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

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

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

As of August 2025, there are 26 flights per day flying from Chicago to Oregon. The most common time of day flights depart is 4:00PM, with 39% of flights taking off in the afternoon.

What airlines fly to Oregon?

United Airlines, Alaska Airlines and American 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 38% 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?

185 flights are operational weekly from Chicago to Oregon as of August 2025. The most popular departure day for this route is Thu, with 19% of flights per week taking off on this day.

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 August 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.

$90 Cheap Flights from Chicago to Oregon in 2025

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Find the cheapest flights from Chicago to Oregon

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:15 am - 11:11 amORD-PDX

6h 56m1 stop

6:05 am - 9:37 amPDX-ORD

25h 32m1 stop

$181

Find Deal

Mon, Sep 8 - Sun, Sep 14

7:15 am - 11:48 amORD-PDX

6h 33m1 stop

12:43 pm - 11:53 pmPDX-ORD

9h 10m1 stop

$182Frontier

Find Deal

Wed, Oct 8 - Wed, Oct 15

4:05 pm - 6:31 pmORD-PDX

4h 26mnonstop

11:59 pm - 5:52 amPDX-ORD

3h 53mnonstop

$203United Airlines

Find Deal

Sat, Oct 25 - Fri, Oct 31

3:45 pm - 6:05 pmMDW-PDX

4h 20mnonstop

10:15 am - 9:30 pmPDX-MDW

9h 15m1 stop

$213Southwest

Find Deal

Sat, Oct 25 - Fri, Oct 31

5:15 pm - 9:35 pmMDW-PDX

6h 20m1 stop

10:15 am - 9:30 pmPDX-MDW

9h 15m1 stop

$222Southwest

Find Deal

Sat, Oct 25 - Fri, Oct 31

8:00 am - 3:12 pmORD-BOI

8h 12m1 stop

8:50 pm - 6:22 amBOI-ORD

8h 32m1 stop

$224Alaska Airlines

Find Deal

Sat, Nov 1 - Fri, Nov 14

9:05 am - 11:41 amORD-PDX

4h 36mnonstop

7:00 am - 1:08 pmPDX-ORD

4h 08mnonstop

$227United Airlines

Find Deal

Sat, Sep 27 - Sat, Oct 4

6:00 am - 2:36 pmORD-BOI

9h 36m1 stop

7:13 am - 6:59 pmBOI-ORD

10h 46m1 stop

$236Alaska Airlines

Find Deal

Sat, Oct 11 - Tue, Oct 14

9:45 am - 12:40 pmORD-BOI

3h 55mnonstop

1:20 pm - 5:55 pmBOI-ORD

3h 35mnonstop

$255American Airlines

Find Deal

Wed, Jan 28 - Sun, Feb 1

9:40 am - 12:27 pmORD-BOI

3h 47mnonstop

1:07 pm - 5:45 pmBOI-ORD

3h 38mnonstop

$264American Airlines

Find Deal

Sat, Sep 27 - Sat, Oct 4

Spirit Airlines flights from Chicago to Oregon

Our best Spirit Airlines deals on Chicago to Oregon flight tickets

Spirit Airlines

Oct 14

ORD6:40 amChicago O'Hare Intl

14h 56m

1 stop

PDX7:36 pmPortland

Oct 18

PDX8:36 pmPortland

6h 59m

1 stop

ORD5:35 amChicago O'Hare Intl

$186

Find similar

Spirit Airlines

Oct 14

ORD6:40 amChicago O'Hare Intl

14h 56m

1 stop

PDX7:36 pmPortland

Oct 18

PDX8:36 pmPortland

6h 59m

1 stop

ORD5:35 amChicago O'Hare Intl

$187

Find similar

Spirit Airlines

Sep 8

ORD6:15 amChicago O'Hare Intl

6h 56m

1 stop

PDX11:11 amPortland

Sep 9

PDX12:07 pmPortland

7h 25m

1 stop

ORD9:32 pmChicago O'Hare Intl

$190

Find similar

Southwest flights from Chicago to Oregon

Our best Southwest deals on Chicago to Oregon flight tickets

Southwest

Oct 25

MDW3:45 pmChicago Midway

4h 20m

PDX6:05 pmPortland

Oct 31

PDX10:15 amPortland

9h 15m

1 stop

MDW9:30 pmChicago Midway

$213

Find similar

Southwest

Oct 25

MDW5:15 pmChicago Midway

6h 20m

1 stop

PDX9:35 pmPortland

Oct 31

PDX10:15 amPortland

9h 15m

1 stop

MDW9:30 pmChicago Midway

$222

Find similar

Southwest

Oct 25

MDW3:45 pmChicago Midway

4h 20m

PDX6:05 pmPortland

Oct 28

PDX6:00 amPortland

3h 55m

MDW11:55 amChicago Midway

$227

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Mon 9/8

6:15 am-11:11 am

1 stop6h 56m

Portland

Sun 9/14

6:05 am-9:37 am

1 stop25h 32m

$181

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 10/8

7:15 am-11:48 am

1 stop6h 33m

Portland

Wed 10/15

12:43 pm-11:53 pm

1 stop9h 10m

$182

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 10/25

4:05 pm-6:31 pm

Nonstop4h 26m

Portland

Fri 10/31

11:59 pm-5:52 am

Nonstop3h 53m

$203

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

3:45 pm-6:05 pm

Nonstop4h 20m

Portland

Fri 10/31

10:15 am-9:30 pm

1 stop9h 15m

$213

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

5:15 pm-9:35 pm

1 stop6h 20m

Portland

Fri 10/31

10:15 am-9:30 pm

1 stop9h 15m

$222

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Sat 11/1

8:00 am-3:12 pm

1 stop8h 12m

Boise Air Term. Gowen Fld

Fri 11/14

8:50 pm-6:22 am

1 stop8h 32m

$224

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 9/27

9:05 am-11:41 am

