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

As of March 2026, there are 8 flights per day flying from Chicago to Oregon. The most common time of day flights depart is 9:00PM, with 42% of flights taking off in the evening.

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

56 flights are operational weekly from Chicago to Oregon as of March 2026. The most popular departure day for this route is Sat, with 43% of flights per week taking off on this day.

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

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

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.

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 March 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.

$74 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.

9:42 pm - 12:27 pm

ORD

BOI

15h 45m

1 stop

1:22 pm - 8:37 pm

BOI

ORD

6h 15m

1 stop

$171Frontier

Mon, May 11 - Thu, May 14

6:20 pm - 11:50 pm

ORD

EUG

7h 30m

1 stop

12:35 pm - 11:55 pm

EUG

ORD

9h 20m

1 stop

$177Delta

Wed, May 27 - Wed, Jun 3

1:55 pm - 10:00 pm

MDW

EUG

10h 05m

2 stops

5:55 pm - 5:00 am

EUG

MDW

9h 05m

1 stop

$180Southwest

Tue, Jun 2 - Tue, Jun 9

1:55 pm - 10:00 pm

MDW

EUG

10h 05m

2 stops

1:40 pm - 12:05 am

EUG

MDW

8h 25m

2 stops

$185Southwest

Tue, Jun 2 - Tue, Jun 9

9:26 pm - 11:57 pm

ORD

PDX

4h 31mnonstop

1:23 pm - 7:32 pm

PDX

ORD

4h 09mnonstop

$216American Airlines

Thu, Apr 16 - Wed, Apr 22

7:40 am - 2:30 pm

ORD

PDX

8h 50m

1 stop

2:30 pm - 8:34 pm

PDX

ORD

4h 04mnonstop

$217United Airlines

Wed, Apr 22 - Wed, Apr 29

5:00 am - 1:25 pm

ORD

MFR

10h 25m

1 stop

2:08 pm - 12:32 am

MFR

ORD

8h 24m

1 stop

$317American Airlines

Wed, Apr 22 - Wed, Apr 29

6:00 am - 12:58 pm

ORD

RDM

8h 58m

1 stop

1:52 pm - 11:59 pm

RDM

ORD

8h 07m

1 stop

$317Alaska Airlines

Wed, Apr 29 - Wed, May 6

3:52 pm - 10:16 pm

ORD

MFR

8h 24m

1 stop

7:08 am - 6:50 pm

MFR

ORD

9h 42m

1 stop

$319Alaska Airlines

Sat, May 9 - Sat, May 16

7:40 am - 1:10 pm

ORD

OTH

7h 30m

1 stop

1:51 pm - 11:29 pm

OTH

ORD

7h 38m

1 stop

$419United Airlines

Fri, Apr 10 - Tue, Apr 14

United Airlines flights from Chicago to Oregon

Our best United Airlines deals on Chicago to Oregon flight tickets

United Airlines

Apr 22

ORD7:40 amChicago O'Hare Intl

8h 50m

1 stop

PDX2:30 pmPortland

Apr 29

PDX2:30 pmPortland

4h 04m

ORD8:34 pmChicago O'Hare Intl

$217

United Airlines

Apr 16

ORD8:00 pmChicago O'Hare Intl

4h 34m

PDX10:34 pmPortland

Apr 22

PDX4:15 pmPortland

6h 15m

1 stop

ORD12:30 amChicago O'Hare Intl

$231

United Airlines

Apr 23

ORD9:30 pmChicago O'Hare Intl

4h 29m

PDX11:59 pmPortland

Apr 25

PDX11:59 pmPortland

4h 04m

ORD6:03 amChicago O'Hare Intl

$235

American Airlines flights from Chicago to Oregon

Our best American Airlines deals on Chicago to Oregon flight tickets

American Airlines

Apr 16

ORD9:26 pmChicago O'Hare Intl

4h 31m

PDX11:57 pmPortland

Apr 22

PDX1:23 pmPortland

4h 09m

ORD7:32 pmChicago O'Hare Intl

$216

American Airlines

Apr 22

ORD8:19 pmChicago O'Hare Intl

4h 37m

PDX10:56 pmPortland

Apr 25

PDX6:22 amPortland

4h 10m

ORD12:32 pmChicago O'Hare Intl

$229

American Airlines

Apr 15

ORD9:54 amChicago O'Hare Intl

3h 55m

BOI12:49 pmBoise Air Term. Gowen Fld

Apr 22

BOI1:29 pmBoise Air Term. Gowen Fld

3h 47m

ORD6:16 pmChicago O'Hare Intl

$251

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoise

ORD - BOI

ORDBOI

Chicago O'Hare Intl

Mon 5/11

9:42 pm-12:27 pm

1 stop15h 45m

Boise Air Term. Gowen Fld

Thu 5/14

1:22 pm-8:37 pm

1 stop6h 15m

$171

ChicagoEugene

ORD - EUG

ORDEUG

Chicago O'Hare Intl

Wed 5/27

6:20 pm-11:50 pm

1 stop7h 30m

Eugene

Wed 6/3

12:35 pm-11:55 pm

1 stop9h 20m

$177

