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

The number of flights available between Portland and Chicago is 10 per day as of May 2026. The most frequent departure time is 7:00AM, with 62% of daily flights leaving at noon.

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

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

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

76 flights are operational weekly from Portland to Chicago as of May 2026. The most popular departure day for this route is Wed, with 37% of flights per week taking off on this day.

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 39% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 7 operators available for flights from Portland Airport to Chicago as of May 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.

$149 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 $422 to $300. The lowest price recently found on this route was $303.

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Find the cheapest flights from Portland to Chicago

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

12:26 pm - 8:52 pm

PDX

ORD

6h 26m

1 stop

7:15 am - 6:04 pm

ORD

PDX

12h 49m

1 stop

$303Frontier

Mon, Aug 3 - Mon, Aug 10

6:59 pm - 5:28 am

PDX

ORD

8h 29m

1 stop

7:15 am - 6:04 pm

ORD

PDX

12h 49m

1 stop

$304Frontier

Fri, Aug 7 - Mon, Aug 10

7:00 am - 1:13 pm

PDX

ORD

4h 13mnonstop

7:55 pm - 10:29 pm

ORD

PDX

4h 34mnonstop

$305United Airlines

Wed, May 27 - Thu, May 28

10:59 pm - 5:00 am

PDX

ORD

4h 01mnonstop

7:20 pm - 9:50 pm

ORD

PDX

4h 30mnonstop

$309American Airlines

Sat, Jun 27 - Fri, Jul 3

11:40 pm - 5:45 am

PDX

ORD

4h 05mnonstop

7:00 am - 9:34 am

ORD

PDX

4h 34mnonstop

$310United Airlines

Sat, Jun 27 - Wed, Jul 1

11:30 pm - 5:20 am

PDX

MDW

3h 50mnonstop

9:10 pm - 11:30 pm

MDW

PDX

4h 20mnonstop

$310Southwest

Wed, Jul 1 - Wed, Jul 8

10:59 pm - 5:00 am

PDX

ORD

4h 01mnonstop

9:30 pm - 12:05 am

ORD

PDX

4h 35mnonstop

$312American Airlines

Sat, Jun 27 - Fri, Jul 3

11:30 pm - 5:20 am

PDX

MDW

3h 50mnonstop

8:25 pm - 10:45 pm

MDW

PDX

4h 20mnonstop

$315Southwest

Sat, Jul 18 - Sat, Jul 25

12:33 am - 8:37 am

PDX

MDW

6h 04m

1 stop

7:16 pm - 11:18 pm

MDW

PDX

6h 02m

1 stop

$330Delta

Fri, Jun 26 - Fri, Jul 3

12:40 am - 8:38 am

PDX

MDW

5h 58m

1 stop

2:00 pm - 8:15 pm

MDW

PDX

8h 15m

1 stop

$335Delta

Mon, Sep 7 - Tue, Sep 15

American Airlines flights from Portland to Chicago

Our best American Airlines deals on Portland to Chicago flight tickets

American Airlines

Jun 27

PDX10:59 pmPortland

4h 01m

ORD5:00 amChicago O'Hare Intl

Jul 3

ORD7:20 pmChicago O'Hare Intl

4h 30m

PDX9:50 pmPortland

$309

American Airlines

Jun 27

PDX10:59 pmPortland

4h 01m

ORD5:00 amChicago O'Hare Intl

Jul 3

ORD9:30 pmChicago O'Hare Intl

4h 35m

PDX12:05 amPortland

$312

American Airlines

Jul 31

PDX11:15 pmPortland

3h 59m

ORD5:14 amChicago O'Hare Intl

Aug 1

ORD9:29 pmChicago O'Hare Intl

4h 35m

PDX12:04 amPortland

$323

Delta flights from Portland to Chicago

Our best Delta deals on Portland to Chicago flight tickets

Delta

May 24

PDX9:39 pmPortland

9h 00m

1 stop

ORD8:39 amChicago O'Hare Intl

May 28

ORD5:19 pmChicago O'Hare Intl

6h 43m

1 stop

PDX10:02 pmPortland

$325

Delta

Jun 26

PDX12:33 amPortland

6h 02m

1 stop

ORD8:35 amChicago O'Hare Intl

Jul 3

ORD5:57 pmChicago O'Hare Intl

7h 21m

1 stop

PDX11:18 pmPortland

$330

Delta

Jun 26

PDX12:33 amPortland

6h 02m

1 stop

ORD8:35 amChicago O'Hare Intl

Jul 7

ORD7:40 pmChicago O'Hare Intl

6h 04m

1 stop

PDX11:44 pmPortland

$335

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 8/3

12:26 pm-8:52 pm

1 stop6h 26m

Chicago O'Hare Intl

Mon 8/10

7:15 am-6:04 pm

1 stop12h 49m

$303

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 8/7

6:59 pm-5:28 am

1 stop8h 29m

Chicago O'Hare Intl

Mon 8/10

7:15 am-6:04 pm

1 stop12h 49m

$304

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 5/27

7:00 am-1:13 pm

Nonstop4h 13m

Chicago O'Hare Intl

Thu 5/28

7:55 pm-10:29 pm

Nonstop4h 34m

$305

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 6/27

10:59 pm-5:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Fri 7/3

7:20 pm-9:50 pm

Nonstop4h 30m

$309

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 6/27

11:40 pm-5:45 am

Nonstop4h 05m

Chicago O'Hare Intl

Wed 7/1

7:00 am-9:34 am

Nonstop4h 34m

$310

Quickest round-trip

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 7/1

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Wed 7/8

9:10 pm-11:30 pm

Nonstop4h 20m

$310

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 6/27

10:59 pm-5:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Fri 7/3

