In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the most popular routes from Oregon to Chicago?

The most popular route from Oregon to Chicago is Portland - Chicago O'Hare Intl. You may also consider Portland - Chicago Midway or Boise Air Term. Gowen Fld - Chicago O'Hare Intl.

What are the cheapest flights from Oregon to Chicago?

Looking for the cheapest flight from Oregon to Chicago? While on average our users pay $858, our data indicates the cheapest price to be $100. The most popular route (Portland - Chicago O'Hare Intl), is priced around $151.

What are the most reliable airlines from Oregon to Chicago?

The top 3 most reliable airlines when flying from Oregon to Chicago are Brussels Airlines (89%), Air Canada (87%) and Finnair (87%).

What are the most popular airlines that fly from Oregon to Chicago?

American Airlines, Alaska Airlines and Delta are the most popular airlines when flying from Oregon to Chicago.

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

Travelers have found it’s best to book a flight 44 days in advance to save up to 40% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 44 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Oregon to Chicago 1-2 weeks in advance for as low as $334, or $368 for flights within the next 24 hours.

What is the cheapest month to fly from Oregon to Chicago?

Our data shows that January tends to be the cheapest month to fly to Chicago from Oregon. Users have commonly found prices around $343 for the month, but tickets can be as low as $178. Due to multiple factors, prepare for potentially higher prices in March.

Can I find deals for flights from Oregon to Chicago that include hotel bookings?

Yes. In addition to deals on Oregon to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Oregon to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Chicago.

Can I find deals for business class flights from Oregon to Chicago?

Yes. Cheapflights offers flight deals from Oregon to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$85+ Flights from Oregon to Chicago

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Oregon to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Oregon to Chicago

Round-trip from	$178 (Kiwi.com)
One-way from	$85 (Kiwi.com)
Popular in	March
Cheapest in	January
Average price	$283
Good round-trip deal	$238 or less
Good one-way deal	$172 or less

From Oregon to Chicago (CHI)

Search Deals

One-way flight from Oregon to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 9% potential increase in price ($36 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in August 2025

Search Deals

Price to beat on a round-trip flight from Oregon to Chicago (CHI).

Search Deals

Price to beat on a one-way flight from Oregon to Chicago (CHI).

Search Deals

Find flight deals from Oregon to Chicago

Cheapest flights from Oregon to Chicago
Explore the most affordable flight options available from Oregon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2025.

