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	$174	Frontier 1 stop 8 hr Thu, Jan 15 — Wed, Jan 21	The cheapest round-trip flight from Portland to Chicago is currently $174
Cheapest one-way flight	$65	Frontier 1 stop 8 hr Thu, Jan 15	The cheapest one-way flight from Portland to Chicago is currently $65
Cheapest nonstop flights	$217	American Nonstop 5 hr Sat, Jan 10 — Sat, Jan 17	The cheapest nonstop round-trip flight from Portland to Chicago is currently $217
Last-minute weekend getaway	$462	Frontier 1 stop 8 hr Sat, Nov 22 — Sun, Nov 23	The cheapest last-minute weekend getaway from Portland to Chicago is currently $462
Cheapest business class flights	$721	American Nonstop 5 hr Sat, Jan 24 — Sat, Jan 31	The cheapest business class round-trip flight from Portland to Chicago is currently $721

Fastest flight	3 hr 53 min	The fastest nonstop flight from Portland to Chicago takes 3 hr 53 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 February. The most expensive month to fly is typically July.

February Cheapest	Typical prices: $125–200
July Most expensive	Typical prices: $195–270

Popular airlines from Portland to Chicago

Southwest

Nonstop

from $217

Typical price: $250–520

7 weekly nonstop flights

PDX - MDW Every day

1896 weekly connecting flights

PDX - MDW, ORD Every day
United

Nonstop

from $217

Typical price: $235–495

21 weekly nonstop flights

PDX - ORD Every day

260 weekly connecting flights

PDX - ORD Every day
Alaska

Nonstop

from $217

Typical price: $235–530

13 weekly nonstop flights

PDX - ORD Every day

114 weekly connecting flights

PDX - ORD Every day
Delta

from $237

Typical price: $255–590

568 weekly connecting flights

PDX - MDW, ORD Every day
American

Nonstop

from $217

Typical price: $235–530

7 weekly nonstop flights

PDX - ORD Every day

216 weekly connecting flights

PDX - ORD Every day
Frontier

from $322

Typical price: $160–420

29 weekly connecting flights

PDX - MDW, ORD Every Mon, Tue, Fri, Sat, Sun

Popular airports near Portland

Portland International Airport (PDX)

Portland United States 19 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 53 min 99 mi
Redmond Municipal Airport (RDM)

Redmond United States 2 hr 57 min 114 mi

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 31 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 26 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 28 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

When are the cheapest days to fly from Portland to Chicago?

The cheapest flights from Portland to Chicago are usually in February. Typical ticket prices in February range from $125 to $200.

Which airlines provide the cheapest flights from Portland to Chicago?

The cheapest round-trip flight from Portland to Chicago recently found on Google Flights was with Frontier from $174. The cheapest one-way flight was with Frontier from $65.

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

The cheapest Southwest flight from Portland to Chicago is $217, flying from Feb 15 to Feb 21.
The cheapest United flight from Portland to Chicago is $217, flying from Jan 10 to Jan 17.
The cheapest Alaska flight from Portland to Chicago is $217, flying from Jan 18 to Jan 27.
The cheapest Delta flight from Portland to Chicago is $237, flying from Jan 10 to Jan 17.
The cheapest American flight from Portland to Chicago is $217, flying from Jan 17 to Jan 24.
The cheapest Frontier flight from Portland to Chicago is $322, flying from Jan 10 to Jan 18.

What are the cheapest flights from Portland to Chicago?

The cheapest round-trip flight from Portland to Chicago starts at $174 from Thu, Jan 15 to Wed, Jan 21. The cheapest one-way flight starts at $65 and departs on Thu, Jan 15.

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

3 hr 53 min is the shortest flight time from Portland to Chicago.

When should you fly to Chicago, United States?

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.

How do I find cheap dates to fly from Portland to Chicago?

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 is the best airline to fly from Portland to Chicago?

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 21 nonstop flights and 260 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 7 nonstop flights and 1,896 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:

Alaska offers 13 nonstop flights and 114 connecting flights per week. Alaska flies from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD) .
Delta offers 568 connecting flights per week. Delta flies from Portland International Airport (PDX) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
American offers 7 nonstop flights and 216 connecting flights per week. American flies from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD) .
Frontier offers 29 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.

Which airlines provide the cheapest flights from Portland to Chicago?

The cheapest round-trip flight from Portland to Chicago recently found on Google Flights was with Frontier from $174. The cheapest one-way flight was with Frontier from $65.

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

The cheapest Southwest flight from Portland to Chicago is $217, flying from Feb 15 to Feb 21.
The cheapest United flight from Portland to Chicago is $217, flying from Jan 10 to Jan 17.
The cheapest Alaska flight from Portland to Chicago is $217, flying from Jan 18 to Jan 27.
The cheapest Delta flight from Portland to Chicago is $237, flying from Jan 10 to Jan 17.
The cheapest American flight from Portland to Chicago is $217, flying from Jan 17 to Jan 24.
The cheapest Frontier flight from Portland to Chicago is $322, flying from Jan 10 to Jan 18.

Which airlines have direct flights from Portland to Chicago?

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

There are 7 Southwest direct flights from Portland to Chicago per week. Flights are available every day.
There are 21 United direct flights from Portland to Chicago per week. Flights are available every day.
There are 13 Alaska direct flights from Portland to Chicago per week. Flights are available every day.
There are 7 American 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.

Which airline provides the cheapest last-minute getaway flight from Portland to Chicago?

The cheapest last-minute deal between Portland and Chicago at price $462 is offered by Frontier from Sat, Nov 22 to Sun, Nov 23.

Which airlines have direct flights from Portland to Chicago?

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

There are 7 Southwest direct flights from Portland to Chicago per week. Flights are available every day.
There are 21 United direct flights from Portland to Chicago per week. Flights are available every day.
There are 13 Alaska direct flights from Portland to Chicago per week. Flights are available every day.
There are 7 American 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.

When are direct flights from Portland to Chicago available?

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

What are the cheapest direct flights from Portland to Chicago?

The cheapest direct (nonstop) round-trip flights between Portland and Chicago start at $217 from Sat, Jan 10 to Sat, Jan 17 with American.

How can I find nonstop flights from Portland to Chicago?

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.

What are the cheapest business class flights from Portland to Chicago?

The cheapest business class round-trip flights between Portland and Chicago start at $721 from Sat, Jan 24 to Sat, Jan 31 with American.

What are the cheapest economy class flights from Portland to Chicago?

The cheapest economy class round-trip flights between Portland and Chicago start at $174 from Thu, Jan 15 to Wed, Jan 21.

How can I book business class trips from Portland to Chicago?

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.

Are there any last-minute deals from Portland to Chicago next weekend?

The best last-minute getaway deal for the next weekend between Portland and Chicago starts at $462 from Sat, Nov 22 to Sun, Nov 23 with Frontier.

Which airline provides the cheapest last-minute getaway flight from Portland to Chicago?

The cheapest last-minute deal between Portland and Chicago at price $462 is offered by Frontier from Sat, Nov 22 to Sun, Nov 23.

How can I find last-minute flight deals from Portland to Chicago?

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.