Cheapest flights 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.
Cheapest one way flight
$88
Alaska Airlines
Direct flight
4h 7m
05/07/2025
The cheapest one-way flight from Portland to Chicago departs on 05/07/2025, is operated by Alaska Airlines and costs $88
Cheapest round trip flight
$250
United Airlines
Direct flight
8h 36m
05/22/2025
The cheapest roundtrip flight from Portland to Chicago departs on 05/22/2025, is operated by United Airlines and costs $250
The fastest flight
3h 56m
Fastest flight from Portland to Chicago takes 3h 56m
Direct flights
Every day
There are direct flights on this route 7 days a week: Su, Mo, Tu, We, Th, Fr, and Sa
Earliest flight
6:15 AM
Latest flight
11:59 PM
Direct flights count
69
Distance
2816km
Timezone difference
2h
The distance between Portland and Chicago is 2816km (1746 miles). There are 69 direct flights from Portland to Chicago. The time difference between Portland and Chicago is 2h . Flights from Portland begin at 6:15 AM. The latest flight from Portland departs at 11:59 PM.
