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

Flights via Las Vegas (LAS) offer the lowest average round-trip price of $135.

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

The number of flights available between Portland and Chicago is 15 per day as of February 2026. The most frequent departure time is 7:00AM, with 82% 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?

Seattle (SEA) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

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

American Airlines, Alaska Airlines, and United Airlines 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.

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.

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

111 flights are operational weekly from Portland to Chicago as of February 2026. The most popular departure day for this route is Tue, with 18% 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 February 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.

$107 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 low for flights on this route. Typical prices usually range from $268 to $536. The lowest price recently found on this route was $215.

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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.

12:52 pm - 6:08 am

PDX

ORD

15h 16m

1 stop

7:39 pm - 11:52 am

ORD

PDX

18h 13m

1 stop

$215Frontier

Mon, Mar 9 - Wed, Mar 11

10:56 pm - 5:00 am

PDX

ORD

4h 04mnonstop

7:20 am - 9:48 am

ORD

PDX

4h 28mnonstop

$217Alaska Airlines

Wed, Jul 8 - Wed, Jul 15

11:55 pm - 5:45 am

PDX

MDW

3h 50mnonstop

8:50 pm - 11:10 pm

MDW

PDX

4h 20mnonstop

$231Southwest

Wed, Apr 1 - Wed, Apr 8

11:15 pm - 8:47 am

PDX

MDW

7h 32m

1 stop

2:12 pm - 8:07 pm

MDW

PDX

7h 55m

1 stop

$232Delta

Thu, Apr 16 - Sat, Apr 18

6:10 pm - 6:00 am

PDX

MDW

9h 50m

1 stop

6:05 pm - 8:25 pm

MDW

PDX

4h 20mnonstop

$234Southwest

Wed, Apr 15 - Sat, Apr 18

11:15 pm - 8:53 am

PDX

MDW

7h 38m

1 stop

2:05 pm - 8:25 pm

MDW

PDX

8h 20m

1 stop

$251Delta

Tue, Mar 31 - Wed, Apr 8

7:46 pm - 7:45 pm

PDX

RFD

21h 59m

1 stop

2:51 pm - 6:56 pm

RFD

PDX

30h 05m

1 stop

$350Allegiant Air

Thu, Apr 23 - Wed, Apr 29

7:46 pm - 7:45 pm

PDX

RFD

21h 59m

1 stop

8:35 pm - 1:02 pm

RFD

PDX

18h 27m

2 stops

$356Multiple Airlines

Thu, Apr 9 - Mon, Apr 13

1:48 pm - 12:00 pm

PDX

RFD

20h 12m

2 stops

2:51 pm - 6:56 pm

RFD

PDX

30h 05m

1 stop

$361Multiple Airlines

Wed, Apr 22 - Wed, Apr 29

7:56 pm - 8:00 pm

PDX

RFD

22h 04m

1 stop

8:20 pm - 7:02 pm

RFD

PDX

24h 42m

1 stop

$515Allegiant Air

Thu, Mar 12 - Wed, Mar 18

Frontier flights from Portland to Chicago

Our best Frontier deals on Portland to Chicago flight tickets

Frontier

Mar 9

PDX12:52 pmPortland

15h 16m

1 stop

ORD6:08 amChicago O'Hare Intl

Mar 11

ORD7:39 pmChicago O'Hare Intl

18h 13m

1 stop

PDX11:52 amPortland

$215

Frontier

Mar 8

PDX9:53 amPortland

16h 56m

1 stop

ORD4:49 amChicago O'Hare Intl

Mar 11

ORD7:39 pmChicago O'Hare Intl

18h 13m

1 stop

PDX11:52 amPortland

$220

Frontier

May 8

PDX9:53 amPortland

17h 57m

1 stop

ORD5:50 amChicago O'Hare Intl

May 11

ORD10:55 amChicago O'Hare Intl

28h 07m

1 stop

PDX1:02 pmPortland

$222

Alaska Airlines flights from Portland to Chicago

Our best Alaska Airlines deals on Portland to Chicago flight tickets

Alaska Airlines

Jul 8

PDX10:56 pmPortland

4h 04m

ORD5:00 amChicago O'Hare Intl

Jul 15

ORD7:20 amChicago O'Hare Intl

4h 28m

PDX9:48 amPortland

$217

Alaska Airlines

Mar 5

PDX1:36 pmPortland

8h 20m

1 stop

ORD11:56 pmChicago O'Hare Intl

Mar 11

ORD2:07 pmChicago O'Hare Intl

4h 43m

PDX4:50 pmPortland

$219

Alaska Airlines

Mar 9

PDX1:36 pmPortland

8h 20m

1 stop

ORD11:56 pmChicago O'Hare Intl

Mar 10

ORD2:07 pmChicago O'Hare Intl

4h 43m

PDX4:50 pmPortland

$221

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 3/9

12:52 pm-6:08 am

1 stop15h 16m

Chicago O'Hare Intl

Wed 3/11

7:39 pm-11:52 am

1 stop18h 13m

$215

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 7/8

10:56 pm-5:00 am

Nonstop4h 04m

Chicago O'Hare Intl

Wed 7/15

7:20 am-9:48 am

Nonstop4h 28m

$217

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 4/1

11:55 pm-5:45 am

Nonstop3h 50m

Chicago Midway

Wed 4/8

8:50 pm-11:10 pm

Nonstop4h 20m

$231

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 4/16

11:15 pm-8:47 am

1 stop7h 32m

Chicago Midway

Sat 4/18

2:12 pm-8:07 pm

1 stop7h 55m

$232

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 4/15

6:10 pm-6:00 am

1 stop9h 50m

Chicago Midway

Sat 4/18

6:05 pm-8:25 pm

Nonstop4h 20m

$234

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 3/31

11:15 pm-8:53 am

1 stop7h 38m

Chicago Midway

Wed 4/8

2:05 pm-8:25 pm

1 stop8h 20m

$251

PortlandChicago

PDX - RFD

PDXRFD

Portland

Thu 4/23

7:46 pm-7:45 pm

1 stop21h 59m

Chicago Greater Rockford

Wed 4/29

2:51 pm-6:56 pm

1 stop30h 05m

$350

PortlandChicago

PDX - RFD

PDXRFD

Portland

Thu 4/9

7:46 pm-7:45 pm

1 stop21h 59m

