What are the cheapest airlines to fly from Oregon to Chicago one-way?

To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $78. American Airlines flights start at $78 while deals on United Airlines start at $83 one-way.

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 $1,457, our data indicates the cheapest price to be $120. The most popular route (Portland - Chicago O'Hare Intl), is priced around $167.

What are the most reliable airlines from Oregon to Chicago?

The top 3 most reliable airlines when flying from Oregon to Chicago are Lufthansa (96%), United Airlines (94%) and Air Canada (94%).

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 49 days in advance to save up to 22% 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 49 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 $307, or $367 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 $341 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.

$78+ Flights from Oregon to Chicago

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

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Cheap flight deals from Oregon to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$180 (Delta)
One-way from	$78 (Southwest)
Popular in	March
Cheapest in	January
Average price	$466
Good round-trip deal	$360 or less
Good one-way deal	$181 or less

Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.

Search Deals

From Oregon to Chicago (CHI)

Search Deals

One-way flight from Oregon to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 8% potential increase in price ($30 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in March 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).

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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 March 31, 2025.

Sat 6/215:00 amBOI - ORD

1 stop5h 42mDelta

Tue 7/12:00 pmORD - BOI

2 stops10h 59mDelta

Deal found 3/30

$180

Fri 9/1212:29 pmBOI - ORD

Nonstop3h 26mUnited Airlines

Tue 9/165:00 amORD - BOI

1 stop5h 43mUnited Airlines

Deal found 3/31

$201

Tue 6/2411:35 pmBOI - MDW

1 stop9h 19mDelta

Thu 7/39:21 amMDW - BOI

1 stop5h 43mDelta

Deal found 3/30

$211

Tue 5/62:41 pmBOI - ORD

1 stop6h 18mMultiple Airlines

Thu 5/89:02 pmORD - BOI

1 stop15h 19mMultiple Airlines

Deal found 3/30

$217

Thu 8/141:17 pmBOI - ORD

Nonstop3h 37mAmerican Airlines

Mon 8/185:00 amORD - BOI

1 stop9h 14mAmerican Airlines

Deal found 3/31

$230

Thu 5/81:50 pmBOI - MDW

1 stop9h 05mSouthwest

Sun 5/115:45 amMDW - BOI

1 stop5h 25mSouthwest

Deal found 3/30

$240

Sat 5/171:37 pmPDX - ORD

2 stops17h 18mSpirit Airlines

Mon 5/1911:50 amORD - PDX

1 stop6h 55mSpirit Airlines

Deal found 3/30

$243

Wed 5/282:30 pmPDX - ORD

1 stop7h 29mAlaska Airlines

Sat 5/317:00 amORD - PDX

Nonstop4h 23mAlaska Airlines

Deal found 3/30

$244

Sun 4/138:59 pmBOI - ORD

1 stop7h 41mHawaiian Airlines

Wed 4/163:16 pmORD - BOI

1 stop9h 43mHawaiian Airlines

Deal found 3/30

$246

Thu 5/85:40 pmPDX - ORD

2 stops13h 15mMultiple Airlines

Sun 5/115:21 pmORD - PDX

1 stop9h 23mMultiple Airlines

Deal found 3/30

$246

Sat 6/145:35 pmPDX - ORD

Nonstop4h 04mHawaiian Airlines

Wed 6/187:00 amORD - PDX

Nonstop4h 25mHawaiian Airlines

Deal found 3/31

$247

Sat 6/1411:13 pmPDX - MDW

1 stop7h 28mDelta

Wed 6/1810:39 amMDW - PDX

1 stop10h 22mDelta

Deal found 3/30

$247

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 March 31, 2025.

