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.

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

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

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 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 43% 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 14 per day as of November 2025. The most frequent departure time is 7:00AM, with 76% of daily flights leaving at noon.

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 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?

102 flights are operational weekly from Portland to Chicago as of November 2025. The most popular departure day for this route is Thu, with 22% of flights per week taking off on this day.

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 November 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.

$114 Cheap Flights from Portland to Chicago in 2025/26

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Find the cheapest flights from Portland to Chicago

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One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:32 am - 8:40 amPDX-ORD

6h 08m1 stop

1:35 pm - 10:40 pmORD-PDX

11h 05m2 stops

$246Delta

Find Deal

dom., dic. 14 - lun., dic. 15

5:55 am - 3:55 pmPDX-MDW

8h 00m1 stop

6:35 pm - 12:15 amMDW-PDX

7h 40m1 stop

$246Southwest

Find Deal

mar., dic. 9 - vie., dic. 12

7:05 am - 1:10 pmPDX-ORD

4h 05mnonstop

3:35 pm - 8:47 pmORD-PDX

7h 12m1 stop

$247Alaska Airlines

Find Deal

dom., feb. 1 - vie., feb. 6

11:20 pm - 8:54 amPDX-MDW

7h 34m1 stop

1:50 pm - 8:52 pmMDW-PDX

9h 02m1 stop

$247Delta

Find Deal

jue., dic. 11 - sáb., dic. 13

12:05 pm - 2:05 pmPDX-MDW

24h 00m1 stop

6:10 am - 11:04 amMDW-PDX

30h 54m2 stops

$248Frontier

Find Deal

jue., ene. 8 - mié., ene. 14

7:10 am - 5:44 pmPDX-ORD

8h 34m2 stops

7:30 am - 12:44 pmORD-PDX

7h 14m1 stop

$248Delta

Find Deal

jue., ene. 8 - mié., ene. 14

12:05 pm - 2:05 pmPDX-MDW

24h 00m1 stop

6:10 am - 11:04 amMDW-PDX

30h 54m2 stops

$249Frontier

Find Deal

jue., ene. 8 - mié., ene. 14

1:28 pm - 7:46 pmPDX-ORD

4h 18mnonstop

9:57 am - 12:38 pmORD-PDX

4h 41mnonstop

$250American Airlines

Find Deal

sáb., dic. 6 - sáb., dic. 13

1:24 pm - 9:15 pmPDX-ORD

5h 51m1 stop

5:16 pm - 11:06 pmORD-PDX

7h 50m1 stop

$252United Airlines

Find Deal

jue., ene. 22 - lun., ene. 26

11:00 pm - 5:02 amPDX-ORD

4h 02mnonstop

8:58 pm - 9:44 amORD-PDX

14h 46m1 stop

$253Alaska Airlines

Find Deal

jue., ene. 1 - dom., ene. 4

American Airlines flights from Portland to Chicago

Our best American Airlines deals on Portland to Chicago flight tickets

American Airlines

Dec 6

PDX1:28 pmPortland

4h 18m

ORD7:46 pmChicago O'Hare Intl

Dec 13

ORD9:57 amChicago O'Hare Intl

4h 41m

PDX12:38 pmPortland

$250

Find similar

American Airlines

Dec 9

PDX11:37 amPortland

4h 15m

ORD5:52 pmChicago O'Hare Intl

Dec 12

ORD9:57 amChicago O'Hare Intl

4h 41m

PDX12:38 pmPortland

$263

Find similar

American Airlines

Dec 3

PDX11:37 amPortland

4h 15m

ORD5:52 pmChicago O'Hare Intl

Dec 9

ORD8:10 amChicago O'Hare Intl

4h 37m

PDX10:47 amPortland

$264

Find similar

Alaska Airlines flights from Portland to Chicago

Our best Alaska Airlines deals on Portland to Chicago flight tickets

Alaska Airlines

Dec 14

PDX9:44 pmPortland

6h 37m

1 stop

ORD6:21 amChicago O'Hare Intl

Dec 17

ORD8:00 amChicago O'Hare Intl

7h 50m

1 stop

PDX1:50 pmPortland

$246

Find similar

Alaska Airlines

Feb 1

PDX7:05 amPortland

4h 05m

ORD1:10 pmChicago O'Hare Intl

Feb 5

ORD8:00 amChicago O'Hare Intl

6h 38m

1 stop

PDX12:38 pmPortland

$247

Find similar

Alaska Airlines

Dec 31

PDX7:00 amPortland

4h 09m

ORD1:09 pmChicago O'Hare Intl

Jan 5

ORD6:00 amChicago O'Hare Intl

8h 13m

1 stop

PDX12:13 pmPortland

$251

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

dom. 12/14

12:32 am-8:40 am

1 stop6h 08m

Chicago O'Hare Intl

lun. 12/15

1:35 pm-10:40 pm

2 stops11h 05m

$246

PortlandChicago

PDX - MDW

PDXMDW

Portland

mar. 12/9

5:55 am-3:55 pm

1 stop8h 00m

Chicago Midway

vie. 12/12

6:35 pm-12:15 am

1 stop7h 40m

$246

PortlandChicago

PDX - ORD

PDXORD

Portland

dom. 2/1

7:05 am-1:10 pm

Nonstop4h 05m

Chicago O'Hare Intl

vie. 2/6

3:35 pm-8:47 pm

1 stop7h 12m

$247

PortlandChicago

PDX - MDW

PDXMDW

Portland

jue. 12/11

11:20 pm-8:54 am

