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

Las Vegas (LAS) was the most common stop: 54% 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 40m.

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 23m.

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

Frontier, Spirit Airlines, and Southwest are the most popular carriers operating from Chicago to Portland

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 40% 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.

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

The number of flights available between Chicago and Portland is 23 per day as of August 2025. The most frequent departure time is 8:00PM, with 39% of daily flights leaving in the evening.

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

As of August 2025, there are 161 flights per week flying from Chicago to Portland. The most common day of the week flights depart is Mon, with 19% of flights taking off on this day.

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 August 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.

$93 Cheap Flights from Chicago to Portland (CHI-PDX) in 2025

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Find the cheapest flights from Chicago to Portland (CHI-PDX)

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:35 am - 7:36 pmORD-PDX

15h 01m1 stop

12:43 pm - 11:53 pmPDX-ORD

9h 10m1 stop

$182

Find Deal

Wed, Oct 8 - Sat, Oct 11

6:00 am - 12:12 amORD-PDX

20h 12m1 stop

6:05 am - 9:37 amPDX-ORD

25h 32m1 stop

$184Frontier

Find Deal

Fri, Oct 3 - Sun, Oct 5

5:35 am - 12:12 amORD-PDX

20h 37m1 stop

12:43 pm - 11:53 pmPDX-ORD

9h 10m1 stop

$185Frontier

Find Deal

Thu, Oct 2 - Wed, Oct 15

7:00 am - 9:39 amORD-PDX

4h 39mnonstop

7:00 am - 1:09 pmPDX-ORD

4h 09mnonstop

$203Alaska Airlines

Find Deal

Fri, Oct 31 - Tue, Nov 11

8:20 am - 10:35 amMDW-PDX

4h 15mnonstop

6:00 am - 12:00 pmPDX-MDW

4h 00mnonstop

$205Southwest

Find Deal

Sat, Sep 6 - Sat, Sep 13

3:45 pm - 6:05 pmMDW-PDX

4h 20mnonstop

10:15 am - 9:30 pmPDX-MDW

9h 15m1 stop

$213Southwest

Find Deal

Sat, Oct 25 - Fri, Oct 31

1:05 pm - 3:25 pmORD-PDX

4h 20mnonstop

11:59 pm - 6:00 amPDX-ORD

4h 01mnonstop

$214United Airlines

Find Deal

Fri, Sep 5 - Thu, Sep 25

4:05 pm - 6:31 pmORD-PDX

4h 26mnonstop

4:07 pm - 11:59 pmPDX-ORD

5h 52m1 stop

$215United Airlines

Find Deal

Sat, Sep 6 - Sat, Sep 13

7:00 am - 9:39 amORD-PDX

4h 39mnonstop

1:38 pm - 12:24 amPDX-ORD

8h 46m1 stop

$218Alaska Airlines

Find Deal

Fri, Oct 31 - Sat, Nov 8

2:07 pm - 4:37 pmORD-PDX

4h 30mnonstop

5:50 pm - 12:04 amPDX-ORD

4h 14mnonstop

$231Hawaiian Airlines

Find Deal

Wed, Sep 17 - Sat, Sep 20

Spirit Airlines flights from Chicago to Portland

Our best Spirit Airlines deals on Chicago to Portland flight tickets

Spirit Airlines

Oct 7

ORD6:40 amChicago O'Hare Intl

14h 56m

1 stop

PDX7:36 pmPortland

Oct 11

PDX8:36 pmPortland

6h 59m

1 stop

ORD5:35 amChicago O'Hare Intl

$186

Find similar

Spirit Airlines

Oct 14

ORD6:40 amChicago O'Hare Intl

14h 56m

1 stop

PDX7:36 pmPortland

Oct 18

PDX8:36 pmPortland

6h 59m

1 stop

ORD5:35 amChicago O'Hare Intl

$188

Find similar

Spirit Airlines

Sep 5

ORD6:15 amChicago O'Hare Intl

6h 56m

1 stop

PDX11:11 amPortland

Sep 10

PDX12:07 pmPortland

7h 25m

1 stop

ORD9:32 pmChicago O'Hare Intl

$195

Find similar

Frontier flights from Chicago to Portland

Our best Frontier deals on Chicago to Portland flight tickets

Frontier

Oct 3

ORD6:00 amChicago O'Hare Intl

20h 12m

1 stop

PDX12:12 amPortland

Oct 5

PDX6:05 amPortland

25h 32m

1 stop

ORD9:37 amChicago O'Hare Intl

$184

Find similar

Frontier

Oct 2

ORD5:35 amChicago O'Hare Intl

20h 37m

1 stop

PDX12:12 amPortland

Oct 15

PDX12:43 pmPortland

9h 10m

1 stop

ORD11:53 pmChicago O'Hare Intl

$185

Find similar

Frontier

Sep 8

MDW4:48 pmChicago Midway

9h 24m

1 stop

PDX12:12 amPortland

Sep 15

PDX6:05 amPortland

7h 48m

1 stop

MDW3:53 pmChicago Midway

$189

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 10/8

6:35 am-7:36 pm

1 stop15h 01m

Portland

Sat 10/11

12:43 pm-11:53 pm

1 stop9h 10m

$182

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 10/3

6:00 am-12:12 am

1 stop20h 12m

Portland

Sun 10/5

6:05 am-9:37 am

1 stop25h 32m

$184

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 10/2

5:35 am-12:12 am

1 stop20h 37m

Portland

Wed 10/15

12:43 pm-11:53 pm

1 stop9h 10m

$185

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 10/31

7:00 am-9:39 am

Nonstop4h 39m

Portland

Tue 11/11

7:00 am-1:09 pm

Nonstop4h 09m

$203

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 9/6

8:20 am-10:35 am

Nonstop4h 15m

Portland

Sat 9/13

6:00 am-12:00 pm

Nonstop4h 00m

$205

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

3:45 pm-6:05 pm

Nonstop4h 20m

Portland

Fri 10/31

10:15 am-9:30 pm

1 stop9h 15m

$213

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 9/5

1:05 pm-3:25 pm

Nonstop4h 20m

Portland

Thu 9/25

11:59 pm-6:00 am

Nonstop4h 01m

$214

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 9/6

4:05 pm-6:31 pm

Nonstop4h 26m

Portland

Sat 9/13

4:07 pm-11:59 pm

1 stop5h 52m

$215

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 10/31

7:00 am-9:39 am

Nonstop4h 39m

Portland

Sat 11/8

1:38 pm-12:24 am

1 stop8h 46m