Sat 6/215:00 amBOI - ORD

1 stop5h 42mDelta

Tue 7/12:00 pmORD - BOI

2 stops10h 59mDelta

Deal found 3/30

$180

Tue 5/62:41 pmBOI - ORD

1 stop6h 18mMultiple Airlines

Thu 5/89:02 pmORD - BOI

1 stop15h 19mMultiple Airlines

Deal found 3/30

$217

Mon 4/145:25 pmBOI - ORD

1 stop5h 27mUnited Airlines

Fri 4/187:35 pmORD - BOI

Nonstop4h 14mUnited Airlines

Deal found 3/30

$237

Thu 5/81:50 pmBOI - MDW

1 stop9h 05mSouthwest

Sun 5/115:45 amMDW - BOI

1 stop5h 25mSouthwest

Deal found 3/30

$240

Sat 5/171:37 pmPDX - ORD

2 stops17h 18mSpirit Airlines

Mon 5/1911:50 amORD - PDX

1 stop6h 55mSpirit Airlines

Deal found 3/30

$243

Wed 5/282:30 pmPDX - ORD

1 stop7h 29mAlaska Airlines

Sat 5/317:00 amORD - PDX

Nonstop4h 23mAlaska Airlines

Deal found 3/30

$244

Sun 4/138:59 pmBOI - ORD

1 stop7h 41mHawaiian Airlines

Wed 4/163:16 pmORD - BOI

1 stop9h 43mHawaiian Airlines

Deal found 3/30

$246

Thu 4/176:40 amPDX - MDW

1 stop15h 41mFrontier

Mon 4/216:45 amMDW - PDX

1 stop19h 52mFrontier

Deal found 3/29

$250

Fri 4/2511:52 pmPDX - ORD

Nonstop4h 05mAmerican Airlines

Mon 4/288:20 pmORD - PDX

Nonstop4h 42mAmerican Airlines

Deal found 3/30

$257

Thu 6/1211:59 pmPDX - ORD

1 stop15h 16mSun Country Air

Mon 6/236:17 pmORD - PDX

1 stop6h 29mSun Country Air

Deal found 3/31

$325

Tue 6/2411:35 pmBOI - MDW

1 stop9h 19mDelta

Thu 7/39:21 amMDW - BOI

1 stop5h 43mDelta

Deal found 3/30

$211

Thu 5/85:40 pmPDX - ORD

2 stops13h 15mMultiple Airlines

Sun 5/115:21 pmORD - PDX

1 stop9h 23mMultiple Airlines

Deal found 3/30

$246

Last-minute flights from Oregon to Chicago
Discover last-minute flight deals from Oregon to Chicago. Data last updated March 31, 2025 and is based on user searches.

Mon 4/79:01 amPDX - ORD

1 stop13h 57mMultiple Airlines

Tue 4/88:00 amORD - PDX

1 stop11h 18mMultiple Airlines

Deal found 3/30

$277

Tue 4/89:59 amPDX - ORD

1 stop12h 11mFrontier

Fri 4/118:01 pmORD - PDX

1 stop14h 46mFrontier

Deal found 3/30

$278

Tue 4/86:35 amBOI - ORD

1 stop7h 50mSouthwest

Thu 4/106:15 amORD - BOI

1 stop8h 00mSouthwest

Deal found 3/31

$345

Tue 4/812:06 pmBOI - ORD

Nonstop3h 57mUnited Airlines

Thu 4/107:35 pmORD - BOI

Nonstop4h 14mUnited Airlines

Deal found 3/31

$419

Wed 4/96:37 amBOI - ORD

1 stop6h 39mHawaiian Airlines

Thu 4/107:00 amORD - BOI

1 stop7h 52mHawaiian Airlines

Deal found 3/29

$353

Thu 4/107:01 pmPDX - ORD

1 stop9h 32mSpirit Airlines

Sun 4/137:12 pmORD - PDX

1 stop16h 00mSpirit Airlines

Deal found 3/30

$249

Thu 4/106:40 amPDX - MDW

1 stop15h 41mFrontier

Sun 4/138:50 pmMDW - PDX

1 stop13h 57mFrontier

Deal found 3/30

$270

Thu 4/1011:30 pmBOI - ORD

1 stop8h 04mDelta

Sun 4/137:20 amORD - BOI

1 stop5h 50mDelta

Deal found 3/30

$303

Thu 4/101:45 pmBOI - MDW

1 stop7h 36mDelta

Sun 4/139:23 amMDW - BOI

2 stops10h 33mDelta

Deal found 3/30

$308

Thu 4/101:23 pmBOI - ORD

1 stop6h 52mAmerican Airlines

Sun 4/136:00 amORD - BOI

1 stop8h 21mAmerican Airlines

Deal found 3/31

$359

Thu 4/102:47 pmBOI - ORD

1 stop8h 12mAlaska Airlines

Mon 4/1410:00 amORD - BOI

1 stop9h 00mAlaska Airlines

Deal found 3/31

$448

Thu 4/107:00 amPDX - ORD

Nonstop4h 05mHawaiian Airlines

Mon 4/143:16 pmORD - PDX

Nonstop4h 34mHawaiian Airlines

Deal found 3/31

$493

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 March 31, 2025.

