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

235 flights are operational weekly from Oregon to Chicago as of May 2026. The most popular departure day for this route is Sun, with 17% 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 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.

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

33 flights are operational daily from Oregon to Chicago as of May 2026. The most popular departure time for this route is 7:00AM, with 60% of flights per day taking off at noon.

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

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

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 40% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 May 2026, there are 7 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.

$105 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.

5:35 pm - 11:41 pm

PDX

ORD

4h 06mnonstop

1:02 pm - 8:39 pm

ORD

PDX

9h 37m

1 stop

$289Multiple Airlines

Fri, Aug 28 - Sun, Sep 13

5:42 pm - 6:17 am

PDX

ORD

10h 35m

1 stop

7:15 am - 6:04 pm

ORD

PDX

12h 49m

1 stop

$290Frontier

Sat, Jul 11 - Mon, Jul 13

11:30 pm - 5:25 am

PDX

MDW

3h 55mnonstop

6:00 pm - 8:15 pm

MDW

PDX

4h 15mnonstop

$305Southwest

Tue, Sep 8 - Sat, Sep 12

11:30 pm - 5:20 am

PDX

MDW

3h 50mnonstop

9:10 pm - 11:30 pm

MDW

PDX

4h 20mnonstop

$310Southwest

Sat, Jun 27 - Wed, Jul 1

5:56 am - 1:21 pm

BOI

ORD

6h 25m

1 stop

3:49 pm - 11:58 pm

ORD

BOI

9h 09m

1 stop

$329Alaska Airlines

Sat, Oct 3 - Sat, Oct 3

2:00 pm - 8:11 pm

EUG

ORD

4h 11mnonstop

9:05 am - 11:50 am

ORD

EUG

4h 45mnonstop

$329United Airlines

Wed, Aug 12 - Mon, Aug 17

11:42 pm - 10:10 am

BOI

ORD

9h 28m

1 stop

7:40 pm - 12:05 am

ORD

BOI

5h 25m

1 stop

$335Delta

Wed, Jul 8 - Wed, Jul 15

4:11 pm - 12:59 am

EUG

ORD

6h 48m

1 stop

9:05 am - 11:50 am

ORD

EUG

4h 45mnonstop

$339United Airlines

Wed, Aug 12 - Mon, Aug 17

6:41 pm - 8:05 am

BOI

ORD

12h 24m

2 stops

6:55 am - 3:12 pm

ORD

BOI

9h 17m

1 stop

$340Delta

Sat, Jun 6 - Tue, Jun 9

7:35 pm - 6:22 am

EUG

ORD

8h 47m

1 stop

9:00 am - 1:44 pm

ORD

EUG

6h 44m

1 stop

$343Alaska Airlines

Tue, Sep 22 - Wed, Sep 23

American Airlines flights from Oregon to Chicago

Our best American Airlines deals on Oregon to Chicago flight tickets

American Airlines

Jun 26

PDX10:59 pmPortland

4h 01m

ORD5:00 amChicago O'Hare Intl

Jul 1

ORD8:00 amChicago O'Hare Intl

4h 25m

PDX10:25 amPortland

$316

American Airlines

Aug 7

PDX11:20 pmPortland

4h 12m

ORD5:32 amChicago O'Hare Intl

Aug 8

ORD9:30 pmChicago O'Hare Intl

4h 26m

PDX11:56 pmPortland

$318

American Airlines

Jun 19

PDX10:59 pmPortland

4h 01m

ORD5:00 amChicago O'Hare Intl

Jun 26

ORD8:00 amChicago O'Hare Intl

4h 25m

PDX10:25 amPortland

$328

Frontier flights from Oregon to Chicago

Our best Frontier deals on Oregon to Chicago flight tickets

Frontier

Jul 11

PDX5:42 pmPortland

10h 35m

1 stop

ORD6:17 amChicago O'Hare Intl

Jul 13

ORD7:15 amChicago O'Hare Intl

12h 49m

1 stop

PDX6:04 pmPortland

$290

Frontier

Jun 11

PDX12:26 pmPortland

6h 17m

1 stop

ORD8:43 pmChicago O'Hare Intl

Jun 13

ORD9:48 pmChicago O'Hare Intl

21h 09m

1 stop

PDX4:57 pmPortland

$291

Frontier

Jun 26

PDX12:26 pmPortland

6h 17m

1 stop

ORD8:43 pmChicago O'Hare Intl

Jul 1

ORD9:48 pmChicago O'Hare Intl

21h 09m

1 stop

PDX4:57 pmPortland

$295

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 8/28

5:35 pm-11:41 pm

Nonstop4h 06m

Chicago O'Hare Intl

Sun 9/13

1:02 pm-8:39 pm

1 stop9h 37m

$289

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 7/11

5:42 pm-6:17 am

1 stop10h 35m

Chicago O'Hare Intl

Mon 7/13

7:15 am-6:04 pm

1 stop12h 49m

$290

Quickest round-trip

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 9/8

11:30 pm-5:25 am

Nonstop3h 55m

Chicago Midway

Sat 9/12

6:00 pm-8:15 pm

Nonstop4h 15m

$305

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 6/27

