What airlines fly to Chicago?

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago from Oregon according to our data. United Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

132 flights are operational weekly from Oregon to Chicago as of November 2026. The most popular departure day for this route is Mon, with 19% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Average flight duration from Oregon to Chicago depends on which airport you fly into and out of. Flying from Portland to Chicago O'Hare Intl Airport is 3h 49m on average, while flying from Eugene to Chicago O'Hare Intl Airport is 4h 13m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

18 flights are operational daily from Oregon to Chicago as of November 2026. The most popular departure time for this route is 7:00AM, with 53% of flights per day taking off at noon.

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

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

When did momondo last update prices for flights from Oregon to Chicago?

Prices for flights from Oregon to Chicago were last updated today.

How many operators does momondo search for flights from Oregon to Chicago?

As of November 2026, there are 6 operators available to choose from for flights from Oregon to Chicago.

How old do you have to be to fly from Oregon to Chicago?

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 Oregon to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$165 Cheap Flights from Oregon to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Oregon to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:59 pm - 5:37 amEUG Eugene-ORD Chicago O'Hare Intl

8h 38m1 stop Seattle/Tacoma Intl

2:13 pm - 11:57 amORD Chicago O'Hare Intl-EUG Eugene

23h 44m1 stop San Diego

$277Alaska Airlines

Sat, Dec 12 - Tue, Dec 15

5:15 am - 1:13 pmEUG Eugene-ORD Chicago O'Hare Intl

5h 58m1 stop Portland

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

7h 11m1 stop Seattle/Tacoma Intl

$327Alaska Airlines

Thu, Feb 4 - Tue, Feb 9

5:10 pm - 12:54 amPDX Portland-ORD Chicago O'Hare Intl

29h 44m1 stop Denver Intl

7:25 am - 1:03 pmORD Chicago O'Hare Intl-PDX Portland

7h 38m1 stop Denver Intl

$345Frontier

Tue, Dec 8 - Thu, Dec 10

5:10 pm - 12:54 amPDX Portland-ORD Chicago O'Hare Intl

29h 44m1 stop Denver Intl

7:25 am - 4:10 pmORD Chicago O'Hare Intl-PDX Portland

10h 45m1 stop Denver Intl

$346Frontier

Tue, Dec 8 - Tue, Dec 15

11:13 pm - 5:07 amPDX Portland-ORD Chicago O'Hare Intl

3h 54mnonstop

5:05 pm - 7:55 pmORD Chicago O'Hare Intl-PDX Portland

4h 50mnonstop

$347American Airlines

Wed, Dec 9 - Tue, Dec 15

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

4h 14mnonstop

9:45 am - 12:37 pmORD Chicago O'Hare Intl-PDX Portland

4h 52mnonstop

$347American Airlines

Wed, Dec 9 - Tue, Dec 15

10:45 am - 4:52 pmPDX Portland-ORD Chicago O'Hare Intl

4h 07mnonstop

4:15 pm - 6:59 pmORD Chicago O'Hare Intl-PDX Portland

4h 44mnonstop

$347United Airlines

Tue, Jan 19 - Wed, Jan 20

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

4h 02mnonstop

12:40 pm - 3:19 pmORD Chicago O'Hare Intl-PDX Portland

4h 39mnonstop

$347United Airlines

Sat, Dec 12 - Tue, Dec 15

8:25 am - 2:20 pmPDX Portland-MDW Chicago Midway

3h 55mnonstop

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

4h 40mnonstop

$347Southwest

Sat, Feb 6 - Tue, Feb 9

8:25 am - 2:20 pmPDX Portland-MDW Chicago Midway

3h 55mnonstop

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

4h 40mnonstop

$347Southwest

Sat, Feb 6 - Tue, Feb 16

Cheap last minute flights

Enter your travel dates to find the best prices.

