Cheap Flights from Portland to Chicago Starting at $88

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

$88

Alaska Airlines
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
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.

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

Airlines operating on route

Starting at $85

Starting at $130

Direct Flights from Portland to Chicago

Chicago city image

PortlandChicago

PDXCHI

05/04/2025

Departure date

Direct flight

Southwest Airlines

WN407

Starting at $326

Chicago city image

PortlandChicago

PDXCHI

05/01/2025

Departure date

Direct flight

Alaska Airlines

AS324

Starting at $376

Chicago city image

PortlandChicago

PDXCHI

05/03/2025

Departure date

Direct flight

Southwest Airlines

WN407

Starting at $250

Chicago city image

PortlandChicago

PDXCHI

05/06/2025

Departure date

Direct flight

Alaska Airlines

AS324

Starting at $153

Chicago city image

PortlandChicago

PDXCHI

05/08/2025

Departure date

Direct flight

United Airlines

UA1490

Starting at $197

Chicago city image

PortlandChicago

PDXCHI

05/09/2025

Departure date

Direct flight

Alaska Airlines

AS324

Starting at $179

Chicago city image

PortlandChicago

PDXCHI

05/25/2025

Departure date

Direct flight

Alaska Airlines

AS324

Starting at $91

Chicago city image

PortlandChicago

PDXCHI

08/04/2025

Departure date

Direct flight

Southwest Airlines

WN4170

Starting at $224

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

PDX
United Airlines
American Airlines
Alaska Airlines
Airlines flying to this airport
$88
Starting at
$165
on average

Chicago airports overview

ORD
United Airlines
American Airlines
Alaska Airlines
Airlines flying to this airport
$88
Starting at
$165
on average

Frequently asked questions (FAQ)

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

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

BellinghamChicagoBoiseChicagoEugeneChicagoSpokaneChicagoEverettChicagoSeattleChicagoYakimaChicagoKelownaChicagoAbbotsfordChicagoPortlandAppletonPortlandKalamazooPortlandChampaignPortlandFort WaynePortlandIndianapolisPortlandLansingPortlandMilwaukeePortlandMuskegonPortlandSouth Bend