Chicago Greater Rockford

Mon 4/13

8:35 pm-1:02 pm

2 stops18h 27m

$356

PortlandChicago

PDX - RFD

PDXRFD

Portland

Wed 4/22

1:48 pm-12:00 pm

2 stops20h 12m

Chicago Greater Rockford

Wed 4/29

2:51 pm-6:56 pm

1 stop30h 05m

$361

PortlandChicago

PDX - RFD

PDXRFD

Portland

Thu 3/12

7:56 pm-8:00 pm

1 stop22h 04m

Chicago Greater Rockford

Wed 3/18

8:20 pm-7:02 pm

1 stop24h 42m

$515

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 January is, on average, the cheapest month to fly to Chicago from Portland, with most prices found around $237. 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 $289.

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 $426. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, 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 $313. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $476.

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 $346 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 $295 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 February 2026, prices for Portland to Chicago flights are approximately 17% 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	$168
Fastest flight time	3h 50m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Portland in the past 72 hours is $168. The best round-trip flight deal from Portland to Chicago found on momondo in the last 72 hours is $327.

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

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 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 February 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 (31.81% of total bookings). The next most popular plane models are Boeing 737 MAX 9 (14.51%), Boeing 737-900 (12.82%), and Boeing 737 MAX 8 (11.66%).
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 American Airlines at 26%, Alaska Airlines at 20%, 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 $86	Free Cancellation	Rating 5.7 3,047 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $93	Free Cancellation	Rating 6.3 8,464 reviews	Search Spirit Airlines flights
Delta	PriceFrom $99	Free Cancellation	Rating 7.9 8,205 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $125	Free Cancellation	Rating 7.8 2,833 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $192	Free Cancellation	Rating 7.2 11,294 reviews	Search American Airlines flights
United Airlines	PriceFrom $199	Free Cancellation	Rating 7.4 9,308 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom $209	Free Cancellation	Rating 8.0 11,891 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $231	Free Cancellation	Rating 8.0 4,289 reviews	Search Southwest flights

Alaska Airlines Flights From Portland to Chicago
Alaska Airlines flies from Portland to Chicago around 6 times per week, with 11,891 momondo users rating the airline 8.0/10. The cheapest Alaska Airlines deal from Portland to Chicago in the last 72 hours was $209 (round-trip), much lower than the average airfare cost of $345 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, 4,289 ratings). Southwest flies from Portland to Chicago around 6 times per week, with deals starting from $231 round-trip and rising to an average price of around $376.

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.

An easier way to manage your Chicago trip

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Fly into one of these airports located in Chicago

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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 3/11. 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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Frontier flights from Portland to Chicago

Our best Frontier deals on Portland to Chicago flight tickets

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Our best Alaska Airlines deals on Portland to Chicago flight tickets

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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?

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?

What is the cheapest Portland to Chicago flight route?

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

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

Can stopping save me money on Portland to Chicago flights?

How have Portland to Chicago flight prices changed over time?

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

What airlines fly to Chicago?

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

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

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

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

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

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

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

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

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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Popular flights according to clicks in the last 7 days on momondo

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