$114+ 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 2/19. 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
Discover tips and strategies to find the most affordable flight options for your journey from Oregon (USOR) to Midway (MDW). 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 January 21, 2025.
Round-trip from | $227 (Southwest) |
|---|---|
One-way from | $114 (Southwest) |
Good round-trip deal | $359 or less |
Good one-way deal | $209 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 January 21, 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 January 21, 2025.
This Southwest deal was found by Cheapflights users on 1/20. 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 FlightHub deal was found by Cheapflights users on 1/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kissandfly.com deal was found by Cheapflights users on 1/20. 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 Kissandfly.com 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 1/20. 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 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 1/21. 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 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 1/20. 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 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 1/21. 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 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 1/20. 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 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 1/20. 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 Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Find flights from Oregon to Midway within your budget
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 January 21, 2025.
Fly from
Fly to
Route
Depart
Return
Price
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sun 3/16
6:32 am-12:17 am
1 stop15h 45m
Chicago Midway
Wed 3/19
6:40 am-12:37 am
1 stop19h 57m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 2/18
12:59 am-9:35 am
1 stop6h 36m
Chicago Midway
Tue 2/25
1:26 pm-5:32 pm
1 stop6h 06m
BoiseChicago
BOI - MDW
BOIMDW
Boise Air Term. Gowen Fld
Tue 3/4
5:30 am-12:42 pm
1 stop6h 12m
Chicago Midway
Tue 3/11
7:09 pm-11:59 pm
1 stop5h 50m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 2/19
9:00 am-2:55 pm
Nonstop3h 55m
Chicago Midway
Wed 2/26
8:35 am-4:45 pm
1 stop10h 10m
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Sat 4/19
5:55 am-6:04 pm
2 stops10h 09m
Chicago Midway
Tue 4/29
1:16 pm-11:30 pm
2 stops12h 14m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Mon 2/10
6:00 am-12:17 am
2 stops16h 17m
Chicago Midway
Wed 2/19
7:05 am-6:15 pm
2 stops13h 10m
EugeneChicago
EUG - MDW
EUGMDW
Eugene
Fri 4/25
5:30 pm-8:42 am
2 stops13h 12m
Chicago Midway
Mon 4/28
3:02 pm-11:45 pm
2 stops10h 43m
BoiseChicago
BOI - MDW
BOIMDW
Boise Air Term. Gowen Fld
Thu 4/10
2:25 pm-12:30 am
1 stop9h 05m
Chicago Midway
Sun 4/13
7:00 am-3:00 pm
1 stop9h 00m
EugeneChicago
EUG - MDW
EUGMDW
Eugene
Wed 2/12
6:35 am-4:50 pm
2 stops8h 15m
Chicago Midway
Wed 2/19
9:40 am-3:15 pm
1 stop7h 35m
MedfordChicago
MFR - MDW
MFRMDW
Medford
Tue 4/1
5:24 pm-8:45 am
2 stops13h 21m
Chicago Midway
Mon 4/7
1:15 pm-11:55 pm
2 stops12h 40m
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.
Travel insights for flights from Oregon to Midway
Get recent, data-driven insights about flights from Oregon to Midway including ideal travel times, pricing trends, and more.
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 January 21, 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 January 21, 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.
Comfort
Crew
Food
Overall
Boarding
Entertainment
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
Crew
Food
Overall
Boarding
Entertainment
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
Crew
Food
Overall
Boarding
Entertainment
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
Crew
Food
Overall
Boarding
Entertainment
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
Crew
Food
Overall
Boarding
Entertainment
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 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 January 21, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$134 | Average$284 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$216 | Average$455 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$233 | Average$504 | FlexibilityNo cancel fee | On-time63% |