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$129+ Cheap flights from Des Moines (DSM) 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Jun 27 — Jul 41
Sat 6/27
Sat 7/4
1 adult, Economy
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Cheap flight deals from Des Moines to Midway

Cheapest flights from Des Moines to Midway
Explore the most affordable flight options available from Des Moines to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 28, 2026.

This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/163:45 pm
DSM
-
MDW
Nonstop1h 20m
Southwest
Wed 6/1710:10 am
MDW
-
DSM
Nonstop1h 20m
Southwest
Deal found 5/26$257
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:20 am
DSM
-
MDW
Nonstop1h 20m
Southwest
Wed 7/157:00 am
MDW
-
DSM
1 stop8h 05m
Southwest
Deal found 5/26$267
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:40 pm
DSM
-
MDW
Nonstop1h 20m
Southwest
Thu 8/208:50 pm
MDW
-
DSM
Nonstop1h 20m
Southwest
Deal found 5/26$269
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/13:45 pm
DSM
-
MDW
Nonstop1h 20m
Southwest
Tue 7/77:00 am
MDW
-
DSM
1 stop8h 05m
Southwest
Deal found 5/26$273
This Delta deal was found by Cheapflights users on 5/26. 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 7/82:45 pm
DSM
-
MDW
1 stop3h 33m
Delta
Wed 7/159:49 am
MDW
-
DSM
1 stop4h 16m
Delta
Deal found 5/26$277
This Southwest deal was found by Cheapflights users on 5/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/232:40 pm
DSM
-
MDW
Nonstop1h 20m
Southwest
Mon 9/288:50 pm
MDW
-
DSM
Nonstop1h 20m
Southwest
Deal found 5/27$282
This Delta deal was found by Cheapflights users on 5/26. 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 8/196:55 am
DSM
-
MDW
1 stop6h 15m
Delta
Thu 8/209:59 am
MDW
-
DSM
1 stop6h 51m
Delta
Deal found 5/26$283
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:15 am
DSM
-
MDW
2 stops9h 45m
Southwest
Mon 9/218:50 pm
MDW
-
DSM
Nonstop1h 20m
Southwest
Deal found 5/26$284
This Delta deal was found by Cheapflights users on 5/27. 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 9/246:00 am
DSM
-
MDW
1 stop6h 34m
Delta
Mon 9/289:49 am
MDW
-
DSM
1 stop6h 52m
Delta
Deal found 5/27$289
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/174:40 pm
DSM
-
MDW
Nonstop1h 20m
Southwest
Tue 7/2110:10 am
MDW
-
DSM
Nonstop1h 20m
Southwest
Deal found 5/26$293
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:40 am
DSM
-
MDW
Nonstop1h 20m
Southwest
Mon 9/710:05 am
MDW
-
DSM
Nonstop1h 20m
Southwest
Deal found 5/26$295

Find flight deals from Des Moines to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Des Moines (DSM) 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 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$257
(Southwest)

One-way from

$129
(Southwest)

Popular in

April

Cheapest in

September

Average price

$280

Good round-trip deal

$386 or less

Good one-way deal

$196 or less
Provider with most accurate pricing for Des Moines-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Des Moines-Chicago Midway flights.
Search Deals
From Des Moines to Chicago Midway
Search Deals
One-way flight from Des Moines to Chicago Midway
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Des Moines to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Des Moines to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Des Moines 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 28, 2026.
Use the filters below to find and compare flights from Des Moines to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 8/14

2:25 pm-8:15 pm

1 stop5h 50m

Chicago Midway

Sun 8/16

9:30 pm-10:50 pm

Nonstop1h 20m

$339

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 8/14

6:00 am-12:39 pm

1 stop6h 39m

Chicago Midway

Sun 8/16

1:27 pm-5:11 pm

1 stop3h 44m

$349

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 7/10

2:45 pm-6:18 pm

1 stop3h 33m

Chicago Midway

Fri 7/17

1:18 pm-5:12 pm

1 stop3h 54m

$349
Quickest round-trip

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 6/19

4:40 pm-6:00 pm

Nonstop1h 20m

Chicago Midway

Sun 6/21

10:25 pm-11:45 pm

Nonstop1h 20m

$367

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 6/18

4:40 pm-6:00 pm

Nonstop1h 20m

Chicago Midway

Sun 6/21

10:25 pm-11:45 pm

Nonstop1h 20m

$379

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 6/26

1:30 pm-8:35 pm

2 stops7h 05m

Chicago Midway

Sun 6/28

10:25 pm-11:45 pm

Nonstop1h 20m

$380

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 7/31

1:30 pm-8:35 pm

2 stops7h 05m

Chicago Midway

Mon 8/3

10:05 pm-11:35 pm

Nonstop1h 30m

$380

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 6/13

6:50 am-1:09 pm

1 stop6h 19m

Chicago Midway

Tue 6/16

1:26 pm-5:23 pm

1 stop3h 57m

$388

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 7/10

1:30 pm-8:35 pm

2 stops7h 05m

Chicago Midway

Fri 7/17

4:15 pm-10:25 pm

1 stop6h 10m

$392

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 6/10

6:08 am-12:46 pm

1 stop6h 38m

Chicago Midway

Sat 6/13

1:26 pm-5:13 pm

1 stop3h 47m

$407

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Des Moines 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 Des Moines 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 Des Moines-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 Des Moines-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Des Moines-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Des Moines-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 Des Moines-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 Des Moines to Midway

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

Cheapflights Insights

Everything you need to know about your flight from Des Moines to Chicago Midway Airport

What is the cheapest time of day to fly from DSM to MDW?

Find hourly flight availability from Des Moines to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 28, 2026.

It’s optimal to fly from Des Moines to Chicago Midway Airport at noon. By choosing this option you can save up to 53% on the cost of your flight, compared to a flight in the evening.

Related info for your journey

Find useful and relevant information for your journey from Des Moines 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 Des Moines to Chicago Midway?

    If you book a flight to Chicago Midway from Des Moines, you will be flying from Des Moines, which is the city’s only airport. Des Moines (DSM) is located 3.6 mi from the center of Des Moines. There is 1 flight from Des Moines to Chicago Midway per day from 0 different airlines.

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

    A quick flight from Des Moines to Chicago Midway Airport can take about 5h 50m. Southwest provides one of the quickest options available for as low as $339. Airlines will cover a distance of 305 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest flights from Des Moines to Chicago Midway Airport?

    While on average a flight from Des Moines to Chicago Midway Airport is generally $331, our data shows the cheapest flight currently is $173. When looking at the most popular route, (Des Moines - Chicago Midway), you can expect to pay $257 for that flight.

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

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

  • How can I find direct flights from Des Moines to Midway?

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

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

    Yes. Cheapflights offers flight deals from Des Moines 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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