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$255+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — MDW
Jun 10 — Jun 171
Wed 6/10
Wed 6/17
1 adult, Economy
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Cheap 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 May 11, 2026.

This Delta deal was found by Cheapflights users on 5/7. 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 6/65:05 am
RDM
-
MDW
2 stops11h 28m
Delta
Sat 6/131:49 pm
MDW
-
RDM
2 stops10h 47m
Delta
Deal found 5/7$379
This Delta deal was found by Cheapflights users on 5/10. 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 8/215:15 am
RDM
-
MDW
2 stops10h 46m
Delta
Mon 8/241:52 pm
MDW
-
RDM
2 stops11h 06m
Delta
Deal found 5/10$399
This Delta deal was found by Cheapflights users on 5/7. 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 12/25:55 am
RDM
-
MDW
2 stops8h 55m
Delta
Tue 12/81:00 pm
MDW
-
RDM
2 stops11h 46m
Delta
Deal found 5/7$413
This Delta deal was found by Cheapflights users on 5/11. 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 12/35:55 am
RDM
-
MDW
2 stops8h 55m
Delta
Mon 12/71:00 pm
MDW
-
RDM
2 stops11h 46m
Delta
Deal found 5/11$444
This Delta deal was found by Cheapflights users on 5/9. 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 8/147:25 pm
RDM
-
MDW
2 stops11h 15m
Delta
Sun 8/161:27 pm
MDW
-
RDM
2 stops12h 22m
Delta
Deal found 5/9$451
This Delta deal was found by Cheapflights users on 5/11. 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 12/45:55 am
RDM
-
MDW
2 stops8h 55m
Delta
Tue 12/81:00 pm
MDW
-
RDM
2 stops12h 40m
Delta
Deal found 5/11$474
This Delta deal was found by Cheapflights users on 5/10. 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 9/195:55 am
RDM
-
MDW
2 stops10h 10m
Delta
Fri 9/251:00 pm
MDW
-
RDM
2 stops11h 47m
Delta
Deal found 5/10$484
This Delta deal was found by Cheapflights users on 5/10. 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 6/305:20 am
RDM
-
MDW
2 stops11h 11m
Delta
Tue 7/71:49 pm
MDW
-
RDM
2 stops11h 08m
Delta
Deal found 5/10$505
This Delta deal was found by Cheapflights users on 5/8. 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 5/95:05 am
RDM
-
MDW
2 stops10h 51m
Delta
Sat 5/161:22 pm
MDW
-
RDM
2 stops10h 52m
Delta
Deal found 5/8$511
This Delta deal was found by Cheapflights users on 5/7. 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 12/25:55 am
RDM
-
MDW
2 stops8h 55m
Delta
Thu 12/101:05 pm
MDW
-
RDM
2 stops12h 35m
Delta
Deal found 5/7$513
This Delta deal was found by Cheapflights users on 5/11. 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 6/106:26 am
RDM
-
MDW
2 stops10h 05m
Delta
Tue 6/161:26 pm
MDW
-
RDM
2 stops12h 33m
Delta
Deal found 5/11$532
This Delta deal was found by Cheapflights users on 5/10. 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 8/215:15 am
RDM
-
MDW
2 stops10h 46m
Delta
Sun 8/231:52 pm
MDW
-
RDM
2 stops11h 06m
Delta
Deal found 5/10$542

Find 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 May 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$379
(Delta)

One-way from

$255
(Kiwi.com)

Popular in

May

Cheapest in

December

Average price

$622
Provider with most accurate pricing for Bend/Redmond-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Bend/Redmond-Chicago Midway flights.
Search Deals
From Bend/Redmond to Chicago Midway
Search Deals
One-way flight from Bend/Redmond to Chicago Midway
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 11, 2026.
Use the filters below to find and compare flights from Redmond to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 8/21

5:15 am-6:01 pm

2 stops10h 46m

Chicago Midway

Mon 8/24

1:52 pm-10:58 pm

2 stops11h 06m

$399

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 8/14

7:25 pm-8:40 am

2 stops11h 15m

Chicago Midway

Sun 8/16

1:27 pm-11:49 pm

2 stops12h 22m

$451

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sat 9/19

5:55 am-6:05 pm

2 stops10h 10m

Chicago Midway

Fri 9/25

1:00 pm-10:47 pm

2 stops11h 47m

$484

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Tue 6/30

5:20 am-6:31 pm

2 stops11h 11m

Chicago Midway

Tue 7/7

1:49 pm-10:57 pm

2 stops11h 08m

$505

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 7/10

7:25 pm-8:37 am

2 stops11h 12m

Chicago Midway

Tue 7/14

1:18 pm-11:58 pm

2 stops12h 40m

$510

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 7/3

7:25 pm-8:37 am

2 stops11h 12m

Chicago Midway

Wed 7/8

1:18 pm-11:58 pm

2 stops12h 40m

$565

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 9/16

6:20 am-6:31 pm

2 stops10h 11m

Chicago Midway

Sat 9/19

1:00 pm-10:47 pm

2 stops11h 47m

$574

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 6/5

7:20 pm-8:43 am

2 stops11h 23m

Chicago Midway

Mon 6/8

1:49 pm-10:58 pm

2 stops11h 09m

$673

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 6/5

7:20 pm-8:43 am

2 stops11h 23m

Chicago Midway

Sun 6/14

9:17 am-6:45 pm

2 stops11h 28m

$792
Cheapest one-way

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Mon 9/14

12:20 pm-10:58 am

2 stops44h 38m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/9

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

Compare providers for flights from Redmond to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Redmond to Midway in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Redmond-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Redmond-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 46m. 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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