$124+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Aug 1 — Aug 81
Round-trip
1 adult, Economy
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Find cheap flights from Des Moines to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Des Moines to Midway
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Best
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One-way
Cheapest flights from Des Moines to MidwayExplore 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 July 2, 2026.
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 July 2, 2026.
This Southwest deal was found by Cheapflights users on 6/29. 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 8/116:10 am
DSM
- MDW
Nonstop1h 20m
Southwest
Tue 8/188:35 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/29![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 6/28. 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.
Sat 8/13:35 pm
DSM
- MDW
Nonstop1h 25m
Southwest
Sat 8/86:00 pm
MDW
- DSM
Nonstop1h 25m
Southwest
Deal found 6/28![Southwest logo]()
$250
This Southwest deal was found by Cheapflights users on 6/29. 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 8/133:50 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Thu 8/2010:05 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/29![Southwest logo]()
$260
This Southwest deal was found by Cheapflights users on 7/1. 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.
Sat 8/85:30 am
DSM
- MDW
Nonstop1h 15m
Southwest
Mon 8/108:50 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 7/1![Southwest logo]()
$263
This Delta deal was found by Cheapflights users on 6/29. 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.
Mon 9/142:46 pm
DSM
- MDW
1 stop3h 33m
Delta
Wed 9/161:19 pm
MDW
- DSM
1 stop4h 00m
Delta
Deal found 6/29![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 6/29. 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.
Mon 9/143:50 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Wed 9/163:50 pm
MDW
- DSM
1 stop5h 10m
Southwest
Deal found 6/29![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 7/1. 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 8/65:40 am
DSM
- MDW
Nonstop1h 20m
Southwest
Mon 8/1010:05 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 7/1![Southwest logo]()
$273
Best flights from Des Moines to MidwayDiscover carefully curated flight deals from Des Moines to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
Discover carefully curated flight deals from Des Moines to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
This Southwest deal was found by Cheapflights users on 6/28. 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 8/65:40 am
DSM
- MDW
Nonstop1h 20m
Southwest
Mon 8/1010:05 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/28![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 6/28. 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.
Sat 8/15:10 am
DSM
- MDW
Nonstop1h 20m
Southwest
Sat 8/86:50 am
MDW
- DSM
1 stop7h 20m
Southwest
Deal found 6/28![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 6/30. 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 9/236:10 am
DSM
- MDW
Nonstop1h 20m
Southwest
Fri 9/258:50 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/30![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 6/29. 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.
Sat 8/2912:10 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Sun 8/309:30 am
MDW
- DSM
1 stop5h 45m
Southwest
Deal found 6/29![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 6/27. 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.
Thu 11/196:00 am
DSM
- MDW
Nonstop1h 25m
Southwest
Sun 11/229:35 pm
MDW
- DSM
Nonstop1h 25m
Southwest
Deal found 6/27![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 6/27. 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.
Mon 8/102:25 pm
DSM
- MDW
1 stop7h 35m
Southwest
Mon 8/1710:05 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/27![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 7/2. 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 8/25:10 am
DSM
- MDW
Nonstop1h 20m
Southwest
Sat 8/810:10 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 7/2![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 6/29. 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 8/213:50 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Sun 8/239:30 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/29![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 6/27. 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.
Thu 7/304:40 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Sun 8/210:25 pm
MDW
- DSM
Nonstop1h 25m
Southwest
Deal found 6/27![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 6/29. 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 7/195:10 am
DSM
- MDW
Nonstop1h 20m
Southwest
Sat 7/2510:15 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/29![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 7/1. 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.
Sat 8/812:10 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Mon 8/102:05 pm
MDW
- DSM
1 stop7h 10m
Southwest
Deal found 7/1![Southwest logo]()
$337
Last-minute flights from Des Moines to MidwayDiscover last-minute flight deals from Des Moines to Midway. Data last updated July 2, 2026 and is based on user searches.
Discover last-minute flight deals from Des Moines to Midway. Data last updated July 2, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/28. 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.
Sat 8/13:35 pm
DSM
- MDW
Nonstop1h 25m
Southwest
Sat 8/86:00 pm
MDW
- DSM
Nonstop1h 25m
Southwest
Deal found 6/28![Southwest logo]()
$250
This Southwest deal was found by Cheapflights users on 7/1. 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 8/65:40 am
DSM
- MDW
Nonstop1h 20m
Southwest
Mon 8/1010:05 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 7/1![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 7/1. 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.
