Find Cheap Flights from Portland to Chicago (PDX - CHI)

Flights overview

Useful information for finding cheap flights from Portland to Chicago and booking your next trip

Cheapest round-trip flights	$204	Frontier 1 stop 12 hr Sat, May 23 — Mon, Jun 1	The cheapest round-trip flight from Portland to Chicago is currently $204
Cheapest one-way flight	$86	Frontier 1 stop 12 hr Sat, May 23	The cheapest one-way flight from Portland to Chicago is currently $86
Cheapest nonstop flights	$215	American Nonstop 5 hr Thu, May 28 — Wed, Jun 3	The cheapest nonstop round-trip flight from Portland to Chicago is currently $215
Last-minute weekend getaway	$381	Frontier 1 stop 16 hr Thu, Apr 30 — Sun, May 3	The cheapest last-minute weekend getaway from Portland to Chicago is currently $381
Cheapest business class flights	$518	Frontier 1 stop 9 hr Sun, Jul 19 — Sun, Jul 26	The cheapest business class round-trip flight from Portland to Chicago is currently $518

Fastest flight	3 hr 50 min	The fastest nonstop flight from Portland to Chicago takes 3 hr 50 min
Nonstop flights	Every day	There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Portland to Chicago is typically September. The most expensive month to fly is typically April.

September Cheapest	Typical prices: $150–235
April Most expensive	Typical prices: $215–405

Popular airlines from Portland to Chicago

Southwest

Nonstop

from $224

Typical price: $235–520

14 weekly nonstop flights

PDX - MDW Every day

2193 weekly connecting flights

PDX - MDW, ORD Every day
United

Nonstop

from $215

Typical price: $225–510

31 weekly nonstop flights

PDX - ORD Every day

272 weekly connecting flights

PDX - ORD Every day
American

Nonstop

from $215

Typical price: $230–530

21 weekly nonstop flights

PDX - ORD Every day

191 weekly connecting flights

PDX - ORD Every day
Delta

from $235

Typical price: $255–570

506 weekly connecting flights

PDX - MDW, ORD Every day
Alaska

Nonstop

from $315

Typical price: $235–540

7 weekly nonstop flights

PDX - ORD Every day

127 weekly connecting flights

PDX - ORD Every day
Frontier

from $250

Typical price: $200–510

36 weekly connecting flights

PDX - MDW, ORD Every day

Popular airports near Portland

Portland International Airport (PDX)

Portland United States 20 min 6 mi
Seattle-Tacoma International Airport (SEA)

Seattle United States 2 hr 37 min 134 mi
Eugene Airport (EUG)

Eugene United States 1 hr 54 min 99 mi
Redmond Municipal Airport (RDM)

Redmond United States 3 hr 114 mi

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 26 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 25 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 23 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Portland to Chicago

The cheapest flights from Portland to Chicago are usually in September. Typical ticket prices in September range from $150 to $235.

The cheapest round-trip flight from Portland to Chicago recently found on Google Flights was with Frontier from $204. The cheapest one-way flight was with Frontier from $86.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Portland to Chicago is $224, flying from Jun 1 to Jun 9.
The cheapest United flight from Portland to Chicago is $215, flying from May 28 to Jun 3.
The cheapest American flight from Portland to Chicago is $215, flying from May 28 to Jun 3.
The cheapest Delta flight from Portland to Chicago is $235, flying from May 28 to Jun 3.
The cheapest Alaska flight from Portland to Chicago is $315, flying from Jul 3 to Jul 11.
The cheapest Frontier flight from Portland to Chicago is $250, flying from Jul 19 to Jul 26.

The cheapest round-trip flight from Portland to Chicago starts at $204 from Sat, May 23 to Mon, Jun 1. The cheapest one-way flight starts at $86 and departs on Sat, May 23.

3 hr 50 min is the shortest flight time from Portland to Chicago.

Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.

It's easy to use Google Flights to find the cheapest days to fly from Portland to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What counts as the best airline for your flights from Portland to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Portland to Chicago.

In terms of nonstop flights, United is the most popular. United offers 31 nonstop flights and 272 connecting flights per week. United flies from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Southwest is the most popular. Southwest offers 14 nonstop flights and 2,193 connecting flights per week. Southwest flies from Portland International Airport (PDX) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Portland to Chicago are:

American offers 21 nonstop flights and 191 connecting flights per week. American flies from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD) .
Delta offers 506 connecting flights per week. Delta flies from Portland International Airport (PDX) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
Alaska offers 7 nonstop flights and 127 connecting flights per week. Alaska flies from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD) .
Frontier offers 36 connecting flights per week. Frontier flies from Portland International Airport (PDX) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

The number of connecting flights refers to distinct flights with at least one stop between Portland and Chicago.

The cheapest round-trip flight from Portland to Chicago recently found on Google Flights was with Frontier from $204. The cheapest one-way flight was with Frontier from $86.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Portland to Chicago is $224, flying from Jun 1 to Jun 9.
The cheapest United flight from Portland to Chicago is $215, flying from May 28 to Jun 3.
The cheapest American flight from Portland to Chicago is $215, flying from May 28 to Jun 3.
The cheapest Delta flight from Portland to Chicago is $235, flying from May 28 to Jun 3.
The cheapest Alaska flight from Portland to Chicago is $315, flying from Jul 3 to Jul 11.
The cheapest Frontier flight from Portland to Chicago is $250, flying from Jul 19 to Jul 26.

Southwest, United, American and Alaska fly direct from Portland to Chicago.

There are 14 Southwest direct flights from Portland to Chicago per week. Flights are available every day.
There are 31 United direct flights from Portland to Chicago per week. Flights are available every day.
There are 21 American direct flights from Portland to Chicago per week. Flights are available every day.
There are 7 Alaska direct flights from Portland to Chicago per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

The cheapest last-minute deal between Portland and Chicago at price $381 is offered by Frontier from Thu, Apr 30 to Sun, May 3.

Southwest, United, American and Alaska fly direct from Portland to Chicago.

There are 14 Southwest direct flights from Portland to Chicago per week. Flights are available every day.
There are 31 United direct flights from Portland to Chicago per week. Flights are available every day.
There are 21 American direct flights from Portland to Chicago per week. Flights are available every day.
There are 7 Alaska direct flights from Portland to Chicago per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

There are direct flights from Portland to Chicago on a daily basis.

The cheapest direct (nonstop) round-trip flights between Portland and Chicago start at $215 from Thu, May 28 to Wed, Jun 3 with American.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Portland to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

The cheapest business class round-trip flights between Portland and Chicago start at $518 from Sun, Jul 19 to Sun, Jul 26 with Frontier.

The cheapest economy class round-trip flights between Portland and Chicago start at $204 from Sat, May 23 to Mon, Jun 1.

To book business class trips from Portland to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

The best last-minute getaway deal for the next weekend between Portland and Chicago starts at $381 from Thu, Apr 30 to Sun, May 3 with Frontier.

The cheapest last-minute deal between Portland and Chicago at price $381 is offered by Frontier from Thu, Apr 30 to Sun, May 3.

To find last-minute flight deals from Portland to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.