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

The number of flights available between Portland and Chicago is 9 per day as of January 2026. The most frequent departure time is 7:00AM, with 63% of daily flights leaving at noon.

What airlines fly to Chicago?

United Airlines, American Airlines and Alaska 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 42% 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: 60% 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 $188.

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

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

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 week?

66 flights are operational weekly from Portland to Chicago as of January 2026. The most popular departure day for this route is Tue, with 29% of flights per week taking off on this day.

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 January 2026.

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.

$109 Cheap Flights from Portland to Chicago in 2026

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

Prices are currently typical for flights on this route. Typical prices usually range from $219 to $462. The lowest price recently found on this route was $219.

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Find the cheapest flights from Portland to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

3:59 pm - 11:52 pm

PDX

ORD

5h 53m1 stop

7:40 am - 12:42 pm

ORD

PDX

7h 02m1 stop

$219Delta

Sat, Feb 14 - Tue, Feb 17

6:00 am - 4:14 pm

PDX

MDW

8h 14m1 stop

1:49 pm - 8:30 pm

MDW

PDX

8h 41m1 stop

$219Delta

Sat, Feb 14 - Tue, Feb 17

5:10 am - 11:05 am

PDX

MDW

3h 55mnonstop

6:45 am - 1:45 pm

MDW

PDX

9h 00m1 stop

$220Southwest

Thu, May 7 - Wed, May 13

12:40 am - 8:40 am

PDX

ORD

6h 00m1 stop

1:50 pm - 8:59 pm

ORD

PDX

9h 09m2 stops

$220Delta

Tue, Jan 27 - Fri, Jan 30

8:45 am - 6:30 pm

PDX

MDW

7h 45m2 stops

8:30 pm - 11:00 pm

MDW

PDX

4h 30mnonstop

$222Southwest

Sat, Jan 31 - Sat, Feb 14

1:24 pm - 9:15 pm

PDX

ORD

5h 51m1 stop

9:10 am - 11:57 am

ORD

PDX

4h 47mnonstop

$223United Airlines

Fri, Feb 6 - Sun, Feb 8

5:05 am - 6:45 pm

PDX

MDW

11h 40m2 stops

3:35 pm - 6:00 pm

MDW

PDX

4h 25mnonstop

$223Southwest

Wed, Jan 28 - Fri, Jan 30

11:48 am - 5:57 pm

PDX

ORD

4h 09mnonstop

8:25 am - 10:58 am

ORD

PDX

4h 33mnonstop

$224American Airlines

Thu, Feb 12 - Sun, Feb 22

7:05 am - 11:56 pm

PDX

ORD

14h 51m1 stop

2:07 pm - 4:50 pm

ORD

PDX

4h 43mnonstop

$225Alaska Airlines

Sun, Feb 22 - Wed, Feb 25

7:05 am - 1:10 pm

PDX

ORD

4h 05mnonstop

3:35 pm - 8:47 pm

ORD

PDX

7h 12m1 stop

$226Alaska Airlines

Tue, Feb 10 - Wed, Feb 11

Delta flights from Portland to Chicago

Our best Delta deals on Portland to Chicago flight tickets

Delta

Feb 14

PDX3:59 pmPortland

5h 53m

1 stop

ORD11:52 pmChicago O'Hare Intl

Feb 17

ORD7:40 amChicago O'Hare Intl

7h 02m

1 stop

PDX12:42 pmPortland

$219

Find similar

Delta

Jan 27

PDX12:40 amPortland

6h 00m

1 stop

ORD8:40 amChicago O'Hare Intl

Jan 30

ORD1:50 pmChicago O'Hare Intl

9h 09m

2 stops

PDX8:59 pmPortland

$220

Find similar

Delta

Jan 29

PDX12:40 amPortland

6h 28m

1 stop

MDW9:08 amChicago Midway

Feb 3

MDW12:46 pmChicago Midway

8h 27m

1 stop

PDX7:13 pmPortland

$224

Find similar

United Airlines flights from Portland to Chicago

Our best United Airlines deals on Portland to Chicago flight tickets

United Airlines

Feb 6

PDX1:24 pmPortland

5h 51m

1 stop

ORD9:15 pmChicago O'Hare Intl

Feb 8

ORD9:10 amChicago O'Hare Intl

4h 47m

PDX11:57 amPortland

$223

Find similar

United Airlines

Jan 30

PDX1:24 pmPortland

5h 51m

1 stop

ORD9:15 pmChicago O'Hare Intl

Feb 3

ORD4:15 pmChicago O'Hare Intl

4h 41m

PDX6:56 pmPortland

$233

Find similar

United Airlines

Mar 5

PDX11:59 pmPortland

3h 54m

ORD5:53 amChicago O'Hare Intl

Mar 8

ORD6:17 amChicago O'Hare Intl

8h 16m

1 stop

PDX12:33 pmPortland

$235

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 2/14

3:59 pm-11:52 pm

1 stop5h 53m

Chicago O'Hare Intl

Tue 2/17

7:40 am-12:42 pm

1 stop7h 02m

$219

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 2/14

6:00 am-4:14 pm

1 stop8h 14m

Chicago Midway

Tue 2/17

1:49 pm-8:30 pm

1 stop8h 41m

$219

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 5/7

5:10 am-11:05 am

Nonstop3h 55m

Chicago Midway

Wed 5/13

6:45 am-1:45 pm

1 stop9h 00m

$220

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 1/27

12:40 am-8:40 am

1 stop6h 00m

Chicago O'Hare Intl

Fri 1/30

1:50 pm-8:59 pm

2 stops9h 09m

$220

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 1/31

8:45 am-6:30 pm

2 stops7h 45m

Chicago Midway

Sat 2/14

8:30 pm-11:00 pm

Nonstop4h 30m

$222

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 2/6

1:24 pm-9:15 pm

1 stop5h 51m

Chicago O'Hare Intl

Sun 2/8

9:10 am-11:57 am

Nonstop4h 47m

$223

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 1/28

5:05 am-6:45 pm

2 stops11h 40m

Chicago Midway

Fri 1/30

3:35 pm-6:00 pm

Nonstop4h 25m

$223

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 2/12

11:48 am-5:57 pm

Nonstop4h 09m

