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

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

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

121 flights are operational weekly from Chicago to Oregon as of November 2025. The most popular departure day for this route is Mon, with 20% of flights per week taking off on this day.

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

As of November 2025, there are 17 flights per day flying from Chicago to Oregon. The most common time of day flights depart is 4:00PM, with 48% of flights taking off in the afternoon.

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 November 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.

$71 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:50 am - 4:37 pmORD-PDX

11h 47m1 stop

5:32 pm - 6:05 amPDX-ORD

10h 33m1 stop

$206Multiple Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

2:05 pm - 4:48 pmORD-PDX

4h 43mnonstop

11:00 pm - 5:02 amPDX-ORD

4h 02mnonstop

$207Alaska Airlines

Find Deal

Mon, Dec 15 - Tue, Dec 30

7:00 am - 11:56 amORD-PDX

6h 56m1 stop

10:40 am - 10:30 pmPDX-ORD

9h 50m1 stop

$208Multiple Airlines

Find Deal

Sun, Dec 7 - Sat, Dec 13

4:50 pm - 7:20 pmMDW-PDX

4h 30mnonstop

6:15 am - 12:10 pmPDX-MDW

3h 55mnonstop

$217Southwest

Find Deal

Tue, Dec 9 - Wed, Dec 10

4:15 pm - 6:56 pmORD-PDX

4h 41mnonstop

1:24 pm - 9:15 pmPDX-ORD

5h 51m1 stop

$223United Airlines

Find Deal

Sat, Jan 24 - Sat, Jan 31

4:50 pm - 7:20 pmMDW-PDX

4h 30mnonstop

10:50 am - 8:05 pmPDX-MDW

7h 15m1 stop

$227Southwest

Find Deal

Tue, Dec 9 - Wed, Dec 10

7:45 am - 12:36 pmORD-PDX

6h 51m1 stop

7:00 am - 1:04 pmPDX-ORD

4h 04mnonstop

$231Hawaiian Airlines

Find Deal

Thu, Feb 12 - Thu, Feb 19

7:10 am - 1:45 pmORD-PDX

8h 35m1 stop

1:24 pm - 9:15 pmPDX-ORD

5h 51m1 stop

$232United Airlines

Find Deal

Tue, Jan 6 - Tue, Jan 13

5:50 pm - 8:24 pmORD-PDX

4h 34mnonstop

6:00 am - 12:12 pmPDX-ORD

4h 12mnonstop

$258American Airlines

Find Deal

Thu, Mar 12 - Tue, Mar 17

9:59 am - 1:06 pmORD-BOI

4h 07mnonstop

1:57 pm - 6:40 pmBOI-ORD

3h 43mnonstop

$272American Airlines

Find Deal

Thu, Dec 4 - Tue, Dec 9

Alaska Airlines flights from Chicago to Oregon

Our best Alaska Airlines deals on Chicago to Oregon flight tickets

Alaska Airlines

Dec 15

ORD2:05 pmChicago O'Hare Intl

4h 43m

PDX4:48 pmPortland

Dec 30

PDX11:00 pmPortland

4h 02m

ORD5:02 amChicago O'Hare Intl

$207

Find similar

Alaska Airlines

Jan 6

ORD2:12 pmChicago O'Hare Intl

4h 38m

PDX4:50 pmPortland

Jan 13

PDX7:05 amPortland

4h 05m

ORD1:10 pmChicago O'Hare Intl

$215

Find similar

Alaska Airlines

Dec 24

ORD7:00 amChicago O'Hare Intl

4h 50m

PDX9:50 amPortland

Dec 31

PDX7:00 amPortland

4h 09m

ORD1:09 pmChicago O'Hare Intl

$217

Find similar

Frontier flights from Chicago to Oregon

Our best Frontier deals on Chicago to Oregon flight tickets

Frontier

Nov 22

ORD7:00 amChicago O'Hare Intl

10h 07m

1 stop

PDX3:07 pmPortland

Nov 25

PDX10:06 amPortland

7h 33m

1 stop

ORD7:39 pmChicago O'Hare Intl

$210

Find similar

Frontier

Dec 12

ORD6:50 amChicago O'Hare Intl

11h 47m

1 stop

PDX4:37 pmPortland

Dec 14

PDX12:51 pmPortland

20h 51m

2 stops

ORD11:42 amChicago O'Hare Intl

$211

Find similar

Frontier

Nov 15

ORD7:15 amChicago O'Hare Intl

6h 41m

1 stop

PDX11:56 amPortland

Nov 17

PDX3:26 pmPortland

6h 49m

1 stop

ORD12:15 amChicago O'Hare Intl

$214

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 12/4

6:50 am-4:37 pm

1 stop11h 47m

Portland

Mon 12/8

5:32 pm-6:05 am

1 stop10h 33m

$206

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Mon 12/15

2:05 pm-4:48 pm

Nonstop4h 43m

Portland

Tue 12/30

11:00 pm-5:02 am

Nonstop4h 02m

$207

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sun 12/7

7:00 am-11:56 am

1 stop6h 56m

Portland

Sat 12/13

10:40 am-10:30 pm

1 stop9h 50m

$208

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 12/9

4:50 pm-7:20 pm

Nonstop4h 30m

Portland

Wed 12/10

6:15 am-12:10 pm

Nonstop3h 55m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 1/24

4:15 pm-6:56 pm

Nonstop4h 41m

Portland

Sat 1/31

1:24 pm-9:15 pm

1 stop5h 51m

$223

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 12/9

4:50 pm-7:20 pm

Nonstop4h 30m

Portland

Wed 12/10

