$91+ Cheap flights from Oregon to Midway (MDW)
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 Midway 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 Midway
Keep the following information in mind while searching for Oregon to Midway flight deals. Data was last updated June 12, 2025.
Round-trip from | $200 (Delta) |
|---|---|
One-way from | $91 (Delta) |
Popular in | March |
Cheapest in | January |
Average price | $341 |
Good round-trip deal | $376 or less |
Good one-way deal | $195 or less |
Find flight deals from Oregon to Midway
Cheapest flights from Oregon to MidwayExplore the most affordable flight options available from Oregon to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
Explore the most affordable flight options available from Oregon to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
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 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 Delta 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 Delta 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 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 FlightHub 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 6/11. 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 Delta 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 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 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 FlightHub 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 FlightHub 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 6/11. 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 Delta 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 Midway 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 June 12, 2025.
Use the filters below to find and compare flights from Oregon to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
BoiseChicago
BOI - MDW
BOIMDW
Boise Air Term. Gowen Fld
Sat 7/12
5:40 am-1:06 pm
1 stop6h 26m
Chicago Midway
Sat 7/19
9:25 am-5:05 pm
2 stops8h 40m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 9/10
11:45 am-9:50 pm
1 stop8h 05m
Chicago Midway
Sun 9/14
10:25 pm-12:40 am
Nonstop4h 15m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 7/15
11:11 pm-8:44 am
1 stop7h 33m
Chicago Midway
Tue 7/22
9:24 am-3:55 pm
1 stop8h 31m
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Sat 10/4
6:20 am-6:07 pm
2 stops9h 47m
Chicago Midway
Sat 10/11
2:00 pm-10:44 pm
2 stops10h 44m
BoiseChicago
BOI - MDW
BOIMDW
Boise Air Term. Gowen Fld
Sat 7/12
12:55 pm-5:15 pm
Nonstop3h 20m
Chicago Midway
Sat 7/19
7:50 am-10:30 am
Nonstop3h 40m
EugeneChicago
EUG - MDW
EUGMDW
Eugene
Fri 7/4
11:00 am-9:00 pm
1 stop8h 00m
Chicago Midway
Thu 7/10
8:20 am-4:05 pm
1 stop9h 45m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fri 6/27
5:50 pm-8:53 pm
1 stop25h 03m
Chicago Midway
Mon 6/30
6:25 am-12:55 pm
1 stop8h 30m
MedfordChicago
MFR - MDW
MFRMDW
Medford
Tue 8/26
6:00 am-6:37 pm
2 stops10h 37m
Chicago Midway
Sat 8/30
1:08 pm-10:21 pm
2 stops11h 13m
BoiseChicago
BOI - MDW
BOIMDW
Boise Air Term. Gowen Fld
Sun 6/22
12:36 pm-11:40 am
1 stop22h 04m
Chicago Midway
Sat 6/28
2:44 pm-11:47 am
1 stop22h 03m
EugeneChicago
EUG - MDW
EUGMDW
Eugene
Tue 7/8
5:20 pm-9:45 am
2 stops14h 25m
Chicago Midway
Mon 7/14
1:46 pm-10:49 pm
2 stops11h 03m
Best time to book a flight from Oregon to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Oregon with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Oregon to Chicago Midway Airport
What is the cheapest month to book a flight from Oregon to Chicago Midway Airport?
Currently, April is the cheapest month in which you can book a flight from Oregon to Chicago Midway Airport (average of $160). Flying from Oregon to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 MDW?
Find hourly flight availability from Oregon to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to Chicago Midway Airport as you normally would.
Rainfall in Midway by month
Plan your trip to Midway by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago Midway Airport 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 Midway Airport when rainfall is around 1.7 in.
Temperature in Midway by month
Plan your trip to Midway by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago Midway Airport, 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 Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated June 12, 2025.
See what other customers who have flown with Southwest, Delta and Frontier from Oregon to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
Boarding
Comfort
Food
Overall
Crew
Reviews
John,May 2025
PVD - BNA
Entertainment
Boarding
Comfort
Food
Overall
Crew
Reviews
John,May 2025
PVD - BNA
Entertainment
Boarding
Comfort
Food
Overall
Crew
Reviews
John,May 2025
PVD - BNA
Entertainment
Boarding
Comfort
Food
Overall
Crew
Reviews
John,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Oregon to Midway. 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?
Book flights to Oregon if you plan to visit one of these locationsBrowse 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 Midway
See prices for flight routes from nearby airports that may be better suited for you.
Top 3 airlines flying from Oregon to Midway
Discover the top 3 airlines that operate flights from Oregon to Midway. 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 June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$261 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$216 | Average$402 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$253 | Average$443 | FlexibilityNo cancel fee | On-time63% |