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$356+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — MDW
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
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 December 23, 2025.

This Delta deal was found by Cheapflights users on 12/22. 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 12/236:05 amRDM - MDW
2 stops9h 14mDelta
Fri 12/2612:45 pmMDW - RDM
2 stops13h 14mDelta
Deal found 12/22$1,890

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 December 23, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$356
(Delta)

Popular in

March

Cheapest in

January

Average price

$324
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
Highest demand for flights based on searches. 21% potential increase in price ($115 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 23, 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 5/27

6:20 am-6:31 pm

2 stops10h 11m

Chicago Midway

Mon 6/1

1:00 pm-10:47 pm

2 stops11h 47m

$356

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Mon 1/5

5:45 am-6:32 pm

2 stops10h 47m

Chicago Midway

Thu 1/8

9:32 am-4:36 pm

2 stops9h 04m

$439

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 5/27

6:20 am-6:31 pm

2 stops10h 11m

Chicago Midway

Wed 6/3

1:00 pm-10:47 pm

2 stops11h 47m

$494

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 3/18

6:19 am-5:54 pm

2 stops9h 35m

Chicago Midway

Tue 3/24

9:35 am-4:13 pm

2 stops8h 38m

$589

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Mon 2/2

5:50 am-6:36 pm

2 stops10h 46m

Chicago Midway

Fri 2/6

1:51 pm-10:47 pm

2 stops10h 56m

$592

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Thu 3/19

6:19 am-5:54 pm

2 stops9h 35m

Chicago Midway

Tue 3/24

9:35 am-4:13 pm

2 stops8h 38m

$704

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Tue 1/6

5:45 am-6:32 pm

2 stops10h 47m

Chicago Midway

Sat 1/10

11:21 am-10:25 pm

2 stops13h 04m

$769

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Tue 12/30

3:32 pm-5:26 pm

2 stops23h 54m

$403

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sun 12/28

3:32 pm-5:26 pm

2 stops23h 54m

$493

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Mon 12/29

5:00 am-10:22 pm

2 stops15h 22m

$573

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

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 11m. 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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