What airlines fly to Oregon?

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Oregon from Chicago 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 Oregon. Keep in mind that there are 8 different airlines that fly to Oregon on a routine basis, so you have a few additional options to choose from.

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

210 flights are operational weekly from Chicago to Oregon as of May 2026. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.

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

As of May 2026, there are 30 flights per day flying from Chicago to Oregon. The most common time of day flights depart is 8:00PM, with 53% of flights taking off in the evening.

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

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

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

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

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

The number of operators available for flights from Chicago to Oregon is 8 as of May 2026.

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

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 Chicago to Oregon.

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

The travel and health documents required for your trip to Oregon can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Oregon. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$115 Cheap Flights from Chicago to Oregon in 2026

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Find the cheapest flights from Chicago to Oregon

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:18 pm - 4:50 pm

ORD

PDX

4h 32mnonstop

7:00 am - 1:22 pm

PDX

ORD

4h 22mnonstop

$304Alaska Airlines

Thu, May 28 - Sat, May 30

9:50 pm - 12:10 am

MDW

PDX

4h 20mnonstop

11:30 pm - 5:20 am

PDX

MDW

3h 50mnonstop

$305Southwest

Fri, May 29 - Wed, Jul 1

7:20 am - 9:45 am

ORD

PDX

4h 25mnonstop

10:59 pm - 5:00 am

PDX

ORD

4h 01mnonstop

$305Alaska Airlines

Wed, Jun 17 - Wed, Jul 1

12:09 pm - 2:35 pm

ORD

PDX

4h 26mnonstop

11:30 am - 5:47 pm

PDX

ORD

4h 17mnonstop

$306American Airlines

Thu, May 28 - Sat, Jun 6

9:25 pm - 11:52 pm

ORD

PDX

4h 27mnonstop

10:59 pm - 5:02 am

PDX

ORD

4h 03mnonstop

$308American Airlines

Thu, May 28 - Sat, May 30

9:07 am - 11:47 am

ORD

EUG

4h 40mnonstop

12:38 pm - 6:48 pm

EUG

ORD

4h 10mnonstop

$329United Airlines

Wed, May 27 - Sun, May 31

8:45 am - 11:17 am

ORD

EUG

4h 32mnonstop

1:57 pm - 12:55 am

EUG

ORD

8h 58m

1 stop

$339United Airlines

Tue, Aug 11 - Tue, Aug 18

9:23 am - 5:50 pm

MDW

BOI

9h 27m

2 stops

11:39 pm - 9:59 am

BOI

MDW

9h 20m

1 stop

$340Delta

Sun, May 24 - Fri, May 29

12:47 pm - 8:34 pm

ORD

BOI

8h 47m

1 stop

5:20 am - 4:29 pm

BOI

ORD

10h 09m

2 stops

$340Delta

Thu, May 28 - Sat, Jun 6

9:48 pm - 12:30 pm

ORD

BOI

15h 42m

1 stop

1:25 pm - 8:03 am

BOI

ORD

17h 38m

2 stops

$343Frontier

Wed, Jun 10 - Tue, Jun 16

Delta flights from Chicago to Oregon

Our best Delta deals on Chicago to Oregon flight tickets

Delta

Jun 23

ORD2:09 pmChicago O'Hare Intl

6h 13m

1 stop

PDX6:22 pmPortland

Jun 29

PDX12:33 amPortland

6h 02m

1 stop

ORD8:35 amChicago O'Hare Intl

$330

Delta

Jul 21

MDW7:06 pmChicago Midway

6h 28m

1 stop

PDX11:34 pmPortland

Aug 3

PDX12:32 amPortland

6h 08m

1 stop

MDW8:40 amChicago Midway

$335

Delta

May 28

ORD12:47 pmChicago O'Hare Intl

8h 47m

1 stop

BOI8:34 pmBoise Air Term. Gowen Fld

Jun 6

BOI5:20 amBoise Air Term. Gowen Fld

10h 09m

2 stops

ORD4:29 pmChicago O'Hare Intl

$340

American Airlines flights from Chicago to Oregon

