What airlines fly to Chicago?

United Airlines, Alaska Airlines and American 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 41% 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.

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

Frontier, United Airlines, and American Airlines are the most popular carriers operating from Oregon to Chicago

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

20 flights are operational daily from Oregon to Chicago as of December 2025. The most popular departure time for this route is 7:00AM, with 66% of flights per day taking off at noon.

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

145 flights are operational weekly from Oregon to Chicago as of December 2025. The most popular departure day for this route is Tue, with 20% 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 44m on average, while flying from Eugene to Chicago O'Hare Intl Airport is 3h 52m on average. Chicago O'Hare Intl Airport is the most popular airport in 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 December 2025, there are 8 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.

$88 Cheap Flights from Oregon to Chicago in 2025/26

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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.

10:10 am - 9:45 pm

BOI

ORD

10h 35m1 stop

12:07 pm - 11:12 am

ORD

BOI

24h 05m1 stop

$195Multiple Airlines

Fri, Jan 23 - Sun, Jan 25

12:38 pm - 1:25 pm

BOI

ORD

23h 47m1 stop

3:07 pm - 11:30 pm

ORD

BOI

9h 23m1 stop

$211Multiple Airlines

Thu, Feb 26 - Mon, Mar 2

2:19 pm - 1:57 pm

BOI

ORD

22h 38m2 stops

12:07 pm - 11:12 am

ORD

BOI

24h 05m1 stop

$212Frontier

Mon, Jan 19 - Sun, Jan 25

12:07 pm - 2:17 pm

BOI

ORD

25h 10m2 stops

12:07 pm - 11:12 am

ORD

BOI

24h 05m1 stop

$220Multiple Airlines

Fri, Jan 23 - Sun, Jan 25

5:40 am - 1:10 pm

BOI

ORD

6h 30m1 stop

3:35 pm - 11:01 pm

ORD

BOI

8h 26m1 stop

$223Alaska Airlines

Tue, Feb 3 - Tue, Feb 3

1:40 pm - 11:53 pm

BOI

ORD

9h 13m1 stop

7:30 am - 4:17 pm

ORD

BOI

9h 47m1 stop

$225Delta

Tue, Jan 20 - Sat, Jan 24

6:23 am - 2:38 pm

BOI

ORD

7h 15m1 stop

8:00 am - 3:10 pm

ORD

BOI

8h 10m1 stop

$227Alaska Airlines

Wed, Jan 21 - Wed, Jan 28

1:24 pm - 9:16 pm

PDX

ORD

5h 52m1 stop

5:40 am - 12:18 pm

ORD

PDX

8h 38m1 stop

$232United Airlines

Tue, Feb 3 - Tue, Feb 10

1:24 pm - 9:15 pm

PDX

ORD

5h 51m1 stop

9:10 am - 11:57 am

ORD

PDX

4h 47mnonstop

$233United Airlines

Sat, Jan 24 - Sun, Jan 25

6:00 am - 4:14 pm

PDX

MDW

8h 14m1 stop

1:49 pm - 8:30 pm

MDW

PDX

8h 41m1 stop

$237Delta

Sat, Feb 14 - Tue, Feb 17

American Airlines flights from Oregon to Chicago

Our best American Airlines deals on Oregon to Chicago flight tickets

American Airlines

Jan 24

EUG3:18 pmEugene

7h 05m

1 stop

ORD12:23 amChicago O'Hare Intl

Jan 25

ORD7:05 amChicago O'Hare Intl

9h 26m

1 stop

EUG2:31 pmEugene

$239

Find similar

American Airlines

Feb 13

BOI1:23 pmBoise Air Term. Gowen Fld

3h 45m

ORD6:08 pmChicago O'Hare Intl

Feb 15

ORD9:45 amChicago O'Hare Intl

4h 08m

BOI12:53 pmBoise Air Term. Gowen Fld

$249

Find similar

American Airlines

Jan 20

BOI3:18 pmBoise Air Term. Gowen Fld

3h 41m

ORD7:59 pmChicago O'Hare Intl

Jan 24

ORD11:41 amChicago O'Hare Intl

4h 10m

BOI2:51 pmBoise Air Term. Gowen Fld

$252

Find similar

United Airlines flights from Oregon to Chicago

Our best United Airlines deals on Oregon to Chicago flight tickets

United Airlines

Feb 3

PDX1:24 pmPortland

5h 52m

1 stop

ORD9:16 pmChicago O'Hare Intl

Feb 10

ORD5:40 amChicago O'Hare Intl

8h 38m

1 stop

PDX12:18 pmPortland

$232

Find similar

United Airlines

Jan 24

PDX1:24 pmPortland

5h 51m

1 stop

ORD9:15 pmChicago O'Hare Intl

Jan 25

ORD9:10 amChicago O'Hare Intl

4h 47m

PDX11:57 amPortland

$233

Find similar

United Airlines

Jan 12

PDX1:24 pmPortland

5h 51m

1 stop

