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

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

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

237 flights are operational weekly from Chicago to Oregon 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 many flights depart from Chicago to Oregon on average per day?

As of June 2026, there are 33 flights per day flying from Chicago to Oregon. The most common time of day flights depart is 6:00PM, with 50% of flights taking off in the evening.

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.

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 June 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.

$136 Cheap Flights from Chicago to Oregon in 2026

Discover deals from 900+ travel sites with momondo.

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.

9:57 pm - 4:36 pm

ORD

PDX

20h 39m

1 stop

12:20 pm - 8:52 pm

PDX

ORD

6h 32m

1 stop

$309Frontier

Tue, Jul 7 - Sat, Jul 11

7:29 am - 6:04 pm

ORD

PDX

12h 35m

1 stop

9:19 am - 7:21 pm

PDX

ORD

8h 02m

1 stop

$311Multiple Airlines

Thu, Aug 6 - Wed, Aug 12

7:20 am - 9:45 am

ORD

PDX

4h 25mnonstop

10:59 pm - 5:00 am

PDX

ORD

4h 01mnonstop

$315Alaska Airlines

Sat, Jul 18 - Sat, Jul 25

6:00 pm - 8:15 pm

MDW

PDX

4h 15mnonstop

11:30 pm - 5:25 am

PDX

MDW

3h 55mnonstop

$325Southwest

Sat, Sep 5 - Tue, Sep 8

10:25 am - 1:10 pm

ORD

EUG

4h 45mnonstop

2:19 pm - 8:30 pm

EUG

ORD

4h 11mnonstop

$329United Airlines

Fri, Aug 21 - Mon, Aug 24

11:35 am - 2:31 pm

ORD

BOI

3h 56mnonstop

3:21 pm - 8:16 pm

BOI

ORD

3h 55mnonstop

$335American Airlines

Tue, Sep 22 - Tue, Sep 29

8:25 pm - 10:50 pm

MDW

PDX

4h 25mnonstop

8:20 pm - 5:45 am

PDX

MDW

7h 25m

1 stop

$335Southwest

Sat, Jul 18 - Sat, Jul 25

11:32 am - 2:22 pm

ORD

BOI

3h 50mnonstop

2:58 pm - 7:49 pm

BOI

ORD

3h 51mnonstop

$336American Airlines

Sat, Aug 1 - Sat, Aug 8

10:25 am - 1:10 pm

ORD

EUG

4h 45mnonstop

1:57 pm - 12:59 am

EUG

ORD

9h 02m

1 stop

$339United Airlines

Fri, Aug 21 - Mon, Aug 24

6:20 am - 1:46 pm

ORD

BOI

8h 26m

1 stop

7:48 pm - 6:20 am

BOI

ORD

9h 32m

1 stop

$339Alaska Airlines

Sat, Aug 15 - Sat, Aug 22

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Alaska Airlines flights from Chicago to Oregon

