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

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

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.

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

Las Vegas (LAS) was the most common stop: 78% of momondo users choosing 1-stop flights on this route connected there.

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

185 flights are operational weekly from Portland to Chicago as of October 2025. The most popular departure day for this route is Thu, with 17% of flights per week taking off on this day.

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 October 2025. The most frequent departure time is 7:00AM, with 63% of daily flights leaving at noon.

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

Flights via Las Vegas (LAS) offer the lowest average round-trip price of $200.

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

Seattle (SEA) has the shortest average layover time for this route: 1h 48m.

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.

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 October 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.

$108 Cheap Flights from Portland to Chicago in 2025/26

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

3:26 pm - 12:16 amPDX-ORD

6h 50m1 stop

5:00 am - 10:56 amORD-PDX

7h 56m1 stop

$213Frontier

Find Deal

Fri, Oct 31 - Sun, Nov 2

11:00 pm - 5:01 amPDX-ORD

4h 01mnonstop

7:00 am - 9:39 amORD-PDX

4h 39mnonstop

$217Alaska Airlines

Find Deal

Thu, Oct 30 - Mon, Nov 3

12:43 pm - 11:53 pmPDX-ORD

9h 10m1 stop

7:00 am - 9:39 amORD-PDX

4h 39mnonstop

$220Multiple Airlines

Find Deal

Sat, Oct 25 - Mon, Oct 27

2:31 pm - 11:59 pmPDX-ORD

7h 28m1 stop

5:00 am - 9:32 amORD-PDX

6h 32m1 stop

$226Alaska Airlines

Find Deal

Wed, Oct 29 - Sun, Nov 2

7:00 am - 1:04 pmPDX-ORD

4h 04mnonstop

7:45 am - 12:36 pmORD-PDX

6h 51m1 stop

$232Hawaiian Airlines

Find Deal

Tue, Mar 10 - Wed, Mar 11

11:30 am - 9:15 pmPDX-MDW

7h 45m1 stop

3:40 pm - 10:05 pmMDW-PDX

8h 25m1 stop

$236Southwest

Find Deal

Thu, Jan 22 - Mon, Jan 26

11:59 pm - 5:52 amPDX-ORD

3h 53mnonstop

6:15 pm - 10:56 pmORD-PDX

6h 41m1 stop

$242United Airlines

Find Deal

Mon, Nov 17 - Sat, Nov 22

7:25 am - 5:15 pmPDX-MDW

7h 50m1 stop

8:10 am - 3:40 pmMDW-PDX

9h 30m2 stops

$242Southwest

Find Deal

Thu, Jan 22 - Mon, Jan 26

11:43 am - 5:55 pmPDX-ORD

4h 12mnonstop

8:14 am - 10:48 amORD-PDX

4h 34mnonstop

$252American Airlines

Find Deal

Tue, Nov 4 - Tue, Nov 11

11:43 am - 5:55 pmPDX-ORD

4h 12mnonstop

8:14 am - 10:48 amORD-PDX

4h 34mnonstop

$253American Airlines

Find Deal

Tue, Nov 4 - Tue, Nov 11

Frontier flights from Portland to Chicago

Our best Frontier deals on Portland to Chicago flight tickets

Frontier

Oct 31

PDX3:26 pmPortland

6h 50m

1 stop

ORD12:16 amChicago O'Hare Intl

Nov 2

ORD5:00 amChicago O'Hare Intl

7h 56m

1 stop

PDX10:56 amPortland

$213

Find similar

Frontier

Oct 22

PDX12:43 pmPortland

9h 10m

1 stop

ORD11:53 pmChicago O'Hare Intl

Oct 26

ORD9:54 pmChicago O'Hare Intl

40h 02m

2 stops

PDX11:56 amPortland

$228

Find similar

Frontier

Nov 7

PDX3:26 pmPortland

30h 03m

1 stop

ORD11:29 pmChicago O'Hare Intl

Nov 9

ORD10:43 pmChicago O'Hare Intl

17h 48m

2 stops

PDX2:31 pmPortland

$229

Find similar

Alaska Airlines flights from Portland to Chicago

Our best Alaska Airlines deals on Portland to Chicago flight tickets

Alaska Airlines

Oct 30

PDX11:00 pmPortland

4h 01m

ORD5:01 amChicago O'Hare Intl

Nov 3

ORD7:00 amChicago O'Hare Intl

4h 39m

PDX9:39 amPortland

$217

Find similar

Alaska Airlines

Oct 29

PDX2:31 pmPortland

7h 28m

1 stop

ORD11:59 pmChicago O'Hare Intl

Nov 2

ORD5:00 amChicago O'Hare Intl

6h 32m

1 stop

PDX9:32 amPortland

$226

Find similar

Alaska Airlines

Nov 18

PDX7:00 amPortland

4h 09m

ORD1:09 pmChicago O'Hare Intl

Nov 27

ORD7:00 amChicago O'Hare Intl

4h 39m

PDX9:39 amPortland

$233

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/31

3:26 pm-12:16 am

1 stop6h 50m

Chicago O'Hare Intl

Sun 11/2

5:00 am-10:56 am

1 stop7h 56m

$213

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 10/30

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Mon 11/3

7:00 am-9:39 am

Nonstop4h 39m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 10/25

12:43 pm-11:53 pm

1 stop9h 10m

Chicago O'Hare Intl

Mon 10/27

7:00 am-9:39 am

Nonstop4h 39m

$220

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 10/29

2:31 pm-11:59 pm

1 stop7h 28m

Chicago O'Hare Intl

Sun 11/2

5:00 am-9:32 am

1 stop6h 32m

$226

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 3/10

7:00 am-1:04 pm

Nonstop4h 04m

Chicago O'Hare Intl

Wed 3/11

7:45 am-12:36 pm

1 stop6h 51m

$232

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 1/22

11:30 am-9:15 pm

1 stop7h 45m

Chicago Midway

Mon 1/26

3:40 pm-10:05 pm

1 stop8h 25m

$236

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 11/17

11:59 pm-5:52 am

Nonstop3h 53m

Chicago O'Hare Intl

Sat 11/22

6:15 pm-10:56 pm

1 stop6h 41m

$242

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 1/22

7:25 am-5:15 pm

1 stop7h 50m

Chicago Midway

Mon 1/26

8:10 am-3:40 pm

2 stops9h 30m

$242

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 11/4

11:43 am-5:55 pm

Nonstop4h 12m

Chicago O'Hare Intl

Tue 11/11

8:14 am-10:48 am

Nonstop4h 34m

$252

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 11/4

11:43 am-5:55 pm

