Cheap Flights from Chicago to Portland

Helping travelers to find the best flight offers

Cheapest flights from Chicago to Portland

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.

Cheapest one way flight

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There is no information about the cheapest one-way flight from Chicago to Portland

Cheapest round trip flight

$174

Spirit Airlines
Spirit Airlines
1 transfer
1d 0h 48m
06/11/2025

The cheapest roundtrip flight from Chicago to Portland departs on 06/11/2025, is operated by Spirit Airlines and costs $174

The fastest flight

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There is no information about the fastest flight from Chicago to Portland

Direct flights

No direct flights

There are no direct flights on this route.

Earliest flight

4:15 PM

Latest flight

10:15 PM

Direct flights count

8

Distance

2816km

Timezone difference

2h

The distance between Chicago and Portland is 2816km (1746 miles). There are 8 direct flights from Chicago to Portland. The time difference between Chicago and Portland is 2h . Flights from Chicago begin at 4:15 PM. The latest flight from Chicago departs at 10:15 PM.

See also:

Cheap flights to United States

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Direct flights airfares to Portland

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Cheapest air tickets to Chicago

Airfare from Chicago to Portland 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 Chicago to Portland

April 2025
Lowest price
on average:
$110
  • Avg Price

Airlines operating on route

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.

Alaska Airlines
Alaska Airlines

Starting at $92

Spirit Airlines
Spirit Airlines

Starting at $107

Frontier Airlines
Frontier Airlines

Starting at $166

Direct 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.

Portland city image

Chicago — Portland

CHI — PDX

04/18/2025

Departure date

Direct flight

Alaska Airlines

AS325

Starting at $299

Portland city image

Chicago — Portland

CHI — PDX

04/26/2025

Departure date

Direct flight

American Airlines

AA2545

Starting at $259

Portland city image

Chicago — Portland

CHI — PDX

05/18/2025

Departure date

Direct flight

United Airlines

UA1634

Starting at $402

Schedule of direct flights from Chicago to Portland

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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Unable to find information about the schedule of direct flights from

Chicago airports overview

ORD
O'Hare International Airport
United Airlines
Alaska Airlines
American Airlines
Airlines flying to this airport
$198
Starting at
$220
on average

Portland airports overview

PDX
Portland International Airport
United Airlines
Alaska Airlines
American Airlines
Airlines flying to this airport
$198
Starting at
$220
on average

Frequently asked questions (FAQ)

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

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

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

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

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

Which airline can fly direct from Chicago to Portland?

The following airlines operate direct flights on the route Chicago — Portland: Alaska Airlines, American Airlines, United Airlines

Special offers and sales on air tickets 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.

Alternative routes

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