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

76 flights are operational weekly from Chicago to Oregon as of November 2026. The most popular departure day for this route is Wed, with 33% 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 43% of people opting to fly with this airline when traveling to Oregon. Keep in mind that there are 7 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 day?

As of November 2026, there are 10 flights per day flying from Chicago to Oregon. The most common time of day flights depart is 5:00PM, with 60% of flights taking off in the afternoon.

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

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 7 as of November 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.

$139 Cheap Flights from Chicago to Oregon in 2026/27

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.

8:00 am - 2:20 pmORD Chicago O'Hare Intl-EUG Eugene

8h 20m1 stop Seattle/Tacoma Intl

2:57 pm - 11:59 pmEUG Eugene-ORD Chicago O'Hare Intl

7h 02m1 stop Seattle/Tacoma Intl

$277Alaska Airlines

Tue, Jan 5 - Tue, Jan 12

6:47 pm - 11:58 pmORD Chicago O'Hare Intl-EUG Eugene

7h 11m1 stop Seattle/Tacoma Intl

2:03 pm - 11:59 pmEUG Eugene-ORD Chicago O'Hare Intl

7h 56m1 stop San Diego

$277Alaska Airlines

Tue, Jan 19 - Wed, Jan 20

7:00 am - 12:09 pmORD Chicago O'Hare Intl-PDX Portland

7h 09m1 stop Denver Intl

11:12 am - 6:00 amPDX Portland-ORD Chicago O'Hare Intl

16h 48m1 stop Las Vegas Harry Reid Intl

$354Frontier

Thu, Dec 24 - Fri, Jan 8

7:58 pm - 9:29 amORD Chicago O'Hare Intl-PDX Portland

15h 31m1 stop San Diego

1:29 pm - 1:07 amPDX Portland-ORD Chicago O'Hare Intl

9h 38m1 stop Denver Intl

$354Multiple Airlines

Sun, Jan 3 - Tue, Jan 12

7:30 am - 10:04 pmORD Chicago O'Hare Intl-PDX Portland

16h 34m1 stop Las Vegas Harry Reid Intl

7:00 am - 1:08 pmPDX Portland-ORD Chicago O'Hare Intl

4h 08mnonstop

$354Multiple Airlines

Thu, Feb 25 - Wed, Mar 3

6:59 am - 1:41 pmORD Chicago O'Hare Intl-PDX Portland

8h 42m1 stop Dallas/Fort Worth

1:30 pm - 7:44 pmPDX Portland-ORD Chicago O'Hare Intl

4h 14mnonstop

$357American Airlines

Tue, Dec 8 - Wed, Dec 16

9:55 am - 12:47 pmORD Chicago O'Hare Intl-PDX Portland

4h 52mnonstop

2:48 pm - 12:33 amPDX Portland-ORD Chicago O'Hare Intl

7h 45m1 stop Phoenix Sky Harbor Intl

$357American Airlines

Tue, Jan 5 - Sat, Jan 9

7:40 pm - 10:20 pmMDW Chicago Midway-PDX Portland

4h 40mnonstop

10:50 am - 7:25 pmPDX Portland-MDW Chicago Midway

6h 35m1 stop Denver Intl

$357Southwest

Wed, Feb 17 - Wed, Feb 24

6:15 am - 10:45 amMDW Chicago Midway-PDX Portland

6h 30m1 stop Denver Intl

6:30 am - 12:25 pmPDX Portland-MDW Chicago Midway

3h 55mnonstop

$357Southwest

Wed, Jan 6 - Wed, Jan 13

7:35 am - 9:33 pmORD Chicago O'Hare Intl-PDX Portland

15h 58m1 stop Las Vegas Harry Reid Intl

4:27 pm - 12:26 amPDX Portland-ORD Chicago O'Hare Intl

5h 59m1 stop Denver Intl

$357Frontier

Sun, Dec 20 - Tue, Jan 5

Cheap last minute flights

Enter your travel dates to find the best prices.