12:02 pm - 12:21 amPDX Portland-ORD Chicago O'Hare Intl

10h 19m1 stop Denver Intl

10:00 pm - 10:28 amORD Chicago O'Hare Intl-PDX Portland

14h 28m1 stop Los Angeles

$374Frontier

Thu, Nov 12 - Sat, Nov 21

12:02 pm - 12:21 amPDX Portland-ORD Chicago O'Hare Intl

10h 19m1 stop Denver Intl

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

6h 37m1 stop Denver Intl

$374Frontier

Thu, Nov 12 - Tue, Nov 17

1:22 pm - 7:44 pmPDX Portland-ORD Chicago O'Hare Intl

4h 22mnonstop

7:20 pm - 10:10 pmORD Chicago O'Hare Intl-PDX Portland

4h 50mnonstop

$527American Airlines

Sat, Nov 14 - Sat, Nov 21

1:22 pm - 7:44 pmPDX Portland-ORD Chicago O'Hare Intl

4h 22mnonstop

5:05 pm - 7:47 pmORD Chicago O'Hare Intl-PDX Portland

4h 42mnonstop

$527American Airlines

Sat, Nov 14 - Wed, Nov 18

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

4h 08mnonstop

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

4h 43mnonstop

$527Alaska Airlines

Sat, Nov 14 - Tue, Nov 17

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

4h 08mnonstop

2:06 pm - 4:52 pmORD Chicago O'Hare Intl-PDX Portland

4h 46mnonstop

$527Alaska Airlines

Sat, Nov 14 - Sat, Nov 21

6:00 am - 11:50 amPDX Portland-MDW Chicago Midway

3h 50mnonstop

8:40 pm - 11:25 pmMDW Chicago Midway-PDX Portland

4h 45mnonstop

$532Southwest

Wed, Nov 11 - Wed, Nov 11

6:00 am - 11:50 amPDX Portland-MDW Chicago Midway

3h 50mnonstop

8:40 pm - 11:25 pmMDW Chicago Midway-PDX Portland

4h 45mnonstop

$537Southwest

Wed, Nov 11 - Wed, Nov 11

5:00 am - 2:55 pmPDX Portland-ORD Chicago O'Hare Intl

7h 55m1 stop Denver Intl

7:45 pm - 10:27 pmORD Chicago O'Hare Intl-PDX Portland

4h 42mnonstop

$537United Airlines

Wed, Nov 11 - Wed, Nov 11

2:27 pm - 8:40 pmEUG Eugene-ORD Chicago O'Hare Intl

4h 13mnonstop

9:01 am - 11:57 amORD Chicago O'Hare Intl-EUG Eugene

4h 56mnonstop

$539United Airlines

Fri, Nov 13 - Fri, Nov 20

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Frontier flights from Oregon to Chicago

