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	$130	Frontier 1 stop 14 hr Thu, Jan 8 — Thu, Jan 15	The cheapest round-trip flight from Chicago to Portland is currently $130
Cheapest one-way flight	$91	Frontier 1 stop 15 hr Thu, Jan 15	The cheapest one-way flight from Chicago to Portland is currently $91
Cheapest nonstop flights	$217	Southwest Nonstop 5 hr Sat, Feb 14 — Fri, Feb 20	The cheapest nonstop round-trip flight from Chicago to Portland is currently $217
Last-minute weekend getaway	$544	United 2 stops 13 hr Thu, Nov 20 — Sun, Nov 23	The cheapest last-minute weekend getaway from Chicago to Portland is currently $544
Cheapest business class flights	$721	American Nonstop 5 hr Sat, Jan 10 — Sat, Jan 17	The cheapest business class round-trip flight from Chicago to Portland is currently $721

Fastest flight	4 hr 25 min	The fastest nonstop flight from Chicago to Portland takes 4 hr 25 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 February. The most expensive month to fly is typically July.

February Cheapest	Typical prices: $125–210
July Most expensive	Typical prices: $195–265

Popular airlines from Chicago to Portland

Southwest

Nonstop

from $217

Typical price: $250–530

7 weekly nonstop flights

MDW - PDX Every day

1899 weekly connecting flights

MDW, ORD - PDX Every day
United

Nonstop

from $217

Typical price: $235–500

21 weekly nonstop flights

ORD - PDX Every day

233 weekly connecting flights

ORD - PDX Every day
Alaska

Nonstop

from $217

Typical price: $235–540

12 weekly nonstop flights

ORD - PDX Every day

121 weekly connecting flights

ORD - PDX Every day
American

Nonstop

from $217

Typical price: $235–550

7 weekly nonstop flights

ORD - PDX Every day

148 weekly connecting flights

ORD - PDX Every day
Delta

from $199

Typical price: $255–590

432 weekly connecting flights

MDW, ORD - PDX Every day
Frontier

from $130

Typical price: $165–425

36 weekly connecting flights

MDW, ORD - PDX Every day

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

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

Frequently asked questions about flying from Chicago to Portland

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

The cheapest flights from Chicago to Portland are usually in February. Typical ticket prices in February range from $125 to $210.

Which airlines provide the cheapest flights from Chicago to Portland?

The cheapest round-trip flight from Chicago to Portland recently found on Google Flights was with Frontier from $130. The cheapest one-way flight was with Frontier from $91.

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

The cheapest Southwest flight from Chicago to Portland is $217, flying from Feb 14 to Feb 20.
The cheapest United flight from Chicago to Portland is $217, flying from Jan 10 to Jan 17.
The cheapest Alaska flight from Chicago to Portland is $217, flying from Feb 14 to Feb 20.
The cheapest American flight from Chicago to Portland is $217, flying from Jan 10 to Jan 17.
The cheapest Delta flight from Chicago to Portland is $199, flying from Jan 24 to Jan 31.
The cheapest Frontier flight from Chicago to Portland is $130, flying from Jan 8 to Jan 15.

What are the cheapest flights from Chicago to Portland?

The cheapest round-trip flight from Chicago to Portland starts at $130 from Thu, Jan 8 to Thu, Jan 15. The cheapest one-way flight starts at $91 and departs on Thu, Jan 15.

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

4 hr 25 min is the shortest flight time from Chicago to Portland.

When should you fly to Portland, United States?

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.

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

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 is the best airline to fly from Chicago to Portland?

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 21 nonstop flights and 233 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 7 nonstop flights and 1,899 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:

Alaska offers 12 nonstop flights and 121 connecting flights per week. Alaska flies from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX) .
American offers 7 nonstop flights and 148 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX) .
Delta offers 432 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX) .
Frontier offers 36 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.

Which airlines provide the cheapest flights from Chicago to Portland?

The cheapest round-trip flight from Chicago to Portland recently found on Google Flights was with Frontier from $130. The cheapest one-way flight was with Frontier from $91.

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

The cheapest Southwest flight from Chicago to Portland is $217, flying from Feb 14 to Feb 20.
The cheapest United flight from Chicago to Portland is $217, flying from Jan 10 to Jan 17.
The cheapest Alaska flight from Chicago to Portland is $217, flying from Feb 14 to Feb 20.
The cheapest American flight from Chicago to Portland is $217, flying from Jan 10 to Jan 17.
The cheapest Delta flight from Chicago to Portland is $199, flying from Jan 24 to Jan 31.
The cheapest Frontier flight from Chicago to Portland is $130, flying from Jan 8 to Jan 15.

Which airlines have direct flights from Chicago to Portland?

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

There are 7 Southwest direct flights from Chicago to Portland per week. Flights are available every day.
There are 21 United direct flights from Chicago to Portland per week. Flights are available every day.
There are 12 Alaska direct flights from Chicago to Portland per week. Flights are available every day.
There are 7 American 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.

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

The cheapest last-minute deal between Chicago and Portland at price $544 is offered by United from Thu, Nov 20 to Sun, Nov 23.

Which airlines have direct flights from Chicago to Portland?

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

There are 7 Southwest direct flights from Chicago to Portland per week. Flights are available every day.
There are 21 United direct flights from Chicago to Portland per week. Flights are available every day.
There are 12 Alaska direct flights from Chicago to Portland per week. Flights are available every day.
There are 7 American 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.

When are direct flights from Chicago to Portland available?

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

What are the cheapest direct flights from Chicago to Portland?

The cheapest direct (nonstop) round-trip flights between Chicago and Portland start at $217 from Sat, Feb 14 to Fri, Feb 20 with Southwest.

How can I find nonstop flights from Chicago to Portland?

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.

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

The cheapest business class round-trip flights between Chicago and Portland start at $721 from Sat, Jan 10 to Sat, Jan 17 with American.

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

The cheapest economy class round-trip flights between Chicago and Portland start at $130 from Thu, Jan 8 to Thu, Jan 15.

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

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.

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

The best last-minute getaway deal for the next weekend between Chicago and Portland starts at $544 from Thu, Nov 20 to Sun, Nov 23 with United.

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

The cheapest last-minute deal between Chicago and Portland at price $544 is offered by United from Thu, Nov 20 to Sun, Nov 23.

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

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.