What airlines fly to Chicago?

United Airlines, Alaska Airlines and American 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 43% 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.

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

Frontier, Alaska Airlines, and American Airlines are the most popular carriers operating from Oregon to Chicago

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 44m on average, while flying from Eugene to Chicago O'Hare Intl Airport is 3h 52m 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?

23 flights are operational daily from Oregon to Chicago as of November 2025. The most popular departure time for this route is 7:00AM, with 76% of flights per day taking off at noon.

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

165 flights are operational weekly from Oregon to Chicago as of November 2025. The most popular departure day for this route is Wed, 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 November 2025, 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.

$71 Cheap Flights from Oregon to Chicago in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

11:59 pm - 5:52 amPDX-ORD

3h 53mnonstop

9:05 am - 11:48 amORD-PDX

4h 43mnonstop

$227United Airlines

Find Deal

Thu, Dec 4 - Wed, Dec 10

1:25 pm - 11:59 pmEUG-ORD

8h 34m1 stop

7:45 am - 12:37 pmORD-EUG

6h 52m1 stop

$229Hawaiian Airlines

Find Deal

Tue, Mar 10 - Wed, Mar 11

3:59 pm - 2:31 pmPDX-MDW

20h 32m1 stop

4:00 pm - 8:04 amMDW-PDX

18h 04m2 stops

$229Frontier

Find Deal

Sun, Nov 23 - Thu, Nov 27

10:06 am - 5:32 amPDX-ORD

17h 26m1 stop

7:00 am - 11:56 amORD-PDX

30h 56m1 stop

$231Multiple Airlines

Find Deal

Tue, Nov 25 - Thu, Dec 4

11:37 am - 5:52 pmPDX-ORD

4h 15mnonstop

9:57 am - 12:38 pmORD-PDX

4h 41mnonstop

$234American Airlines

Find Deal

Wed, Dec 3 - Sun, Dec 7

7:04 am - 1:09 pmPDX-ORD

4h 05mnonstop

7:00 am - 9:50 amORD-PDX

4h 50mnonstop

$235Alaska Airlines

Find Deal

Mon, Dec 15 - Thu, Dec 18

1:30 pm - 11:59 pmRDM-ORD

8h 29m1 stop

10:00 am - 5:04 pmORD-RDM

9h 04m1 stop

$236Alaska Airlines

Find Deal

Tue, Dec 2 - Tue, Dec 9

12:47 pm - 12:12 amPDX-ORD

9h 25m1 stop

7:44 pm - 3:00 pmORD-PDX

21h 16m2 stops

$239Multiple Airlines

Find Deal

Thu, Dec 25 - Tue, Dec 30

12:47 pm - 12:12 amPDX-ORD

9h 25m1 stop

10:01 pm - 10:34 amORD-PDX

14h 33m1 stop

$240Frontier

Find Deal

Sun, Dec 21 - Sun, Jan 11

11:37 am - 5:52 pmPDX-ORD

4h 15mnonstop

9:57 am - 12:38 pmORD-PDX

4h 41mnonstop

$243American Airlines

Find Deal

Wed, Dec 10 - Fri, Dec 12

American Airlines flights from Oregon to Chicago

Our best American Airlines deals on Oregon to Chicago flight tickets

American Airlines

Dec 3

PDX11:37 amPortland

4h 15m

ORD5:52 pmChicago O'Hare Intl

Dec 7

ORD9:57 amChicago O'Hare Intl

4h 41m

PDX12:38 pmPortland

$234

Find similar

American Airlines

Dec 10

PDX11:37 amPortland

4h 15m

ORD5:52 pmChicago O'Hare Intl

Dec 12

ORD9:57 amChicago O'Hare Intl

4h 41m

PDX12:38 pmPortland

$243

Find similar

American Airlines

Dec 8

RDM2:28 pmBend/Redmond

8h 03m

1 stop

ORD12:31 amChicago O'Hare Intl

Dec 10

ORD7:02 amChicago O'Hare Intl

9h 25m

1 stop

RDM2:27 pmBend/Redmond

$246

Find similar

Alaska Airlines flights from Oregon to Chicago

Our best Alaska Airlines deals on Oregon to Chicago flight tickets

Alaska Airlines

Dec 15

PDX7:04 amPortland

4h 05m

ORD1:09 pmChicago O'Hare Intl

Dec 18

ORD7:00 amChicago O'Hare Intl

4h 50m

PDX9:50 amPortland

$235

Find similar

Alaska Airlines

Dec 10

PDX10:30 amPortland

7h 24m

1 stop

ORD7:54 pmChicago O'Hare Intl

Dec 15

ORD8:00 amChicago O'Hare Intl

7h 50m

1 stop

PDX1:50 pmPortland

$236

Find similar

Alaska Airlines

Dec 21

EUG5:56 amEugene

9h 16m

1 stop

ORD5:12 pmChicago O'Hare Intl

Dec 27

ORD6:00 amChicago O'Hare Intl

20h 22m

1 stop

EUG12:22 amEugene

$239

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 12/4

11:59 pm-5:52 am

Nonstop3h 53m

Chicago O'Hare Intl

Wed 12/10

9:05 am-11:48 am

Nonstop4h 43m

$227

EugeneChicago

EUG - ORD

EUGORD

Eugene

Tue 3/10

1:25 pm-11:59 pm

1 stop8h 34m

Chicago O'Hare Intl

Wed 3/11

7:45 am-12:37 pm

1 stop6h 52m

$229

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sun 11/23

3:59 pm-2:31 pm

1 stop20h 32m

Chicago Midway

Thu 11/27

4:00 pm-8:04 am

2 stops18h 04m

$229

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 11/25

10:06 am-5:32 am

1 stop17h 26m

Chicago O'Hare Intl

Thu 12/4

7:00 am-11:56 am

1 stop30h 56m

$231

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 12/3

11:37 am-5:52 pm

Nonstop4h 15m

Chicago O'Hare Intl

Sun 12/7

9:57 am-12:38 pm

Nonstop4h 41m

$234