Sat 8/85:30 am
DSM
- MDW
Nonstop1h 15m
Southwest
Mon 8/108:50 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 7/1![Southwest logo]()
$263
This Southwest deal was found by Cheapflights users on 6/29. 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 8/116:10 am
DSM
- MDW
Nonstop1h 20m
Southwest
Tue 8/188:35 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/29![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 6/29. 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 8/133:50 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Thu 8/2010:05 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/29![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 6/29. 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 8/226:00 am
DSM
- MDW
1 stop6h 39m
Delta
Mon 8/241:25 pm
MDW
- DSM
1 stop3h 46m
Delta
Deal found 6/29![Delta logo]()
$283
One-way flights from Des Moines to MidwaySearch for one-way flight options from Des Moines to Midway. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
Search for one-way flight options from Des Moines to Midway. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
This Southwest deal was found by Cheapflights users on 6/28. 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 8/256:10 am
DSM
- MDW
Nonstop1h 20m
Southwest
Deal found 6/28![Southwest logo]()
$124
This Southwest deal was found by Cheapflights users on 6/30. 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 7/283:45 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Deal found 6/30![Southwest logo]()
$127
This Delta deal was found by Cheapflights users on 6/29. 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 8/256:00 am
DSM
- MDW
1 stop6h 39m
Delta
Deal found 6/29![Delta logo]()
$134
This Delta deal was found by Cheapflights users on 7/1. 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 7/282:45 pm
DSM
- MDW
1 stop3h 33m
Delta
Deal found 7/1![Delta logo]()
$137
This Southwest deal was found by Cheapflights users on 6/30. 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 8/127:15 am
DSM
- MDW
2 stops9h 45m
Southwest
Deal found 6/30![Southwest logo]()
$142
This Delta deal was found by Cheapflights users on 7/1. 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.
Mon 9/282:46 pm
DSM
- MDW
1 stop3h 33m
Delta
Deal found 7/1![Delta logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Sun 9/271:58 pm
DSM
- MDW
2 stops45h 00m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Sun 8/95:12 pm
DSM
- MDW
2 stops40h 39m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Thu 9/241:58 pm
DSM
- MDW
2 stops45h 00m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Thu 8/135:12 pm
DSM
- MDW
2 stops40h 39m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$164
This Southwest deal was found by Cheapflights users on 6/29. 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 9/273:50 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Deal found 6/29![Southwest logo]()
$165
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 July 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $247 (Southwest) |
One-way from | $124 (Southwest) |
Popular in | May |
Cheapest in | September |
Average price | $274 |
Good round-trip deal | $416 or less |
Good one-way deal | $229 or less |
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 July 2, 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
Cheapest round-trip
Quickest round-trip
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Thu 8/6
5:40 am-7:00 am
Nonstop1h 20m
Chicago Midway
Mon 8/10
10:05 am-11:25 am
Nonstop1h 20m
$273
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Sat 8/1
5:10 am-6:30 am
Nonstop1h 20m
Chicago Midway
Sat 8/8
6:50 am-2:10 pm
1 stop7h 20m
$273
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Wed 9/23
6:10 am-7:30 am
Nonstop1h 20m
Chicago Midway
Fri 9/25
8:50 pm-10:10 pm
Nonstop1h 20m
$291
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Sat 8/29
12:10 pm-1:30 pm
Nonstop1h 20m
Chicago Midway
Sun 8/30
9:30 am-3:15 pm
1 stop5h 45m
$298
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Thu 11/19
6:00 am-7:25 am
Nonstop1h 25m
Chicago Midway
Sun 11/22
9:35 pm-11:00 pm
Nonstop1h 25m
$301
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Mon 8/10
2:25 pm-10:00 pm
1 stop7h 35m
Chicago Midway
Mon 8/17
10:05 am-11:25 am
Nonstop1h 20m
$302
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Sun 8/2
5:10 am-6:30 am
Nonstop1h 20m
Chicago Midway
Sat 8/8
10:10 am-11:30 am
Nonstop1h 20m
$315
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Fri 8/21
3:50 pm-5:10 pm
Nonstop1h 20m
Chicago Midway
Sun 8/23
9:30 pm-10:50 pm
Nonstop1h 20m
$329
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Thu 7/30
4:40 pm-6:00 pm
Nonstop1h 20m
Chicago Midway
Sun 8/2
10:25 pm-11:50 pm
Nonstop1h 25m
$329
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Sun 7/19
5:10 am-6:30 am
Nonstop1h 20m
Chicago Midway
Sat 7/25
10:15 am-11:35 am
Nonstop1h 20m
$335
Showing 1-10 of 23 resultsSorted by cheapest first
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 July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
DSM-MDW
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
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter
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