Nonstop4h 36m

Portland

Sat 10/4

7:00 am-1:08 pm

Nonstop4h 08m

$227

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Sat 10/11

6:00 am-2:36 pm

1 stop9h 36m

Boise Air Term. Gowen Fld

Tue 10/14

7:13 am-6:59 pm

1 stop10h 46m

$236

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Wed 1/28

9:45 am-12:40 pm

Nonstop3h 55m

Boise Air Term. Gowen Fld

Sun 2/1

1:20 pm-5:55 pm

Nonstop3h 35m

$255

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Sat 9/27

9:40 am-12:27 pm

Nonstop3h 47m

Boise Air Term. Gowen Fld

Sat 10/4

1:07 pm-5:45 pm

Nonstop3h 38m

$264

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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 September is, on average, the cheapest month to fly to Oregon from Chicago, with most prices found around $271. The month of January is another great option to travel to Oregon, with average flight prices from Chicago averaging around $274.

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 $331. 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 $404.

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 $317. 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 $435. 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 $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 $284 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?

No. A direct flight is the cheapest option for a flight between Chicago to Oregon.

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	$98
Fastest flight time	3h 42m
Direct flights	Every day
Airports in Oregon	1 airport

The best one-way flight to Oregon from Chicago in the past 72 hours is $98. The best round-trip flight deal from Chicago to Oregon found on momondo in the last 72 hours is $249.

The fastest flight from Chicago to Oregon takes 3h 42m

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 August 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 20.79% of the total bookings. Other popular models include Boeing 737 MAX 9 with 17.20%, Boeing 737-900 with 11.89%, and Airbus A321neo with 11.12%.

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 8,028 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $108	Free Cancellation	Rating 5.8 3,204 reviews	Search Frontier flights
Delta	PriceFrom $123	Free Cancellation	Rating 7.9 7,977 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $134	Free Cancellation	Rating 7.8 2,690 reviews	Search Hawaiian Airlines flights
Alaska Airlines	PriceFrom $183	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $216	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $227	Free Cancellation	Rating 7.4 8,944 reviews	Search United Airlines flights
Southwest	PriceFrom $238	Free Cancellation	Rating 8.0 4,242 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 $38

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Flights to Chicagofrom $46

Flights to Orlandofrom $39

Flights to Las Vegasfrom $38

Flights to San Franciscofrom $38

Flights to Washington, D.C.from $38

Flights to Bostonfrom $58

Flights to Atlantafrom $38

Flights to Dallasfrom $52

Flights to Seattlefrom $85

Cheap flights from Chicago to Oregon from $90

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 11/27. 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

Price Alerts

Price Alerts

Find the cheapest flights from Chicago to Oregon

Cheap round-trip flights

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Cheap last minute flights

Cheap direct flights

Spirit Airlines flights from Chicago to Oregon

Our best Spirit 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.

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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 September is, on average, the cheapest month to fly to Oregon from Chicago, with most prices found around $271. The month of January is another great option to travel to Oregon, with average flight prices from Chicago averaging around $274.

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?

No. A direct flight is the cheapest option for a flight between Chicago to Oregon.

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

Southwest, Hawaiian Airlines, and Frontier 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 August 2025, there are 26 flights per day flying from Chicago to Oregon. The most common time of day flights depart is 4:00PM, with 39% of flights taking off in the afternoon.

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

185 flights are operational weekly from Chicago to Oregon as of August 2025. The most popular departure day for this route is Thu, with 19% 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