What is the cheapest airline that flies from Oregon to Chicago O'Hare Intl?

Frontier, Alaska Airlines, and Hawaiian Airlines are the most popular carriers operating from Oregon to Chicago O'Hare Intl

What airlines fly to Chicago O'Hare Intl Airport?

United Airlines, Alaska Airlines and American Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Oregon according to our data. United Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 7 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

How many flights depart from Oregon to Chicago O'Hare Intl Airport on average per day?

32 flights are operational daily from Oregon to Chicago O'Hare Intl Airport as of September 2025. The most popular departure time for this route is 7:00AM, with 69% of flights per day taking off at noon.

How many flights depart from Oregon to Chicago O'Hare Intl Airport on average per week?

The number of flights available between Oregon and Chicago O'Hare Intl Airport is 227 per week as of September 2025. The most frequent departure day is Thu, with 18% of weekly flights leaving on this day.

How long does it take to fly to Chicago O'Hare Intl Airport?

On average, it takes 3h 53m to fly from Oregon to Chicago O'Hare Intl Airport if you fly out of Portland (the most popular airport in Oregon) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago O'Hare Intl Airport). If you’re flying out of Eugene and into Chicago O'Hare Intl Airport, then the flight time is around 5h 34m.

When did momondo last update prices for flights from Oregon to Chicago O'Hare Intl Airport?

Prices for flights from Oregon to Chicago O'Hare Intl Airport are refreshed on a daily basis.

How many operators does momondo search for flights from Oregon to Chicago O'Hare Intl Airport?

There are 8 operators available for flights from Oregon to Chicago O'Hare Intl Airport as of September 2025.

How old do you have to be to fly from Oregon to Chicago O'Hare Intl Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Oregon to Chicago O'Hare Intl Airport.

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$102 Cheap Flights from Oregon to Chicago O'Hare Intl Airport in 2025/26

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Find the cheapest flights from Oregon to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

12:43 pm - 12:59 amPDX-ORD

10h 16m1 stop

2:05 pm - 4:41 pmORD-PDX

4h 36mnonstop

$193Multiple Airlines

Find Deal

Fri, Oct 24 - Fri, Oct 31

12:52 pm - 11:29 pmPDX-ORD

8h 37m1 stop

6:20 pm - 11:56 amORD-PDX

19h 36m2 stops

$194Frontier

Find Deal

Sat, Nov 15 - Mon, Nov 17

12:32 am - 10:29 amPDX-ORD

7h 57m1 stop

6:13 pm - 10:40 pmORD-PDX

6h 27m1 stop

$195Delta

Find Deal

Fri, Dec 5 - Mon, Dec 8

11:00 pm - 5:01 amPDX-ORD

4h 01mnonstop

2:54 pm - 8:46 pmORD-PDX

7h 52m1 stop

$201Alaska Airlines

Find Deal

Fri, Oct 31 - Wed, Nov 5

7:00 am - 1:04 pmPDX-ORD

4h 04mnonstop

7:00 am - 9:39 amORD-PDX

4h 39mnonstop

$209Alaska Airlines

Find Deal

Tue, Oct 21 - Fri, Oct 31

3:50 pm - 12:54 amPDX-ORD

7h 04m1 stop

7:15 am - 9:40 amORD-PDX

4h 25mnonstop

$213United Airlines

Find Deal

Wed, Oct 15 - Mon, Oct 20

11:00 pm - 5:01 amPDX-ORD

4h 01mnonstop

8:00 am - 12:38 pmORD-PDX

6h 38m1 stop

$217Hawaiian Airlines

Find Deal

Fri, Oct 31 - Sat, Nov 8

11:00 pm - 5:01 amPDX-ORD

4h 01mnonstop

7:00 am - 9:39 amORD-PDX

4h 39mnonstop

$222Hawaiian Airlines

Find Deal

Fri, Oct 31 - Mon, Nov 3

12:25 pm - 9:24 pmRDM-ORD

6h 59m1 stop

7:40 pm - 11:59 pmORD-RDM

6h 19m1 stop

$223Delta

Find Deal

Tue, Dec 9 - Fri, Dec 12

1:09 pm - 10:39 pmMFR-ORD

7h 30m1 stop

6:15 am - 12:07 pmORD-MFR

7h 52m1 stop

$223United Airlines

Find Deal

Wed, Oct 15 - Mon, Oct 20

American Airlines flights from Oregon to Chicago O'Hare Intl Airport

Our best American Airlines deals on Oregon to Chicago O'Hare Intl Airport flight tickets

