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 41% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 8 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 day?

17 flights are operational daily from Oregon to Chicago as of February 2026. The most popular departure time for this route is 7:00AM, with 91% of flights per day taking off at noon.

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 52m on average, while flying from Eugene to Chicago O'Hare Intl Airport is 3h 53m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

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

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

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

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 February 2026, there are 8 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.

$104 Cheap Flights from Oregon to Chicago in 2026

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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.

6:30 am - 9:18 pm

EUG

ORD

12h 48m

2 stops

6:00 pm - 11:10 pm

ORD

EUG

7h 10m

1 stop

$192Delta

Mon, Apr 20 - Wed, Apr 22

2:00 pm - 11:59 pm

MFR

ORD

7h 59m

1 stop

7:00 am - 1:02 pm

ORD

MFR

8h 02m

1 stop

$197Alaska Airlines

Tue, Mar 10 - Wed, Mar 11

6:30 am - 6:07 pm

EUG

ORD

9h 37m

2 stops

2:09 pm - 11:10 pm

ORD

EUG

11h 01m

2 stops

$198Delta

Mon, Apr 20 - Wed, Apr 22

1:55 pm - 12:59 am

RDM

ORD

9h 04m

1 stop

6:25 am - 11:55 am

ORD

RDM

7h 30m

1 stop

$212United Airlines

Wed, Apr 15 - Sat, Apr 18

1:48 pm - 6:47 am

PDX

ORD

14h 59m

2 stops

10:55 am - 11:42 am

ORD

PDX

26h 47m

1 stop

$212Frontier

Tue, Apr 21 - Fri, Apr 24

1:48 pm - 9:50 am

PDX

ORD

18h 02m

1 stop

10:55 am - 11:42 am

ORD

PDX

26h 47m

1 stop

$216Frontier

Wed, Apr 29 - Fri, May 1

2:05 pm - 11:59 pm

PDX

ORD

7h 54m

1 stop

4:40 pm - 7:14 pm

ORD

PDX

4h 34mnonstop

$217United Airlines

Thu, Mar 5 - Sat, Mar 7

7:15 pm - 5:00 am

PDX

MDW

7h 45m

1 stop

8:10 pm - 1:40 am

MDW

PDX

7h 30m

1 stop

$218Southwest

Thu, Mar 5 - Sat, Mar 7

6:55 am - 2:30 pm

PDX

MDW

5h 35m

1 stop

8:10 pm - 1:40 am

MDW

PDX

7h 30m

1 stop

$220Southwest

Sat, Feb 28 - Sat, Mar 7

11:48 am - 9:50 am

PDX

ORD

20h 02m

1 stop

8:53 pm - 11:03 am

ORD

PDX

16h 10m

2 stops

$223Multiple Airlines

Thu, Apr 30 - Sun, May 3

American Airlines flights from Oregon to Chicago

Our best American Airlines deals on Oregon to Chicago flight tickets

American Airlines

Mar 14

PDX11:59 pmPortland

3h 57m

ORD5:56 amChicago O'Hare Intl

Mar 15

ORD9:44 pmChicago O'Hare Intl

4h 31m

PDX12:15 amPortland

$225

American Airlines

Apr 23

PDX3:16 pmPortland

4h 18m

ORD9:34 pmChicago O'Hare Intl

Apr 26

ORD9:22 pmChicago O'Hare Intl

4h 31m

PDX11:53 pmPortland

$242

American Airlines

Mar 24

PDX11:59 pmPortland

3h 57m

ORD5:56 amChicago O'Hare Intl

Mar 31

ORD9:49 pmChicago O'Hare Intl

4h 31m

PDX12:20 amPortland

$253

Frontier flights from Oregon to Chicago

Our best Frontier deals on Oregon to Chicago flight tickets

Frontier

Apr 21

PDX1:48 pmPortland

14h 59m

2 stops

ORD6:47 amChicago O'Hare Intl

Apr 24

ORD10:55 amChicago O'Hare Intl

26h 47m

1 stop

PDX11:42 amPortland

$212

Frontier

Apr 29

PDX1:48 pmPortland

18h 02m

1 stop

ORD9:50 amChicago O'Hare Intl

May 1

ORD10:55 amChicago O'Hare Intl

26h 47m

1 stop

PDX11:42 amPortland

$216

Frontier

Apr 23

PDX11:48 amPortland

20h 02m

1 stop

ORD9:50 amChicago O'Hare Intl

Apr 26

ORD9:18 pmChicago O'Hare Intl

13h 41m

1 stop

PDX8:59 amPortland

$222

Fly from

Fly to

Route

Depart

Return

Price

EugeneChicago

EUG - ORD

EUGORD

Eugene

Mon 4/20

6:30 am-9:18 pm

2 stops12h 48m

Chicago O'Hare Intl

Wed 4/22

6:00 pm-11:10 pm

1 stop7h 10m

$192

MedfordChicago

MFR - ORD

MFRORD

Medford

Tue 3/10

2:00 pm-11:59 pm

1 stop7h 59m

Chicago O'Hare Intl

Wed 3/11

7:00 am-1:02 pm

1 stop8h 02m

$197

EugeneChicago

EUG - ORD

EUGORD

Eugene

Mon 4/20

6:30 am-6:07 pm

2 stops9h 37m

Chicago O'Hare Intl

Wed 4/22

2:09 pm-11:10 pm

2 stops11h 01m

$198

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 4/15

1:55 pm-12:59 am

1 stop9h 04m

Chicago O'Hare Intl

Sat 4/18

6:25 am-11:55 am

1 stop7h 30m

$212

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 4/21

1:48 pm-6:47 am

2 stops14h 59m

Chicago O'Hare Intl

Fri 4/24

10:55 am-11:42 am

1 stop26h 47m

$212

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 4/29

1:48 pm-9:50 am

1 stop18h 02m

Chicago O'Hare Intl

Fri 5/1

10:55 am-11:42 am

1 stop26h 47m

$216

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 3/5

2:05 pm-11:59 pm

1 stop7h 54m

Chicago O'Hare Intl

Sat 3/7

4:40 pm-7:14 pm

Nonstop4h 34m

$217

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 3/5

7:15 pm-5:00 am

1 stop7h 45m

Chicago Midway

Sat 3/7

8:10 pm-1:40 am

1 stop7h 30m

$218

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 2/28

6:55 am-2:30 pm

1 stop5h 35m

Chicago Midway

Sat 3/7

8:10 pm-1:40 am

1 stop7h 30m

$220

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 4/30

11:48 am-9:50 am

1 stop20h 02m

Chicago O'Hare Intl

Sun 5/3

