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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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$175
(Delta)

One-way from

$88
(Southwest)

Popular in

March

Cheapest in

January

Average price

$338

Good round-trip deal

$387 or less

Good one-way deal

$209 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
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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. 10% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/30. 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 6/1410:24 amBOI - MDW
1 stop5h 48mDelta
Sat 6/217:21 pmMDW - BOI
1 stop5h 30mDelta
Deal found 4/30$175
This Delta deal was found by Cheapflights users on 4/30. 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 5/247:29 pmRDM - MDW
2 stops11h 07mDelta
Sat 5/319:20 amMDW - RDM
2 stops11h 29mDelta
Deal found 4/30$230
This Trip.com deal was found by Cheapflights users on 4/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/56:35 amPDX - MDW
1 stop12h 18mFrontier
Mon 6/96:25 amMDW - PDX
1 stop8h 30mFrontier
Deal found 4/30$236
This Southwest deal was found by Cheapflights users on 4/30. 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.
Mon 6/309:15 pmPDX - MDW
1 stop8h 20mSouthwest
Fri 7/46:20 amMDW - PDX
1 stop10h 35mSouthwest
Deal found 4/30$239
This Delta deal was found by Cheapflights users on 4/30. 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 8/911:11 pmPDX - MDW
1 stop7h 28mDelta
Sat 8/165:50 pmMDW - PDX
1 stop7h 14mDelta
Deal found 4/30$247
This Booking.com deal was found by Cheapflights users on 4/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2712:36 pmBOI - MDW
1 stop7h 17mFrontier
Sat 5/312:44 pmMDW - BOI
1 stop22h 03mFrontier
Deal found 4/30$280
This Southwest deal was found by Cheapflights users on 4/30. 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 7/102:50 pmBOI - MDW
Nonstop3h 20mSouthwest
Mon 7/147:05 pmMDW - BOI
1 stop7h 00mSouthwest
Deal found 4/30$296
This Southwest deal was found by Cheapflights users on 4/30. 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.
Tue 7/2212:20 pmEUG - MDW
2 stops9h 45mSouthwest
Tue 7/295:25 pmMDW - EUG
1 stop8h 05mSouthwest
Deal found 4/30$351
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 6/195:24 pmEUG - MDW
2 stops13h 17mDelta
Tue 6/241:47 pmMDW - EUG
2 stops11h 58mDelta
Deal found 4/30$370
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/125:15 amMFR - MDW
2 stops9h 55mDelta
Mon 7/141:09 pmMDW - MFR
2 stops12h 49mDelta
Deal found 4/29$431
This Mytrip deal was found by Cheapflights users on 4/30. 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 6/1212:12 pmPDX - MDW
3 stops23h 51mMultiple Airlines
Sun 6/1511:45 amMDW - PDX
2 stops28h 55mMultiple Airlines
Deal found 4/30$477

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 May 1, 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

Sat 6/14

10:24 am-5:12 pm

1 stop5h 48m

Chicago Midway

Sat 6/21

7:21 pm-11:51 pm

1 stop5h 30m

$175

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sat 5/24

7:29 pm-8:36 am

2 stops11h 07m

Chicago Midway

Sat 5/31

9:20 am-6:49 pm

2 stops11h 29m

$230

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 6/5

6:35 am-8:53 pm

1 stop12h 18m

Chicago Midway

Mon 6/9

6:25 am-12:55 pm

1 stop8h 30m

$236

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 6/30

9:15 pm-7:35 am

1 stop8h 20m

Chicago Midway

Fri 7/4

6:20 am-2:55 pm

1 stop10h 35m

$239

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 8/9

11:11 pm-8:39 am

1 stop7h 28m

Chicago Midway

Sat 8/16

5:50 pm-11:04 pm

1 stop7h 14m

$247

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 5/27

12:36 pm-8:53 pm

1 stop7h 17m

Chicago Midway

Sat 5/31

2:44 pm-11:47 am

1 stop22h 03m

$280

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Thu 7/10

2:50 pm-7:10 pm

Nonstop3h 20m

Chicago Midway

Mon 7/14

7:05 pm-1:05 am

1 stop7h 00m

$296

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Tue 7/22

12:20 pm-12:05 am

2 stops9h 45m

Chicago Midway

Tue 7/29

5:25 pm-11:30 pm

1 stop8h 05m

$351

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Thu 6/19

5:24 pm-8:41 am

2 stops13h 17m

Chicago Midway

Tue 6/24

1:47 pm-11:45 pm

2 stops11h 58m

$370

MedfordChicago

MFR - MDW

MFRMDW

Medford

Sat 7/12

5:15 am-5:10 pm

2 stops9h 55m

Chicago Midway

Mon 7/14

1:09 pm-11:58 pm

2 stops12h 49m

$431

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 23 results
1
2
3

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 May 1, 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 May 1, 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
4,294 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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?

    $88 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 $93 and $109, 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 $124. While the most popular route (Portland - Chicago Midway) can be booked for $204 on average our data indicates $349 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
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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$288FlexibilityNo cancel feeOn-time62%
DeltaCheapest$215Average$402FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$249Average$445FlexibilityNo cancel feeOn-time63%

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