What airlines fly to Portland?

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Portland from Chicago according to our data. United Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Portland. Keep in mind that there are 7 different airlines that fly to Portland on a routine basis, so you have a few additional options to choose from.

How many flights depart from Chicago to Portland on average per day?

The number of flights available between Chicago and Portland is 11 per day as of January 2026. The most frequent departure time is 4:00PM, with 63% of daily flights leaving in the afternoon.

What is the cheapest airline that flies from Chicago to Portland?

Southwest, Delta, and United Airlines are the most popular carriers operating from Chicago to Portland

Which layover airport has the shortest connection time from Chicago to Portland?

Las Vegas (LAS) has the shortest average layover time for this route: 3h 40m.

Which layover airport has the shortest travel time from Chicago to Portland?

Flights connecting via Las Vegas (LAS) have the shortest average one-way travel time: 9h 46m.

Which layover airport offers the lowest fares from Chicago to Portland?

Flights via Las Vegas (LAS) offer the lowest average round-trip price of $173.

How many flights depart from Chicago to Portland on average per week?

As of January 2026, there are 82 flights per week flying from Chicago to Portland. The most common day of the week flights depart is Mon, with 22% of flights taking off on this day.

Which airport is the most popular layover for flights between Chicago and Portland?

Las Vegas (LAS) was the most common stop: 55% of momondo users choosing 1-stop flights on this route connected there.

When did momondo last update prices for flights from Chicago to Portland Airport?

Prices for flights from Chicago to Portland Airport refresh daily.

How many operators does momondo search for flights from Chicago to Portland Airport?

As of January 2026, there are 7 operators available to choose from for flights from Chicago to Portland Airport.

How old do you have to be to fly from Chicago to Portland Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Portland Airport.

What documentation or ID do you need to fly to Portland Airport?

The travel and health documents required for your trip to Portland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Portland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$119 Cheap Flights from Chicago to Portland in 2026

