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 07m 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?

28 flights are operational daily from Oregon to Chicago as of September 2026. The most popular departure time for this route is 11:00AM, with 76% of flights per day taking off at noon.

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

197 flights are operational weekly from Oregon to Chicago as of September 2026. The most popular departure day for this route is Fri, with 17% of flights per week taking off on this day.

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 44% 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.

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

Southwest, United Airlines, and Alaska Airlines 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 September 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.

$116 Cheap Flights from Oregon to Chicago in 2026/27

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Find the cheapest flights from Oregon to Chicago

Round-trip

One-way

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Cheap round-trip flights

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1:10 pm - 12:50 amEUG Eugene-MDW Chicago Midway

9h 40m1 stop San Diego

6:05 am - 10:40 amMDW Chicago Midway-EUG Eugene

6h 35m1 stop Denver Intl

$231Southwest

Thu, Oct 29 - Tue, Nov 10

2:30 pm - 12:20 amEUG Eugene-MDW Chicago Midway

7h 50m1 stop Denver Intl

5:20 am - 1:55 pmMDW Chicago Midway-EUG Eugene

10h 35m2 stops Phoenix Sky Harbor Intl Las Vegas Harry Reid Intl

$236Southwest

Thu, Oct 29 - Tue, Nov 10

8:28 am - 6:59 pmEUG Eugene-ORD Chicago O'Hare Intl

8h 31m1 stop San Diego

9:01 pm - 5:45 pmORD Chicago O'Hare Intl-EUG Eugene

22h 44m1 stop San Diego

$315Alaska Airlines

Thu, Nov 19 - Sun, Nov 22

12:39 pm - 11:59 pmEUG Eugene-ORD Chicago O'Hare Intl

9h 20m1 stop San Diego

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

23h 44m1 stop San Diego

$331Alaska Airlines

Thu, Dec 3 - Tue, Dec 8

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

10h 19m1 stop Denver Intl

9:30 am - 3:13 pmORD Chicago O'Hare Intl-PDX Portland

7h 43m1 stop Seattle/Tacoma Intl

$342Multiple Airlines

Tue, Oct 27 - Wed, Nov 4

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

10h 19m1 stop Denver Intl

3:49 pm - 9:56 pmORD Chicago O'Hare Intl-PDX Portland

8h 07m1 stop Seattle/Tacoma Intl

$342Multiple Airlines

Tue, Oct 27 - Sat, Oct 31

11:06 am - 6:34 amPDX Portland-ORD Chicago O'Hare Intl

17h 28m1 stop Los Angeles

1:30 pm - 3:56 pmORD Chicago O'Hare Intl-PDX Portland

4h 26mnonstop

$344Frontier

Thu, Oct 15 - Wed, Oct 21

6:29 pm - 6:15 amPDX Portland-ORD Chicago O'Hare Intl

9h 46m1 stop Los Angeles

5:19 am - 12:36 pmORD Chicago O'Hare Intl-PDX Portland

9h 17m1 stop Las Vegas Harry Reid Intl

$344Frontier

Thu, Nov 26 - Mon, Nov 30

1:12 pm - 7:35 pmPDX Portland-ORD Chicago O'Hare Intl

4h 23mnonstop

9:21 pm - 11:59 pmORD Chicago O'Hare Intl-PDX Portland

4h 38mnonstop

$356American Airlines

Thu, Oct 15 - Wed, Oct 21

11:09 pm - 5:07 amPDX Portland-ORD Chicago O'Hare Intl

3h 58mnonstop

9:45 am - 12:28 pmORD Chicago O'Hare Intl-PDX Portland

4h 43mnonstop

$357American Airlines

Thu, Nov 5 - Mon, Nov 9

Cheap last minute flights

Enter your travel dates to find the best prices.