Chicago O'Hare Intl

Sun 2/22

8:25 am-10:58 am

Nonstop4h 33m

$224

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 2/22

7:05 am-11:56 pm

1 stop14h 51m

Chicago O'Hare Intl

Wed 2/25

2:07 pm-4:50 pm

Nonstop4h 43m

$225

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 2/10

7:05 am-1:10 pm

Nonstop4h 05m

Chicago O'Hare Intl

Wed 2/11

3:35 pm-8:47 pm

1 stop7h 12m

$226

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

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 $291. 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 $430. 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 $533.

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 $320. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $483.

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 $350 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?

You could potentially save up to 1% on your flight if you consider stops on a Portland to Chicago flight.

How have Portland to Chicago flight prices changed over time?

As of January 2026, prices for Portland to Chicago flights are approximately 9% 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	$148
Fastest flight time	3h 44m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Portland in the past 72 hours is $148. The best round-trip flight deal from Portland to Chicago found on momondo in the last 72 hours is $303.

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

Direct flights go from Portland to Chicago every day.

There are 3 airports in Chicago. From Portland there are direct flights to 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 44m.
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 January 2026.
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 737-800 (23.92% of total bookings). The next most popular plane models are Boeing 737 MAX 9 (16.46%), Boeing 737-900 (16.13%), and Boeing 737 MAX 8 (15.19%).
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 American Airlines at 24%, Alaska Airlines at 21%, 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
Frontier	PriceFrom $96	Free Cancellation	Rating 5.7 3,063 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $119	Free Cancellation	Rating 6.3 8,285 reviews	Search Spirit Airlines flights
Delta	PriceFrom $123	Free Cancellation	Rating 7.9 8,023 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $125	Free Cancellation	Rating 7.8 2,824 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $196	Free Cancellation	Rating 7.2 11,091 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $218	Free Cancellation	Rating 8.0 11,660 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $220	Free Cancellation	Rating 7.4 9,138 reviews	Search United Airlines flights
Southwest	PriceFrom $238	Free Cancellation	Rating 8.0 4,249 reviews	Search Southwest flights

Alaska Airlines Flights From Portland to Chicago
Alaska Airlines flies from Portland to Chicago around 3 times per week, with 11,660 momondo users rating the airline 8.0/10. The cheapest Alaska Airlines deal from Portland to Chicago in the last 72 hours was $218 (round-trip), much lower than the average airfare cost of $350 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, 4,249 ratings). Southwest flies from Portland to Chicago around 5 times per week, with deals starting from $238 round-trip and rising to an average price of around $377.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

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 $38

Cheap flights from Portland to Chicago from $109

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 2/14. 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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Filter for what you want

Filter for what you want

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Delta flights from Portland to Chicago

Our best Delta deals on Portland to Chicago flight tickets

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Our best United 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

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 August is, on average, the cheapest month to fly to Chicago from Portland, with most prices found around $291. 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 $320. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $483.

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?

You could potentially save up to 1% on your flight if you consider stops on a Portland to Chicago flight.

How have Portland to Chicago flight prices changed over time?

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

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

United Airlines, Alaska Airlines, and Delta 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: 60% 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 $188.

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 9 per day as of January 2026. 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?

66 flights are operational weekly from Portland to Chicago as of January 2026. The most popular departure day for this route is Tue, with 29% 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