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

Las Vegas (LAS) was the most common stop: 53% of momondo users choosing 1-stop flights on this route connected there.

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

Flights connecting via Seattle (SEA) have the shortest average one-way travel time: 6h 00m.

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

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

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

Denver (DEN) has the shortest average layover time for this route: 1h 35m.

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

184 flights are operational weekly from Portland to Chicago as of August 2025. The most popular departure day for this route is Thu, with 20% of flights per week taking off on this day.

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

Flights via Denver (DEN) offer the lowest average round-trip price of $135.

What airlines fly to Chicago?

United Airlines, Alaska Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Portland according to our data. United Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 8 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

The number of flights available between Portland and Chicago is 26 per day as of August 2025. The most frequent departure time is 7:00AM, with 56% of daily flights leaving at noon.

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

Prices for flights from Portland Airport to Chicago are refreshed on a daily basis.

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

There are 8 operators available for flights from Portland Airport to Chicago as of August 2025.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$106 Cheap Flights from Portland to Chicago (PDX-CHI) in 2025

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

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

7:15 am - 9:28 pmPDX-ORD

12h 13m1 stop

10:42 am - 12:12 amORD-PDX

15h 30m1 stop

$179Frontier

Find Deal

Tue, Sep 9 - Mon, Sep 15

1:20 pm - 7:15 pmPDX-MDW

3h 55mnonstop

2:10 pm - 4:25 pmMDW-PDX

4h 15mnonstop

$179Southwest

Find Deal

Sun, Aug 31 - Sat, Sep 6

3:26 pm - 12:15 amPDX-ORD

6h 49m1 stop

6:00 am - 11:56 amORD-PDX

7h 56m1 stop

$181Frontier

Find Deal

Fri, Nov 7 - Mon, Nov 10

7:52 pm - 4:50 amPDX-ORD

6h 58m1 stop

9:00 am - 11:11 amORD-PDX

28h 11m1 stop

$184Spirit Airlines

Find Deal

Wed, Sep 3 - Tue, Sep 9

12:07 pm - 9:32 pmPDX-ORD

7h 25m1 stop

7:09 pm - 11:11 amORD-PDX

18h 02m2 stops

$192Spirit Airlines

Find Deal

Tue, Sep 9 - Tue, Sep 16

6:07 am - 12:12 pmPDX-ORD

4h 05mnonstop

8:05 am - 10:28 amORD-PDX

4h 23mnonstop

$227American Airlines

Find Deal

Wed, Sep 24 - Sat, Sep 27

2:15 pm - 8:25 pmPDX-ORD

4h 10mnonstop

7:55 pm - 10:30 pmORD-PDX

4h 35mnonstop

$229United Airlines

Find Deal

Tue, Sep 16 - Tue, Sep 30

10:51 am - 4:59 pmPDX-ORD

4h 08mnonstop

7:50 pm - 10:25 pmORD-PDX

4h 35mnonstop

$231United Airlines

Find Deal

Sat, Sep 13 - Tue, Sep 16

12:40 am - 8:46 amPDX-MDW

6h 06m1 stop

2:00 pm - 8:25 pmMDW-PDX

8h 25m1 stop

$234Delta

Find Deal

Wed, Nov 19 - Mon, Nov 24

6:00 am - 3:23 pmPDX-MDW

7h 23m1 stop

1:43 pm - 8:59 pmMDW-PDX

9h 16m1 stop

$239Delta

Find Deal

Sun, Aug 31 - Sat, Sep 6

Frontier flights from Portland to Chicago

Our best Frontier deals on Portland to Chicago flight tickets

Frontier

Sep 9

PDX7:15 amPortland

12h 13m

1 stop

ORD9:28 pmChicago O'Hare Intl

Sep 15

ORD10:42 amChicago O'Hare Intl

15h 30m

1 stop

PDX12:12 amPortland

$179

Find similar

Frontier

Nov 7

PDX3:26 pmPortland

6h 49m

1 stop

ORD12:15 amChicago O'Hare Intl

Nov 10

ORD6:00 amChicago O'Hare Intl

7h 56m

1 stop

PDX11:56 amPortland

$181

Find similar

Frontier

Sep 17

PDX7:15 amPortland

12h 13m

1 stop

ORD9:28 pmChicago O'Hare Intl

Sep 20

ORD8:25 amChicago O'Hare Intl

16h 09m

1 stop

PDX10:34 pmPortland

$186

Find similar

Spirit Airlines flights from Portland to Chicago

Our best Spirit Airlines deals on Portland to Chicago flight tickets

Spirit Airlines

Sep 3

PDX7:52 pmPortland

6h 58m

1 stop

ORD4:50 amChicago O'Hare Intl

Sep 9

ORD9:00 amChicago O'Hare Intl