Sat 9/68:18 pmPDX - ORD

1 stop13h 33mSpirit Airlines

Wed 9/107:09 pmORD - PDX

2 stops26h 14mSpirit Airlines

Deal found 8/11

$178

Wed 8/277:52 pmPDX - ORD

1 stop6h 58mSpirit Airlines

Sat 8/306:00 amORD - PDX

1 stop14h 57mSpirit Airlines

Deal found 8/11

$182

Wed 9/2412:07 pmPDX - ORD

1 stop7h 25mSpirit Airlines

Tue 9/3011:15 amORD - PDX

1 stop10h 08mSpirit Airlines

Deal found 8/11

$184

Wed 9/2412:07 pmPDX - ORD

1 stop7h 25mSpirit Airlines

Mon 9/299:00 amORD - PDX

1 stop12h 23mSpirit Airlines

Deal found 8/10

$185

Thu 10/28:18 pmPDX - ORD

1 stop13h 33mSpirit Airlines

Tue 10/711:15 amORD - PDX

1 stop10h 08mSpirit Airlines

Deal found 8/11

$186

Thu 9/412:07 pmPDX - ORD

1 stop7h 25mSpirit Airlines

Mon 9/86:15 amORD - PDX

1 stop6h 56mSpirit Airlines

Deal found 8/12

$187

Thu 9/2512:07 pmPDX - ORD

1 stop7h 25mSpirit Airlines

Mon 9/296:15 amORD - PDX

1 stop15h 08mSpirit Airlines

Deal found 8/11

$188

Sat 8/307:52 pmPDX - ORD

1 stop6h 58mSpirit Airlines

Tue 9/97:09 pmORD - PDX

2 stops26h 14mSpirit Airlines

Deal found 8/11

$189

Thu 9/188:18 pmPDX - ORD

1 stop13h 33mSpirit Airlines

Mon 9/226:15 amORD - PDX

1 stop6h 56mSpirit Airlines

Deal found 8/12

$190

Fri 9/198:18 pmPDX - ORD

1 stop13h 33mSpirit Airlines

Mon 9/226:15 amORD - PDX

1 stop15h 08mSpirit Airlines

Deal found 8/11

$191

Tue 9/1612:07 pmPDX - ORD

1 stop7h 25mMultiple Airlines

Sat 9/202:07 pmORD - PDX

Nonstop4h 30mMultiple Airlines

Deal found 8/11

$192

Fri 9/2612:07 pmPDX - ORD

1 stop7h 25mSpirit Airlines

Tue 9/309:00 amORD - PDX

1 stop12h 23mSpirit Airlines

Deal found 8/12

$193

Best flights from Oregon to Chicago
Discover carefully curated flight deals from Oregon to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2025.

Wed 10/228:04 pmPDX - ORD

1 stop16h 23mSpirit Airlines

Wed 10/296:00 amORD - PDX

1 stop15h 36mSpirit Airlines

Deal found 8/12

$184

Wed 9/1712:07 pmPDX - ORD

1 stop7h 25mMultiple Airlines

Sat 9/202:07 pmORD - PDX

Nonstop4h 30mMultiple Airlines

Deal found 8/12

$195

Sun 8/311:20 pmPDX - MDW

Nonstop3h 55mSouthwest

Sat 9/68:20 amMDW - PDX

Nonstop4h 15mSouthwest

Deal found 8/12

$205

Sat 10/412:35 pmBOI - ORD

Nonstop3h 33mUnited Airlines

Thu 10/165:01 amORD - BOI

1 stop5h 41mUnited Airlines

Deal found 8/12

$232

Sun 2/12:45 pmBOI - ORD

1 stop8h 14mHawaiian Airlines

Thu 2/52:00 pmORD - BOI

1 stop9h 20mHawaiian Airlines

Deal found 8/11

$234

Tue 9/302:28 pmBOI - ORD

1 stop6h 39mAlaska Airlines

Mon 10/67:59 pmORD - BOI

1 stop16h 35mAlaska Airlines

Deal found 8/12

$234

Fri 9/2611:35 pmBOI - MDW

1 stop9h 13mDelta

Fri 10/37:15 pmMDW - BOI

1 stop5h 44mDelta

Deal found 8/12

$235

Thu 9/1112:07 pmPDX - ORD

1 stop7h 25mSpirit Airlines

Wed 9/179:00 amORD - PDX

1 stop12h 23mSpirit Airlines

Deal found 8/12

$186

Wed 9/37:52 pmPDX - ORD

1 stop6h 58mMultiple Airlines

Sat 9/67:00 amORD - PDX

Nonstop4h 25mMultiple Airlines

Deal found 8/11

$197

Fri 9/198:18 pmPDX - ORD

1 stop13h 33mSpirit Airlines

Mon 9/226:15 amORD - PDX

1 stop15h 08mSpirit Airlines

Deal found 8/11

$191

Sat 8/305:35 amPDX - MDW

1 stop8h 55mSouthwest

Sat 9/62:10 pmMDW - PDX

Nonstop4h 15mSouthwest

Deal found 8/11

$215

Fri 8/155:50 pmPDX - ORD

1 stop28h 42mMultiple Airlines

Tue 9/1611:15 amORD - PDX

1 stop10h 08mMultiple Airlines

Deal found 8/11

$198

Last-minute flights from Oregon to Chicago
Discover last-minute flight deals from Oregon to Chicago. Data last updated August 13, 2025 and is based on user searches.

