$91+ 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 8/16. 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
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
Keep the following information in mind while searching for Oregon to Chicago flight deals. Data was last updated junio 12, 2025.
Round-trip from | $191 (Cheapflightsfares) |
|---|---|
One-way from | $91 (Delta) |
Popular in | March |
Cheapest in | January |
Average price | $341 |
Good round-trip deal | $342 or less |
Good one-way deal | $171 or less |
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 junio 12, 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 junio 12, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Cheapflightsfares deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Hawaiian Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Alaska Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Hawaiian Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Cheapflights Fare Finder
Customize your flight search to find flights from Oregon to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated junio 12, 2025.
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
sáb. 9/6
9:49 pm-2:16 pm
1 stop15h 27m
Chicago O'Hare Intl
sáb. 9/13
6:00 am-8:44 pm
1 stop15h 44m
BoiseChicago
BOI - ORD
BOIORD
Boise Air Term. Gowen Fld
mar. 7/15
4:20 pm-11:56 pm
1 stop6h 36m
Chicago O'Hare Intl
mar. 7/22
7:20 pm-12:09 am
1 stop5h 49m
BoiseChicago
BOI - MDW
BOIMDW
Boise Air Term. Gowen Fld
sáb. 7/12
5:40 am-1:06 pm
1 stop6h 26m
Chicago Midway
sáb. 7/19
9:25 am-5:05 pm
2 stops8h 40m
PortlandChicago
PDX - ORD
PDXORD
Portland
mié. 6/25
6:39 pm-10:50 am
1 stop14h 11m
Chicago O'Hare Intl
dom. 6/29
10:15 pm-11:17 am
1 stop15h 02m
PortlandChicago
PDX - MDW
PDXMDW
Portland
mié. 9/10
11:45 am-9:50 pm
1 stop8h 05m
Chicago Midway
dom. 9/14
10:25 pm-12:40 am
Nonstop4h 15m
PortlandChicago
PDX - ORD
PDXORD
Portland
mar. 9/2
6:10 am-2:10 pm
1 stop6h 00m
Chicago O'Hare Intl
jue. 9/18
1:30 pm-8:10 pm
1 stop8h 40m
PortlandChicago
PDX - ORD
PDXORD
Portland
jue. 8/14
5:35 pm-11:39 pm
Nonstop4h 04m
Chicago O'Hare Intl
dom. 8/17
7:00 am-9:25 am
Nonstop4h 25m
EugeneChicago
EUG - ORD
EUGORD
Eugene
mié. 8/13
1:30 pm-5:40 am
1 stop14h 10m
Chicago O'Hare Intl
sáb. 8/16
5:55 pm-11:59 pm
1 stop8h 04m
PortlandChicago
PDX - ORD
PDXORD
Portland
jue. 10/30
2:31 pm-11:59 pm
1 stop7h 28m
Chicago O'Hare Intl
dom. 11/2
7:00 am-9:38 am
Nonstop4h 38m
MedfordChicago
MFR - ORD
MFRORD
Medford
jue. 7/10
9:51 pm-2:13 pm
1 stop14h 22m
Chicago O'Hare Intl
mié. 7/16
3:18 pm-3:26 pm
1 stop26h 08m
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?
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?
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 junio 12, 2025.
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
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 junio 12, 2025.
The most flights from USOR to CHI are scheduled on a Thursday (33 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals 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
Plan your trip to Chicago by taking into account the average temperature totals 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
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated junio 12, 2025.
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.
Food
Overall
Comfort
Entertainment
Boarding
Crew
Reviews
James,Apr 2025
LAX - SFO
Food
Overall
Comfort
Entertainment
Boarding
Crew
Reviews
James,Apr 2025
LAX - SFO
Food
Overall
Comfort
Entertainment
Boarding
Crew
Reviews
James,Apr 2025
LAX - SFO
Food
Overall
Comfort
Entertainment
Boarding
Crew
Reviews
James,Apr 2025
LAX - SFO
Food
Overall
Comfort
Entertainment
Boarding
Crew
Reviews
James,Apr 2025
LAX - SFO
Food
Overall
Comfort
Entertainment
Boarding
Crew
Reviews
James,Apr 2025
LAX - SFO
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.
Traveling to a place near Oregon?
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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
Discover the top 8 airlines that operate flights from Oregon to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated junio 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$135 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$219 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$123 | Average$377 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$186 | Average$462 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$202 | Average$294 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$217 | Average$500 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$226 | Average$440 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$253 | Average$443 | FlexibilityNo cancel fee | On-time63% |