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Tue 6/2

1:55 pm-10:00 pm

2 stops10h 05m

Eugene

Tue 6/9

5:55 pm-5:00 am

1 stop9h 05m

$180

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Tue 6/2

1:55 pm-10:00 pm

2 stops10h 05m

Eugene

Tue 6/9

1:40 pm-12:05 am

2 stops8h 25m

$185

Quickest round-trip

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 4/16

9:26 pm-11:57 pm

Nonstop4h 31m

Portland

Wed 4/22

1:23 pm-7:32 pm

Nonstop4h 09m

$216

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 4/22

7:40 am-2:30 pm

1 stop8h 50m

Portland

Wed 4/29

2:30 pm-8:34 pm

Nonstop4h 04m

$217

ChicagoMedford

ORD - MFR

ORDMFR

Chicago O'Hare Intl

Wed 4/22

5:00 am-1:25 pm

1 stop10h 25m

Medford

Wed 4/29

2:08 pm-12:32 am

1 stop8h 24m

$317

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 4/29

6:00 am-12:58 pm

1 stop8h 58m

Bend/Redmond

Wed 5/6

1:52 pm-11:59 pm

1 stop8h 07m

$317

ChicagoMedford

ORD - MFR

ORDMFR

Chicago O'Hare Intl

Sat 5/9

3:52 pm-10:16 pm

1 stop8h 24m

Medford

Sat 5/16

7:08 am-6:50 pm

1 stop9h 42m

$319

ChicagoNorth Bend

ORD - OTH

ORDOTH

Chicago O'Hare Intl

Fri 4/10

7:40 am-1:10 pm

1 stop7h 30m

North Bend

Tue 4/14

1:51 pm-11:29 pm

1 stop7h 38m

$419

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 January is, on average, the cheapest month to fly to Oregon from Chicago, with most prices found around $257. The month of May is another great option to travel to Oregon, with average flight prices from Chicago averaging around $269.

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 $322. 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 $374.

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 $309. 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 $458. 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 $321 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 $260 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	$153
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 $153. The best round-trip flight deal from Chicago to Oregon found on momondo in the last 72 hours is $289.

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

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 March 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 36.42% of the total bookings. Other popular models include Boeing 737 MAX 8 with 16.26%, Boeing 737-900 with 11.29%, and Boeing 737 MAX 9 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 8,551 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 8,359 reviews	Search Delta flights
Frontier	PriceFrom $150	Free Cancellation	Rating 5.7 3,013 reviews	Search Frontier flights
United Airlines	PriceFrom $192	Free Cancellation	Rating 7.4 9,508 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom $193	Free Cancellation	Rating 7.9 12,134 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $200	Free Cancellation	Rating 7.1 11,518 reviews	Search American Airlines flights
Southwest	PriceFrom $227	Free Cancellation	Rating 8.0 4,333 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 $58

Flights to Los Angelesfrom $53

Flights to Orlandofrom $49

Flights to Miamifrom $53

Flights to Chicagofrom $56

Flights to San Franciscofrom $55

Flights to Las Vegasfrom $35

Flights to Washington, D.C.from $51

Flights to Bostonfrom $76

Flights to Atlantafrom $49

Flights to Dallasfrom $56

Flights to Seattlefrom $80

Cheap flights from Chicago to Oregon from $74

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 5/11. 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 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

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

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According to popular flight searches on momondo this year

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