6:30 am - 11:07 amORD Chicago O'Hare Intl-PDX Portland

6h 37m1 stop Denver Intl

11:23 am - 5:10 amPDX Portland-ORD Chicago O'Hare Intl

15h 47m1 stop Las Vegas Harry Reid Intl

$372Frontier

Tue, Nov 17 - Sun, Nov 22

6:30 am - 11:12 amORD Chicago O'Hare Intl-PDX Portland

6h 42m1 stop Denver Intl

11:23 am - 5:10 amPDX Portland-ORD Chicago O'Hare Intl

15h 47m1 stop Las Vegas Harry Reid Intl

$376Frontier

Sun, Nov 15 - Sun, Nov 22

2:15 pm - 10:52 pmORD Chicago O'Hare Intl-PDX Portland

10h 37m1 stop San Diego

7:01 am - 1:09 pmPDX Portland-ORD Chicago O'Hare Intl

4h 08mnonstop

$397Alaska Airlines

Mon, Nov 16 - Tue, Nov 17

2:07 pm - 4:50 pmORD Chicago O'Hare Intl-PDX Portland

4h 43mnonstop

10:10 pm - 5:10 amPDX Portland-ORD Chicago O'Hare Intl

29h 00m1 stop Las Vegas Harry Reid Intl

$441Multiple Airlines

Wed, Nov 18 - Sat, Nov 21

2:07 pm - 4:50 pmORD Chicago O'Hare Intl-PDX Portland

4h 43mnonstop

10:10 pm - 5:10 amPDX Portland-ORD Chicago O'Hare Intl

29h 00m1 stop Las Vegas Harry Reid Intl

$446Multiple Airlines

Fri, Nov 13 - Sat, Nov 21

4:25 pm - 7:12 pmORD Chicago O'Hare Intl-PDX Portland

4h 47mnonstop

2:26 pm - 8:28 pmPDX Portland-ORD Chicago O'Hare Intl

4h 02mnonstop

$452United Airlines

Fri, Nov 13 - Tue, Dec 15

9:15 pm - 11:55 pmMDW Chicago Midway-PDX Portland

4h 40mnonstop

11:20 am - 5:05 pmPDX Portland-MDW Chicago Midway

3h 45mnonstop

$452Southwest

Fri, Nov 13 - Tue, Dec 15

4:25 pm - 7:12 pmORD Chicago O'Hare Intl-PDX Portland

4h 47mnonstop

7:25 pm - 5:25 amPDX Portland-ORD Chicago O'Hare Intl

8h 00m1 stop San Francisco

$462United Airlines

Fri, Nov 13 - Tue, Dec 15

7:20 am - 1:37 pmORD Chicago O'Hare Intl-PDX Portland

8h 17m1 stop San Diego

7:01 am - 1:09 pmPDX Portland-ORD Chicago O'Hare Intl

4h 08mnonstop

$462Alaska Airlines

Mon, Nov 16 - Tue, Nov 17

10:10 am - 4:55 pmMDW Chicago Midway-PDX Portland

8h 45m1 stop San Jose

11:20 am - 5:05 pmPDX Portland-MDW Chicago Midway

3h 45mnonstop

$462Southwest

Fri, Nov 13 - Tue, Dec 15

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American Airlines flights from Chicago to Oregon

