HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Oregon

$78+ Cheap flights from Midway (MDW) to Oregon

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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Oregon 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 Midway to Oregon

Keep the following information in mind while searching for Midway to Oregon flight deals. Data was last updated March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$232
(Delta)

One-way from

$78
(Southwest)

Popular in

March

Cheapest in

September

Average price

$447

Good round-trip deal

$395 or less

Good one-way deal

$209 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
Search Deals
From Chicago Midway to Oregon
Search Deals
One-way flight from Chicago Midway to Oregon
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($39 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 Chicago Midway to Oregon.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Oregon.
Search Deals

Find flight deals from Midway to Oregon

Cheapest flights from Midway to Oregon
Explore the most affordable flight options available from Midway to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 28, 2025.

This Delta deal was found by Cheapflights users on 3/27. 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.
Tue 5/67:00 pmMDW - BOI
1 stop6h 03mDelta
Tue 5/135:35 amBOI - MDW
1 stop6h 40mDelta
Deal found 3/27$232
This Southwest deal was found by Cheapflights users on 3/26. 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.
Sat 4/194:15 pmMDW - PDX
Nonstop4h 20mSouthwest
Sat 4/2611:50 amPDX - MDW
1 stop8h 25mSouthwest
Deal found 3/26$242
This Delta deal was found by Cheapflights users on 3/27. 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.
Sat 4/195:59 pmMDW - PDX
1 stop6h 36mDelta
Sat 4/2610:59 pmPDX - MDW
1 stop7h 41mDelta
Deal found 3/27$251
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/118:36 pmMDW - PDX
1 stop14h 20mFrontier
Tue 4/159:59 amPDX - MDW
1 stop12h 22mFrontier
Deal found 3/27$258
This Delta deal was found by Cheapflights users on 3/27. 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.
Sat 5/101:08 pmMDW - RDM
2 stops11h 58mDelta
Sat 5/177:29 pmRDM - MDW
2 stops11h 11mDelta
Deal found 3/27$259
This Southwest deal was found by Cheapflights users on 3/27. 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.
Thu 6/58:00 pmMDW - BOI
1 stop5h 30mSouthwest
Thu 6/124:10 pmBOI - MDW
1 stop7h 20mSouthwest
Deal found 3/27$287
This Trip.com deal was found by Cheapflights users on 3/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/118:36 pmMDW - PDX
1 stop14h 20mMultiple Airlines
Sun 4/1310:25 amPDX - MDW
1 stop16h 55mMultiple Airlines
Deal found 3/27$289
This Delta deal was found by Cheapflights users on 3/25. 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.
Fri 5/91:08 pmMDW - MFR
2 stops12h 01mDelta
Fri 5/166:15 amMFR - MDW
2 stops10h 30mDelta
Deal found 3/25$377
This Southwest deal was found by Cheapflights users on 3/27. 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.
Wed 6/185:15 amMDW - EUG
2 stops8h 20mSouthwest
Tue 6/245:25 amEUG - MDW
1 stop6h 10mSouthwest
Deal found 3/27$393
This Delta deal was found by Cheapflights users on 3/27. 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.
Fri 5/91:08 pmMDW - EUG
2 stops11h 49mDelta
Tue 5/137:15 amEUG - MDW
2 stops9h 30mDelta
Deal found 3/27$478

Cheapflights Fare Finder

Customize your flight search to find flights from Midway to Oregon 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 March 28, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Oregon that are best for you.