10:50 am-8:05 pm

1 stop7h 15m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 2/12

7:45 am-12:36 pm

1 stop6h 51m

Portland

Thu 2/19

7:00 am-1:04 pm

Nonstop4h 04m

$231

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 1/6

7:10 am-1:45 pm

1 stop8h 35m

Portland

Tue 1/13

1:24 pm-9:15 pm

1 stop5h 51m

$232

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 3/12

5:50 pm-8:24 pm

Nonstop4h 34m

Portland

Tue 3/17

6:00 am-12:12 pm

Nonstop4h 12m

$258

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Thu 12/4

9:59 am-1:06 pm

Nonstop4h 07m

Boise Air Term. Gowen Fld

Tue 12/9

1:57 pm-6:40 pm

Nonstop3h 43m

$272

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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 $271. The month of September is another great option to travel to Oregon, with average flight prices from Chicago averaging around $278.

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 $332. 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 $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 $492. 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 $336 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 $272 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.

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 51m
Direct flights	Every day
Airports in Oregon	1 airport

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 51m

Direct flights go from Chicago to Oregon every day.

There is 1 airport near Oregon: 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 November 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 25.58% of the total bookings. Other popular models include Boeing 737 MAX 9 with 14.97%, Boeing 737-900 with 13.39%, and Airbus A321neo with 9.66%.

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 8,112 reviews	Search Spirit Airlines flights
Delta	PriceFrom $88	Free Cancellation	Rating 7.9 8,002 reviews	Search Delta flights
Frontier	PriceFrom $110	Free Cancellation	Rating 5.8 3,116 reviews	Search Frontier flights
Hawaiian Airlines	PriceFrom $134	Free Cancellation	Rating 7.8 2,799 reviews	Search Hawaiian Airlines flights
Alaska Airlines	PriceFrom $208	Free Cancellation	Rating 8.0 11,237 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $213	Free Cancellation	Rating 7.2 11,038 reviews	Search American Airlines flights
United Airlines	PriceFrom $225	Free Cancellation	Rating 7.4 8,998 reviews	Search United Airlines flights
Southwest	PriceFrom $238	Free Cancellation	Rating 8.0 4,237 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 $49

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Flights to Chicagofrom $54

Flights to Orlandofrom $47

Flights to Las Vegasfrom $49

Flights to San Franciscofrom $54

Flights to Washington, D.C.from $54

Flights to Bostonfrom $40

Flights to Atlantafrom $40

Flights to Dallasfrom $49

Flights to Seattlefrom $68

Cheap flights from Chicago to Oregon from $71

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 1/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

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Price Alerts

Find the cheapest flights from Chicago to Oregon

Cheap round-trip flights

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Alaska Airlines flights from Chicago to Oregon

Our best Alaska Airlines 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.

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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

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 $271. The month of September is another great option to travel to Oregon, with average flight prices from Chicago averaging around $278.

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.

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

Frontier, Alaska Airlines, and Southwest 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 November 2025, there are 17 flights per day flying from Chicago to Oregon. The most common time of day flights depart is 4:00PM, with 48% of flights taking off in the afternoon.

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

121 flights are operational weekly from Chicago to Oregon as of November 2025. The most popular departure day for this route is Mon, with 20% 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