Schedule of direct flights from Portland to Chicago
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Portland to Chicago:
Portland airports overview
Chicago airports overview
Frequently asked questions (FAQ)
Answers to questions about the route that travelers are most interested in.
Special offers and sales on air tickets 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.
Alternative routes
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Cheapest one way flight
$58
Frontier Airlines
1 transfer
9h 13m
04/14/2025
The cheapest one-way flight from Portland to Chicago departs on 04/14/2025, is operated by Frontier Airlines and costs $58
Cheapest round trip flight
$126
United Airlines
Direct flight
8h 33m
07/24/2025
The cheapest roundtrip flight from Portland to Chicago departs on 07/24/2025, is operated by United Airlines and costs $126
The fastest flight
7h 39m
Fastest flight from Portland to Chicago takes 7h 39m
Direct flights
No direct flights
There are no direct flights on this route.
Earliest flight
7:00 AM
Latest flight
11:59 PM
Direct flights count
32
Distance
2816km
Timezone difference
2h
The distance between Portland and Chicago is 2816km (1746 miles).There are 32 direct flights from Portland to Chicago.The time difference between Portland and Chicago is 2h .Flights from Portland begin at 7:00 AM.The latest flight from Portland departs at 11:59 PM.
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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.
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
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.
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.
