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$165+ Cheap flights from Redmond (RDM) 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Redmond to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Redmond (RDM) 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 September 17, 2025.

Round-trip from

$309
(Delta)

One-way from

$165
(Delta)

Popular in

February

Cheapest in

May

Average price

$411
From Bend/Redmond to Chicago Midway
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One-way flight from Bend/Redmond to Chicago Midway
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Highest demand for flights based on searches. 22% potential increase in price ($131 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Redmond to Midway

Cheapest flights from Redmond to Midway
Explore the most affordable flight options available from Redmond to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Delta deal was found by Cheapflights users on 9/14. 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 11/87:00 amRDM - MDW
2 stops8h 43mDelta
Tue 11/111:47 pmMDW - RDM
2 stops11h 06mDelta
Deal found 9/14$309
This Delta deal was found by Cheapflights users on 9/14. 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 11/77:26 pmRDM - MDW
2 stops13h 04mDelta
Tue 11/111:47 pmMDW - RDM
2 stops11h 06mDelta
Deal found 9/14$319
This Delta deal was found by Cheapflights users on 9/16. 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 9/207:30 pmRDM - MDW
2 stops11h 19mDelta
Wed 9/241:08 pmMDW - RDM
2 stops11h 48mDelta
Deal found 9/16$441
This Delta deal was found by Cheapflights users on 9/17. 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 10/167:26 pmRDM - MDW
2 stops11h 29mDelta
Mon 10/201:48 pmMDW - RDM
2 stops10h 47mDelta
Deal found 9/17$489
This Delta deal was found by Cheapflights users on 9/16. 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 9/197:30 pmRDM - MDW
2 stops11h 23mDelta
Tue 9/231:43 pmMDW - RDM
2 stops11h 13mDelta
Deal found 9/16$496
This Delta deal was found by Cheapflights users on 9/17. 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 10/47:30 pmRDM - MDW
2 stops11h 23mDelta
Mon 10/61:08 pmMDW - RDM
2 stops12h 38mDelta
Deal found 9/17$500
This Delta deal was found by Cheapflights users on 9/17. 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 9/237:30 pmRDM - MDW
2 stops11h 23mDelta
Thu 9/251:08 pmMDW - RDM
2 stops11h 48mDelta
Deal found 9/17$507
This Delta deal was found by Cheapflights users on 9/16. 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.
Wed 10/17:30 pmRDM - MDW
2 stops11h 23mDelta
Mon 10/612:48 pmMDW - RDM
2 stops11h 47mDelta
Deal found 9/16$525
This Delta deal was found by Cheapflights users on 9/16. 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 10/317:00 amRDM - MDW
2 stops13h 14mDelta
Fri 11/71:48 pmMDW - RDM
2 stops10h 47mDelta
Deal found 9/16$531
This Delta deal was found by Cheapflights users on 9/16. 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 9/305:55 amRDM - MDW
2 stops9h 40mDelta
Wed 10/19:35 amMDW - RDM
2 stops11h 15mDelta
Deal found 9/16$573
This Delta deal was found by Cheapflights users on 9/15. 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 10/27:30 pmRDM - MDW
2 stops11h 10mDelta
Mon 10/612:48 pmMDW - RDM
2 stops11h 47mDelta
Deal found 9/15$584
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 9/247:30 pmRDM - MDW
2 stops11h 23mDelta
Fri 9/269:35 amMDW - RDM
2 stops11h 15mDelta
Deal found 9/17$618

Cheapflights Fare Finder

 
Customize your flight search to find flights from Redmond 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 September 17, 2025.
Use the filters below to find and compare flights from Redmond to Chicago Midway Airport that are best for you.

Fly from

Redmond

Fly to

Midway

Route

Depart

Return

Price

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Tue 3/10

7:25 pm-8:50 am

2 stops11h 25m

Chicago Midway

Wed 3/11

2:00 pm-10:42 pm

2 stops10h 42m

$309

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sat 11/8

7:00 am-5:43 pm

2 stops8h 43m

Chicago Midway

Tue 11/11

1:47 pm-10:53 pm

2 stops11h 06m

$309

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 11/7

7:26 pm-10:30 am

2 stops13h 04m

Chicago Midway

Tue 11/11

1:47 pm-10:53 pm

2 stops11h 06m

$319

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Thu 10/16

7:26 pm-8:55 am

2 stops11h 29m

Chicago Midway

Mon 10/20

1:48 pm-10:35 pm

2 stops10h 47m

$489

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sat 10/4

7:30 pm-8:53 am

2 stops11h 23m

Chicago Midway

Mon 10/6

1:08 pm-11:46 pm

2 stops12h 38m

$500

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 10/1

7:30 pm-8:53 am

2 stops11h 23m

Chicago Midway

Mon 10/6

12:48 pm-10:35 pm

2 stops11h 47m

$525

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 10/31

7:00 am-10:14 pm

2 stops13h 14m

Chicago Midway

Fri 11/7

1:48 pm-10:35 pm

2 stops10h 47m

$531

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Tue 9/30

5:55 am-5:35 pm

2 stops9h 40m

Chicago Midway

Wed 10/1

9:35 am-6:50 pm

2 stops11h 15m

$573

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Thu 10/2

7:30 pm-8:40 am

2 stops11h 10m

Chicago Midway

Mon 10/6

12:48 pm-10:35 pm

2 stops11h 47m

$584

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 11/14

7:34 pm-8:52 am

2 stops11h 18m

$165

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 21 results
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Best time to book a flight from Redmond to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Redmond 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.

Related info for your journey

Find useful and relevant information for your journey from Redmond to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Redmond to Chicago Midway?

    Bend/Redmond (RDM) is the airport you will fly out of if you book a flight from Redmond to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Bend/Redmond; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Redmond airport to Chicago Midway. It is only a 1.8 mi journey to Bend/Redmond (RDM) from Redmond’s city center.

  • How long is the flight from Redmond to Chicago Midway Airport?

    There are many flights that can get you from Redmond to Chicago Midway Airport in 11h 25m. Fly via Delta to get the fastest option. The distance between Redmond and Chicago Midway Airport is about 1683 mi.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Redmond to Chicago Midway Airport (average of $160). Flying from Redmond 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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