American Airlines

Oct 24

BOI1:26 pmBoise Air Term. Gowen Fld

3h 48m

ORD6:14 pmChicago O'Hare Intl

Oct 28

ORD9:56 amChicago O'Hare Intl

3h 50m

BOI12:46 pmBoise Air Term. Gowen Fld

$252

Find similar

American Airlines

Nov 17

BOI1:40 pmBoise Air Term. Gowen Fld

3h 47m

ORD6:27 pmChicago O'Hare Intl

Nov 19

ORD9:55 amChicago O'Hare Intl

4h 11m

BOI1:06 pmBoise Air Term. Gowen Fld

$255

Find similar

American Airlines

Oct 5

BOI1:07 pmBoise Air Term. Gowen Fld

3h 38m

ORD5:45 pmChicago O'Hare Intl

Nov 1

ORD9:56 amChicago O'Hare Intl

3h 50m

BOI12:46 pmBoise Air Term. Gowen Fld

$262

Find similar

Frontier flights from Oregon to Chicago O'Hare Intl Airport

Our best Frontier deals on Oregon to Chicago O'Hare Intl Airport flight tickets

Frontier

Nov 15

PDX12:52 pmPortland

8h 37m

1 stop

ORD11:29 pmChicago O'Hare Intl

Nov 17

ORD6:20 pmChicago O'Hare Intl

19h 36m

2 stops

PDX11:56 amPortland

$194

Find similar

Frontier

Oct 17

PDX12:43 pmPortland

10h 16m

1 stop

ORD12:59 amChicago O'Hare Intl

Oct 25

ORD7:05 amChicago O'Hare Intl

6h 43m

1 stop

PDX11:48 amPortland

$196

Find similar

Frontier

Oct 1

PDX7:15 amPortland

12h 13m

1 stop

ORD9:28 pmChicago O'Hare Intl

Oct 8

ORD7:15 amChicago O'Hare Intl

27h 08m

2 stops

PDX8:23 amPortland

$203

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Oregon to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/24

12:43 pm-12:59 am

1 stop10h 16m

Chicago O'Hare Intl

Fri 10/31

2:05 pm-4:41 pm

Nonstop4h 36m

$193

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 11/15

12:52 pm-11:29 pm

1 stop8h 37m

Chicago O'Hare Intl

Mon 11/17

6:20 pm-11:56 am

2 stops19h 36m

$194

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 12/5

12:32 am-10:29 am

1 stop7h 57m

Chicago O'Hare Intl

Mon 12/8

6:13 pm-10:40 pm

1 stop6h 27m

$195

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/31

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Wed 11/5

2:54 pm-8:46 pm

1 stop7h 52m

$201

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 10/21

7:00 am-1:04 pm

Nonstop4h 04m

Chicago O'Hare Intl

Fri 10/31

7:00 am-9:39 am

Nonstop4h 39m

$209

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 10/15

3:50 pm-12:54 am

1 stop7h 04m

Chicago O'Hare Intl

Mon 10/20

7:15 am-9:40 am

Nonstop4h 25m

$213

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/31

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Sat 11/8

8:00 am-12:38 pm

1 stop6h 38m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/31

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Mon 11/3

7:00 am-9:39 am

Nonstop4h 39m

$222

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 12/9

12:25 pm-9:24 pm

1 stop6h 59m

Chicago O'Hare Intl

Fri 12/12

7:40 pm-11:59 pm

1 stop6h 19m

$223

MedfordChicago

MFR - ORD

MFRORD

Medford

Wed 10/15

1:09 pm-10:39 pm

1 stop7h 30m

Chicago O'Hare Intl

Mon 10/20

6:15 am-12:07 pm

1 stop7h 52m

$223

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 Oregon to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Oregon averaging around $298.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $453. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Oregon because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $576.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Oregon in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $312 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $523. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Oregon to Chicago O'Hare Intl flight route?

Fly from Portland to Chicago O'Hare Intl for the best Oregon - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Oregon when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $360 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Oregon for as low as $293 on momondo.