12:38 pm - 12:23 amPDX Portland-ORD Chicago O'Hare Intl

9h 45m1 stop Denver Intl

8:01 pm - 10:11 amORD Chicago O'Hare Intl-PDX Portland

16h 10m1 stop Los Angeles

$361Frontier

Thu, Oct 1 - Sat, Oct 10

12:39 pm - 5:38 amPDX Portland-ORD Chicago O'Hare Intl

14h 59m1 stop Las Vegas Harry Reid Intl

1:21 pm - 11:36 amORD Chicago O'Hare Intl-PDX Portland

24h 15m1 stop Las Vegas Harry Reid Intl

$361Frontier

Mon, Sep 28 - Wed, Sep 30

11:08 pm - 5:08 amPDX Portland-ORD Chicago O'Hare Intl

4h 00mnonstop

9:21 pm - 11:59 pmORD Chicago O'Hare Intl-PDX Portland

4h 38mnonstop

$427American Airlines

Tue, Sep 29 - Thu, Oct 15

11:48 am - 6:12 pmPDX Portland-ORD Chicago O'Hare Intl

4h 24mnonstop

6:17 pm - 11:55 pmORD Chicago O'Hare Intl-PDX Portland

7h 38m1 stop Phoenix Sky Harbor Intl

$437American Airlines

Tue, Sep 29 - Thu, Oct 15

12:38 pm - 12:23 amPDX Portland-ORD Chicago O'Hare Intl

9h 45m1 stop Denver Intl

2:14 pm - 4:51 pmORD Chicago O'Hare Intl-PDX Portland

4h 37mnonstop

$440Multiple Airlines

Fri, Oct 2 - Tue, Oct 6

12:39 pm - 5:38 amPDX Portland-ORD Chicago O'Hare Intl

14h 59m1 stop Las Vegas Harry Reid Intl

2:22 pm - 4:50 pmORD Chicago O'Hare Intl-PDX Portland

4h 28mnonstop

$440Multiple Airlines

Mon, Sep 28 - Wed, Sep 30

3:21 pm - 11:57 pmPDX Portland-ORD Chicago O'Hare Intl

6h 36m1 stop Seattle/Tacoma Intl

5:30 pm - 9:56 pmORD Chicago O'Hare Intl-PDX Portland

6h 26m1 stop Seattle/Tacoma Intl

$447Delta

Tue, Sep 29 - Thu, Oct 15

5:30 am - 6:04 pmPDX Portland-ORD Chicago O'Hare Intl

10h 34m2 stops Seattle/Tacoma Intl Salt Lake City

5:30 pm - 9:56 pmORD Chicago O'Hare Intl-PDX Portland

6h 26m1 stop Seattle/Tacoma Intl

$452Delta

Tue, Sep 29 - Thu, Oct 15

7:08 am - 7:21 pmEUG Eugene-ORD Chicago O'Hare Intl

10h 13m1 stop San Diego

7:49 pm - 9:47 pmORD Chicago O'Hare Intl-EUG Eugene

27h 58m1 stop San Diego

$475Alaska Airlines

Wed, Sep 30 - Mon, Oct 19

7:06 am - 1:26 pmPDX Portland-ORD Chicago O'Hare Intl

4h 20mnonstop

2:22 pm - 4:50 pmORD Chicago O'Hare Intl-PDX Portland

4h 28mnonstop

$497Alaska Airlines

Tue, Sep 29 - Wed, Sep 30

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Frontier flights from Oregon to Chicago

