Airlines operating on route
Starting at $103
Helping travelers to find the best flight offers
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 Chicago to Portland. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
Starting at $103
A direct flight is the most convenient and comfortable way to fly from Chicago to Portland, 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 Chicago to Portland:
Unable to find information about the schedule of direct flights from
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.
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 Chicago to Portland
Below you will find a list of airlines operating flights on the Chicago — Portland route and the starting prices for flights of each specific airline on it.
The cheapest one-way flight from Chicago to Portland departs on 07/27/2025, is operated by American Airlines and costs $130
The cheapest roundtrip flight from Chicago to Portland departs on 07/08/2025, is operated by American Airlines and costs $190
Fastest flight from Chicago to Portland takes 2h 34m
There are direct flights on this route 1 day a week: Su
The distance between Chicago and Portland is 1424km (883 miles). There are 33 direct flights from Chicago to Portland. The time difference between Chicago and Portland is 1h . Flights from Chicago begin at 8:00 AM. The latest flight from Chicago departs at 7:09 PM.
Chicago — Portland
07/27/2025
Departure date
Direct flight
AA4403
Starting at $121
The cheapest flight ticket from Chicago to Portland according to data for the last 48 hours costs $130
Often the best time to buy tickets from Chicago to Portland is 2 months before departure.
The fastest flights from Chicago to Portland start from 2 hours 34 minutes in the air.
The following airlines operate direct flights on the route Chicago — Portland: American Airlines
We couldn't find any special offers for flights from Chicago to Portland
