Cheap Flights from Portland to Chicago Starting at $84

Helping travelers to find the best flight offers

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

$84

Spirit Airlines
Spirit Airlines
1 transfer
15h 15m
05/30/2025

The cheapest one-way flight from Portland to Chicago departs on 05/30/2025, is operated by Spirit Airlines and costs $84

Cheapest round trip flight

$163

Spirit Airlines
Spirit Airlines
1 transfer
16h 40m
05/31/2025

The cheapest roundtrip flight from Portland to Chicago departs on 05/31/2025, is operated by Spirit Airlines and costs $163

The fastest flight

4 hours

Fastest flight from Portland to Chicago takes 4 hours

Direct flights

Several times a week

There are direct flights on this route 3 days a week: Su, Mo, and Fr

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.

See also:

Cheap flights to United States

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Direct flights airfares to Chicago

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Cheapest air tickets to Portland

Airfare from Portland to Chicago by month

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

September 2025
Lowest price
on average:
$123
  • Avg Price

Airlines operating on route

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.

Spirit Airlines
Spirit Airlines

Starting at $84

American Airlines
American Airlines

Starting at $89

Frontier Airlines
Frontier Airlines

Starting at $116

Alaska Airlines
Alaska Airlines

Starting at $123

Direct Flights 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.

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There appear to be no direct flights from Portland to Chicago at this time.... Well, or something went wrong on our side and we couldn't find anything

Schedule of direct flights from Portland to Chicago

A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Portland to Chicago:

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Unable to find information about the schedule of direct flights from

Portland airports overview

Chicago airports overview

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Unfortunately, we were unable to find any airports in Chicago. We'll try to look better another time

Frequently asked questions (FAQ)

Answers to questions about the route that travelers are most interested in.

How much is the cheapest flight ticket from Portland to Chicago?

The cheapest flight ticket from Portland to Chicago according to data for the last 48 hours costs $84

When is the best time to buy air tickets on the route Portland — Chicago?

Often the best time to buy tickets from Portland to Chicago is 2 months before departure.

When is the cheapest time of year to fly from Portland to Chicago?

Based on statistics over the past years, the lowest prices for flights from Portland to Chicago can be found flying in these months: September.

How long does it take to fly from Portland to Chicago?

The fastest flights from Portland to Chicago start from 4 hours in the air.

Which airline can fly direct from Portland to Chicago?

The following airlines operate direct flights on the route Portland — Chicago:

Special offers and sales on air tickets 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.

Alternative routes

Bellingham ➜ Chicago•Boise ➜ Chicago•Eugene ➜ Chicago•Spokane ➜ Chicago•Everett ➜ Chicago•Seattle ➜ Chicago•Yakima ➜ Chicago•Kelowna ➜ Chicago•Abbotsford ➜ Chicago•Portland ➜ Appleton•Portland ➜ Kalamazoo•Portland ➜ Champaign•Portland ➜ Fort Wayne•Portland ➜ Indianapolis•Portland ➜ Lansing•Portland ➜ Milwaukee•Portland ➜ Muskegon•Portland ➜ South Bend