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

162 flights are operational weekly from Chicago to Oregon as of December 2025. The most popular departure day for this route is Fri, with 15% of flights per week taking off on this day.

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 37% 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.

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

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

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

As of December 2025, there are 23 flights per day flying from Chicago to Oregon. The most common time of day flights depart is 4:00PM, with 36% of flights taking off in the afternoon.

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 December 2025.

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.

$105 Cheap Flights from Chicago to Oregon in 2025/26

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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.

5:54 pm - 8:27 pm

ORD

PDX

4h 33mnonstop

6:00 am - 12:15 pm

PDX

ORD

4h 15mnonstop

$219American Airlines

Sat, Jan 17 - Sat, Jan 24

7:50 pm - 11:17 am

ORD

BOI

16h 27m1 stop

12:07 pm - 6:45 pm

BOI

ORD

5h 38m1 stop

$221Frontier

Thu, Jan 8 - Mon, Jan 12

9:10 am - 11:57 am

ORD

PDX

4h 47mnonstop

1:24 pm - 9:15 pm

PDX

ORD

5h 51m1 stop

$223United Airlines

Wed, Jan 21 - Tue, Jan 27

4:16 pm - 11:11 am

ORD

BOI

19h 55m1 stop

11:56 am - 4:53 pm

BOI

ORD

27h 57m2 stops

$226Frontier

Thu, Feb 19 - Fri, Feb 27

7:50 pm - 10:32 pm

ORD

PDX

4h 42mnonstop

10:47 am - 4:48 pm

PDX

ORD

4h 01mnonstop

$227United Airlines

Fri, Jan 16 - Sat, Jan 31

3:35 pm - 11:59 pm

ORD

BOI

9h 24m1 stop

6:23 am - 5:10 pm

BOI

ORD

9h 47m1 stop

$227Alaska Airlines

Mon, Jan 12 - Wed, Jan 21

8:35 am - 11:15 am

MDW

PDX

4h 40mnonstop

8:45 am - 4:25 pm

PDX

MDW

5h 40m1 stop

$227Southwest

Sat, Jan 17 - Sat, Jan 24

3:54 pm - 10:40 pm

ORD

BOI

7h 46m1 stop

8:27 pm - 2:11 pm

BOI

ORD

16h 44m1 stop

$228Alaska Airlines

Thu, Feb 19 - Mon, Feb 23

8:35 am - 11:15 am

MDW

PDX

4h 40mnonstop

8:45 am - 6:30 pm

PDX

MDW

7h 45m2 stops

$232Southwest

Sat, Jan 17 - Sat, Jan 24

8:00 am - 12:38 pm

ORD

PDX

6h 38m1 stop

1:38 pm - 11:50 pm

PDX

ORD

8h 12m1 stop

$240Hawaiian Airlines

Sat, Jan 17 - Sat, Jan 24

Southwest flights from Chicago to Oregon

Our best Southwest deals on Chicago to Oregon flight tickets

Southwest

Jan 17

MDW8:35 amChicago Midway

4h 40m

PDX11:15 amPortland

Jan 24

PDX8:45 amPortland

5h 40m

1 stop

MDW4:25 pmChicago Midway

$227

Find similar

Southwest

Jan 17

MDW8:35 amChicago Midway

4h 40m

PDX11:15 amPortland

Jan 24

PDX8:45 amPortland

7h 45m

2 stops

MDW6:30 pmChicago Midway

$232

Find similar

Southwest

Jan 17

MDW4:05 pmChicago Midway

6h 25m

1 stop

PDX8:30 pmPortland

Jan 18

PDX7:25 amPortland

7h 50m

1 stop

MDW5:15 pmChicago Midway

$236

Find similar

Frontier flights from Chicago to Oregon

Our best Frontier deals on Chicago to Oregon flight tickets

Frontier

Jan 8

ORD7:50 pmChicago O'Hare Intl

16h 27m

1 stop

BOI11:17 amBoise Air Term. Gowen Fld

Jan 12

BOI12:07 pmBoise Air Term. Gowen Fld

5h 38m

1 stop

ORD6:45 pmChicago O'Hare Intl

$221

Find similar

Frontier

Feb 19

ORD4:16 pmChicago O'Hare Intl

19h 55m

1 stop

BOI11:11 amBoise Air Term. Gowen Fld

Feb 27

BOI11:56 amBoise Air Term. Gowen Fld

27h 57m

2 stops

ORD4:53 pmChicago O'Hare Intl

$226

Find similar

Frontier

Jan 8

ORD6:15 amChicago O'Hare Intl

8h 08m

1 stop

PDX12:23 pmPortland

Jan 11

PDX12:10 pmPortland

6h 47m

1 stop

ORD8:57 pmChicago O'Hare Intl

$267

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 1/17

5:54 pm-8:27 pm

Nonstop4h 33m

Portland

Sat 1/24

6:00 am-12:15 pm

Nonstop4h 15m

$219

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Thu 1/8

7:50 pm-11:17 am

1 stop16h 27m

Boise Air Term. Gowen Fld

Mon 1/12

12:07 pm-6:45 pm

1 stop5h 38m

$221

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 1/21

9:10 am-11:57 am

Nonstop4h 47m

Portland

Tue 1/27

1:24 pm-9:15 pm

1 stop5h 51m

$223

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Thu 2/19

4:16 pm-11:11 am

1 stop19h 55m

Boise Air Term. Gowen Fld

Fri 2/27

11:56 am-4:53 pm

2 stops27h 57m

$226

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 1/16

7:50 pm-10:32 pm

Nonstop4h 42m

Portland

Sat 1/31

10:47 am-4:48 pm

Nonstop4h 01m

$227

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Mon 1/12

3:35 pm-11:59 pm

1 stop9h 24m

Boise Air Term. Gowen Fld

Wed 1/21

6:23 am-5:10 pm

1 stop9h 47m

$227

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 1/17

8:35 am-11:15 am

Nonstop4h 40m

Portland

Sat 1/24

8:45 am-4:25 pm

1 stop5h 40m

$227

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Thu 2/19

3:54 pm-10:40 pm

1 stop7h 46m

Boise Air Term. Gowen Fld

Mon 2/23

8:27 pm-2:11 pm

1 stop16h 44m

$228

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 1/17

8:35 am-11:15 am

Nonstop4h 40m

Portland

Sat 1/24

8:45 am-6:30 pm

2 stops7h 45m

$232

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 1/17

8:00 am-12:38 pm

1 stop6h 38m

Portland

Sat 1/24

1:38 pm-11:50 pm

1 stop8h 12m

$240