Our best Alaska Airlines deals on Chicago to Oregon flight tickets

Alaska Airlines

Jul 18

ORD7:20 amChicago O'Hare Intl

4h 25m

PDX9:45 amPortland

Jul 25

PDX10:59 pmPortland

4h 01m

ORD5:00 amChicago O'Hare Intl

$315

Alaska Airlines

Aug 8

ORD7:20 amChicago O'Hare Intl

4h 25m

PDX9:45 amPortland

Aug 18

PDX7:00 amPortland

4h 13m

ORD1:13 pmChicago O'Hare Intl

$325

Alaska Airlines

Aug 8

ORD7:20 amChicago O'Hare Intl

4h 25m

PDX9:45 amPortland

Aug 15

PDX10:59 pmPortland

4h 01m

ORD5:00 amChicago O'Hare Intl

$326

Southwest flights from Chicago to Oregon

Our best Southwest deals on Chicago to Oregon flight tickets

Southwest

Sep 5

MDW6:00 pmChicago Midway

4h 15m

PDX8:15 pmPortland

Sep 8

PDX11:30 pmPortland

3h 55m

MDW5:25 amChicago Midway

$325

Southwest

Jul 18

MDW8:25 pmChicago Midway

4h 25m

PDX10:50 pmPortland

Jul 25

PDX8:20 pmPortland

7h 25m

1 stop

MDW5:45 amChicago Midway

$335

Southwest

Aug 18

MDW8:55 pmChicago Midway

4h 15m

PDX11:10 pmPortland

Sep 1

PDX5:50 amPortland

8h 45m

2 stops

MDW4:35 pmChicago Midway

$336

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 7/7

9:57 pm-4:36 pm

1 stop20h 39m

Portland

Sat 7/11

12:20 pm-8:52 pm

1 stop6h 32m

$309

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 8/6

7:29 am-6:04 pm

1 stop12h 35m

Portland

Wed 8/12

9:19 am-7:21 pm

1 stop8h 02m

$311

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 7/18

7:20 am-9:45 am

Nonstop4h 25m

Portland

Sat 7/25

10:59 pm-5:00 am

Nonstop4h 01m

$315

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 9/5

6:00 pm-8:15 pm

Nonstop4h 15m

Portland

Tue 9/8

11:30 pm-5:25 am

Nonstop3h 55m

$325

ChicagoEugene

ORD - EUG

ORDEUG

Chicago O'Hare Intl

Fri 8/21

10:25 am-1:10 pm

Nonstop4h 45m

Eugene

Mon 8/24

2:19 pm-8:30 pm

Nonstop4h 11m

$329

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Tue 9/22

11:35 am-2:31 pm

Nonstop3h 56m

Boise Air Term. Gowen Fld

Tue 9/29

3:21 pm-8:16 pm

Nonstop3h 55m

$335

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 7/18

8:25 pm-10:50 pm

Nonstop4h 25m

Portland

Sat 7/25

8:20 pm-5:45 am

1 stop7h 25m

$335

Quickest round-trip

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Sat 8/1

11:32 am-2:22 pm

Nonstop3h 50m

Boise Air Term. Gowen Fld

Sat 8/8

2:58 pm-7:49 pm

Nonstop3h 51m

$336

ChicagoEugene

ORD - EUG

ORDEUG

Chicago O'Hare Intl

Fri 8/21

10:25 am-1:10 pm

Nonstop4h 45m

Eugene

Mon 8/24

1:57 pm-12:59 am

1 stop9h 02m

$339

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Sat 8/15

6:20 am-1:46 pm

1 stop8h 26m

Boise Air Term. Gowen Fld

Sat 8/22

7:48 pm-6:20 am

1 stop9h 32m

$339

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 May is, on average, the cheapest month to fly to Oregon from Chicago, with most prices found around $115. 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 $334. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Oregon is Monday, with ticket prices averaging around $403.

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 $333. 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 $457. 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 $332 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 $268 on momondo.

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

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

You could potentially save up to 11% 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	$168
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 $168. The best round-trip flight deal from Chicago to Oregon found on momondo in the last 72 hours is $315.

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 June 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 31.74% of the total bookings. Other popular models include Airbus A321-100/200 with 15.78%, Airbus A321neo with 13.17%, and Boeing 737 MAX 8 with 9.27%.

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
Hawaiian Airlines	PriceFrom $124	Free Cancellation	Rating 7.8 2,826 reviews	Search Hawaiian Airlines flights
Frontier	PriceFrom $150	Free Cancellation	Rating 5.6 2,863 reviews	Search Frontier flights
JetBlue	PriceFrom $191	Free Cancellation	Rating 7.1 3,014 reviews	Search JetBlue flights
Delta	PriceFrom $192	Free Cancellation	Rating 7.8 8,453 reviews	Search Delta flights
Alaska Airlines	PriceFrom $196	Free Cancellation	Rating 7.9 12,582 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $202	Free Cancellation	Rating 7.1 11,776 reviews	Search American Airlines flights
United Airlines	PriceFrom $205	Free Cancellation	Rating 7.4 9,898 reviews	Search United Airlines flights
Southwest	PriceFrom $227	Free Cancellation	Rating 7.9 4,246 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 $77

Flights to Los Angelesfrom $56

Flights to Orlandofrom $62

Flights to Miamifrom $79

Flights to Chicagofrom $62

Flights to San Franciscofrom $50

Flights to Las Vegasfrom $49

Flights to Washington, D.C.from $55

Flights to Bostonfrom $72

Flights to Atlantafrom $56

Flights to Fort Lauderdalefrom $58

Flights to Dallasfrom $105

Cheap flights from Chicago to Oregon from $136

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 8/12. 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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Alaska Airlines flights from Chicago to Oregon

Our best Alaska Airlines deals on Chicago to Oregon flight tickets

Southwest flights from Chicago to Oregon

Our best Southwest deals on Chicago to Oregon flight tickets

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Use the filters below to find and compare flights from Chicago to Oregon that are best for you.

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?

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

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

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

Chicago flight routes

According to popular flight searches on momondo this year

Oregon flight routes

According to popular flight searches on momondo this year

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