Airlines operating on route
Starting at $137
Helping travelers to find the best flight offers
Starting at $137
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to Portland:
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.
Chicago — Portland
10/08/2025
Departure date
Direct flight
AA3272
Starting at $93
Chicago — Portland
10/11/2025
Departure date
Direct flight
AS413
Starting at $68
Chicago — Portland
10/12/2025
Departure date
Direct flight
WN3337
Starting at $321
Chicago — Portland
10/15/2025
Departure date
Direct flight
UA2494
Starting at $101
Chicago — Portland
06/02/2025
Departure date
Direct flight
AS413
Starting at $357
Chicago — Portland
06/25/2025
Departure date
Direct flight
WN3874
Starting at $161
Chicago — Portland
07/08/2025
Departure date
Direct flight
WN1656
Starting at $182
Chicago — Portland
07/08/2025
Departure date
Direct flight
AA3320
Starting at $111
Chicago — Portland
08/02/2025
Departure date
Direct flight
AA2977
Starting at $127
Chicago — Portland
08/02/2025
Departure date
Direct flight
AS413
Starting at $200
Unable to find information about the schedule of direct flights from
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.
The cheapest flight ticket from Chicago to Portland according to data for the last 48 hours costs $68
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 4 hours 15 minutes in the air.
The following airlines operate direct flights on the route Chicago — Portland: American Airlines, Alaska Airlines, Southwest Airlines
The cheapest one-way flight from Chicago to Portland departs on 10/11/2025, is operated by Alaska Airlines and costs $68
The cheapest roundtrip flight from Chicago to Portland departs on 10/07/2025, is operated by Alaska Airlines and costs $143
Fastest flight from Chicago to Portland takes 4h 15m
There are direct flights on this route 3 days a week: Su, Mo, and Sa
The distance between Chicago and Portland is 2816km (1746 miles). There are 77 direct flights from Chicago to Portland. The time difference between Chicago and Portland is 2h . Flights from Chicago begin at 7:00 AM. The latest flight from Chicago departs at 8:25 PM.
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.
We couldn't find any special offers for flights from Chicago to Portland
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.
