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$155+ 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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$309
(Delta)

One-way from

$155
(Delta)

Popular in

March

Cheapest in

January

Average price

$426
Provider with most accurate pricing for Bend/Redmond-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Bend/Redmond-Chicago Midway flights.
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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. 17% potential increase in price ($93 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 12/105:55 amRDM - MDW
2 stops10h 23mDelta
Sat 12/131:14 pmMDW - RDM
2 stops11h 36mDelta
Deal found 10/29$309
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 12/87:34 pmRDM - MDW
2 stops11h 45mDelta
Fri 12/1212:50 pmMDW - RDM
2 stops13h 09mDelta
Deal found 10/29$329
This Delta deal was found by Cheapflights users on 10/28. 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 11/177:34 pmRDM - MDW
2 stops11h 27mDelta
Wed 11/199:41 amMDW - RDM
2 stops11h 13mDelta
Deal found 10/28$447
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 12/157:34 pmRDM - MDW
2 stops11h 20mDelta
Fri 12/191:50 pmMDW - RDM
2 stops12h 09mDelta
Deal found 10/29$455
This Delta deal was found by Cheapflights users on 10/29. 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.
Fri 11/217:34 pmRDM - MDW
2 stops11h 27mDelta
Mon 11/241:15 pmMDW - RDM
2 stops12h 41mDelta
Deal found 10/29$479
This Delta deal was found by Cheapflights users on 10/30. 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 11/177:34 pmRDM - MDW
2 stops11h 20mDelta
Fri 11/211:15 pmMDW - RDM
2 stops11h 38mDelta
Deal found 10/30$517
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 11/187:00 amRDM - MDW
2 stops9h 18mDelta
Sun 11/2312:47 pmMDW - RDM
2 stops13h 09mDelta
Deal found 10/29$524
This Delta deal was found by Cheapflights users on 10/29. 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.
Sun 11/27:26 pmRDM - MDW
2 stops11h 29mDelta
Tue 11/41:08 pmMDW - RDM
2 stops12h 38mDelta
Deal found 10/29$532
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/305:00 amRDM - MDW
2 stops10h 19mDelta
Tue 1/209:34 amMDW - RDM
2 stops9h 02mDelta
Deal found 10/29$644
This Delta deal was found by Cheapflights users on 10/30. 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 11/77:26 pmRDM - MDW
2 stops11h 14mDelta
Sun 11/99:34 amMDW - RDM
2 stops11h 20mDelta
Deal found 10/30$712
This Delta deal was found by Cheapflights users on 10/30. 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 11/77:26 pmRDM - MDW
2 stops15h 42mDelta
Mon 11/101:47 pmMDW - RDM
2 stops12h 09mDelta
Deal found 10/30$857
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 11/257:34 pmRDM - MDW
2 stops11h 27mDelta
Sat 11/291:15 pmMDW - RDM
2 stops11h 38mDelta
Deal found 10/29$1,044

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 October 30, 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

Wed 12/10

5:55 am-6:18 pm

2 stops10h 23m

Chicago Midway

Sat 12/13

1:14 pm-10:50 pm

2 stops11h 36m

$309

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Mon 12/8

7:34 pm-9:19 am

2 stops11h 45m

Chicago Midway

Fri 12/12

12:50 pm-11:59 pm

2 stops13h 09m

$329

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Mon 11/17

7:34 pm-9:01 am

2 stops11h 27m

Chicago Midway

Wed 11/19

9:41 am-6:54 pm

2 stops11h 13m

$447

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Mon 12/15

7:34 pm-8:54 am

2 stops11h 20m

Chicago Midway

Fri 12/19

1:50 pm-11:59 pm

2 stops12h 09m

$455

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 11/21

7:34 pm-9:01 am

2 stops11h 27m

Chicago Midway

Mon 11/24

1:15 pm-11:56 pm

2 stops12h 41m

$479

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Mon 11/17

7:34 pm-8:54 am

2 stops11h 20m

Chicago Midway

Fri 11/21

1:15 pm-10:53 pm

2 stops11h 38m

$517

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Tue 11/18

7:00 am-6:18 pm

2 stops9h 18m

Chicago Midway

Sun 11/23

12:47 pm-11:56 pm

2 stops13h 09m

$524

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sun 11/2

7:26 pm-8:55 am

2 stops11h 29m

Chicago Midway

Tue 11/4

1:08 pm-11:46 pm

2 stops12h 38m

$532

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Tue 12/30

5:00 am-5:19 pm

2 stops10h 19m

Chicago Midway

Tue 1/13

9:34 am-4:36 pm

2 stops9h 02m

$644

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Tue 12/30

5:00 am-5:19 pm

2 stops10h 19m

Chicago Midway

Tue 1/20

9:34 am-4:36 pm

2 stops9h 02m

$644

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 18 results
1
2
  • Most accurate provider: When it comes to deals on Redmond-Chicago Midway Airport flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Redmond-Chicago Midway Airport flight deals on Cheapflights vs. Expedia 90-95% of the time. Price accuracy is based on data collected from Redmond-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Redmond-Chicago Midway Airport flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Redmond-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 10h 23m. 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.

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
Porter
Benton Harbor

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