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Wed 7/1

9:10 pm-11:30 pm

Nonstop4h 20m

$310

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Sat 10/3

5:56 am-1:21 pm

1 stop6h 25m

Chicago O'Hare Intl

Sat 10/3

3:49 pm-11:58 pm

1 stop9h 09m

$329

EugeneChicago

EUG - ORD

EUGORD

Eugene

Wed 8/12

2:00 pm-8:11 pm

Nonstop4h 11m

Chicago O'Hare Intl

Mon 8/17

9:05 am-11:50 am

Nonstop4h 45m

$329

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 7/8

11:42 pm-10:10 am

1 stop9h 28m

Chicago O'Hare Intl

Wed 7/15

7:40 pm-12:05 am

1 stop5h 25m

$335

EugeneChicago

EUG - ORD

EUGORD

Eugene

Wed 8/12

4:11 pm-12:59 am

1 stop6h 48m

Chicago O'Hare Intl

Mon 8/17

9:05 am-11:50 am

Nonstop4h 45m

$339

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Sat 6/6

6:41 pm-8:05 am

2 stops12h 24m

Chicago O'Hare Intl

Tue 6/9

6:55 am-3:12 pm

1 stop9h 17m

$340

EugeneChicago

EUG - ORD

EUGORD

Eugene

Tue 9/22

7:35 pm-6:22 am

1 stop8h 47m

Chicago O'Hare Intl

Wed 9/23

9:00 am-1:44 pm

1 stop6h 44m

$343

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 November is, on average, the cheapest month to fly to Chicago from Oregon, with most prices found around $103. If you’re not able to fly to Chicago in November, then December is your next best option. Flight prices from Oregon to Chicago during December average around $108.

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 $424. 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 $519.

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 $324. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $466.

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 $339 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 $274 on momondo.

Can stopping save me money on Oregon to Chicago flights?

You could potentially save up to 14% 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	$143
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 $143. The best round-trip flight deal from Oregon to Chicago found on momondo in the last 72 hours is $371.

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 May 2026, there are 7 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 31.58% of the total bookings. Other popular models include Boeing 737-900 with 13.06%, Airbus A321-100/200 with 12.51%, and Boeing 737 MAX 8 with 10.00%.

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 $96	Free Cancellation	Rating 5.6 2,955 reviews	Search Frontier flights
Delta	PriceFrom $99	Free Cancellation	Rating 7.9 8,453 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $113	Free Cancellation	Rating 7.8 2,837 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $170	Free Cancellation	Rating 7.1 11,668 reviews	Search American Airlines flights
Southwest	PriceFrom $179	Free Cancellation	Rating 7.9 4,301 reviews	Search Southwest flights
Alaska Airlines	PriceFrom $198	Free Cancellation	Rating 7.9 12,349 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $214	Free Cancellation	Rating 7.4 9,694 reviews	Search United Airlines 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 $105

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 6/30. 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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American Airlines flights from Oregon to Chicago

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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?

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

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

Best Price Found

Fastest flight time

Direct flights

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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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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

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

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

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