ORD9:15 pmChicago O'Hare Intl

Jan 13

ORD5:40 amChicago O'Hare Intl

8h 38m

1 stop

PDX12:18 pmPortland

$242

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Fri 1/23

10:10 am-9:45 pm

1 stop10h 35m

Chicago O'Hare Intl

Sun 1/25

12:07 pm-11:12 am

1 stop24h 05m

$195

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Thu 2/26

12:38 pm-1:25 pm

1 stop23h 47m

Chicago O'Hare Intl

Mon 3/2

3:07 pm-11:30 pm

1 stop9h 23m

$211

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Mon 1/19

2:19 pm-1:57 pm

2 stops22h 38m

Chicago O'Hare Intl

Sun 1/25

12:07 pm-11:12 am

1 stop24h 05m

$212

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Fri 1/23

12:07 pm-2:17 pm

2 stops25h 10m

Chicago O'Hare Intl

Sun 1/25

12:07 pm-11:12 am

1 stop24h 05m

$220

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Tue 2/3

5:40 am-1:10 pm

1 stop6h 30m

Chicago O'Hare Intl

Tue 2/3

3:35 pm-11:01 pm

1 stop8h 26m

$223

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Tue 1/20

1:40 pm-11:53 pm

1 stop9h 13m

Chicago O'Hare Intl

Sat 1/24

7:30 am-4:17 pm

1 stop9h 47m

$225

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 1/21

6:23 am-2:38 pm

1 stop7h 15m

Chicago O'Hare Intl

Wed 1/28

8:00 am-3:10 pm

1 stop8h 10m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 2/3

1:24 pm-9:16 pm

1 stop5h 52m

Chicago O'Hare Intl

Tue 2/10

5:40 am-12:18 pm

1 stop8h 38m

$232

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 1/24

1:24 pm-9:15 pm

1 stop5h 51m

Chicago O'Hare Intl

Sun 1/25

9:10 am-11:57 am

Nonstop4h 47m

$233

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

$237

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 August is, on average, the cheapest month to fly to Chicago from Oregon, with most prices found around $291. If you’re not able to fly to Chicago in August, then January is your next best option. Flight prices from Oregon to Chicago during January 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 $431. 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 $538.

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 $320. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $486.

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 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 $353 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 $293 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.

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	$148
Fastest flight time	3h 24m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Oregon in the past 72 hours is $148. The best round-trip flight deal from Oregon to Chicago found on momondo in the last 72 hours is $325.

The fastest flight from Oregon to Chicago takes 3h 24m

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

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 December 2025, there are 8 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 23.14% of the total bookings. Other popular models include Boeing 737 MAX 9 with 17.21%, Boeing 737-900 with 16.13%, and Boeing 737 MAX 8 with 13.93%.

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
Frontier	PriceFrom $96	Free Cancellation	Rating 5.8 3,073 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $119	Free Cancellation	Rating 6.3 8,194 reviews	Search Spirit Airlines flights
Delta	PriceFrom $123	Free Cancellation	Rating 7.9 8,015 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $125	Free Cancellation	Rating 7.8 2,820 reviews	Search Hawaiian Airlines flights
Southwest	PriceFrom $179	Free Cancellation	Rating 8.0 4,256 reviews	Search Southwest flights
American Airlines	PriceFrom $196	Free Cancellation	Rating 7.2 11,050 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $217	Free Cancellation	Rating 8.0 11,517 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $222	Free Cancellation	Rating 7.4 9,109 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.