$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 1/23. 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
Discover tips and strategies to find the most affordable flight options for your journey from Oregon (USOR) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.
Round-trip from | $228 (Delta) |
|---|---|
One-way from | $91 (FlightHub) |
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 December 22, 2024.
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 December 22, 2024.
This Mytrip deal was found by Cheapflights users on 12/21. 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 FlightHub deal was found by Cheapflights users on 12/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 12/21. 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 American 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 12/21. 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 Cheapflightsfares deal was found by Cheapflights users on 12/21. 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 Alaska Airlines deal was found by Cheapflights users on 12/19. 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 Gotogate deal was found by Cheapflights users on 12/20. 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 Gotogate 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 12/19. 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 12/19. 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 American Airlines deal was found by Cheapflights users on 12/19. 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 American Airlines 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 12/20. 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 Gotogate deal was found by Cheapflights users on 12/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Find flights from Oregon to Chicago within your budget
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 December 22, 2024.
Fly from
Fly to
Route
Depart
Return
Price
BoiseChicago
BOI - ORD
BOIORD
Boise Air Term. Gowen Fld
Sun 1/19
5:55 am-2:12 pm
1 stop7h 17m
Chicago O'Hare Intl
Sun 1/26
6:15 am-2:05 pm
1 stop8h 50m
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 4/1
9:54 am-12:15 am
1 stop12h 21m
Chicago O'Hare Intl
Tue 4/8
6:45 am-12:37 am
1 stop19h 52m
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 4/15
7:00 am-1:05 pm
Nonstop4h 05m
Chicago O'Hare Intl
Sat 4/26
2:00 pm-7:19 pm
1 stop7h 19m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sun 1/19
12:45 am-9:39 am
1 stop6h 54m
Chicago Midway
Mon 1/27
1:26 pm-8:35 pm
1 stop9h 09m
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 1/11
7:00 am-1:01 pm
Nonstop4h 01m
Chicago O'Hare Intl
Wed 1/15
4:00 pm-6:43 pm
Nonstop4h 43m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Thu 1/16
5:26 pm-11:44 am
2 stops16h 18m
Chicago Midway
Wed 1/22
1:26 pm-8:36 pm
1 stop9h 10m
PortlandChicago
PDX - ORD
PDXORD
Portland
Mon 4/14
12:40 am-8:35 am
1 stop5h 55m
Chicago O'Hare Intl
Tue 4/22
6:50 pm-11:52 pm
1 stop7h 02m
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 1/18
5:30 pm-2:15 pm
3 stops18h 45m
Chicago O'Hare Intl
Sat 1/25
8:00 am-4:35 pm
1 stop10h 35m
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 12/31
7:48 pm-5:30 am
1 stop7h 42m
Chicago O'Hare Intl
Wed 1/29
8:00 am-9:21 am
2 stops27h 21m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Mon 2/10
11:17 am-4:16 pm
2 stops26h 59m
Chicago Midway
Sat 2/22
4:48 pm-12:37 am
2 stops33h 49m
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.
Travel insights for flights from Oregon to Chicago
Get recent, data-driven insights about flights from Oregon to Chicago including ideal travel times, pricing trends, and more.
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 $317). 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 December 22, 2024.
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 December 22, 2024.
The most flights from USOR to CHI are scheduled on a Saturday (19 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 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 December 22, 2024.
Read reviews from past customers who have flown United Airlines, Frontier and Alaska Airlines 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.
Comfort
Boarding
Entertainment
Overall
Crew
Food
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Comfort
Boarding
Entertainment
Overall
Crew
Food
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Comfort
Boarding
Entertainment
Overall
Crew
Food
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Comfort
Boarding
Entertainment
Overall
Crew
Food
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Comfort
Boarding
Entertainment
Overall
Crew
Food
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Comfort
Boarding
Entertainment
Overall
Crew
Food
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
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.
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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 7 airlines flying from Oregon to Chicago
Discover the top 7 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 December 22, 2024.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$82 | Average$136 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$240 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$179 | Average$480 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$188 | Average$438 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$216 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$218 | Average$535 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$233 | Average$551 | FlexibilityNo cancel fee | On-time63% |