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

The number of flights available between Chicago and Portland is 10 per day as of November 2025. The most frequent departure time is 4:00PM, with 48% of daily flights leaving in the afternoon.

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

Denver (DEN) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

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.

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

As of November 2025, there are 74 flights per week flying from Chicago to Portland. The most common day of the week flights depart is Thu, with 24% of flights taking off on this day.

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 41% of people opting to fly with this airline when traveling to Portland. Keep in mind that there are 8 different airlines that fly to Portland on a routine basis, so you have a few additional options to choose from.

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.

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

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

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 November 2025, there are 8 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.

$118 Cheap Flights from Chicago to Portland in 2025/26

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

Prices are currently low for flights on this route. Typical prices usually range from $284 to $548. The lowest price recently found on this route was $228.

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1:49 pm - 8:32 pmMDW-PDX

8h 43m1 stop

12:40 am - 9:08 amPDX-MDW

6h 28m1 stop

$228Delta

Find Deal

Fri, Jan 23 - Mon, Jan 26

2:20 pm - 6:50 pmORD-PDX

6h 30m1 stop

12:40 am - 10:25 amPDX-ORD

7h 45m1 stop

$228Delta

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Fri, Feb 6 - Fri, Feb 6

2:30 pm - 11:04 amORD-PDX

22h 34m1 stop

7:05 am - 1:10 pmPDX-ORD

4h 05mnonstop

$229Multiple Airlines

Find Deal

Thu, Jan 15 - Tue, Jan 20

9:59 pm - 10:33 amORD-PDX

14h 34m1 stop

7:05 am - 1:10 pmPDX-ORD

4h 05mnonstop

$230Multiple Airlines

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Thu, Jan 15 - Sun, Jan 18

7:00 am - 9:32 amORD-PDX

4h 32mnonstop

11:00 pm - 5:07 amPDX-ORD

4h 07mnonstop

$231Alaska Airlines

Find Deal

Wed, Mar 18 - Wed, Mar 25

2:36 pm - 9:12 pmORD-PDX

8h 36m1 stop

1:24 pm - 9:15 pmPDX-ORD

5h 51m1 stop

$232United Airlines

Find Deal

Tue, Feb 3 - Sat, Feb 7

8:45 am - 3:20 pmMDW-PDX

8h 35m1 stop

3:55 pm - 12:05 amPDX-MDW

6h 10m1 stop

$233Southwest

Find Deal

Tue, Dec 9 - Fri, Dec 12

4:25 pm - 10:30 pmORD-PDX

8h 05m1 stop

5:10 am - 3:25 pmPDX-ORD

8h 15m1 stop

$233Southwest

Find Deal

Tue, Dec 9 - Fri, Dec 12

2:06 pm - 4:48 pmORD-PDX

4h 42mnonstop

7:05 am - 1:10 pmPDX-ORD

4h 05mnonstop

$237Alaska Airlines

Find Deal

Thu, Feb 5 - Sun, Feb 8

5:54 pm - 8:27 pmORD-PDX

4h 33mnonstop

6:00 am - 12:15 pmPDX-ORD

4h 15mnonstop

$238American Airlines

Find Deal

Fri, Jan 9 - Fri, Jan 16

Delta flights from Chicago to Portland

Our best Delta deals on Chicago to Portland flight tickets

Delta

Jan 23

MDW1:49 pmChicago Midway

8h 43m

1 stop

PDX8:32 pmPortland

Jan 26

PDX12:40 amPortland

6h 28m

1 stop

MDW9:08 amChicago Midway

$228

Find similar

Delta

Dec 11

ORD6:10 pmChicago O'Hare Intl

8h 05m

1 stop

PDX12:15 amPortland

Dec 14

PDX10:10 pmPortland

10h 04m

1 stop

ORD10:14 amChicago O'Hare Intl

$234

Find similar

Delta

Feb 2

MDW1:49 pmChicago Midway

8h 43m

1 stop

PDX8:32 pmPortland

Feb 8

PDX6:00 amPortland

8h 16m

1 stop

MDW4:16 pmChicago Midway

$236

Find similar

Alaska Airlines flights from Chicago to Portland

Our best Alaska Airlines deals on Chicago to Portland flight tickets

Alaska Airlines

Mar 18

ORD7:00 amChicago O'Hare Intl

4h 32m

PDX9:32 amPortland

Mar 25

PDX11:00 pmPortland

4h 07m

ORD5:07 amChicago O'Hare Intl

$231

Find similar

Alaska Airlines

Feb 5

ORD2:06 pmChicago O'Hare Intl

4h 42m

PDX4:48 pmPortland

Feb 8

PDX7:05 amPortland

4h 05m

ORD1:10 pmChicago O'Hare Intl

$237

Find similar

Alaska Airlines

Feb 28

ORD2:07 pmChicago O'Hare Intl

4h 43m

PDX4:50 pmPortland

Mar 11

PDX7:00 amPortland

4h 11m

ORD1:11 pmChicago O'Hare Intl

$243

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 1/23

1:49 pm-8:32 pm

1 stop8h 43m

Portland

Mon 1/26

12:40 am-9:08 am

1 stop6h 28m

$228

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 2/6

2:20 pm-6:50 pm

1 stop6h 30m

Portland

Fri 2/6

12:40 am-10:25 am

1 stop7h 45m

$228

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 1/15

2:30 pm-11:04 am

1 stop22h 34m

Portland

Tue 1/20

7:05 am-1:10 pm

Nonstop4h 05m

$229

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 1/15

9:59 pm-10:33 am

1 stop14h 34m

Portland

Sun 1/18

7:05 am-1:10 pm

Nonstop4h 05m

$230

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 3/18

7:00 am-9:32 am

Nonstop4h 32m

Portland

Wed 3/25

11:00 pm-5:07 am

Nonstop4h 07m

$231

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/3

2:36 pm-9:12 pm

1 stop8h 36m

Portland

Sat 2/7

1:24 pm-9:15 pm

1 stop5h 51m

$232

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 12/9

8:45 am-3:20 pm

1 stop8h 35m

Portland

Fri 12/12

3:55 pm-12:05 am

1 stop6h 10m

$233

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 12/9

4:25 pm-10:30 pm

1 stop8h 05m

