Airlines operating on route
Starting at $86
Starting at $90
Starting at $118
Starting at $125
Helping travelers to find the best flight offers
Starting at $86
Starting at $90
Starting at $118
Starting at $125
A direct flight is the most convenient and comfortable way to fly from Portland to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Portland to Chicago:
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
Below you will find a list of airlines operating flights on the Portland — Chicago route and the starting prices for flights of each specific airline on it.
Unable to find information about the schedule of direct flights from
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Portland to Chicago
Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Portland to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
Portland — Chicago
08/13/2025
Departure date
Direct flight
UA1490
Starting at $129
Portland — Chicago
08/13/2025
Departure date
Direct flight
UA1045
Starting at $188
Portland — Chicago
06/27/2025
Departure date
Direct flight
AA2846
Starting at $477
Portland — Chicago
06/28/2025
Departure date
Direct flight
UA1693
Starting at $418
Portland — Chicago
06/30/2025
Departure date
Direct flight
UA1490
Starting at $346
Portland — Chicago
07/03/2025
Departure date
Direct flight
AA2846
Starting at $318
Portland — Chicago
07/08/2025
Departure date
Direct flight
WN4170
Starting at $246
Portland — Chicago
08/09/2025
Departure date
Direct flight
UA1490
Starting at $135
Portland — Chicago
08/09/2025
Departure date
Direct flight
WN2678
Starting at $317
The cheapest flight ticket from Portland to Chicago according to data for the last 48 hours costs $95
Often the best time to buy tickets from Portland to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Portland to Chicago can be found flying in these months: August.
The fastest flights from Portland to Chicago start from 4 hours 4 minutes in the air.
The following airlines operate direct flights on the route Portland — Chicago: United Airlines, American Airlines, Southwest Airlines
We couldn't find any special offers for flights from Portland to Chicago
The cheapest one-way flight from Portland to Chicago departs on 07/04/2025, is operated by Spirit Airlines and costs $95
The cheapest roundtrip flight from Portland to Chicago departs on 08/18/2025, is operated by Spirit Airlines and costs $231
Fastest flight from Portland to Chicago takes 4h 4m
There are direct flights on this route 1 day a week: We
The distance between Portland and Chicago is 2816km (1746 miles). There are 23 direct flights from Portland to Chicago. The time difference between Portland and Chicago is 2h . Flights from Portland begin at 5:50 AM. The latest flight from Portland departs at 2:30 PM.