Our best American Airlines deals on Chicago to Oregon flight tickets

American Airlines

May 28

ORD12:09 pmChicago O'Hare Intl

4h 26m

PDX2:35 pmPortland

Jun 6

PDX11:30 amPortland

4h 17m

ORD5:47 pmChicago O'Hare Intl

$306

American Airlines

May 28

ORD9:25 pmChicago O'Hare Intl

4h 27m

PDX11:52 pmPortland

May 30

PDX10:59 pmPortland

4h 03m

ORD5:02 amChicago O'Hare Intl

$308

American Airlines

Jul 3

ORD9:30 pmChicago O'Hare Intl

4h 35m

PDX12:05 amPortland

Jul 11

PDX6:07 amPortland

4h 10m

ORD12:17 pmChicago O'Hare Intl

$310

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 5/28

2:18 pm-4:50 pm

Nonstop4h 32m

Portland

Sat 5/30

7:00 am-1:22 pm

Nonstop4h 22m

$304

Quickest round-trip

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 5/29

9:50 pm-12:10 am

Nonstop4h 20m

Portland

Wed 7/1

11:30 pm-5:20 am

Nonstop3h 50m

$305

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 6/17

7:20 am-9:45 am

Nonstop4h 25m

Portland

Wed 7/1

10:59 pm-5:00 am

Nonstop4h 01m

$305

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 5/28

12:09 pm-2:35 pm

Nonstop4h 26m

Portland

Sat 6/6

11:30 am-5:47 pm

Nonstop4h 17m

$306

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 5/28

9:25 pm-11:52 pm

Nonstop4h 27m

Portland

Sat 5/30

10:59 pm-5:02 am

Nonstop4h 03m

$308

ChicagoEugene

ORD - EUG

ORDEUG

Chicago O'Hare Intl

Wed 5/27

9:07 am-11:47 am

Nonstop4h 40m

Eugene

Sun 5/31

12:38 pm-6:48 pm

Nonstop4h 10m

$329

ChicagoEugene

ORD - EUG

ORDEUG

Chicago O'Hare Intl

Tue 8/11

8:45 am-11:17 am

Nonstop4h 32m

Eugene

Tue 8/18

1:57 pm-12:55 am

1 stop8h 58m

$339

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Sun 5/24

9:23 am-5:50 pm

2 stops9h 27m

Boise Air Term. Gowen Fld

Fri 5/29

11:39 pm-9:59 am

1 stop9h 20m

$340

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Thu 5/28

12:47 pm-8:34 pm

1 stop8h 47m

Boise Air Term. Gowen Fld

Sat 6/6

5:20 am-4:29 pm

2 stops10h 09m

$340

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Wed 6/10

9:48 pm-12:30 pm

1 stop15h 42m

Boise Air Term. Gowen Fld

Tue 6/16

1:25 pm-8:03 am

2 stops17h 38m

$343

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 Chicago to Oregon

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 Oregon?

The month of September is, on average, the cheapest month to fly to Oregon from Chicago, with most prices found around $105. The month of January is another great option to travel to Oregon, with average flight prices from Chicago averaging around $123.

What is the cheapest day to depart on your flight to Oregon?

On average, the least expensive day to fly to Oregon from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $324. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Oregon is Sunday, with ticket prices averaging around $388.

What is the cheapest time of day to depart on your flight to Oregon?

According to our data, the cheapest time of day to fly to Oregon is in the evening. momondo users have found flights departing from Chicago to Oregon in the evening for as low as $325. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Oregon are more costly at noon, with an average ticket price of $465. Departure times at noon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Oregon flight route?

Fly from Chicago O'Hare Intl to Portland for the best Chicago - Oregon flight prices

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

You are more likely to see cheaper flights to Oregon from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Oregon for around $327 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Oregon from Chicago for as low as $256 on momondo.

Can stopping save me money on Chicago to Oregon flights?

