Cheap Flights from Portland to Chicago

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

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

Cheapest round trip flight

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There is no information about the cheapest roundtrip flight from Portland to Chicago

The fastest flight

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

Direct flights

No direct flights

There are no direct flights on this route.

Earliest flight

6:00 AM

Latest flight

4:20 PM

Direct flights count

23

Distance

1424km

Timezone difference

1h

The distance between Portland and Chicago is 1424km (883 miles). There are 23 direct flights from Portland to Chicago. The time difference between Portland and Chicago is 1h . Flights from Portland begin at 6:00 AM. The latest flight from Portland departs at 4:20 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

  • 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.

Southwest Airlines
Southwest 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.

Chicago city image

Portland — Chicago

PWM — CHI

05/02/2025

Departure date

Direct flight

United Airlines

UA5880

Starting at $234

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

PWM
Portland International Jetport
United Airlines
Airlines flying to this airport
$179
Starting at
$179
on average

Chicago airports overview

ORD
O'Hare International Airport
United Airlines
Airlines flying to this airport
$179
Starting at
$179
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 Portland — Chicago?

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

Which airline can fly direct from Portland to Chicago?

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

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

Boston ➜ Chicago•New Bedford ➜ Chicago•Manchester ➜ Chicago•Providence ➜ Chicago•Montreal ➜ Chicago•Portland ➜ Appleton•Portland ➜ Kalamazoo•Portland ➜ Champaign•Portland ➜ Fort Wayne•Portland ➜ Indianapolis•Portland ➜ Lansing•Portland ➜ Milwaukee•Portland ➜ Muskegon•Portland ➜ South Bend