $353Find
- NK - Spirit Airlinesfrom $301Find
Airports
You can fly from Chicago to Portland from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).
Chicago airports
- O'Hare International-ORDfrom $282Find
- Midway-MDWfrom $552Find
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Portland airports
- Portland Intl Jetport-PWMFind
Airplanes
There are flights to Portland from Chicago by 9 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.
- Airbus A321from $282Find
- Embraer 175 (short wing)from $353Find
- Boeing 737 MAX 8from $365Find
- Boeing 757-200from $374Find
- Boeing 737-800from $376Find
- Boeing 737-900from $376Find
- Airbus A319from $495Find
- Canadair Regional Jet 900from $525Find
- Boeing 717from $525Find
- Embraer 170from $534Find
Top Domestic Destinations from Chicago
You may also consider searching for discounted plane tickets to some other popular places from Chicago within United States.
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Top International Destinations from Chicago
Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.
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How to book a plane ticket yourself?
- Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
- Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
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- That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
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