Our best Frontier deals on Oregon to Chicago flight tickets

Frontier

Oct 15

PDX11:06 amPortland

17h 28m

1 stop

ORD6:34 amChicago O'Hare Intl

Oct 21

ORD1:30 pmChicago O'Hare Intl

4h 26m

PDX3:56 pmPortland

$344

Frontier

Oct 19

PDX12:25 pmPortland

40h 09m

2 stops

ORD6:34 amChicago O'Hare Intl

Oct 22

ORD6:30 amChicago O'Hare Intl

6h 24m

1 stop

PDX10:54 amPortland

$345

Frontier

Oct 13

PDX11:49 amPortland

10h 35m

1 stop

ORD12:24 amChicago O'Hare Intl

Oct 17

ORD8:01 pmChicago O'Hare Intl

16h 10m

1 stop

PDX10:11 amPortland

$350

American Airlines flights from Oregon to Chicago

Our best American Airlines deals on Oregon to Chicago flight tickets

American Airlines

Oct 15

PDX1:12 pmPortland

4h 23m

ORD7:35 pmChicago O'Hare Intl

Oct 21

ORD9:21 pmChicago O'Hare Intl

4h 38m

PDX11:59 pmPortland

$356

American Airlines

Oct 15

PDX2:25 pmPortland

7h 34m

1 stop

ORD11:59 pmChicago O'Hare Intl

Oct 21

ORD9:21 pmChicago O'Hare Intl

4h 38m

PDX11:59 pmPortland

$366

American Airlines

Nov 21

PDX2:34 pmPortland

7h 46m

1 stop

ORD12:20 amChicago O'Hare Intl

Nov 27

ORD6:50 amChicago O'Hare Intl

8h 43m

1 stop

PDX1:33 pmPortland

$391

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

EugeneChicago

EUG Eugene - MDW Chicago Midway

EUGMDW

Eugene

Thu 10/29

1:10 pm-12:50 am

1 stop9h 40m

Chicago Midway

Tue 11/10

6:05 am-10:40 am

1 stop6h 35m

$231

EugeneChicago

EUG Eugene - MDW Chicago Midway

EUGMDW

Eugene

Thu 10/29

2:30 pm-12:20 am

1 stop7h 50m

Chicago Midway

Tue 11/10

5:20 am-1:55 pm

2 stops10h 35m

$236

EugeneChicago

EUG Eugene - ORD Chicago O'Hare Intl

EUGORD

Eugene

Thu 11/19

8:28 am-6:59 pm

1 stop8h 31m

Chicago O'Hare Intl

Sun 11/22

9:01 pm-5:45 pm

1 stop22h 44m

$315

EugeneChicago

EUG Eugene - ORD Chicago O'Hare Intl

EUGORD

Eugene

Thu 12/3

12:39 pm-11:59 pm

1 stop9h 20m

Chicago O'Hare Intl

Tue 12/8

2:13 pm-11:57 am

1 stop23h 44m

$331

PortlandChicago

PDX Portland - ORD Chicago O'Hare Intl

PDXORD

Portland

Tue 10/27

12:02 pm-12:21 am

1 stop10h 19m

Chicago O'Hare Intl

Wed 11/4

9:30 am-3:13 pm

1 stop7h 43m

$342

PortlandChicago

PDX Portland - ORD Chicago O'Hare Intl

PDXORD

Portland

Tue 10/27

12:02 pm-12:21 am

1 stop10h 19m

Chicago O'Hare Intl

Sat 10/31

3:49 pm-9:56 pm

1 stop8h 07m

$342

PortlandChicago

PDX Portland - ORD Chicago O'Hare Intl

PDXORD

Portland

Thu 10/15

11:06 am-6:34 am

1 stop17h 28m

Chicago O'Hare Intl

Wed 10/21

1:30 pm-3:56 pm

Nonstop4h 26m

$344

PortlandChicago

PDX Portland - ORD Chicago O'Hare Intl

PDXORD

Portland

Thu 11/26

6:29 pm-6:15 am

1 stop9h 46m

Chicago O'Hare Intl

Mon 11/30

5:19 am-12:36 pm

1 stop9h 17m

$344

PortlandChicago

PDX Portland - ORD Chicago O'Hare Intl

PDXORD

Portland

Thu 10/15

1:12 pm-7:35 pm

Nonstop4h 23m

Chicago O'Hare Intl

Wed 10/21

9:21 pm-11:59 pm

Nonstop4h 38m

$356

Quickest round-trip

PortlandChicago

PDX Portland - ORD Chicago O'Hare Intl

PDXORD

Portland

Thu 11/5

11:09 pm-5:07 am

Nonstop3h 58m

Chicago O'Hare Intl

Mon 11/9

9:45 am-12:28 pm

Nonstop4h 43m

$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 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 $294. 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 $297.

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 $446. 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 $551.

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 $370. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $504.

What is the cheapest Oregon to Chicago flight route?

Fly from Portland to Chicago O'Hare Intl 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 $380 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 39% 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	$116
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 $116. The best round-trip flight deal from Oregon to Chicago found on momondo in the last 72 hours is $231.

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

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 September 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 27.70% of the total bookings. Other popular models include Airbus A321neo with 13.38%, Airbus A321-100/200 with 13.11%, and Boeing 737 MAX 8 with 10.55%.

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 8,609 reviews	Search Delta flights
Alaska Airlines	PriceFrom $198	Free Cancellation	Rating 7.9 12,977 reviews	Search Alaska Airlines flights
JetBlue	PriceFrom $216	Free Cancellation	Rating 7.1 3,039 reviews	Search JetBlue flights
American Airlines	PriceFrom $223	Free Cancellation	Rating 7.0 12,103 reviews	Search American Airlines flights
United Airlines	PriceFrom $244	Free Cancellation	Rating 7.4 10,247 reviews	Search United Airlines flights
Southwest	PriceFrom $266	Free Cancellation	Rating 8.0 4,201 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 $116

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 10/30. 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

American Airlines flights from Oregon to Chicago

Our best American 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

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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.

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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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