Unable to find information about the schedule of direct flights from
Helping travelers to find the best flight offers
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
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.
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.
Starting at $242
The cheapest one-way flight from Portland to Chicago departs on 06/12/2025, is operated by Southwest Airlines and costs $242
The cheapest roundtrip flight from Portland to Chicago departs on 09/15/2025, is operated by JetBlue Airways and costs $193
Fastest flight from Portland to Chicago takes 2h 35m
There are direct flights on this route 1 day a week: Th
The distance between Portland and Chicago is 1424km (883 miles). There are 8 direct flights from Portland to Chicago. The time difference between Portland and Chicago is 1h . Flights from Portland begin at 6:55 PM. The latest flight from Portland departs at 7:55 PM.
Portland — Chicago
06/12/2025
Departure date
Direct flight
UA1564
Starting at $274
The cheapest flight ticket from Portland to Chicago according to data for the last 48 hours costs $242
Often the best time to buy tickets from Portland to Chicago is 2 months before departure.
The fastest flights from Portland to Chicago start from 2 hours 35 minutes in the air.
The following airlines operate direct flights on the route Portland — Chicago: United Airlines
We couldn't find any special offers for flights from Portland to Chicago