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12:46 pm - 7:13 pm

MDW

PDX

8h 27m

1 stop

12:40 am - 9:06 am

PDX

MDW

6h 26m

1 stop

$217Delta

Wed, Feb 11 - Mon, Feb 16

6:15 am - 12:44 pm

ORD

PDX

8h 29m

1 stop

1:32 pm - 9:52 pm

PDX

ORD

6h 20m

1 stop

$217Delta

Sat, Feb 14 - Sat, Feb 21

5:54 pm - 8:27 pm

ORD

PDX

4h 33mnonstop

11:35 pm - 5:32 am

PDX

ORD

3h 57mnonstop

$218American Airlines

Sat, Feb 7 - Sat, Feb 14

2:16 pm - 8:58 am

MDW

PDX

20h 42m

1 stop

9:53 am - 10:45 pm

PDX

MDW

34h 52m

2 stops

$218Frontier

Sun, Mar 8 - Sun, Mar 15

3:07 pm - 11:57 pm

ORD

PDX

10h 50m

1 stop

7:00 am - 1:11 pm

PDX

ORD

4h 11mnonstop

$219Hawaiian Airlines

Fri, Feb 27 - Fri, Mar 6

5:55 pm - 10:30 pm

MDW

PDX

6h 35m

1 stop

3:15 pm - 12:50 am

PDX

MDW

7h 35m

1 stop

$220Southwest

Sat, Feb 28 - Sat, Mar 7

6:15 am - 5:35 pm

MDW

PDX

13h 20m

1 stop

5:40 am - 11:35 am

PDX

MDW

3h 55mnonstop

$222Southwest

Sat, Apr 11 - Tue, Apr 14

4:15 pm - 6:56 pm

ORD

PDX

4h 41mnonstop

1:24 pm - 9:15 pm

PDX

ORD

5h 51m

1 stop

$223United Airlines

Tue, Feb 3 - Tue, Feb 10

2:07 pm - 4:50 pm

ORD

PDX

4h 43mnonstop

1:36 pm - 11:56 pm

PDX

ORD

8h 20m

1 stop

$227Alaska Airlines

Wed, Feb 18 - Tue, Feb 24

9:44 pm - 12:15 am

ORD

PDX

4h 31mnonstop

11:46 am - 5:55 pm

PDX

ORD

4h 09mnonstop

$228American Airlines

Wed, Mar 25 - Mon, Mar 30

Delta flights from Chicago to Portland

Our best Delta deals on Chicago to Portland flight tickets

Delta

Feb 14

ORD6:15 amChicago O'Hare Intl

8h 29m

1 stop

PDX12:44 pmPortland

Feb 21

PDX1:53 pmPortland

5h 37m

1 stop

ORD9:30 pmChicago O'Hare Intl

$217

Delta

Feb 5

MDW1:51 pmChicago Midway

8h 41m

1 stop

PDX8:32 pmPortland

Feb 10

PDX12:40 amPortland

6h 28m

1 stop

MDW9:08 amChicago Midway

$227

Delta

Feb 19

MDW1:49 pmChicago Midway

8h 41m

1 stop

PDX8:30 pmPortland

Feb 23

PDX9:45 pmPortland

10h 09m

1 stop

MDW9:54 amChicago Midway

$237

American Airlines flights from Chicago to Portland

Our best American Airlines deals on Chicago to Portland flight tickets

American Airlines

Feb 7

ORD5:54 pmChicago O'Hare Intl

4h 33m

PDX8:27 pmPortland

Feb 14

PDX11:35 pmPortland

3h 57m

ORD5:32 amChicago O'Hare Intl

$218

American Airlines

Mar 25

ORD9:44 pmChicago O'Hare Intl

4h 31m

PDX12:15 amPortland

Mar 30

PDX11:46 amPortland

4h 09m

ORD5:55 pmChicago O'Hare Intl

$228

American Airlines

Feb 27

ORD8:29 amChicago O'Hare Intl

4h 33m

PDX11:02 amPortland

Mar 6

PDX11:35 pmPortland

3h 57m

ORD5:32 amChicago O'Hare Intl

$238

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 2/11

12:46 pm-7:13 pm

1 stop8h 27m

Portland

Mon 2/16

12:40 am-9:06 am

1 stop6h 26m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 2/14

6:15 am-12:44 pm

1 stop8h 29m

Portland

Sat 2/21

1:32 pm-9:52 pm

1 stop6h 20m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 2/7

5:54 pm-8:27 pm

Nonstop4h 33m

Portland

Sat 2/14

11:35 pm-5:32 am

Nonstop3h 57m

$218

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sun 3/8

2:16 pm-8:58 am

1 stop20h 42m

Portland

Sun 3/15

9:53 am-10:45 pm

2 stops34h 52m

$218

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 2/27

3:07 pm-11:57 pm

1 stop10h 50m

Portland

Fri 3/6

7:00 am-1:11 pm

Nonstop4h 11m

$219

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 2/28

5:55 pm-10:30 pm

1 stop6h 35m

Portland

Sat 3/7

3:15 pm-12:50 am

1 stop7h 35m

$220

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 4/11

6:15 am-5:35 pm

1 stop13h 20m

Portland

Tue 4/14

5:40 am-11:35 am

Nonstop3h 55m

$222

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/3

4:15 pm-6:56 pm

Nonstop4h 41m

Portland

Tue 2/10

1:24 pm-9:15 pm

1 stop5h 51m

$223

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 2/18

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Tue 2/24

1:36 pm-11:56 pm

1 stop8h 20m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 3/25

9:44 pm-12:15 am

Nonstop4h 31m

Portland

Mon 3/30

11:46 am-5:55 pm

Nonstop4h 09m

$228

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How to get the cheapest flight ticket from Chicago to Portland

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

Other information

What is the typical price of a round-trip flight between Chicago and Portland?