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 12/15

7:04 am-1:09 pm

Nonstop4h 05m

Chicago O'Hare Intl

Thu 12/18

7:00 am-9:50 am

Nonstop4h 50m

$235

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 12/2

1:30 pm-11:59 pm

1 stop8h 29m

Chicago O'Hare Intl

Tue 12/9

10:00 am-5:04 pm

1 stop9h 04m

$236

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 12/25

12:47 pm-12:12 am

1 stop9h 25m

Chicago O'Hare Intl

Tue 12/30

7:44 pm-3:00 pm

2 stops21h 16m

$239

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 12/21

12:47 pm-12:12 am

1 stop9h 25m

Chicago O'Hare Intl

Sun 1/11

10:01 pm-10:34 am

1 stop14h 33m

$240

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 12/10

11:37 am-5:52 pm

Nonstop4h 15m

Chicago O'Hare Intl

Fri 12/12

9:57 am-12:38 pm

Nonstop4h 41m

$243

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 $293. 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 $434. 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 $557.

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 $316. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $493.

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 $358 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 $293 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	$186
Fastest flight time	3h 22m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Oregon in the past 72 hours is $186. The best round-trip flight deal from Oregon to Chicago found on momondo in the last 72 hours is $287.

The fastest flight from Oregon to Chicago takes 3h 22m

Direct flights go from Oregon to Chicago every day.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

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 November 2025, 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 MAX 9, making up 19.50% of the total bookings. Other popular models include Boeing 737-800 with 19.01%, Boeing 737-900 with 13.18%, and Airbus A321neo with 10.17%.

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 $94	Free Cancellation	Rating 5.8 3,115 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $119	Free Cancellation	Rating 6.3 8,113 reviews	Search Spirit Airlines flights
Delta	PriceFrom $123	Free Cancellation	Rating 7.9 8,004 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $125	Free Cancellation	Rating 7.8 2,800 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $192	Free Cancellation	Rating 7.2 11,039 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $197	Free Cancellation	Rating 8.0 11,241 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $222	Free Cancellation	Rating 7.4 9,001 reviews	Search United Airlines flights
Southwest	PriceFrom $246	Free Cancellation	Rating 8.0 4,239 reviews	Search Southwest flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

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.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Fri 12/5

Fri 12/12

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Popular cities in the United States

Flights to New Yorkfrom $44

Flights to Los Angelesfrom $49

Flights to Miamifrom $49

Flights to Orlandofrom $49

Flights to Las Vegasfrom $42

Flights to San Franciscofrom $57

Flights to Washington, D.C.from $49

Flights to Bostonfrom $49

Flights to Atlantafrom $40

Flights to Dallasfrom $59

Flights to Seattlefrom $58

Flights to Denverfrom $57

Cheap flights from Oregon to Chicago from $71

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 1/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Oregon to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

American Airlines flights from Oregon to Chicago

Our best American Airlines 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

momondo Fare Finder

Use the filters below to find and compare flights from Oregon to Chicago that are best for you.

See travel insights to Chicago from

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

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 $293. 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 $316. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $493.

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?

Frontier, Alaska Airlines, and American 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?

23 flights are operational daily from Oregon to Chicago as of November 2025. The most popular departure time for this route is 7:00AM, with 76% of flights per day taking off at noon.

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

165 flights are operational weekly from Oregon to Chicago as of November 2025. The most popular departure day for this route is Wed, 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