28h 11m

1 stop

PDX11:11 amPortland

$184

Find similar

Spirit Airlines

Sep 9

PDX12:07 pmPortland

7h 25m

1 stop

ORD9:32 pmChicago O'Hare Intl

Sep 16

ORD7:09 pmChicago O'Hare Intl

18h 02m

2 stops

PDX11:11 amPortland

$192

Find similar

Spirit Airlines

Aug 30

PDX7:52 pmPortland

6h 58m

1 stop

ORD4:50 amChicago O'Hare Intl

Sep 2

ORD6:00 amChicago O'Hare Intl

14h 57m

1 stop

PDX6:57 pmPortland

$194

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 9/9

7:15 am-9:28 pm

1 stop12h 13m

Chicago O'Hare Intl

Mon 9/15

10:42 am-12:12 am

1 stop15h 30m

$179

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sun 8/31

1:20 pm-7:15 pm

Nonstop3h 55m

Chicago Midway

Sat 9/6

2:10 pm-4:25 pm

Nonstop4h 15m

$179

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 11/7

3:26 pm-12:15 am

1 stop6h 49m

Chicago O'Hare Intl

Mon 11/10

6:00 am-11:56 am

1 stop7h 56m

$181

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 9/3

7:52 pm-4:50 am

1 stop6h 58m

Chicago O'Hare Intl

Tue 9/9

9:00 am-11:11 am

1 stop28h 11m

$184

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 9/9

12:07 pm-9:32 pm

1 stop7h 25m

Chicago O'Hare Intl

Tue 9/16

7:09 pm-11:11 am

2 stops18h 02m

$192

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 9/24

6:07 am-12:12 pm

Nonstop4h 05m

Chicago O'Hare Intl

Sat 9/27

8:05 am-10:28 am

Nonstop4h 23m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 9/16

2:15 pm-8:25 pm

Nonstop4h 10m

Chicago O'Hare Intl

Tue 9/30

7:55 pm-10:30 pm

Nonstop4h 35m

$229

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 9/13

10:51 am-4:59 pm

Nonstop4h 08m

Chicago O'Hare Intl

Tue 9/16

7:50 pm-10:25 pm

Nonstop4h 35m

$231

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 11/19

12:40 am-8:46 am

1 stop6h 06m

Chicago Midway

Mon 11/24

2:00 pm-8:25 pm

1 stop8h 25m

$234

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sun 8/31

6:00 am-3:23 pm

1 stop7h 23m

Chicago Midway

Sat 9/6

1:43 pm-8:59 pm

1 stop9h 16m

$239

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Portland to Chicago

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 Portland and Chicago?

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Portland, with most prices found around $272. If you’re not able to fly to Chicago in January, then August is your next best option. Flight prices from Portland to Chicago during August average around $283.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $452. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Portland to Chicago for around $569.

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

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Portland to Chicago during this time can be as low as $309. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $507.

What is the cheapest Portland to Chicago flight route?

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

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

You are more likely to see cheaper flights to Chicago from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $359 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Portland for as low as $298 on momondo.

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

There are 4 cabin classes available to choose from on Portland to Chicago 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 Portland to Chicago flights?

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

How have Portland to Chicago flight prices changed over time?

As of August 2025, prices for Portland to Chicago flights are approximately 57% cheaper when compared to flights at the same time last year.

When to book flights from Portland to Chicago

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

Estimated round-trip price

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

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

Best Price Found	$167
Fastest flight time	3h 50m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Portland in the past 72 hours is $167. The best round-trip flight deal from Portland to Chicago found on momondo in the last 72 hours is $238.

