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

Flights overview

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

Cheapest round-trip flights	$230	Frontier 1 stop 17 hr Fri, Jun 5 — Sun, Jun 14	The cheapest round-trip flight from Chicago to Portland is currently $230
Cheapest one-way flight	$111	Frontier 1 stop 17 hr Fri, Jun 5	The cheapest one-way flight from Chicago to Portland is currently $111
Cheapest nonstop flights	$251	Southwest Nonstop 5 hr Sat, May 9 — Sat, May 16	The cheapest nonstop round-trip flight from Chicago to Portland is currently $251
Last-minute weekend getaway	$336	Frontier 1 stop 27 hr Fri, Apr 17 — Sun, Apr 19	The cheapest last-minute weekend getaway from Chicago to Portland is currently $336
Cheapest business class flights	$478	Frontier 1 stop 17 hr Fri, Jun 5 — Sun, Jun 14	The cheapest business class round-trip flight from Chicago to Portland is currently $478

Fastest flight	4 hr 15 min	The fastest nonstop flight from Chicago to Portland takes 4 hr 15 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 Chicago to Portland is typically September. The most expensive month to fly is typically December.

September Cheapest	Typical prices: $150–230
December Most expensive	Typical prices: $220–465

Popular airlines from Chicago to Portland

Southwest

Nonstop

from $251

Typical price: $235–510

14 weekly nonstop flights

MDW - PDX Every day

1811 weekly connecting flights

MDW, ORD - PDX Every day
United

Nonstop

from $251

Typical price: $225–510

31 weekly nonstop flights

ORD - PDX Every day

182 weekly connecting flights

ORD - PDX Every day
American

Nonstop

from $251

Typical price: $235–540

21 weekly nonstop flights

ORD - PDX Every day

121 weekly connecting flights

ORD - PDX Every day
Delta

from $271

Typical price: $255–560

447 weekly connecting flights

MDW, ORD - PDX Every day
Alaska

Nonstop

from $326

Typical price: $235–540

7 weekly nonstop flights

ORD - PDX Every day

79 weekly connecting flights

ORD - PDX Every day
Frontier

from $230

Typical price: $200–560

25 weekly connecting flights

MDW, ORD - PDX Every day

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 25 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 24 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

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 2 hr 59 min 114 mi

Frequently asked questions about flying from Chicago to Portland

The cheapest flights from Chicago to Portland are usually in September. Typical ticket prices in September range from $150 to $230.

The cheapest round-trip flight from Chicago to Portland recently found on Google Flights was with Frontier from $230. The cheapest one-way flight was with Frontier from $111.

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

The cheapest Southwest flight from Chicago to Portland is $251, flying from May 9 to May 16.
The cheapest United flight from Chicago to Portland is $251, flying from May 9 to May 16.
The cheapest American flight from Chicago to Portland is $251, flying from May 9 to May 16.
The cheapest Delta flight from Chicago to Portland is $271, flying from May 9 to May 16.
The cheapest Alaska flight from Chicago to Portland is $326, flying from Jul 9 to Jul 15.
The cheapest Frontier flight from Chicago to Portland is $230, flying from May 3 to May 11.

The cheapest round-trip flight from Chicago to Portland starts at $230 from Fri, Jun 5 to Sun, Jun 14. The cheapest one-way flight starts at $111 and departs on Fri, Jun 5.

4 hr 15 min is the shortest flight time from Chicago to Portland.

Most travelers choose to visit in late spring and summer (May–Aug), when the days are mild to warm, and generally dry (especially Jul–Aug). The long-standing Portland Rose Festival (May–Jun) is a several-week event featuring floral parades, carnival rides, waterfront activities and fireworks. In Jul, the Oregon Brewers Festival draws thousands for craft beer tastings, demonstrations and live music along the river. The Waterfront Blues Festival is also held in Jul. Weather Nov–Apr is cool and rainy.

It's easy to use Google Flights to find the cheapest days to fly from Chicago to Portland.
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 Chicago to Portland 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 Chicago to Portland.

In terms of nonstop flights, United is the most popular. United offers 31 nonstop flights and 182 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX) .

In terms of flights, Southwest is the most popular. Southwest offers 14 nonstop flights and 1,811 connecting flights per week. Southwest flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX) .

Other popular airlines flying from Chicago to Portland are:

American offers 21 nonstop flights and 121 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX) .
Delta offers 447 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX) .
Alaska offers 7 nonstop flights and 79 connecting flights per week. Alaska flies from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX) .
Frontier offers 25 connecting flights per week. Frontier flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX) .

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

The cheapest round-trip flight from Chicago to Portland recently found on Google Flights was with Frontier from $230. The cheapest one-way flight was with Frontier from $111.

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

The cheapest Southwest flight from Chicago to Portland is $251, flying from May 9 to May 16.
The cheapest United flight from Chicago to Portland is $251, flying from May 9 to May 16.
The cheapest American flight from Chicago to Portland is $251, flying from May 9 to May 16.
The cheapest Delta flight from Chicago to Portland is $271, flying from May 9 to May 16.
The cheapest Alaska flight from Chicago to Portland is $326, flying from Jul 9 to Jul 15.
The cheapest Frontier flight from Chicago to Portland is $230, flying from May 3 to May 11.

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

There are 14 Southwest direct flights from Chicago to Portland per week. Flights are available every day.
There are 31 United direct flights from Chicago to Portland per week. Flights are available every day.
There are 21 American direct flights from Chicago to Portland per week. Flights are available every day.
There are 7 Alaska direct flights from Chicago to Portland 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 Chicago and Portland at price $336 is offered by Frontier from Fri, Apr 17 to Sun, Apr 19.

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

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

The cheapest direct (nonstop) round-trip flights between Chicago and Portland start at $251 from Sat, May 9 to Sat, May 16 with Southwest.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to Portland, 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 Chicago and Portland start at $478 from Fri, Jun 5 to Sun, Jun 14 with Frontier.

The cheapest economy class round-trip flights between Chicago and Portland start at $230 from Fri, Jun 5 to Sun, Jun 14.

To book business class trips from Chicago to Portland, 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 Chicago and Portland starts at $336 from Fri, Apr 17 to Sun, Apr 19 with Frontier.

The cheapest last-minute deal between Chicago and Portland at price $336 is offered by Frontier from Fri, Apr 17 to Sun, Apr 19.

To find last-minute flight deals from Chicago to Portland, 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.