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Midway

$78+ 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 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
1 adult, Economy
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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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$211
(Delta)

One-way from

$78
(Southwest)

Popular in

March

Cheapest in

January

Average price

$466

Good round-trip deal

$406 or less

Good one-way deal

$209 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
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From Oregon to Chicago Midway
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One-way flight from Oregon to Chicago Midway
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Highest demand for flights based on searches. 8% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Oregon to Chicago Midway.
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Price to beat on a one-way flight from Oregon to Chicago Midway.
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Find flight deals from Oregon to Midway

Cheapest flights from Oregon to Midway
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 March 31, 2025.

This Delta deal was found by Cheapflights users on 3/30. 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 6/2411:35 pmBOI - MDW
1 stop9h 19mDelta
Thu 7/39:21 amMDW - BOI
1 stop5h 43mDelta
Deal found 3/30$211
This Southwest deal was found by Cheapflights users on 3/30. 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 5/81:50 pmBOI - MDW
1 stop9h 05mSouthwest
Sun 5/115:45 amMDW - BOI
1 stop5h 25mSouthwest
Deal found 3/30$240
This Delta deal was found by Cheapflights users on 3/30. 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 6/1411:13 pmPDX - MDW
1 stop7h 28mDelta
Wed 6/1810:39 amMDW - PDX
1 stop10h 22mDelta
Deal found 3/30$247
This Southwest deal was found by Cheapflights users on 3/30. 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 4/306:35 pmPDX - MDW
1 stop8h 45mSouthwest
Sun 5/410:15 pmMDW - PDX
Nonstop4h 20mSouthwest
Deal found 3/30$248
This CheapOair deal was found by Cheapflights users on 3/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/176:40 amPDX - MDW
1 stop15h 41mFrontier
Mon 4/216:45 amMDW - PDX
1 stop19h 52mFrontier
Deal found 3/29$250
This Southwest deal was found by Cheapflights users on 3/30. 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 8/712:00 pmEUG - MDW
2 stops9h 25mSouthwest
Mon 8/115:25 amMDW - EUG
1 stop9h 15mSouthwest
Deal found 3/30$356
This Delta deal was found by Cheapflights users on 3/30. 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 4/295:30 pmMFR - MDW
2 stops13h 10mDelta
Tue 5/61:16 pmMDW - MFR
2 stops12h 25mDelta
Deal found 3/30$357
This Delta deal was found by Cheapflights users on 3/30. 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.
Mon 4/285:36 pmRDM - MDW
2 stops13h 04mDelta
Fri 5/23:02 pmMDW - RDM
2 stops10h 56mDelta
Deal found 3/30$369
This Delta deal was found by Cheapflights users on 3/30. 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 8/85:30 pmEUG - MDW
2 stops13h 10mDelta
Tue 8/121:00 pmMDW - EUG
2 stops12h 17mDelta
Deal found 3/30$425
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Thu 5/296:30 pmPDX - MDW
2 stops21h 40mMultiple Airlines
Sun 6/111:03 amMDW - PDX
2 stops29h 37mMultiple Airlines
Deal found 3/30$456

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 March 31, 2025.
Use the filters below to find and compare flights from Oregon to Chicago Midway Airport that are best for you.

Fly from

Oregon

Fly to

Midway

Route

Depart

Return

Price

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 6/24

11:35 pm-9:54 am

1 stop9h 19m

Chicago Midway

Thu 7/3

9:21 am-2:04 pm

1 stop5h 43m

$211

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Thu 5/8

1:50 pm-11:55 pm

1 stop9h 05m

Chicago Midway

Sun 5/11

5:45 am-10:10 am

1 stop5h 25m

$240

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 6/14

11:13 pm-8:41 am

1 stop7h 28m

Chicago Midway

Wed 6/18

10:39 am-7:01 pm

1 stop10h 22m

$247

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 4/30

6:35 pm-5:20 am

1 stop8h 45m

Chicago Midway

Sun 5/4

10:15 pm-12:35 am

Nonstop4h 20m

$248

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 4/17

6:40 am-12:21 am

1 stop15h 41m

Chicago Midway

Mon 4/21

6:45 am-12:37 am

1 stop19h 52m

$250

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Thu 8/7

12:00 pm-11:25 pm

2 stops9h 25m

Chicago Midway

Mon 8/11

5:25 am-12:40 pm

1 stop9h 15m

$356

MedfordChicago

MFR - MDW

MFRMDW

Medford

Tue 4/29

5:30 pm-8:40 am

2 stops13h 10m

Chicago Midway

Tue 5/6

1:16 pm-11:41 pm

2 stops12h 25m

$357

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Mon 4/28

5:36 pm-8:40 am

2 stops13h 04m

Chicago Midway

Fri 5/2

3:02 pm-11:58 pm

2 stops10h 56m

$369

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Fri 8/8

5:30 pm-8:40 am

2 stops13h 10m

Chicago Midway

Tue 8/12

1:00 pm-11:17 pm

2 stops12h 17m

$425

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 5/29

6:30 pm-6:10 pm

2 stops21h 40m

Chicago Midway

Sun 6/1

11:03 am-2:40 pm

2 stops29h 37m

$456

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 23 results
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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.
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 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 March 31, 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 March 31, 2025.
See what other customers who have flown with Southwest, Delta and Allegiant Air from Oregon to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,276 reviews

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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
8.0
Very good
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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
7,899 reviews
Southwest
8.0
Very good
4,276 reviews

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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
8.0
Very good
4,276 reviews

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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
3,276 reviews
Southwest
8.0
Very good
4,276 reviews

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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 Oregon to Midway. 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 Oregon to Chicago Midway Airport one-way?

    $78 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and Frontier, with prices starting from $98 and $126, respectively.

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

    When deciding which route to take from Oregon to Chicago Midway Airport consider Portland - Chicago Midway, Eugene - Chicago Midway or Boise Air Term. Gowen Fld - Chicago Midway as they are the most popular.

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

    Looking at all options, your cheapest flight can be booked for $113. While the most popular route (Portland - Chicago Midway) can be booked for $214 on average our data indicates $364 when flying from Oregon to Chicago Midway Airport.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oregon to Midway 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 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.

See more FAQs

Traveling to a place near Oregon?

Book flights to Oregon if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Oregon to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$288FlexibilityNo cancel feeOn-time62%
DeltaCheapest$215Average$402FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$249Average$432FlexibilityNo cancel feeOn-time63%
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