What cabin class options are available on Oregon to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Oregon to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Oregon to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oregon to Chicago O'Hare Intl Airport

Best Price Found	$169
Fastest flight time	3h 31m
Direct flights	Every day

The best one-way flight to Chicago O'Hare Intl Airport from Oregon in the past 72 hours is $169. The best round-trip flight deal from Oregon to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $324.

The fastest flight from Oregon to Chicago O'Hare Intl Airport takes 3h 31m

Direct flights go from Oregon to Chicago O'Hare Intl Airport every day.

Search flight deals

When did momondo last update prices for flights from Oregon to Chicago O'Hare Intl Airport?
Prices for flights from Oregon to Chicago O'Hare Intl Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Oregon to Chicago O'Hare Intl Airport?
There are 8 operators available for flights from Oregon to Chicago O'Hare Intl Airport as of September 2025.
How old do you have to be to fly from Oregon to Chicago O'Hare Intl Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Oregon to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Oregon to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Oregon to Chicago O'Hare Intl Airport is Boeing 737 MAX 9 (20.96% of total bookings). The next most popular plane models are Boeing 737-800 (15.39%), Boeing 737-900 (12.24%), and Airbus A321neo (11.70%).

Best airlines flying from Oregon to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Oregon to Chicago O'Hare Intl Airport with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $93	Free Cancellation	Rating 6.3 8,030 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $108	Free Cancellation	Rating 5.8 3,171 reviews	Search Frontier flights
Delta	PriceFrom $123	Free Cancellation	Rating 7.9 7,964 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $125	Free Cancellation	Rating 7.8 2,732 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $195	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $200	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $226	Free Cancellation	Rating 7.4 8,926 reviews	Search United Airlines flights

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Orland Park

Tinley Park

Elgin

Aurora

Janesville

Benton Harbor

Why use momondo?

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

Finding the right flight to Chicago from Oregon is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Chicago from Oregon with this policy.

How can momondo help me find flights from Oregon to Chicago?

Once all potential Oregon to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Oregon to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Oregon to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Chicago O'Hare Intl Airport trip

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Cheap flights from Oregon to Chicago from $102

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oregon to Chicago departing on 10/23. 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 Oregon to Chicago O'Hare Intl Airport

Our best American Airlines deals on Oregon to Chicago O'Hare Intl Airport flight tickets

Frontier flights from Oregon to Chicago O'Hare Intl Airport

Our best Frontier deals on Oregon to Chicago O'Hare Intl Airport flight tickets

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Use the filters below to find and compare flights from Oregon to Chicago O'Hare Intl Airport that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Oregon to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Oregon averaging around $298.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest Oregon to Chicago O'Hare Intl flight route?

Fly from Portland to Chicago O'Hare Intl for the best Oregon - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

What cabin class options are available on Oregon to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Oregon to Chicago O'Hare Intl 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 Oregon to Chicago O'Hare Intl?

Frontier, Alaska Airlines, and Hawaiian Airlines are the most popular carriers operating from Oregon to Chicago O'Hare Intl

What airlines fly to Chicago O'Hare Intl Airport?

How many flights depart from Oregon to Chicago O'Hare Intl Airport on average per day?

32 flights are operational daily from Oregon to Chicago O'Hare Intl Airport as of September 2025. The most popular departure time for this route is 7:00AM, with 69% of flights per day taking off at noon.

How many flights depart from Oregon to Chicago O'Hare Intl Airport on average per week?

The number of flights available between Oregon and Chicago O'Hare Intl Airport is 227 per week as of September 2025. The most frequent departure day is Thu, with 18% of weekly flights leaving on this day.

How long does it take to fly to Chicago O'Hare Intl Airport?

Cheap Oregon to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oregon to Chicago O'Hare Intl Airport

Best Price Found

Fastest flight time

Direct flights

When did momondo last update prices for flights from Oregon to Chicago O'Hare Intl Airport?

How many operators does momondo search for flights from Oregon to Chicago O'Hare Intl Airport?

How old do you have to be to fly from Oregon to Chicago O'Hare Intl Airport?

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

What is the most popular plane model from Oregon to Chicago O'Hare Intl Airport?

Best airlines flying from Oregon to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Oregon to Chicago O'Hare Intl Airport with momondo

Traveling to a place near Chicago?

Why use momondo?

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

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

How can momondo help me find flights from Oregon to Chicago?

I’m not ready to book a flight from Oregon to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago O'Hare Intl Airport 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 Chicago

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo