Cheap Flights from Portland, ME to Chicago, IL from $99
On Cheapflightsplus.com you will find 10 direct and 388 connecting flights from Portland to Chicago. You can compare airfare deals from 4 airlines and multiple travel sites from $99, book and save on cheap plane tickets and last minute offers. Also check out PWM-CHI 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 Portland to Chicago depends on and how to choose the most interesting flight option for you.
Distance between Portland and Chicago is 1425 miles. Time difference between the cities is 1h. Airplanes depart 05:35 to 20:52 from 1 Portland airport and arrive 05:35 to 20:52 to 7 Chicago airports. Average flight time is 2h 59m.
- The fastest flight 2h 51m
- Average flight time 2h 59m
- The earliest flight 05:35
- The latest flight 20:52
- Distance 886 ml
Best Flights from Portland to Chicago Today
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $127 | 06:00 Portland Portland Intl Jetport | 07:53 Chicago O'Hare International | 2h 53m | United Airlines | UA1834 |
| from $99 | 16:57 Portland Portland Intl Jetport | 00:04+1 день Chicago O'Hare International | 8h 7m layover 1h 39m - Orlando | Frontier Airlines | F91929 F92791 |
| from $131 | 19:26 Portland Portland Intl Jetport | 23:15 Chicago O'Hare International | 4h 49m layover 0h 55m - Washington D.C. | United Airlines | UA3582 UA1738 |
The cheapest months to travel to Chicago are may (from 99 $), july (from 112 $), september (from 112 $).
The most expensive months are june (from 144 $), october (from 141 $), august (from 129 $).
What is the lowest airfare Portland to Chicago?
The cheapest plane ticket found by our users is $99. This airfare is for economy class on one-way F91929 flight by Frontier Airlines for May 24, 2025 which leaves Portland Intl Jetport in Portland at 16:57 am and arrives at Chicago O'Hare International at 00:04.
Flight Schedule Portland (Maine) to Chicago (Illinois)
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Popular Airlines on the Route
The flight Portland — Chicago is served by 4 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by Frontier Airlines - 5 departures per week at the price of from $ 99 . And the most expensive tickets are offered by United Airlines airline - from $ 812.
Direct flights
There are 10 nonstop flights on the route. The fastest direct flight is UA1857 by United Airlines takes 2h 51m and the cheapest is F91929 by Frontier Airlines for $127.
- UA - United Airlinesfrom $127Find
Connecting Flights
There are 388 flights with layovers on the route. The fastest connecting flight is UA3582 by United Airlines takes 4h 49m and the cheapest is F91929 by Frontier Airlines for $99.
- F9 - Frontier Airlinesfrom $99Find
- SY - Sun Country Airlinesfrom $158Find
- MX - Mexicanafrom $235Find
- UA - United Airlinesfrom $131Find
Airports
You can fly from Portland to Chicago from 1 airports (Portland Intl Jetport).
Portland airports
- Portland Intl Jetport-PWMfrom $99Find
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Airplanes
There are flights to Chicago from Portland by 4 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.
Top Domestic Destinations from Portland
You may also consider searching for discounted plane tickets to some other popular places from Portland within United States.
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Top International Destinations from Portland
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.
- Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
- Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
- 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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