You could potentially save up to 5% on your flight if you consider stops on a Chicago to Oregon flight.

Cheap Chicago to Oregon flight deals and tips

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

Best Price Found	$163
Fastest flight time	3h 30m
Direct flights	Every day
Airports in Oregon	64 airports

The best one-way flight to Oregon from Chicago in the past 72 hours is $163. The best round-trip flight deal from Chicago to Oregon found on momondo in the last 72 hours is $305.

The fastest flight from Chicago to Oregon takes 3h 30m

Direct flights go from Chicago to Oregon every day.

There are 64 airports in Oregon. From Chicago there are direct flights to Boise Air Term. Gowen Fld (BOI).

Search flight deals

Frequently asked questions about flying from Chicago to Oregon

When did momondo last update prices for flights from Chicago to Oregon?
Prices for flights from Chicago to Oregon were last updated today.
How many operators does momondo search for flights from Chicago to Oregon?
The number of operators available for flights from Chicago to Oregon is 8 as of May 2026.
How old do you have to be to fly from Chicago to Oregon?
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 Chicago to Oregon.
What documentation or ID do you need to fly to Oregon?
The travel and health documents required for your trip to Oregon can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Oregon. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Oregon?
Based on momondo bookings for flights between Chicago and Oregon, the leading plane model is Boeing 737-800, making up 35.02% of the total bookings. Other popular models include Boeing 737 MAX 8 with 13.42%, Airbus A321-100/200 with 12.51%, and Boeing 737-900 with 10.71%.

Best airlines flying from Chicago to Oregon

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

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $86	Free Cancellation	Rating 6.3 8,635 reviews	Search Spirit Airlines flights
Hawaiian Airlines	PriceFrom $124	Free Cancellation	Rating 7.8 2,837 reviews	Search Hawaiian Airlines flights
Delta	PriceFrom $139	Free Cancellation	Rating 7.9 8,454 reviews	Search Delta flights
Frontier	PriceFrom $150	Free Cancellation	Rating 5.6 2,955 reviews	Search Frontier flights
Alaska Airlines	PriceFrom $189	Free Cancellation	Rating 7.9 12,348 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $197	Free Cancellation	Rating 7.1 11,667 reviews	Search American Airlines flights
United Airlines	PriceFrom $199	Free Cancellation	Rating 7.4 9,694 reviews	Search United Airlines flights
Southwest	PriceFrom $227	Free Cancellation	Rating 8.0 4,304 reviews	Search Southwest flights

Why use momondo?

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

It is quick and easy to find Chicago to Oregon flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Oregon that suits you.

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

Flights from Chicago to Oregon 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 Chicago to Oregon?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Oregon.

I’m not ready to book a flight from Chicago to Oregon right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Oregon from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Oregon trip

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Popular cities in Oregon

Flights to New Yorkfrom $54

Flights to Los Angelesfrom $56

Flights to Orlandofrom $50

Flights to Miamifrom $56

Flights to Chicagofrom $58

Flights to San Franciscofrom $56

Flights to Las Vegasfrom $46

Flights to Washington, D.C.from $56

Flights to Bostonfrom $83

Flights to Atlantafrom $56

Flights to Fort Lauderdalefrom $56

Flights to Dallasfrom $72

Cheap flights from Chicago to Oregon from $115

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Oregon departing on 6/3. 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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See travel insights to Oregon from

How to get the cheapest flight ticket from Chicago to Oregon

What is the cheapest month to fly to Oregon?

What is the cheapest day to depart on your flight to Oregon?

What is the cheapest time of day to depart on your flight to Oregon?

What is the cheapest Chicago to Oregon flight route?

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

Can stopping save me money on Chicago to Oregon flights?

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

What airlines fly to Oregon?

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

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

Cheap Chicago to Oregon flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Oregon

Frequently asked questions about flying from Chicago to Oregon

Best airlines flying from Chicago to Oregon

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

Why use momondo?

An easier way to manage your Oregon 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 Oregon

Popular cities in Oregon

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