$218

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 9/17

2:07 pm-4:37 pm

Nonstop4h 30m

Portland

Sat 9/20

5:50 pm-12:04 am

Nonstop4h 14m

$231

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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 $271, 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 January to fly from Chicago, when ticket prices are also cheap, with an average price of $274.

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 $403.

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 $433 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 $332 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 $284 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.

Can stopping save me money on Chicago to Portland flights?

No. A direct flight is the cheapest option for a flight between Chicago to Portland.

How have Chicago to Portland flight prices changed over time?

As of August 2025, prices for Chicago to Portland flights are approximately 60% cheaper 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	$98
Fastest flight time	4h 10m
Direct flights	Every day
Airports in Portland	1 airport

The best one-way flight to Portland from Chicago in the past 72 hours is $98. The best round-trip flight deal from Chicago to Portland found on momondo in the last 72 hours is $249.

The fastest flight from Chicago to Portland takes 4h 10m

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 15m, 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 August 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 20.79% of all bookings. The subsequent popular models are Boeing 737 MAX 9 at 17.20%, Boeing 737-900 at 11.89%, and Airbus A321neo at 11.12%.
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 Alaska Airlines (27%), American Airlines (20%), 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 $86	Free Cancellation	Rating 6.3 8,029 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $108	Free Cancellation	Rating 5.8 3,201 reviews	Search Frontier flights
Delta	PriceFrom $123	Free Cancellation	Rating 7.9 7,981 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $134	Free Cancellation	Rating 7.8 2,679 reviews	Search Hawaiian Airlines flights
Alaska Airlines	PriceFrom $183	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $216	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $227	Free Cancellation	Rating 7.4 8,940 reviews	Search United Airlines flights
Southwest	PriceFrom $238	Free Cancellation	Rating 8.0 4,243 reviews	Search Southwest flights

Alaska Airlines Flights From Chicago to Portland
Alaska Airlines flight deals from Chicago to Portland start from $183 round-trip. Over the 9 Alaska Airlines flights for this route in a normal week, average airfare is usually $290 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, 4,243 ratings). Southwest flies from Chicago to Portland around 11 times per week, with deals starting from $238 round-trip and rising to an average price of around $443.

Lincoln City

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Salem

Astoria

Long Beach

Depoe Bay

Beaverton

Rockaway Beach

Hillsboro

Hood River

Gresham

McMinnville

Longview

Tigard

The Dalles

Pacific City

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.

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Cheap flights from Chicago to Portland from $93

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 10/24. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Chicago to Portland (CHI-PDX)

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Spirit Airlines flights from Chicago to Portland

Our best Spirit Airlines deals on Chicago to Portland flight tickets

Frontier flights from Chicago to Portland

Our best Frontier deals on Chicago to Portland flight tickets

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Use the filters below to find and compare flights from Chicago to Portland that are best for you.

See travel insights to Portland from

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 $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 $403.

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 $433 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.

Can stopping save me money on Chicago to Portland flights?

No. A direct flight is the cheapest option for a flight between Chicago to Portland.

How have Chicago to Portland flight prices changed over time?

As of August 2025, prices for Chicago to Portland flights are approximately 60% cheaper when compared to flights at the same time last year.

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

Frontier, Spirit Airlines, and Southwest 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: 54% 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 40m.

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 23m.

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

The number of flights available between Chicago and Portland is 23 per day as of August 2025. The most frequent departure time is 8:00PM, with 39% of daily flights leaving in the evening.

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

As of August 2025, there are 161 flights per week flying from Chicago to Portland. The most common day of the week flights depart is Mon, with 19% 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.