What is the cheapest month to fly to Portland?

The cheapest month to fly to Portland from Chicago is in September. Flight prices, which tend to average around $280, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in September, then you should wait until May to fly from Chicago, when ticket prices are also cheap, with an average price of $285.

What is the cheapest day to depart on your flight to Portland?

The cheapest day to depart on your flight to Portland is on a Wednesday when prices can be found for as low as $331. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Portland is Monday, with ticket prices averaging around $396.

What is the cheapest time of day to depart on your flight to Portland?

The cheapest time of day to fly to Portland is in the evening when flights can be purchased for as low as $319. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $470 per ticket.

What is the cheapest Chicago to Portland flight route?

Fly from Chicago Midway to Portland for the best Chicago - Portland flight prices

How far in advance should I book a flight to Portland?

You are more likely to see cheaper flights to Portland from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland for around $327 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland from Chicago for as low as $267 on momondo.

What cabin class options are available on Chicago to Portland flights?

There are 4 cabin classes available to choose from on Chicago to Portland flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Portland flight prices changed over time?

As of January 2026, prices for Chicago to Portland flights are approximately 9% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Portland

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Portland according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Portland (CHI to PDX) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Portland

Best Price Found	$136
Fastest flight time	4h 20m
Direct flights	Every day
Airports in Portland	1 airport

The best one-way flight to Portland from Chicago in the past 72 hours is $136. The best round-trip flight deal from Chicago to Portland found on momondo in the last 72 hours is $227.

The fastest flight from Chicago to Portland takes 4h 20m

Direct flights go from Chicago to Portland every day.

There is 1 airport in Portland. From Chicago there are direct flights to Portland (PDX).

Search flight deals

How far is Chicago to Portland by plane?
A flight from Chicago to Portland will travel around 1753.4 mi. Flights usually cover this in 4h 20m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago to Portland Airport?
Prices for flights from Chicago to Portland Airport refresh daily.
How many operators does momondo search for flights from Chicago to Portland Airport?
As of January 2026, there are 7 operators available to choose from for flights from Chicago to Portland Airport.
How old do you have to be to fly from Chicago to Portland Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Portland Airport.
What documentation or ID do you need to fly to Portland Airport?
The travel and health documents required for your trip to Portland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Portland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Portland?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Portland is Boeing 737-800, representing 24.95% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 18.45%, Boeing 737 MAX 9 at 15.94%, and Boeing 737-900 at 12.25%.
What is the most popular airline from Chicago to Portland?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Portland is United Airlines (33% of total bookings). The next most popular airlines are American Airlines (27%), Alaska Airlines (21%), and Southwest (8%).

Best airlines flying from Chicago to Portland

Compare and see reviews for airlines that fly from Chicago to Portland with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $93	Free Cancellation	Rating 6.3 8,305 reviews	Search Spirit Airlines flights
Hawaiian Airlines	PriceFrom $134	Free Cancellation	Rating 7.8 2,827 reviews	Search Hawaiian Airlines flights
Frontier	PriceFrom $150	Free Cancellation	Rating 5.7 3,056 reviews	Search Frontier flights
Alaska Airlines	PriceFrom $198	Free Cancellation	Rating 7.9 11,698 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $212	Free Cancellation	Rating 7.4 9,152 reviews	Search United Airlines flights
American Airlines	PriceFrom $213	Free Cancellation	Rating 7.2 11,116 reviews	Search American Airlines flights
Southwest	PriceFrom $238	Free Cancellation	Rating 8.0 4,257 reviews	Search Southwest flights

Southwest Flights From Chicago to Portland
Southwest flight deals from Chicago to Portland start from $238 round-trip. Over the 4 Southwest flights for this route in a normal week, average airfare is usually $417 round-trip - but some users have found much cheaper deals with momondo.
Alaska Airlines Flights From Chicago to Portland
Another popular option for Chicago to Portland flights is Alaska Airlines (7.9/10, 11,698 ratings). Alaska Airlines flies from Chicago to Portland around 5 times per week, with deals starting from $198 round-trip and rising to an average price of around $309.