Nonstop4h 12m

Chicago O'Hare Intl

Tue 11/11

8:14 am-10:48 am

Nonstop4h 34m

$253

Flights are sorted by cheapest round-trip flights first.

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 cheapest month to fly to Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from Portland, with most prices found around $293. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Portland to Chicago during September average around $293.

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 $440. 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 $555.

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 $314. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $495.

What is the cheapest Portland to Chicago flight route?

Fly from Portland to Chicago O'Hare Intl 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 $360 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 $293 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 October 2025, prices for Portland to Chicago flights are approximately 36% more expensive 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	$173
Fastest flight time	3h 44m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Portland in the past 72 hours is $173. The best round-trip flight deal from Portland to Chicago found on momondo in the last 72 hours is $320.

The fastest flight from Portland to Chicago takes 3h 44m

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 October 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 (20.70% of total bookings). The next most popular plane models are Boeing 737-800 (16.87%), Boeing 737-900 (11.87%), and Airbus A321neo (11.17%).
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 34% of all bookings. The subsequent popular airlines are Alaska Airlines at 23%, American Airlines at 21%, and Southwest at 11%.

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
Frontier	PriceFrom $94	Free Cancellation	Rating 5.8 3,144 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $119	Free Cancellation	Rating 6.3 8,083 reviews	Search Spirit Airlines flights
Delta	PriceFrom $123	Free Cancellation	Rating 7.9 7,968 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $125	Free Cancellation	Rating 7.8 2,774 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $192	Free Cancellation	Rating 7.2 11,043 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $197	Free Cancellation	Rating 8.0 11,045 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $223	Free Cancellation	Rating 7.4 8,966 reviews	Search United Airlines flights
Southwest	PriceFrom $238	Free Cancellation	Rating 8.0 4,236 reviews	Search Southwest flights

Alaska Airlines Flights From Portland to Chicago
Alaska Airlines flies from Portland to Chicago around 9 times per week, with 11,045 momondo users rating the airline 8.0/10. The cheapest Alaska Airlines deal from Portland to Chicago in the last 72 hours was $197 (round-trip), much lower than the average airfare cost of $322 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, 4,236 ratings). Southwest flies from Portland to Chicago around 12 times per week, with deals starting from $238 round-trip and rising to an average price of around $409.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

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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Cheap flights from Portland to Chicago from $108

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 11/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

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Price Alerts

Find the cheapest flights from Portland to Chicago

Cheap round-trip flights

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Cheap last minute flights

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Frontier flights from Portland to Chicago

Our best Frontier deals on Portland to Chicago flight tickets

Alaska Airlines flights from Portland to Chicago

Our best Alaska 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 cheapest month to fly to Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from Portland, with most prices found around $293. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Portland to Chicago during September average around $293.

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 $314. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $495.

What is the cheapest Portland to Chicago flight route?

Fly from Portland to Chicago O'Hare Intl 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 October 2025, prices for Portland to Chicago flights are approximately 36% more expensive when compared to flights at the same time last year.

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

Alaska Airlines, Delta, and Frontier 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: 78% 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 Las Vegas (LAS) offer the lowest average round-trip price of $200.

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?

Seattle (SEA) has the shortest average layover time for this route: 1h 48m.

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 October 2025. The most frequent departure time is 7:00AM, with 63% of daily flights leaving at noon.

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

185 flights are operational weekly from Portland to Chicago as of October 2025. The most popular departure day for this route is Thu, with 17% 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.

Get notified when prices go down