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$93+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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Find 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 October 23, 2025.

This Delta deal was found by Cheapflights users on 10/21. 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 12/66:17 amDSM - MDW
1 stop6h 17mDelta
Sat 12/139:59 amMDW - DSM
1 stop4h 27mDelta
Deal found 10/21$204
This Delta deal was found by Cheapflights users on 10/22. 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.
Wed 11/192:45 pmDSM - MDW
1 stop3h 33mDelta
Sat 11/229:41 amMDW - DSM
1 stop4h 27mDelta
Deal found 10/22$209
This Delta deal was found by Cheapflights users on 10/20. 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 12/56:17 amDSM - MDW
1 stop6h 17mDelta
Fri 12/129:34 amMDW - DSM
1 stop6h 42mDelta
Deal found 10/20$236
This Southwest deal was found by Cheapflights users on 10/21. 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 11/184:15 pmDSM - MDW
1 stop4h 30mSouthwest
Sun 11/236:45 amMDW - DSM
1 stop4h 15mSouthwest
Deal found 10/21$243
This Delta deal was found by Cheapflights users on 10/21. 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 11/136:50 amDSM - MDW
1 stop6h 17mDelta
Sat 11/159:41 amMDW - DSM
1 stop4h 27mDelta
Deal found 10/21$244
This Southwest deal was found by Cheapflights users on 10/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/44:15 pmDSM - MDW
1 stop4h 30mSouthwest
Wed 11/56:20 amMDW - DSM
1 stop5h 05mSouthwest
Deal found 10/22$249
This Southwest deal was found by Cheapflights users on 10/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:15 pmDSM - MDW
1 stop4h 30mSouthwest
Sun 12/74:10 pmMDW - DSM
2 stops7h 25mSouthwest
Deal found 10/22$250
This Southwest deal was found by Cheapflights users on 10/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/145:45 amDSM - MDW
1 stop4h 10mSouthwest
Fri 12/197:55 amMDW - DSM
1 stop3h 05mSouthwest
Deal found 10/22$261
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:58 pmDSM - MDW
2 stops48h 47mFrontier
Fri 12/1212:18 pmMDW - DSM
1 stop6h 45mFrontier
Deal found 10/21$264
This Southwest deal was found by Cheapflights users on 10/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/145:45 amDSM - MDW
1 stop4h 10mSouthwest
Sat 12/204:40 pmMDW - DSM
2 stops7h 15mSouthwest
Deal found 10/22$266

Cheap 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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$190
(Southwest)

One-way from

$93
(Southwest)

Popular in

July

Cheapest in

September

Average price

$271

Good round-trip deal

$651 or less

Good one-way deal

$244 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. 7% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 23, 2025.
Use the filters below to find and compare flights from Des Moines to Chicago Midway Airport that are best for you.

Fly from

Des Moines

Fly to

Midway

Route

Depart

Return

Price

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 1/8

3:20 pm-10:05 pm

2 stops6h 45m

Chicago Midway

Mon 1/12

6:10 am-11:25 am

1 stop5h 15m

$190

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 12/6

6:17 am-12:34 pm

1 stop6h 17m

Chicago Midway

Sat 12/13

9:59 am-2:26 pm

1 stop4h 27m

$204

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 11/18

2:45 pm-6:18 pm

1 stop3h 33m

Chicago Midway

Sat 11/22

9:41 am-2:08 pm

1 stop4h 27m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 11/18

2:45 pm-6:18 pm

1 stop3h 33m

Chicago Midway

Mon 11/24

9:34 am-4:19 pm

1 stop6h 45m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 11/19

6:17 am-12:34 pm

1 stop6h 17m

Chicago Midway

Wed 11/26

9:34 am-4:19 pm

1 stop6h 45m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 11/20

6:50 am-1:07 pm

1 stop6h 17m

Chicago Midway

Mon 11/24

9:34 am-4:19 pm

1 stop6h 45m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 11/19

6:50 am-1:07 pm

1 stop6h 17m

Chicago Midway

Sun 11/23

9:34 am-4:19 pm

1 stop6h 45m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 11/20

6:17 am-12:34 pm

1 stop6h 17m

Chicago Midway

Sat 11/22

9:41 am-2:08 pm

1 stop4h 27m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Mon 1/19

5:20 am-10:20 am

1 stop5h 00m

Chicago Midway

Wed 1/28

2:20 pm-9:10 pm

2 stops6h 50m

$224

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 12/5

6:17 am-12:34 pm

1 stop6h 17m

Chicago Midway

Fri 12/12

9:34 am-4:16 pm

1 stop6h 42m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

Showing 1-10 of 20 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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.

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 are 0 flights 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 6h 17m. Southwest provides one of the quickest options available for as low as $204. 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 airlines to fly from Des Moines to Chicago Midway Airport one-way?

    $93 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Frontier and Delta, with prices starting from $105 and $105, respectively.

  • 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 $499, our data shows the cheapest flight currently is $182. When looking at the most popular route, (Des Moines - Chicago Midway), you can expect to pay $157 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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