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$360+ Cheap flights from Redmond (RDM) to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/13. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — MDW
Feb 15 — Feb 221
Sun 2/15
Sun 2/22
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 January 16, 2026.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$360
(Delta)

Popular in

January

Cheapest in

December

Average price

$615
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
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 16, 2026.

This Delta deal was found by Cheapflights users on 1/13. 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 3/135:15 am
RDM
-
MDW
2 stops10h 39m
Delta
Mon 3/161:10 pm
MDW
-
RDM
2 stops12h 37m
Delta
Deal found 1/13$360
This Delta deal was found by Cheapflights users on 1/14. 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.
Thu 1/295:50 am
RDM
-
MDW
2 stops10h 05m
Delta
Mon 2/21:51 pm
MDW
-
RDM
2 stops10h 56m
Delta
Deal found 1/14$440
This Delta deal was found by Cheapflights users on 1/15. 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.
Sat 1/175:45 am
RDM
-
MDW
2 stops14h 22m
Delta
Tue 1/209:32 am
MDW
-
RDM
2 stops9h 04m
Delta
Deal found 1/15$480
This Delta deal was found by Cheapflights users on 1/13. 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 2/287:00 am
RDM
-
MDW
2 stops13h 31m
Delta
Sat 3/71:29 pm
MDW
-
RDM
2 stops11h 16m
Delta
Deal found 1/13$482
This Delta deal was found by Cheapflights users on 1/14. 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.
Sun 1/185:45 am
RDM
-
MDW
2 stops10h 47m
Delta
Tue 1/201:49 pm
MDW
-
RDM
2 stops12h 03m
Delta
Deal found 1/14$527
This Delta deal was found by Cheapflights users on 1/15. 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.
Fri 5/16:05 am
RDM
-
MDW
2 stops9h 49m
Delta
Wed 5/62:12 pm
MDW
-
RDM
2 stops11h 47m
Delta
Deal found 1/15$528
This Delta deal was found by Cheapflights users on 1/14. 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.
Wed 4/156:05 am
RDM
-
MDW
2 stops10h 40m
Delta
Sun 4/199:27 am
MDW
-
RDM
2 stops9h 34m
Delta
Deal found 1/14$548
This Delta deal was found by Cheapflights users on 1/14. 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 4/176:05 am
RDM
-
MDW
2 stops9h 49m
Delta
Sun 4/199:27 am
MDW
-
RDM
2 stops9h 34m
Delta
Deal found 1/14$578
This Delta deal was found by Cheapflights users on 1/13. 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 2/115:50 am
RDM
-
MDW
2 stops10h 46m
Delta
Sat 2/141:29 pm
MDW
-
RDM
2 stops11h 16m
Delta
Deal found 1/13$588
This Delta deal was found by Cheapflights users on 1/15. 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 5/216:20 am
RDM
-
MDW
2 stops10h 11m
Delta
Tue 5/261:00 pm
MDW
-
RDM
2 stops11h 47m
Delta
Deal found 1/15$627
This Delta deal was found by Cheapflights users on 1/15. 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.
Wed 6/36:20 am
RDM
-
MDW
2 stops10h 11m
Delta
Sat 6/61:00 pm
MDW
-
RDM
2 stops11h 47m
Delta
Deal found 1/15$686
This Delta deal was found by Cheapflights users on 1/15. 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.
Tue 3/245:15 am
RDM
-
MDW
2 stops10h 39m
Delta
Mon 3/302:05 pm
MDW
-
RDM
2 stops10h 53m
Delta
Deal found 1/15$738

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 January 16, 2026.
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

Fri 3/13

5:15 am-5:54 pm

2 stops10h 39m

Chicago Midway

Mon 3/16

1:10 pm-11:47 pm

2 stops12h 37m

$360

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 1/30

5:50 am-6:36 pm

2 stops10h 46m

Chicago Midway

Tue 2/3

9:53 am-4:31 pm

2 stops8h 38m

$440

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sat 2/28

7:00 am-10:31 pm

2 stops13h 31m

Chicago Midway

Sat 3/7

1:29 pm-10:45 pm

2 stops11h 16m

$482

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 5/1

6:05 am-5:54 pm

2 stops9h 49m

Chicago Midway

Wed 5/6

2:12 pm-11:59 pm

2 stops11h 47m

$528

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 4/15

6:05 am-6:45 pm

2 stops10h 40m

Chicago Midway

Sun 4/19

9:27 am-5:01 pm

2 stops9h 34m

$548

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Thu 4/16

5:45 am-6:45 pm

2 stops11h 00m

Chicago Midway

Sun 4/19

1:10 pm-11:44 pm

2 stops12h 34m

$548

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 4/17

6:05 am-5:54 pm

2 stops9h 49m

Chicago Midway

Sun 4/19

9:27 am-5:01 pm

2 stops9h 34m

$578

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 2/11

5:50 am-6:36 pm

2 stops10h 46m

Chicago Midway

Sat 2/14

1:29 pm-10:45 pm

2 stops11h 16m

$588

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Thu 5/21

6:20 am-6:31 pm

2 stops10h 11m

Chicago Midway

Tue 5/26

1:00 pm-10:47 pm

2 stops11h 47m

$627

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 6/3

6:20 am-6:31 pm

2 stops10h 11m

Chicago Midway

Sat 6/6

1:00 pm-10:47 pm

2 stops11h 47m

$686

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/13

Showing 1-10 of 12 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 39m. 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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