Our best American Airlines deals on Chicago to Oregon flight tickets

American Airlines

Dec 5

ORD9:45 amChicago O'Hare Intl

4h 52m

PDX12:37 pmPortland

Dec 12

PDX11:13 pmPortland

3h 54m

ORD5:07 amChicago O'Hare Intl

$360

American Airlines

Dec 5

ORD9:45 amChicago O'Hare Intl

4h 52m

PDX12:37 pmPortland

Dec 12

PDX11:13 pmPortland

3h 54m

ORD5:07 amChicago O'Hare Intl

$361

American Airlines

Dec 12

ORD5:00 pmChicago O'Hare Intl

4h 47m

PDX7:47 pmPortland

Dec 19

PDX11:36 pmPortland

4h 09m

ORD5:45 amChicago O'Hare Intl

$391

Frontier flights from Chicago to Oregon

Our best Frontier deals on Chicago to Oregon flight tickets

Frontier

Dec 24

ORD7:00 amChicago O'Hare Intl

7h 09m

1 stop

PDX12:09 pmPortland

Jan 8

PDX11:12 amPortland

16h 48m

1 stop

ORD6:00 amChicago O'Hare Intl

$354

Frontier

Dec 22

ORD7:35 amChicago O'Hare Intl

15h 58m

1 stop

PDX9:33 pmPortland

Jan 7

PDX4:27 pmPortland

5h 59m

1 stop

ORD12:26 amChicago O'Hare Intl

$362

Frontier

Jan 18

ORD1:33 pmChicago O'Hare Intl

25h 01m

2 stops

PDX12:34 pmPortland

Jan 24

PDX4:27 pmPortland

6h 08m

1 stop

ORD12:35 amChicago O'Hare Intl

$366

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoEugene

ORD Chicago O'Hare Intl - EUG Eugene

ORDEUG

Chicago O'Hare Intl

Tue 1/5

8:00 am-2:20 pm

1 stop8h 20m

Eugene

Tue 1/12

2:57 pm-11:59 pm

1 stop7h 02m

$277

ChicagoEugene

ORD Chicago O'Hare Intl - EUG Eugene

ORDEUG

Chicago O'Hare Intl

Tue 1/19

6:47 pm-11:58 pm

1 stop7h 11m

Eugene

Wed 1/20

2:03 pm-11:59 pm

1 stop7h 56m

$277

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Thu 12/24

7:00 am-12:09 pm

1 stop7h 09m

Portland

Fri 1/8

11:12 am-6:00 am

1 stop16h 48m

$354

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Sun 1/3

7:58 pm-9:29 am

1 stop15h 31m

Portland

Tue 1/12

1:29 pm-1:07 am

1 stop9h 38m

$354

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Thu 2/25

7:30 am-10:04 pm

1 stop16h 34m

Portland

Wed 3/3

7:00 am-1:08 pm

Nonstop4h 08m

$354

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Tue 12/8

6:59 am-1:41 pm

1 stop8h 42m

Portland

Wed 12/16

1:30 pm-7:44 pm

Nonstop4h 14m

$357

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Tue 1/5

9:55 am-12:47 pm

Nonstop4h 52m

Portland

Sat 1/9

2:48 pm-12:33 am

1 stop7h 45m

$357

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Wed 2/17

7:40 pm-10:20 pm

Nonstop4h 40m

Portland

Wed 2/24

10:50 am-7:25 pm

1 stop6h 35m

$357

Quickest round-trip

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Wed 1/6

6:15 am-10:45 am

1 stop6h 30m

Portland

Wed 1/13

6:30 am-12:25 pm

Nonstop3h 55m

$357

ChicagoPortland

ORD Chicago O'Hare Intl - PDX Portland

ORDPDX

Chicago O'Hare Intl

Sun 12/20

7:35 am-9:33 pm

1 stop15h 58m

Portland

Tue 1/5

4:27 pm-12:26 am

1 stop5h 59m

$357

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 February is, on average, the cheapest month to fly to Oregon from Chicago, with most prices found around $313. The month of January is another great option to travel to Oregon, with average flight prices from Chicago averaging around $315.

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 $358. 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 $449.

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 $351. 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 $462. 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 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 $376 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 6% 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	$139
Fastest flight time	3h 51m
Direct flights	Every day
Airports in Oregon	64 airports

The best one-way flight to Oregon from Chicago in the past 72 hours is $139. The best round-trip flight deal from Chicago to Oregon found on momondo in the last 72 hours is $277.

The fastest flight from Chicago to Oregon takes 3h 51m

Direct flights go from Chicago to Oregon every day.

There are 64 airports in Oregon. From Chicago there are direct flights to Portland (PDX).

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 7 as of November 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 27.52% of the total bookings. Other popular models include Boeing 737 MAX 8 with 16.25%, Airbus A321-100/200 with 15.05%, and Airbus A321neo with 13.43%.

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
Frontier	PriceFrom $155	Free Cancellation	Rating 5.5 2,505 reviews	Search Frontier flights
JetBlue	PriceFrom $191	Free Cancellation	Rating 7.1 3,071 reviews	Search JetBlue flights
Alaska Airlines	PriceFrom $197	Free Cancellation	Rating 7.9 13,157 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $218	Free Cancellation	Rating 7.3 10,478 reviews	Search United Airlines flights
American Airlines	PriceFrom $222	Free Cancellation	Rating 7.0 12,224 reviews	Search American Airlines flights
Southwest	PriceFrom $239	Free Cancellation	Rating 8.0 4,216 reviews	Search Southwest flights
Delta	PriceFrom $256	Free Cancellation	Rating 7.8 8,708 reviews	Search Delta 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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Popular cities in Oregon

Flights to New Yorkfrom $62

Flights to Los Angelesfrom $38

Flights to Orlandofrom $44

Flights to Miamifrom $42

Flights to San Franciscofrom $37

Flights to Chicagofrom $90

Flights to Las Vegasfrom $38

Flights to Washington, D.C.from $46

Flights to Fort Lauderdalefrom $43

Flights to Bostonfrom $83

Flights to Atlantafrom $38

Flights to Dallasfrom $93

Cheap flights from Chicago to Oregon from $139

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 2/23. 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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American Airlines flights from Chicago to Oregon

Our best American 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.

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

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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