1 stop7h 34m

Chicago Midway

sáb. 12/13

1:50 pm-8:52 pm

1 stop9h 02m

$247

PortlandChicago

PDX - MDW

PDXMDW

Portland

jue. 1/8

12:05 pm-2:05 pm

1 stop24h 00m

Chicago Midway

mié. 1/14

6:10 am-11:04 am

2 stops30h 54m

$248

PortlandChicago

PDX - ORD

PDXORD

Portland

jue. 1/8

7:10 am-5:44 pm

2 stops8h 34m

Chicago O'Hare Intl

mié. 1/14

7:30 am-12:44 pm

1 stop7h 14m

$248

PortlandChicago

PDX - MDW

PDXMDW

Portland

jue. 1/8

12:05 pm-2:05 pm

1 stop24h 00m

Chicago Midway

mié. 1/14

6:10 am-11:04 am

2 stops30h 54m

$249

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 12/6

1:28 pm-7:46 pm

Nonstop4h 18m

Chicago O'Hare Intl

sáb. 12/13

9:57 am-12:38 pm

Nonstop4h 41m

$250

PortlandChicago

PDX - ORD

PDXORD

Portland

jue. 1/22

1:24 pm-9:15 pm

1 stop5h 51m

Chicago O'Hare Intl

lun. 1/26

5:16 pm-11:06 pm

1 stop7h 50m

$252

PortlandChicago

PDX - ORD

PDXORD

Portland

jue. 1/1

11:00 pm-5:02 am

Nonstop4h 02m

Chicago O'Hare Intl

dom. 1/4

8:58 pm-9:44 am

1 stop14h 46m

$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 $434. 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 $557.

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 $316. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $493.

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 $356 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 November 2025, prices for Portland to Chicago flights are approximately 12% 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	$186
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 $186. The best round-trip flight deal from Portland to Chicago found on momondo in the last 72 hours is $287.

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 55m.
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 November 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 (19.50% of total bookings). The next most popular plane models are Boeing 737-800 (19.01%), Boeing 737-900 (13.18%), and Airbus A321neo (10.17%).
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 35% of all bookings. The subsequent popular airlines are American Airlines at 22%, Alaska Airlines at 22%, 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 3,105 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $119	Free Cancellation	Rating 6.3 8,156 reviews	Search Spirit Airlines flights
Delta	PriceFrom $123	Free Cancellation	Rating 7.9 8,002 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $125	Free Cancellation	Rating 7.8 2,811 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $192	Free Cancellation	Rating 7.2 11,045 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $197	Free Cancellation	Rating 8.0 11,321 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $222	Free Cancellation	Rating 7.4 9,027 reviews	Search United Airlines flights
Southwest	PriceFrom $246	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 7 times per week, with 11,321 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 $314 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 2 times per week, with deals starting from $246 round-trip and rising to an average price of around $404.

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 $114

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 2/18. 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

Trusted and free

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Find the cheapest flights from Portland to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

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American Airlines flights from Portland to Chicago

Our best American Airlines 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 $316. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $493.

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 November 2025, prices for Portland to Chicago flights are approximately 12% 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, Southwest, and Alaska Airlines 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 14 per day as of November 2025. The most frequent departure time is 7:00AM, with 76% of daily flights leaving at noon.

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

102 flights are operational weekly from Portland to Chicago as of November 2025. The most popular departure day for this route is Thu, with 22% 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