Mon 8/185:50 pmPDX - ORD

1 stop25h 52mMultiple Airlines

Sat 8/236:00 amORD - PDX

1 stop14h 57mMultiple Airlines

Deal found 8/12

$236

Tue 8/196:51 amPDX - ORD

1 stop12h 51mMultiple Airlines

Tue 8/266:00 amORD - PDX

1 stop14h 57mMultiple Airlines

Deal found 8/12

$191

Tue 8/196:51 amPDX - ORD

1 stop12h 51mFrontier

Sat 8/237:00 amORD - PDX

1 stop17h 39mFrontier

Deal found 8/12

$243

Wed 8/206:51 amPDX - ORD

1 stop12h 51mMultiple Airlines

Tue 8/266:00 amORD - PDX

1 stop14h 57mMultiple Airlines

Deal found 8/12

$196

Wed 8/207:52 pmPDX - ORD

1 stop13h 51mSpirit Airlines

Mon 8/256:00 amORD - PDX

1 stop14h 57mSpirit Airlines

Deal found 8/13

$237

Thu 8/2112:18 pmPDX - ORD

1 stop10h 14mMultiple Airlines

Tue 8/266:00 amORD - PDX

1 stop14h 57mMultiple Airlines

Deal found 8/11

$206

Thu 8/217:52 pmPDX - ORD

1 stop6h 58mSpirit Airlines

Sat 8/306:00 amORD - PDX

1 stop14h 57mSpirit Airlines

Deal found 8/12

$218

Thu 8/2112:18 pmPDX - ORD

1 stop10h 14mFrontier

Mon 8/256:00 amORD - PDX

1 stop7h 23mFrontier

Deal found 8/10

$235

Fri 8/227:52 pmPDX - ORD

1 stop6h 58mSpirit Airlines

Mon 8/256:00 amORD - PDX

1 stop14h 57mSpirit Airlines

Deal found 8/12

$210

Fri 8/226:06 pmBOI - ORD

1 stop9h 44mSpirit Airlines

Sun 8/246:00 amORD - BOI

1 stop12h 11mSpirit Airlines

Deal found 8/10

$254

Fri 8/226:06 pmBOI - ORD

1 stop9h 44mMultiple Airlines

Sun 8/246:00 amORD - BOI

1 stop6h 38mMultiple Airlines

Deal found 8/11

$261

Sat 8/237:52 pmPDX - ORD

1 stop6h 58mSpirit Airlines

Mon 8/256:00 amORD - PDX

1 stop14h 57mSpirit Airlines

Deal found 8/12

$202

One-way flights from Oregon to Chicago
Search for one-way flight options from Oregon to Chicago. Find affordable one-way fares based on user searches. Data last updated August 13, 2025.