Sat 6/712:55 pmBOI - MDW

Nonstop3h 20mSouthwest

Deal found 3/30

$78

Sat 6/141:15 pmBOI - ORD

Nonstop3h 37mAmerican Airlines

Deal found 3/30

$78

Sat 6/287:15 pmBOI - ORD

1 stop9h 24mUnited Airlines

Deal found 3/30

$83

Mon 5/1212:16 pmBOI - ORD

1 stop21h 39mSpirit Airlines

Deal found 3/30

$84

Tue 5/62:41 pmBOI - ORD

1 stop6h 18mAlaska Airlines

Deal found 3/31

$87

Sat 5/103:10 pmBOI - ORD

1 stop6h 55mSouthwest

Deal found 3/31

$88

Wed 6/41:37 pmPDX - ORD

1 stop13h 48mSpirit Airlines

Deal found 3/30

$91

Sat 5/35:30 amBOI - MDW

1 stop7h 52mDelta

Deal found 3/30

$98

Fri 5/3012:50 pmBOI - ORD

1 stop7h 50mDelta

Deal found 3/31

$98

Sat 5/175:51 pmPDX - ORD

Nonstop4h 05mHawaiian Airlines

Deal found 3/31

$114

Sat 5/106:45 amPDX - MDW

Nonstop4h 00mSouthwest

Deal found 3/31

$114

Mon 4/286:41 pmPDX - ORD

1 stop8h 33mFrontier

Deal found 3/30

$119

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Sat 6/21

5:00 am-11:42 am

1 stop5h 42m

Chicago O'Hare Intl

Mon 6/30

2:20 pm-11:50 pm

2 stops10h 30m

$180

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Fri 9/12

12:29 pm-4:55 pm

Nonstop3h 26m

Chicago O'Hare Intl

Tue 9/16

5:00 am-9:43 am

1 stop5h 43m

$201

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 6/24

11:35 pm-9:54 am

1 stop9h 19m

Chicago Midway

Thu 7/3

9:21 am-2:04 pm

1 stop5h 43m

$211

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Tue 5/6

2:41 pm-9:59 pm

1 stop6h 18m

Chicago O'Hare Intl

Thu 5/8

9:02 pm-11:21 am

1 stop15h 19m

$217

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Thu 8/14

1:17 pm-5:54 pm

Nonstop3h 37m

Chicago O'Hare Intl

Mon 8/18

5:00 am-1:14 pm

1 stop9h 14m

$230

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Thu 5/8

1:50 pm-11:55 pm

1 stop9h 05m

Chicago Midway

Sun 5/11

5:45 am-10:10 am

1 stop5h 25m

$240

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 5/17

1:37 pm-8:55 am

2 stops17h 18m

Chicago O'Hare Intl

Mon 5/19

11:50 am-4:45 pm

1 stop6h 55m

$243

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 5/28

2:30 pm-11:59 pm

1 stop7h 29m

Chicago O'Hare Intl

Sat 5/31

7:00 am-9:23 am

Nonstop4h 23m

$244

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Sun 4/13

8:59 pm-5:40 am

1 stop7h 41m

Chicago O'Hare Intl

Wed 4/16

3:16 pm-11:59 pm

1 stop9h 43m

$246

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 5/8

5:40 pm-8:55 am

2 stops13h 15m

Chicago O'Hare Intl

Sun 5/11

5:21 pm-12:44 am

1 stop9h 23m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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 $323). 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 Sunday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

Rainfall in Chicago by month

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.

Temperature in Chicago by month

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).

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Oregon to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Alaska Airlines

8.0

Very good

9,818 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines

8.0

Very good

9,818 reviews

Alaska Airlines

8.0

Very good

9,818 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Southwest

8.0

Very good

4,275 reviews

Alaska Airlines

8.0

Very good

9,818 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta

8.0

Very good

7,899 reviews

Alaska Airlines

8.0

Very good

9,818 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Hawaiian Airlines

7.9

Good

2,344 reviews

Alaska Airlines

8.0

Very good

9,818 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines

7.4

Good

8,614 reviews

Alaska Airlines

8.0

Very good

9,818 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

What are the cheapest airlines to fly from Oregon to Chicago one-way?
To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $78. American Airlines flights start at $78 while deals on United Airlines start at $83 one-way.
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 Lufthansa (96%), United Airlines (94%) and Air Canada (94%).
What are the cheapest flights from Oregon to Chicago?
Looking for the cheapest flight from Oregon to Chicago? While on average our users pay $1,457, our data indicates the cheapest price to be $120. The most popular route (Portland - Chicago O'Hare Intl), is priced around $167.
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 $323). 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

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Top 8 airlines flying from Oregon to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$82	Average$135	FlexibilityNo cancel fee	On-time65%
Frontier	Cheapest$108	Average$241	FlexibilityNo cancel fee	On-time62%
Alaska Airlines	Cheapest$185	Average$488	FlexibilityNo cancel fee	On-time75%
American Airlines	Cheapest$189	Average$420	FlexibilityNo cancel fee	On-time71%
Hawaiian Airlines	Cheapest$202	Average$383	FlexibilityNo cancel fee	On-time85%
Delta	Cheapest$207	Average$407	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$215	Average$533	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$249	Average$435	FlexibilityNo cancel fee	On-time63%

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$78+ 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 6/7. 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

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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 March 31, 2025.

Most accurate provider

Most trusted provider

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 March 31, 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 March 31, 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 March 31, 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 March 31, 2025.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Oregon to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

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 cheapest airlines to fly from Oregon to Chicago one-way?

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 Oregon?

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Alternative routes for Oregon to Chicago

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Top 8 airlines flying from Oregon to Chicago

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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 March 31, 2025.