8:53 pm-11:03 am

2 stops16h 10m

$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

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 August is, on average, the cheapest month to fly to Chicago from Oregon, with most prices found around $289. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Oregon to Chicago during September average around $293.

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 Friday when prices can be found for as low as $427. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Oregon to Chicago for around $532.

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 $314. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $478.

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 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 $347 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 $303 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?

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

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	$161
Fastest flight time	3h 20m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Oregon in the past 72 hours is $161. The best round-trip flight deal from Oregon to Chicago found on momondo in the last 72 hours is $315.

The fastest flight from Oregon to Chicago takes 3h 20m

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

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 February 2026, there are 8 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 30.35% of the total bookings. Other popular models include Boeing 737 MAX 9 with 15.37%, Boeing 737-900 with 12.74%, and Boeing 737 MAX 8 with 12.41%.

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
Frontier	PriceFrom $86	Free Cancellation	Rating 5.7 3,052 reviews	Search Frontier flights
Delta	PriceFrom $99	Free Cancellation	Rating 7.9 8,172 reviews	Search Delta flights
Spirit Airlines	PriceFrom $119	Free Cancellation	Rating 6.3 8,430 reviews	Search Spirit Airlines flights
Hawaiian Airlines	PriceFrom $125	Free Cancellation	Rating 7.8 2,829 reviews	Search Hawaiian Airlines flights
Southwest	PriceFrom $179	Free Cancellation	Rating 8.0 4,280 reviews	Search Southwest flights
United Airlines	PriceFrom $184	Free Cancellation	Rating 7.4 9,254 reviews	Search United Airlines flights
American Airlines	PriceFrom $196	Free Cancellation	Rating 7.2 11,249 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $215	Free Cancellation	Rating 8.0 11,851 reviews	Search Alaska Airlines flights

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Saint Joseph

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Valparaiso

Munster

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Chesterton

Monticello

Porter

Griffith

Saint John

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.

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.

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Cheap flights from Oregon to Chicago from $103

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 2/19. 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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Find the cheapest flights from Oregon to Chicago

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American Airlines flights from Oregon to Chicago

Our best American Airlines deals on Oregon to Chicago flight tickets

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Our best Frontier 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?

The month of August is, on average, the cheapest month to fly to Chicago from Oregon, with most prices found around $289. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Oregon to Chicago during September average around $293.

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?

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 $314. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $478.

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 to Chicago?

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?

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

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

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

What airlines fly to Chicago?

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

17 flights are operational daily from Oregon to Chicago as of February 2026. The most popular departure time for this route is 7:00AM, with 91% of flights per day taking off at noon.

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

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

How long does it take to fly to Chicago?

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

Fastest flight time

Direct flights

Airports in Chicago

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

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

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

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

What is the most popular plane model 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?

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 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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