9:30 pm-12:05 am

Nonstop4h 35m

$312

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 7/18

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Sat 7/25

8:25 pm-10:45 pm

Nonstop4h 20m

$315

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 6/26

12:33 am-8:37 am

1 stop6h 04m

Chicago Midway

Fri 7/3

7:16 pm-11:18 pm

1 stop6h 02m

$330

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 9/7

12:40 am-8:38 am

1 stop5h 58m

Chicago Midway

Tue 9/15

2:00 pm-8:15 pm

1 stop8h 15m

$335

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

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 September is, on average, the cheapest month to fly to Chicago from Portland, with most prices found around $93. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from Portland to Chicago during May average around $102.

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 Wednesday 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 $523.

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 $328. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $468.

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 from Portland 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 $339 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 $274 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 14% 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 May 2026, prices for Portland to Chicago flights are approximately 65% 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	$199
Fastest flight time	3h 45m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Portland in the past 72 hours is $199. The best round-trip flight deal from Portland to Chicago found on momondo in the last 72 hours is $373.

The fastest flight from Portland to Chicago takes 3h 45m

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

Frequently asked questions about flying from Portland to Chicago

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 45m.
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 7 operators available for flights from Portland Airport to Chicago as of May 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 (31.16% of total bookings). The next most popular plane models are Airbus A321-100/200 (13.39%), Boeing 737-900 (12.85%), and Boeing 737 MAX 8 (9.75%).
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 28%, Alaska Airlines at 18%, and Southwest at 12%.

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 5.6 2,945 reviews	Search Frontier flights
Delta	PriceFrom $99	Free Cancellation	Rating 7.9 8,452 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $113	Free Cancellation	Rating 7.8 2,836 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $170	Free Cancellation	Rating 7.1 11,643 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $212	Free Cancellation	Rating 7.9 12,386 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $214	Free Cancellation	Rating 7.4 9,739 reviews	Search United Airlines flights
Southwest	PriceFrom $217	Free Cancellation	Rating 7.9 4,284 reviews	Search Southwest flights

Alaska Airlines Flights From Portland to Chicago
Alaska Airlines flies from Portland to Chicago around 7 times per week, with 12,386 momondo users rating the airline 7.9/10. The cheapest Alaska Airlines deal from Portland to Chicago in the last 72 hours was $212 (round-trip), much lower than the average airfare cost of $333 for Alaska Airlines flights on this route.
Southwest Flights From Portland to Chicago
Another popular option for Portland to Chicago flights is Southwest (7.9/10, 4,284 ratings). Southwest flies from Portland to Chicago around 12 times per week, with deals starting from $217 round-trip and rising to an average price of around $357.

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Munster

Schererville

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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Cheap flights from Portland to Chicago from $149

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 7/4. 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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American Airlines flights from Portland to Chicago

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Our best Delta deals on Portland to Chicago flight tickets

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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 from Portland 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?

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

Frequently asked questions about flying 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?

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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