The fastest flight from Portland to Chicago takes 3h 50m

Direct flights go from Portland to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

How far is Portland to Chicago by plane?
Portland and Chicago are 1753.4 mi apart from one another. A reasonable flight in good conditions will take 3h 50m.
When did momondo last update prices for flights from Portland Airport to Chicago?
Prices for flights from Portland Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Portland Airport to Chicago?
There are 8 operators available for flights from Portland Airport to Chicago as of August 2025.
How old do you have to be to fly from Portland Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Portland to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Portland to Chicago is Boeing 737 MAX 9 (20.28% of total bookings). The next most popular plane models are Boeing 737-900 (11.98%), Airbus A321neo (11.87%), and Boeing 737-800 (11.81%).
What is the most popular airline from Portland to Chicago?
momondo data reveals that the most frequently booked airline on the route from Portland to Chicago is United Airlines, representing 35% of all bookings. The subsequent popular airlines are Alaska Airlines at 25%, American Airlines at 18%, and Southwest at 10%.

Best airlines flying from Portland to Chicago

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

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $96	Free Cancellation	Rating 6.3 8,035 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $108	Free Cancellation	Rating 5.8 3,207 reviews	Search Frontier flights
Delta	PriceFrom $123	Free Cancellation	Rating 7.9 7,981 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $125	Free Cancellation	Rating 7.8 2,672 reviews	Search Hawaiian Airlines flights
Alaska Airlines	PriceFrom $195	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $199	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $223	Free Cancellation	Rating 7.4 8,930 reviews	Search United Airlines flights
Southwest	PriceFrom $233	Free Cancellation	Rating 8.0 4,245 reviews	Search Southwest flights

Alaska Airlines Flights From Portland to Chicago
Alaska Airlines flies from Portland to Chicago around 7 times per week, with 10,000 momondo users rating the airline 8.0/10. The cheapest Alaska Airlines deal from Portland to Chicago in the last 72 hours was $195 (round-trip), much lower than the average airfare cost of $341 for Alaska Airlines flights on this route.
Southwest Flights From Portland to Chicago
Another popular option for Portland to Chicago flights is Southwest (8.0/10, 4,245 ratings). Southwest flies from Portland to Chicago around 15 times per week, with deals starting from $233 round-trip and rising to an average price of around $416.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Portland.

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

Flights from Portland to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Portland to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Portland to Chicago 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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Flights to Denverfrom $50

Cheap flights from Portland to Chicago from $106

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland to Chicago departing on 9/20. 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 Portland to Chicago (PDX-CHI)

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

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Frontier flights from Portland to Chicago

Our best Frontier deals on Portland to Chicago flight tickets

Spirit Airlines flights from Portland to Chicago

Our best Spirit Airlines deals on Portland to Chicago flight tickets

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Portland to Chicago

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 Portland and Chicago?

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Portland, with most prices found around $272. If you’re not able to fly to Chicago in January, then August is your next best option. Flight prices from Portland to Chicago during August average around $283.

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Portland to Chicago during this time can be as low as $309. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $507.

What is the cheapest Portland to Chicago flight route?

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

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

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

There are 4 cabin classes available to choose from on Portland to Chicago 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 Portland to Chicago flights?

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

How have Portland to Chicago flight prices changed over time?

As of August 2025, prices for Portland to Chicago flights are approximately 57% cheaper when compared to flights at the same time last year.

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

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

What airlines fly to Chicago?

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

Las Vegas (LAS) was the most common stop: 53% of momondo users choosing 1-stop flights on this route connected there.

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

Flights via Denver (DEN) offer the lowest average round-trip price of $135.

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

Flights connecting via Seattle (SEA) have the shortest average one-way travel time: 6h 00m.

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

Denver (DEN) has the shortest average layover time for this route: 1h 35m.

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

The number of flights available between Portland and Chicago is 26 per day as of August 2025. The most frequent departure time is 7:00AM, with 56% of daily flights leaving at noon.

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

184 flights are operational weekly from Portland to Chicago as of August 2025. The most popular departure day for this route is Thu, with 20% of flights per week taking off on this day.

When to book flights from Portland to Chicago

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Portland to Chicago by plane?

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

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

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

What documentation or ID do you need to fly to Chicago?

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

What is the most popular airline from Portland to Chicago?

Best airlines flying from Portland to Chicago

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

Alaska Airlines Flights From Portland to Chicago

Southwest Flights From Portland to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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.