Fly from

Midway

Fly to

Oregon

Route

Depart

Return

Price

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Tue 5/6

7:00 pm-12:03 am

1 stop6h 03m

Boise Air Term. Gowen Fld

Tue 5/13

5:35 am-1:15 pm

1 stop6h 40m

$232

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 4/19

4:15 pm-6:35 pm

Nonstop4h 20m

Portland

Sat 4/26

11:50 am-10:15 pm

1 stop8h 25m

$242

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 4/19

5:59 pm-10:35 pm

1 stop6h 36m

Portland

Sat 4/26

10:59 pm-8:40 am

1 stop7h 41m

$251

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 4/11

8:36 pm-8:56 am

1 stop14h 20m

Portland

Tue 4/15

9:59 am-12:21 am

1 stop12h 22m

$258

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Sat 5/10

1:08 pm-11:06 pm

2 stops11h 58m

Bend/Redmond

Sat 5/17

7:29 pm-8:40 am

2 stops11h 11m

$259

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Thu 6/5

8:00 pm-12:30 am

1 stop5h 30m

Boise Air Term. Gowen Fld

Thu 6/12

4:10 pm-12:30 am

1 stop7h 20m

$287

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 4/11

8:36 pm-8:56 am

1 stop14h 20m

Portland

Sun 4/13

10:25 am-5:20 am

1 stop16h 55m

$289

ChicagoMedford

MDW - MFR

MDWMFR

Chicago Midway

Fri 5/9

1:08 pm-11:09 pm

2 stops12h 01m

Medford

Fri 5/16

6:15 am-6:45 pm

2 stops10h 30m

$377

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Wed 6/18

5:15 am-11:35 am

2 stops8h 20m

Eugene

Tue 6/24

5:25 am-1:35 pm

1 stop6h 10m

$393

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Fri 5/9

1:08 pm-10:57 pm

2 stops11h 49m

Eugene

Tue 5/13

7:15 am-6:45 pm

2 stops9h 30m

$478

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 25 results
1
2
3

Best time to book a flight from Midway to Oregon

Have a flexible travel schedule? Discover the best time to fly to Oregon from Midway 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 Chicago Midway Airport to Oregon

What is the cheapest month to book a flight from Chicago Midway Airport to Oregon?

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Oregon (average of $277). Flying from Chicago Midway Airport to Oregon in March is currently the most expensive (average of $370). 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 MDW to OR?

Find hourly flight availability from Midway to Oregon. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 28, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Oregon as you normally would.

Rainfall in Oregon by month

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

In terms of precipitation, rainfall in Oregon ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Oregon when rainfall is around 0.7 in.

Temperature in Oregon by month

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

If weather is an important factor for your trip to Oregon, 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 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

Reviews of airlines servicing Oregon

Get insights into the airlines that provide service to Oregon. 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 Oregon. Reviews last updated March 28, 2025.
Read through reviews of airlines operating flights from Chicago to Oregon, such as Southwest, Delta and Allegiant Air. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,896 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,271 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Midway to Oregon. 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 Chicago Midway Airport to Oregon one-way?

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Oregon are Southwest ($78), Delta ($88), and Frontier ($118).

  • What are the most popular routes from Chicago Midway Airport to Oregon?

    Most travelers choose Chicago Midway - Portland, Chicago Midway - Boise Air Term. Gowen Fld or Chicago Midway - Eugene when deciding on the best route from Chicago Midway Airport to Oregon.

  • What are the cheapest flights from Chicago Midway Airport to Oregon?

    Looking for the cheapest flight from Chicago Midway Airport to Oregon? While on average our users pay $402, our data indicates the cheapest price to be $124. The most popular route (Chicago Midway - Portland), is priced around $237.

  • Can I find deals for flights from Midway to Oregon that include hotel bookings?

    Yes. In addition to deals on Midway to Oregon flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Oregon?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Oregon.

  • Can I find deals for business class flights from Midway to Oregon?

    Yes. Cheapflights offers flight deals from Midway to Oregon 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 Chicago Midway Airport to Oregon?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Oregon (average of $277). Flying from Chicago Midway Airport to Oregon in March is currently the most expensive (average of $370). 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

Browse 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 Midway to Oregon

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Newark flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Miami flights
O'Hare Intl to Orlando flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Seattle flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Boston flights
Midway to Newark flights
O'Hare Intl to Baltimore flights
Midway to John F Kennedy Intl flights
O'Hare Intl to San Francisco flights
O'Hare Intl to San Diego flights
O'Hare Intl to Nashville flights
O'Hare Intl to Denver flights
O'Hare Intl to Honolulu flights
Midway to Las Vegas flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Dulles Intl flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Reagan-National flights
Midway to Atlanta flights
O'Hare Intl to Tampa flights
Midway to Miami flights
O'Hare Intl to Austin flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Ontario flights
Midway to Seattle flights
O'Hare Intl to Charleston flights
Midway to LaGuardia flights
Midway to Los Angeles flights
O'Hare Intl to Hobby flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Portland flights
O'Hare Intl to Burbank flights
O'Hare Intl to Raleigh flights
O'Hare Intl to Charlotte flights
Midway to San Francisco flights
Midway to Orlando flights
O'Hare Intl to Love Field flights
Midway to Hobby flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to San Antonio flights

Top 2 airlines flying from Midway to Oregon

Discover the top 2 airlines that operate flights from Midway to Oregon. 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$179FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$237Average$432FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.