Cheap Flights from Portland, ME to Chicago, IL from $90

Return flight: Chicago – Portland
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On Cheapflightsplus.com you will find 1 direct and 6 connecting flights from Portland to Chicago. You can compare airfare deals from 2 airlines and multiple travel sites from $90, 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.

Find One-Way and Round-Trip Portland to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $90 (one-way), $154 (round-trip).
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Best Flights from Portland to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Portland to Chicago with the lowest price of $90. The fastest direct flight takes 3h 6m and the fastest connecting – 5h 22m.
Price Departure Arrival Flight Duration Airline Flight
from $243
Find flight
16:20
Portland
Portland Intl Jetport
 18:26
Chicago
O'Hare International
 3h 6m United Airlines
UA3651
from $90
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12:23
Portland
Portland Intl Jetport
 18:48
Chicago
Midway
 7h 25m
layover
1h 9m - Tampa
 Frontier Airlines
F92245
F91185
from $254
Find flight
15:55
Portland
Portland Intl Jetport
 20:17
Chicago
O'Hare International
 5h 22m
layover
0h 48m - Newark
 United Airlines
UA3620
UA254
from $254
Find flight
12:15
Portland
Portland Intl Jetport
 17:02
Chicago
O'Hare International
 5h 47m
layover
1h 17m - Newark
 United Airlines
UA3578
UA1144
from $254
Find flight
06:01
Portland
Portland Intl Jetport
 13:11
Chicago
O'Hare International
 8h 10m
layover
3h 48m - Newark
 United Airlines
UA2455
UA1875
from $289
Find flight
12:15
Portland
Portland Intl Jetport
 18:55
Chicago
O'Hare International
 7h 40m
layover
3h 9m - Newark
 United Airlines
UA3578
UA661
from $391
Find flight
13:30
Portland
Portland Intl Jetport
 18:52
Chicago
O'Hare International
 6h 22m
layover
1h 54m - Washington D.C.
 United Airlines
UA4254
UA2497
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on March 02, 2025
Full flight schedule will help you in detecting at what time planes fly from Portland to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
16:20 — 18:26
16:20 — 18:26 UA3651 United Airlines
Portland — Chicago
3h 6m
Find flight
from$243
06:01 — 13:11
06:00 — 07:34 UA2455 United Airlines
Portland — Newark
3h 48m stop
11:44 — 13:15 UA1875 United Airlines
Newark — Chicago
8h 10m
including layover
Find flight
from$254
12:15 — 17:02
12:15 — 14:01 UA3578 United Airlines
Portland — Newark
1h 17m stop
15:18 — 17:02 UA1144 United Airlines
Newark — Chicago
5h 47m
including layover
Find flight
from$254
12:15 — 18:55
12:15 — 14:01 UA3578 United Airlines
Portland — Newark
3h 9m stop
17:10 — 18:55 UA661 United Airlines
Newark — Chicago
7h 40m
including layover
Find flight
from$289
12:23 — 18:48
12:23 — 15:56 F92245 Frontier Airlines
Portland — Tampa
1h 9m stop
17:05 — 18:48 F91185 Frontier Airlines
Tampa — Chicago
7h 25m
including layover
Find flight
from$90
13:30 — 18:52
13:30 — 15:31 UA4254 United Airlines
Portland — Washington D.C.
1h 54m stop
17:25 — 18:52 UA2497 United Airlines
Washington D.C. — Chicago
6h 22m
including layover
Find flight
from$391
15:55 — 20:17
15:55 — 17:42 UA3620 United Airlines
Portland — Newark
48m stop
18:30 — 20:17 UA254 United Airlines
Newark — Chicago
5h 22m
including layover
Find flight
from$254
*Departure and arrival times - local. Updated on March 2, 2025

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 06:01 to 16:20 from 1 Portland airport and arrive 06:01 to 16:20 to 7 Chicago airports. Average flight time is 3h 6m.

  • The fastest flight 3h 6m
  • Average flight time 3h 6m
  • The earliest flight 06:01
  • The latest flight 16:20
  • Distance 886 ml

The cheapest months to travel to Chicago are february (from 90 $), december (from 275 $).

What is the lowest airfare Portland to Chicago?

The cheapest plane ticket found by our users is $90. This airfare is for economy class on one-way F92245 flight by Frontier Airlines for February 21, 2025 which leaves Portland Intl Jetport in Portland at 12:23 am and arrives at Chicago Midway at 18:48.

Economy class
$90
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Business class
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First class
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Popular Airlines on the Route

The flight Portland — Chicago is served by 2 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by Frontier Airlines - 1 departures per week at the price of from $ 90 . And the most expensive tickets are offered by United Airlines airline - from $ 391.

Direct flights

There are 1 nonstop flights on the route. The fastest direct flight is UA3651 by United Airlines takes 3h 6m and the cheapest is F92245 by Frontier Airlines for $243.

  • UA - United Airlines
    from $243
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Connecting Flights

There are 6 flights with layovers on the route. The fastest connecting flight is UA3620 by United Airlines takes 5h 22m and the cheapest is F92245 by Frontier Airlines for $90.

  • F9 - Frontier Airlines
    from $90
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  • UA - United Airlines
    from $254
    Find
See more connecting flights

Airports

You can fly from Portland to Chicago from 1 airports (Portland Intl Jetport).

Portland airports

  • Portland Intl Jetport-PWM
    from $90
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Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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Airplanes

There are flights to Chicago from Portland by 2 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.

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.

How to book a plane ticket yourself?

How to book an air 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.

    To find a plane ticket, please select dates.

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