Thu 9/252:16 pmBOI - MDW

1 stop29h 36mMultiple Airlines

Deal found 8/12

$85

Fri 9/129:26 pmBOI - ORD

1 stop13h 25mSpirit Airlines

Deal found 8/12

$85

Tue 9/91:07 pmBOI - ORD

Nonstop3h 38mAmerican Airlines

Deal found 8/12

$87

Mon 9/89:26 pmBOI - ORD

1 stop20h 25mSpirit Airlines

Deal found 8/11

$93

Tue 9/232:28 pmBOI - ORD

1 stop8h 35mHawaiian Airlines

Deal found 8/12

$96

Tue 10/2811:43 amBOI - ORD

1 stop8h 57mHawaiian Airlines

Deal found 8/12

$96

Wed 12/102:45 pmBOI - ORD

1 stop8h 14mHawaiian Airlines

Deal found 8/12

$96

Wed 9/34:34 pmBOI - ORD

1 stop6h 29mHawaiian Airlines

Deal found 8/12

$96

Wed 2/46:00 amBOI - ORD

1 stop6h 04mHawaiian Airlines

Deal found 8/12

$96

Wed 11/1211:43 amBOI - ORD

1 stop8h 57mHawaiian Airlines

Deal found 8/12

$96

Wed 1/72:45 pmBOI - ORD

1 stop8h 14mHawaiian Airlines

Deal found 8/12

$96

Tue 9/91:30 pmBOI - MDW

1 stop6h 56mDelta

Deal found 8/12

$97

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 10/22

8:04 pm-2:27 pm

1 stop16h 23m

Chicago O'Hare Intl

Wed 10/29

6:00 am-7:36 pm

1 stop15h 36m

$184

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 9/11

12:07 pm-9:32 pm

1 stop7h 25m

Chicago O'Hare Intl

Wed 9/17

9:00 am-7:23 pm

1 stop12h 23m

$186

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 9/19

8:18 pm-11:51 am

1 stop13h 33m

Chicago O'Hare Intl

Mon 9/22

6:15 am-7:23 pm

1 stop15h 08m

$191

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 10/20

8:04 pm-5:25 am

1 stop7h 21m

Chicago O'Hare Intl

Mon 10/27

12:31 pm-7:04 pm

1 stop8h 33m

$194

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 9/17

12:07 pm-9:32 pm

1 stop7h 25m

Chicago O'Hare Intl

Sat 9/20

2:07 pm-4:37 pm

Nonstop4h 30m

$195

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 9/26

8:18 pm-11:51 am

1 stop13h 33m

Chicago O'Hare Intl

Mon 9/29

6:15 am-7:23 pm

1 stop15h 08m

$196

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 9/1

7:52 pm-4:50 am

1 stop6h 58m

Chicago O'Hare Intl

Fri 9/5

6:15 am-11:11 am

1 stop6h 56m

$196

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 9/3

7:52 pm-4:50 am

1 stop6h 58m

Chicago O'Hare Intl

Sat 9/6

7:00 am-9:25 am

Nonstop4h 25m

$197

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 8/15

5:50 pm-12:32 am

1 stop28h 42m

Chicago O'Hare Intl

Tue 9/16

11:15 am-7:23 pm

1 stop10h 08m

$198

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 9/12

8:18 pm-11:51 am

1 stop13h 33m

Chicago O'Hare Intl

Mon 9/15

6:15 am-11:11 am

1 stop6h 56m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 60 results

...

Best time to book a flight from Oregon to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Oregon with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Oregon to Chicago

What is the cheapest month to book a flight from Oregon to Chicago?

Currently, August is the cheapest month in which you can book a flight from Oregon to Chicago (average of $245). Flying from Oregon to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OR to CHI?

When flying from Oregon to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Oregon to Chicago

The most flights from USOR to CHI are scheduled on a Tuesday (33 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

Related info for your journey

What are the most popular routes from Oregon to Chicago?
The most popular route from Oregon to Chicago is Portland - Chicago O'Hare Intl. You may also consider Portland - Chicago Midway or Boise Air Term. Gowen Fld - Chicago O'Hare Intl.
What are the most reliable airlines from Oregon to Chicago?
The top 3 most reliable airlines when flying from Oregon to Chicago are Brussels Airlines (89%), Air Canada (87%) and Finnair (87%).
What are the cheapest flights from Oregon to Chicago?
Looking for the cheapest flight from Oregon to Chicago? While on average our users pay $858, our data indicates the cheapest price to be $100. The most popular route (Portland - Chicago O'Hare Intl), is priced around $151.
Can I find deals for flights from Oregon to Chicago that include hotel bookings?
Yes. In addition to deals on Oregon to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Oregon to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Chicago.
Can I find deals for business class flights from Oregon to Chicago?
Yes. Cheapflights offers flight deals from Oregon to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Oregon to Chicago?
Currently, August is the cheapest month in which you can book a flight from Oregon to Chicago (average of $245). Flying from Oregon to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Merrillville

Lansing

Hammond

Benton Harbor

Porter

Valparaiso

Chesterton

Browse thousands of different options on Cheapflights for your next trip

Top 8 airlines flying from Oregon to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$86	Average$181	FlexibilityNo cancel fee	On-time65%
Frontier	Cheapest$108	Average$248	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$123	Average$362	FlexibilityNo cancel fee	On-timeN/A
Hawaiian Airlines	Cheapest$178	Average$333	FlexibilityNo cancel fee	On-time85%
Alaska Airlines	Cheapest$191	Average$430	FlexibilityNo cancel fee	On-time75%
American Airlines	Cheapest$218	Average$434	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$226	Average$454	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$238	Average$436	FlexibilityNo cancel fee	On-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$85+ Cheap flights from Oregon to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/25. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Oregon to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Oregon to Chicago

Keep the following information in mind while searching for Oregon to Chicago flight deals. Data was last updated August 13, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Oregon to Chicago

Cheapest flights from Oregon to ChicagoExplore the most affordable flight options available from Oregon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2025.

Explore the most affordable flight options available from Oregon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Oregon to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Oregon with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Oregon to Chicago

What is the cheapest month to book a flight from Oregon to Chicago?

What is the cheapest time of day to fly from OR to CHI?

Find hourly flight availability from Oregon to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 13, 2025.

Weekly flight availability from Oregon to Chicago

Explore weekly flight availability from Oregon to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 13, 2025.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What are the most popular routes from Oregon to Chicago?

What are the most reliable airlines from Oregon to Chicago?

What are the cheapest flights from Oregon to Chicago?

Can I find deals for flights from Oregon to Chicago that include hotel bookings?

How can I find direct flights from Oregon to Chicago?

Can I find deals for business class flights from Oregon to Chicago?

What is the cheapest month to book a flight from Oregon to Chicago?

Traveling to a place near Chicago?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oregon to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 8 airlines flying from Oregon to Chicago

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from Oregon to Chicago
Explore the most affordable flight options available from Oregon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2025.