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

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

What airlines fly to Chicago?

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago from Oregon according to our data. United Airlines is the first choice among our users, with 40% 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.

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

252 flights are operational weekly from Oregon to Chicago as of June 2026. The most popular departure day for this route is Mon, with 18% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Average flight duration from Oregon to Chicago depends on which airport you fly into and out of. Flying from Portland to Chicago O'Hare Intl Airport is 3h 52m on average, while flying from Eugene to Chicago O'Hare Intl Airport is 4h 10m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

36 flights are operational daily from Oregon to Chicago as of June 2026. The most popular departure time for this route is 7:00AM, with 51% of flights per day taking off at noon.

When did momondo last update prices for flights from Oregon to Chicago?

Prices for flights from Oregon to Chicago were last updated today.

How many operators does momondo search for flights from Oregon to Chicago?

As of June 2026, there are 7 operators available to choose from for flights from Oregon to Chicago.

How old do you have to be to fly from Oregon to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oregon to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$123 Cheap Flights from Oregon to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Oregon to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:34 pm - 10:01 am

PDX

ORD

19h 27m

1 stop

2:17 pm - 4:54 pm

ORD

PDX

4h 37mnonstop

$321Multiple Airlines

Fri, Oct 23 - Tue, Oct 27

6:49 pm - 5:37 am

PDX

ORD

8h 48m

1 stop

7:20 am - 9:45 am

ORD

PDX

4h 25mnonstop

$322Multiple Airlines

Thu, Jul 16 - Fri, Jul 24

3:47 pm - 10:01 am

PDX

ORD

16h 14m

1 stop

10:40 pm - 4:35 pm

ORD

PDX

19h 55m

1 stop

$324Frontier

Fri, Oct 30 - Sun, Nov 1

10:59 pm - 5:00 am

PDX

ORD

4h 01mnonstop

7:20 am - 9:45 am

ORD

PDX

4h 25mnonstop

$325Alaska Airlines

Wed, Jul 29 - Wed, Aug 5

11:30 pm - 5:20 am

PDX

MDW

3h 50mnonstop

8:25 pm - 10:50 pm

MDW

PDX

4h 25mnonstop

$325Southwest

Sat, Jul 18 - Sat, Jul 25

11:30 pm - 5:20 am

PDX

MDW

3h 50mnonstop

9:35 pm - 11:55 pm

MDW

PDX

4h 20mnonstop

$326Southwest

Wed, Jul 22 - Fri, Jul 24

11:40 pm - 5:45 am

PDX

ORD

4h 05mnonstop

8:59 am - 11:37 am

ORD

PDX

4h 38mnonstop

$326United Airlines

Wed, Jul 29 - Sun, Aug 9

5:16 pm - 8:52 pm

PDX

ORD

25h 36m

1 stop

9:57 pm - 4:51 pm

ORD

PDX

20h 54m

1 stop

$327Frontier

Tue, Jul 21 - Sun, Jul 26

12:50 pm - 7:00 pm

EUG

ORD

4h 10mnonstop

8:53 am - 11:37 am

ORD

EUG

4h 44mnonstop

$329United Airlines

Fri, Jul 17 - Mon, Jul 20

7:57 am - 6:57 pm

BOI

ORD

10h 00m

1 stop

6:01 am - 2:02 pm

ORD

BOI

9h 01m

1 stop

$335Alaska Airlines

Wed, Aug 12 - Wed, Aug 19

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Frontier flights from Oregon to Chicago

