starting at $82
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Compare airlines, prices, and flight durations for your trip
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.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to Portland:
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Answers to questions about the route that travelers are most interested in.
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.
More than 6 airlines operate flights from Chicago to Portland, including Southwest Airlines, Grumeti Air, Alaska Airlines, Hawaiian Airlines, American Airlines, and Frontier Airlines. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $82, and our service lets you instantly compare all options. The variety of offers simplifies planning: you can choose budget fares or more comfortable options with baggage included or extra services. We help you find the best deals so your trip is cost-efficient.
starting at $82
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Chicago — Portland
03/01/2026
Departure
Direct flight
WN2905
starting at $82
Chicago — Portland
04/04/2026
Departure
Direct flight
WN3975
starting at $82
Chicago — Portland
03/04/2026
Departure
Direct flight
0G6293
starting at $95
Chicago — Portland
04/02/2026
Departure
Direct flight
WN3976
starting at $96
Chicago — Portland
04/01/2026
Departure
Direct flight
WN3976
starting at $96
Chicago — Portland
04/02/2026
Departure
Direct flight
AS325
starting at $105
Chicago — Portland
02/20/2026
Departure
Direct flight
HA6293
starting at $111
Chicago — Portland
02/02/2026
Departure
Direct flight
0G6293
starting at $113
Chicago — Portland
02/10/2026
Departure
Direct flight
AS325
starting at $114
Chicago — Portland
03/02/2026
Departure
Direct flight
AA1937
starting at $115
Unable to find information about the schedule of direct flights from
A non-stop 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.
The cheapest one-way flight from Chicago to Portland departs on 03/01/2026, is operated by Southwest Airlines and costs $82
The cheapest roundtrip flight from Chicago to Portland departs on 03/23/2026, is operated by Southwest Airlines and costs $206
Fastest flight from Chicago to Portland takes 4h 20m
There are direct flights on this route 7 days a week: Su, Mo, Tu, We, Th, Fr, and Sa
The distance between Chicago and Portland is 2816km (1746 miles). There are 6 direct flights from Chicago to Portland. The time difference between Chicago and Portland is 2h. Flights from Chicago begin at 9:10 AM. The latest flight from Chicago departs at 7:50 PM
We couldn't find any special offers for flights from Chicago to Portland
The cheapest flight ticket from Chicago to Portland according to data for the last 48 hours costs $82
Often the best time to buy tickets from Chicago to Portland is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Chicago to Portland can be found flying in these months: February, March, January.
The fastest flights from Chicago to Portland start from 4 hours 20 minutes in the air.
The following airlines operate direct flights on the route Chicago — Portland: Southwest Airlines, Grumeti Air, Alaska Airlines
The cost of a one-way flight from Chicago to Portland ranges from $111 (February 2026) to $294 (January 2026). On average, the ticket price is about $173–$409.