Lincoln City

Seaside

Cannon Beach

Vancouver

Salem

Astoria

Long Beach

Depoe Bay

Rockaway Beach

Beaverton

Hillsboro

Hood River

McMinnville

Longview

Gresham

Tigard

Pacific City

The Dalles

Manzanita

Newberg

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Portland?

It is quick and easy to find Chicago to Portland flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Portland that suits you.

Can I find flights from Chicago to Portland with flexible booking policies on momondo?

All flight searches from Chicago to Portland on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Portland?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Portland.

I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Portland flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Portland trip

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Cheap flights from Chicago to Portland from $119

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Portland departing on 3/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Delta flights from Chicago to Portland

Our best Delta deals on Chicago to Portland flight tickets

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How to get the cheapest flight ticket from Chicago to Portland

What is the typical price of a round-trip flight between Chicago and Portland?

What is the cheapest month to fly to Portland?

What is the cheapest day to depart on your flight to Portland?

The cheapest day to depart on your flight to Portland is on a Wednesday when prices can be found for as low as $331. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Portland is Monday, with ticket prices averaging around $396.

What is the cheapest time of day to depart on your flight to Portland?

The cheapest time of day to fly to Portland is in the evening when flights can be purchased for as low as $319. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $470 per ticket.

What is the cheapest Chicago to Portland flight route?

Fly from Chicago Midway to Portland for the best Chicago - Portland flight prices

How far in advance should I book a flight to Portland?

What cabin class options are available on Chicago to Portland flights?

There are 4 cabin classes available to choose from on Chicago to Portland flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Portland flight prices changed over time?

As of January 2026, prices for Chicago to Portland flights are approximately 9% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Chicago to Portland?

Southwest, Delta, and United Airlines are the most popular carriers operating from Chicago to Portland

What airlines fly to Portland?

Which airport is the most popular layover for flights between Chicago and Portland?

Las Vegas (LAS) was the most common stop: 55% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to Portland?

Flights via Las Vegas (LAS) offer the lowest average round-trip price of $173.

Which layover airport has the shortest travel time from Chicago to Portland?

Flights connecting via Las Vegas (LAS) have the shortest average one-way travel time: 9h 46m.

Which layover airport has the shortest connection time from Chicago to Portland?

Las Vegas (LAS) has the shortest average layover time for this route: 3h 40m.

How many flights depart from Chicago to Portland on average per day?

The number of flights available between Chicago and Portland is 11 per day as of January 2026. The most frequent departure time is 4:00PM, with 63% of daily flights leaving in the afternoon.

How many flights depart from Chicago to Portland on average per week?

As of January 2026, there are 82 flights per week flying from Chicago to Portland. The most common day of the week flights depart is Mon, with 22% of flights taking off on this day.

When to book flights from Chicago to Portland

Cheap Chicago to Portland (CHI to PDX) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Portland

Best Price Found

Fastest flight time

Direct flights

Airports in Portland

How far is Chicago to Portland by plane?

When did momondo last update prices for flights from Chicago to Portland Airport?

How many operators does momondo search for flights from Chicago to Portland Airport?

How old do you have to be to fly from Chicago to Portland Airport?

What documentation or ID do you need to fly to Portland Airport?

What is the most popular plane model from Chicago to Portland?

What is the most popular airline from Chicago to Portland?

Best airlines flying from Chicago to Portland

Compare and see reviews for airlines that fly from Chicago to Portland with momondo

Southwest Flights From Chicago to Portland

Alaska Airlines Flights From Chicago to Portland

Traveling to a place near Portland?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Portland?

Can I find flights from Chicago to Portland with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Portland?

I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?

An easier way to manage your Portland trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States