Portland

Fri 12/12

5:10 am-3:25 pm

1 stop8h 15m

$233

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 2/5

2:06 pm-4:48 pm

Nonstop4h 42m

Portland

Sun 2/8

7:05 am-1:10 pm

Nonstop4h 05m

$237

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 1/9

5:54 pm-8:27 pm

Nonstop4h 33m

Portland

Fri 1/16

6:00 am-12:15 pm

Nonstop4h 15m

$238

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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 January. Flight prices, which tend to average around $265, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in January, then you should wait until September to fly from Chicago, when ticket prices are also cheap, with an average price of $278.

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 $333. 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 $409.

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 $327. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $487 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 $335 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 $272 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 November 2025, prices for Chicago to Portland flights are approximately 16% 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	$118
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 $118. The best round-trip flight deal from Chicago to Portland found on momondo in the last 72 hours is $268.

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

Direct flights go from Chicago to Portland every day.

There is 1 airport near Portland: 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 25m, 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 November 2025, there are 8 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 25.59% of all bookings. The subsequent popular models are Boeing 737 MAX 9 at 14.97%, Boeing 737-900 at 13.39%, and Airbus A321neo at 9.66%.
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 (25%), Alaska Airlines (23%), and Southwest (9%).

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 $86	Free Cancellation	Rating 6.3 8,156 reviews	Search Spirit Airlines flights
Delta	PriceFrom $88	Free Cancellation	Rating 7.9 8,002 reviews	Search Delta flights
Frontier	PriceFrom $110	Free Cancellation	Rating 5.8 3,105 reviews	Search Frontier flights
Hawaiian Airlines	PriceFrom $134	Free Cancellation	Rating 7.8 2,811 reviews	Search Hawaiian Airlines flights
Alaska Airlines	PriceFrom $208	Free Cancellation	Rating 8.0 11,321 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $213	Free Cancellation	Rating 7.2 11,045 reviews	Search American Airlines flights
United Airlines	PriceFrom $225	Free Cancellation	Rating 7.4 9,027 reviews	Search United Airlines flights
Southwest	PriceFrom $238	Free Cancellation	Rating 8.0 4,249 reviews	Search Southwest flights

Alaska Airlines Flights From Chicago to Portland
Alaska Airlines flight deals from Chicago to Portland start from $208 round-trip. Over the 2 Alaska Airlines flights for this route in a normal week, average airfare is usually $304 round-trip - but some users have found much cheaper deals with momondo.
Southwest Flights From Chicago to Portland
Another popular option for Chicago to Portland flights is Southwest (8.0/10, 4,249 ratings). Southwest flies from Chicago to Portland around 2 times per week, with deals starting from $238 round-trip and rising to an average price of around $436.

Lincoln City

Seaside

Cannon Beach

Vancouver

Salem

Astoria

Long Beach

Depoe Bay

Rockaway Beach

Beaverton

Hillsboro

Hood River

Gresham

McMinnville

Longview

The Dalles

Pacific City

Tigard

Manzanita

Tillamook

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

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.

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Cheap flights from Chicago to Portland from $118

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 1/6. 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

Alaska Airlines flights from Chicago to Portland

Our best Alaska Airlines deals on Chicago to Portland flight tickets

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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

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 $333. 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 $409.

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 $327. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $487 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 November 2025, prices for Chicago to Portland flights are approximately 16% more expensive when compared to flights at the same time last year.

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

Southwest, Alaska Airlines, and Delta 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?

Denver (DEN) was the most common stop: 50% 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 10 per day as of November 2025. The most frequent departure time is 4:00PM, with 48% of daily flights leaving in the afternoon.

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

As of November 2025, there are 74 flights per week flying from Chicago to Portland. The most common day of the week flights depart is Thu, with 24% 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

Alaska Airlines Flights From Chicago to Portland

Southwest 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.