Our best Frontier deals on Oregon to Chicago flight tickets

Frontier

Oct 30

PDX3:47 pmPortland

16h 14m

1 stop

ORD10:01 amChicago O'Hare Intl

Nov 1

ORD10:40 pmChicago O'Hare Intl

19h 55m

1 stop

PDX4:35 pmPortland

$324

Frontier

Jul 21

PDX5:16 pmPortland

25h 36m

1 stop

ORD8:52 pmChicago O'Hare Intl

Jul 26

ORD9:57 pmChicago O'Hare Intl

20h 54m

1 stop

PDX4:51 pmPortland

$327

Frontier

Jul 10

PDX5:49 pmPortland

9h 48m

1 stop

ORD5:37 amChicago O'Hare Intl

Jul 13

ORD9:57 pmChicago O'Hare Intl

20h 34m

1 stop

PDX4:31 pmPortland

$328

Alaska Airlines flights from Oregon to Chicago

Our best Alaska Airlines deals on Oregon to Chicago flight tickets

Alaska Airlines

Jul 29

PDX10:59 pmPortland

4h 01m

ORD5:00 amChicago O'Hare Intl

Aug 5

ORD7:20 amChicago O'Hare Intl

4h 25m

PDX9:45 amPortland

$325

Alaska Airlines

Jul 14

PDX10:59 pmPortland

4h 01m

ORD5:00 amChicago O'Hare Intl

Jul 18

ORD7:20 amChicago O'Hare Intl

4h 25m

PDX9:45 amPortland

$331

Alaska Airlines

Aug 12

BOI7:57 amBoise Air Term. Gowen Fld

10h 00m

1 stop

ORD6:57 pmChicago O'Hare Intl

Aug 19

ORD6:01 amChicago O'Hare Intl

9h 01m

1 stop

BOI2:02 pmBoise Air Term. Gowen Fld

$335

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/23

12:34 pm-10:01 am

1 stop19h 27m

Chicago O'Hare Intl

Tue 10/27

2:17 pm-4:54 pm

Nonstop4h 37m

$321

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 7/16

6:49 pm-5:37 am

1 stop8h 48m

Chicago O'Hare Intl

Fri 7/24

7:20 am-9:45 am

Nonstop4h 25m

$322

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/30

3:47 pm-10:01 am

1 stop16h 14m

Chicago O'Hare Intl

Sun 11/1

10:40 pm-4:35 pm

1 stop19h 55m

$324

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 7/29

10:59 pm-5:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Wed 8/5

7:20 am-9:45 am

Nonstop4h 25m

$325

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 7/18

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Sat 7/25

8:25 pm-10:50 pm

Nonstop4h 25m

$325

Quickest round-trip

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 7/22

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Fri 7/24

9:35 pm-11:55 pm

Nonstop4h 20m

$326

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 7/29

11:40 pm-5:45 am

Nonstop4h 05m

Chicago O'Hare Intl

Sun 8/9

8:59 am-11:37 am

Nonstop4h 38m

$326

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 7/21

5:16 pm-8:52 pm

1 stop25h 36m

Chicago O'Hare Intl

Sun 7/26

9:57 pm-4:51 pm

1 stop20h 54m

$327

EugeneChicago

EUG - ORD

EUGORD

Eugene

Fri 7/17

12:50 pm-7:00 pm

Nonstop4h 10m

Chicago O'Hare Intl

Mon 7/20

8:53 am-11:37 am

Nonstop4h 44m

$329

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 8/12

7:57 am-6:57 pm

1 stop10h 00m

Chicago O'Hare Intl

Wed 8/19

6:01 am-2:02 pm

1 stop9h 01m

$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 Oregon 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 cheapest month to fly to Chicago?

The month of December is, on average, the cheapest month to fly to Chicago from Oregon, with most prices found around $108. If you’re not able to fly to Chicago in December, then April is your next best option. Flight prices from Oregon to Chicago during April average around $108.

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 $429. 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 Oregon to Chicago for around $527.

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 Oregon to Chicago during this time can be as low as $360. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $474.

What is the cheapest Oregon to Chicago flight route?

Fly from Portland to Chicago Midway for the best Oregon - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Oregon 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 Oregon for as low as $298 on momondo.

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

There are 4 cabin classes available to choose from on Oregon 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 Oregon to Chicago flights?

You could potentially save up to 29% on your flight if you consider stops on a Oregon to Chicago flight.

Cheap Oregon to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oregon to Chicago

Best Price Found	$216
Fastest flight time	3h 20m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Oregon in the past 72 hours is $216. The best round-trip flight deal from Oregon to Chicago found on momondo in the last 72 hours is $390.

The fastest flight from Oregon to Chicago takes 3h 20m

Direct flights go from Oregon to Chicago every day.

There are 3 airports in Chicago. From Oregon there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Oregon to Chicago

When did momondo last update prices for flights from Oregon to Chicago?
Prices for flights from Oregon to Chicago were last updated today.
How many operators does momondo search for flights from Oregon to Chicago?
As of June 2026, there are 7 operators available to choose from for flights from Oregon to Chicago.
How old do you have to be to fly from Oregon to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oregon to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Oregon to Chicago?
Based on momondo bookings for flights between Oregon and Chicago, the leading plane model is Boeing 737-800, making up 29.24% of the total bookings. Other popular models include Airbus A321-100/200 with 15.02%, Boeing 737-900 with 11.33%, and Airbus A321neo with 10.24%.

Best airlines flying from Oregon to Chicago

Compare and see reviews for airlines that fly from Oregon to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Hawaiian Airlines	PriceFrom $93	Free Cancellation	Rating 7.8 2,827 reviews	Search Hawaiian Airlines flights
Frontier	PriceFrom $96	Free Cancellation	Rating 5.6 2,871 reviews	Search Frontier flights
Delta	PriceFrom $108	Free Cancellation	Rating 7.8 8,422 reviews	Search Delta flights
American Airlines	PriceFrom $173	Free Cancellation	Rating 7.1 11,737 reviews	Search American Airlines flights
Southwest	PriceFrom $179	Free Cancellation	Rating 7.9 4,243 reviews	Search Southwest flights
Alaska Airlines	PriceFrom $198	Free Cancellation	Rating 7.9 12,561 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $221	Free Cancellation	Rating 7.4 9,875 reviews	Search United Airlines flights

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Why use momondo?

Why should I use momondo to find a flight deal from Oregon to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Oregon to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Oregon to Chicago with flexible booking policies on momondo?

Flights from Oregon 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 Oregon to Chicago?

Once all potential Oregon 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 Oregon to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Oregon and alert you when they change.

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Cheap flights from Oregon to Chicago from $123

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oregon to Chicago departing on 9/15. 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 Oregon to Chicago

Our best Frontier deals on Oregon to Chicago flight tickets

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How to get the cheapest flight ticket from Oregon to 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 Oregon to Chicago flight route?

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

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

Can stopping save me money on Oregon to Chicago flights?

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

What airlines fly to Chicago?

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

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

How long does it take to fly to Chicago?

Cheap Oregon to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oregon to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Oregon to Chicago

Best airlines flying from Oregon to Chicago

Compare and see reviews for airlines that fly from Oregon to Chicago with momondo

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.

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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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