Our best Frontier deals on Oregon to Chicago flight tickets

Frontier

Dec 8

PDX5:10 pmPortland

29h 44m

1 stop

ORD12:54 amChicago O'Hare Intl

Dec 10

ORD7:25 amChicago O'Hare Intl

7h 38m

1 stop

PDX1:03 pmPortland

$345

Frontier

Dec 8

PDX5:10 pmPortland

29h 44m

1 stop

ORD12:54 amChicago O'Hare Intl

Dec 15

ORD7:25 amChicago O'Hare Intl

10h 45m

1 stop

PDX4:10 pmPortland

$346

Frontier

Nov 22

PDX6:29 pmPortland

9h 45m

1 stop

ORD6:14 amChicago O'Hare Intl

Nov 25

ORD10:00 pmChicago O'Hare Intl

14h 28m

1 stop

PDX10:28 amPortland

$349

Alaska Airlines flights from Oregon to Chicago

Our best Alaska Airlines deals on Oregon to Chicago flight tickets

Alaska Airlines

Dec 12

EUG6:59 pmEugene

8h 38m

1 stop

ORD5:37 amChicago O'Hare Intl

Dec 15

ORD2:13 pmChicago O'Hare Intl

23h 44m

1 stop

EUG11:57 amEugene

$277

Alaska Airlines

Feb 4

EUG5:15 amEugene

5h 58m

1 stop

ORD1:13 pmChicago O'Hare Intl

Feb 9

ORD6:47 pmChicago O'Hare Intl

7h 11m

1 stop

EUG11:58 pmEugene

$327

Alaska Airlines

Dec 5

EUG5:28 amEugene

5h 42m

1 stop

ORD1:10 pmChicago O'Hare Intl

Dec 9

ORD9:00 amChicago O'Hare Intl

8h 00m

1 stop

EUG3:00 pmEugene

$333

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

EugeneChicago

EUG Eugene - ORD Chicago O'Hare Intl

EUGORD

Eugene

Sat 12/12

6:59 pm-5:37 am

1 stop8h 38m

Chicago O'Hare Intl

Tue 12/15

2:13 pm-11:57 am

1 stop23h 44m

$277

EugeneChicago

EUG Eugene - ORD Chicago O'Hare Intl

EUGORD

Eugene

Thu 2/4

5:15 am-1:13 pm

1 stop5h 58m

Chicago O'Hare Intl

Tue 2/9

6:47 pm-11:58 pm

1 stop7h 11m

$327

PortlandChicago

PDX Portland - ORD Chicago O'Hare Intl

PDXORD

Portland

Tue 12/8

5:10 pm-12:54 am

1 stop29h 44m

Chicago O'Hare Intl

Thu 12/10

7:25 am-1:03 pm

1 stop7h 38m

$345

PortlandChicago

PDX Portland - ORD Chicago O'Hare Intl

PDXORD

Portland

Tue 12/8

5:10 pm-12:54 am

1 stop29h 44m

Chicago O'Hare Intl

Tue 12/15

7:25 am-4:10 pm

1 stop10h 45m

$346

PortlandChicago

PDX Portland - ORD Chicago O'Hare Intl

PDXORD

Portland

Wed 12/9

11:13 pm-5:07 am

Nonstop3h 54m

Chicago O'Hare Intl

Tue 12/15

5:05 pm-7:55 pm

Nonstop4h 50m

$347

PortlandChicago

PDX Portland - ORD Chicago O'Hare Intl

PDXORD

Portland

Wed 12/9

1:30 pm-7:44 pm

Nonstop4h 14m

Chicago O'Hare Intl

Tue 12/15

9:45 am-12:37 pm

Nonstop4h 52m

$347

PortlandChicago

PDX Portland - ORD Chicago O'Hare Intl

PDXORD

Portland

Tue 1/19

10:45 am-4:52 pm

Nonstop4h 07m

Chicago O'Hare Intl

Wed 1/20

4:15 pm-6:59 pm

Nonstop4h 44m

$347

PortlandChicago

PDX Portland - ORD Chicago O'Hare Intl

PDXORD

Portland

Sat 12/12

2:26 pm-8:28 pm

Nonstop4h 02m

Chicago O'Hare Intl

Tue 12/15

12:40 pm-3:19 pm

Nonstop4h 39m

$347

Quickest round-trip

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Sat 2/6

8:25 am-2:20 pm

Nonstop3h 55m

Chicago Midway

Tue 2/9

7:40 pm-10:20 pm

Nonstop4h 40m

$347

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Sat 2/6

8:25 am-2:20 pm

Nonstop3h 55m

Chicago Midway

Tue 2/16

7:40 pm-10:20 pm

Nonstop4h 40m

$347

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

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?

The month of February is, on average, the cheapest month to fly to Chicago from Oregon, with most prices found around $302. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Oregon to Chicago during January average around $320.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $457. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Oregon to Chicago for around $561.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Oregon to Chicago during this time can be as low as $354. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $519.

What is the cheapest Oregon to Chicago flight route?

Fly from Portland to Chicago Midway for the best Oregon - Chicago flight prices

How far in advance should I book a flight from Oregon to Chicago?

You are more likely to see cheaper flights to Chicago from Oregon when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $398 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Oregon for as low as $309 on momondo.

What cabin class options are available on Oregon to Chicago flights?

There are 4 cabin classes available to choose from on Oregon to Chicago 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 Oregon to Chicago flights?

You could potentially save up to 23% on your flight if you consider stops on a Oregon to Chicago flight.

Cheap Oregon to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oregon to Chicago

Best Price Found	$165
Fastest flight time	3h 24m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Oregon in the past 72 hours is $165. The best round-trip flight deal from Oregon to Chicago found on momondo in the last 72 hours is $277.

The fastest flight from Oregon to Chicago takes 3h 24m

Direct flights go from Oregon to Chicago every day.

There are 3 airports in Chicago. From Oregon there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Oregon to Chicago

When did momondo last update prices for flights from Oregon to Chicago?
Prices for flights from Oregon to Chicago were last updated today.
How many operators does momondo search for flights from Oregon to Chicago?
As of November 2026, there are 6 operators available to choose from for flights from Oregon to Chicago.
How old do you have to be to fly from Oregon to Chicago?
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 Oregon to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Oregon to Chicago?
Based on momondo bookings for flights between Oregon and Chicago, the leading plane model is Boeing 737-800, making up 25.63% of the total bookings. Other popular models include Airbus A321-100/200 with 14.87%, Airbus A321neo with 12.01%, and Boeing 737 MAX 8 with 11.93%.

Best airlines flying from Oregon to Chicago

Compare and see reviews for airlines that fly from Oregon to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $108	Free Cancellation	Rating 7.8 8,703 reviews	Search Delta flights
Alaska Airlines	PriceFrom $198	Free Cancellation	Rating 7.9 13,157 reviews	Search Alaska Airlines flights
JetBlue	PriceFrom $216	Free Cancellation	Rating 7.1 3,069 reviews	Search JetBlue flights
American Airlines	PriceFrom $226	Free Cancellation	Rating 7.0 12,228 reviews	Search American Airlines flights
United Airlines	PriceFrom $250	Free Cancellation	Rating 7.3 10,471 reviews	Search United Airlines flights
Southwest	PriceFrom $276	Free Cancellation	Rating 8.0 4,219 reviews	Search Southwest flights

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Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Oregon to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Oregon to Chicago 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 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?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Oregon and alert you when they change.

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Cheap flights from Oregon to Chicago from $165

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 12/20. 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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Frontier flights from Oregon to Chicago

Our best Frontier deals on Oregon to Chicago flight tickets

Alaska Airlines flights from Oregon to Chicago

Our best Alaska Airlines deals on Oregon to Chicago flight tickets

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How to get the cheapest flight ticket from Oregon to Chicago

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Oregon to Chicago flight route?

How far in advance should I book a flight from Oregon to Chicago?

What cabin class options are available on Oregon to Chicago flights?

Can stopping save me money on Oregon to Chicago flights?

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

What airlines fly to Chicago?

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

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

How long does it take to fly to Chicago?

Cheap Oregon to Chicago flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Oregon to Chicago

Best airlines flying from Oregon to Chicago

Compare and see reviews for airlines that fly from Oregon to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago 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 the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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

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