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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 January is, on average, the cheapest month to fly to Oregon from Chicago, with most prices found around $266. The month of September is another great option to travel to Oregon, with average flight prices from Chicago averaging around $280.

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 Wednesday. momondo users have found tickets for Wednesday departures for as low as $330. 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 $410.

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 $319. 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 $481. 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 Midway to Portland for the best Chicago - Oregon flight prices

How far in advance should I book a flight 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 $335 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 $267 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 8% 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	$118
Fastest flight time	3h 35m
Direct flights	Every day
Airports in Oregon	64 airports

The best one-way flight to Oregon from Chicago in the past 72 hours is $118. The best round-trip flight deal from Chicago to Oregon found on momondo in the last 72 hours is $268.

The fastest flight from Chicago to Oregon takes 3h 35m

Direct flights go from Chicago to Oregon every day.

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

Search flight deals

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 December 2025.
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 25.09% of the total bookings. Other popular models include Boeing 737 MAX 8 with 16.55%, Boeing 737 MAX 9 with 15.32%, and Boeing 737-900 with 13.59%.

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 $93	Free Cancellation	Rating 6.3 8,208 reviews	Search Spirit Airlines flights
Hawaiian Airlines	PriceFrom $134	Free Cancellation	Rating 7.8 2,820 reviews	Search Hawaiian Airlines flights
Frontier	PriceFrom $138	Free Cancellation	Rating 5.8 3,070 reviews	Search Frontier flights
Alaska Airlines	PriceFrom $199	Free Cancellation	Rating 8.0 11,542 reviews	Search Alaska Airlines flights
Delta	PriceFrom $203	Free Cancellation	Rating 7.9 8,016 reviews	Search Delta flights
United Airlines	PriceFrom $211	Free Cancellation	Rating 7.4 9,116 reviews	Search United Airlines flights
American Airlines	PriceFrom $213	Free Cancellation	Rating 7.2 11,066 reviews	Search American Airlines flights
Southwest	PriceFrom $238	Free Cancellation	Rating 8.0 4,258 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

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 Oregon

Popular cities in Oregon

Flights to New Yorkfrom $50

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Flights to Miamifrom $50

Flights to Chicagofrom $51

Flights to Orlandofrom $49

Flights to San Franciscofrom $59

Flights to Las Vegasfrom $49

Flights to Washington, D.C.from $58

Flights to Bostonfrom $51

Flights to Atlantafrom $44

Flights to Dallasfrom $51

Flights to Seattlefrom $57

Cheap flights from Chicago to Oregon from $105

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 2/21. 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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Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

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Find the cheapest flights from Chicago to Oregon

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Southwest flights from Chicago to Oregon

Our best Southwest deals on Chicago to Oregon flight tickets

Frontier flights from Chicago to Oregon

Our best Frontier 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?

The month of January is, on average, the cheapest month to fly to Oregon from Chicago, with most prices found around $266. The month of September is another great option to travel to Oregon, with average flight prices from Chicago averaging around $280.

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?

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

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

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 8% on your flight if you consider stops on a Chicago to Oregon flight.

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

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

What airlines fly to Oregon?

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

As of December 2025, there are 23 flights per day flying from Chicago to Oregon. The most common time of day flights depart is 4:00PM, with 36% of flights taking off in the afternoon.

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

162 flights are operational weekly from Chicago to Oregon as of December 2025. The most popular departure day for this route is Fri, with 15% of flights per week taking off on this day.

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

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

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

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

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

What is the most popular plane model 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?

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

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

How can momondo help me find flights 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?

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