$119+ Cheap flights from Des Moines (DSM) 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Oct 5 — Oct 121
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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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 September 5, 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 September 5, 2026.
This Southwest deal was found by Cheapflights users on 9/3. 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 9/245:40 am -
Nonstop1h 20m
Sat 9/266:00 pm -
Nonstop1h 30m
Deal found 9/3![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 9/2. 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.
Mon 10/127:10 pm -
1 stop5h 10m
Tue 10/1310:05 am -
Nonstop1h 25m
Deal found 9/2![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 8/31. 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 -
Nonstop1h 20m
Fri 9/258:50 pm -
Nonstop1h 25m
Deal found 8/31![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 9/2. 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.
Tue 9/297:15 am -
2 stops9h 45m
Thu 10/19:50 pm -
Nonstop1h 20m
Deal found 9/2![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 8/31. 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 10/164:30 pm -
Nonstop1h 20m
Fri 10/239:50 pm -
Nonstop1h 25m
Deal found 8/31![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 9/3. 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 10/197:10 pm -
1 stop5h 10m
Wed 10/211:05 pm -
2 stops7h 35m
Deal found 9/3![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 8/31. 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 10/157:10 pm -
1 stop5h 10m
Thu 10/224:50 pm -
1 stop5h 20m
Deal found 8/31![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 9/1. 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 10/177:00 am -
2 stops11h 00m
Sat 10/2410:40 am -
Nonstop1h 20m
Deal found 9/1![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 9/3. 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 11/193:30 pm -
Nonstop1h 25m
Fri 11/2010:05 am -
Nonstop1h 25m
Deal found 9/3![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 September 5, 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 September 5, 2026.
This Southwest deal was found by Cheapflights users on 9/3. 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 9/307:15 am -
2 stops9h 45m
Thu 10/89:45 am -
Nonstop1h 25m
Deal found 9/3![Southwest logo]()
$264
This Southwest deal was found by Cheapflights users on 9/2. 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.
Tue 9/297:15 am -
1 stop7h 05m
Thu 10/19:50 pm -
Nonstop1h 20m
Deal found 9/2![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 9/3. 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 11/197:00 am -
2 stops10h 05m
Fri 11/205:55 am -
1 stop7h 15m
Deal found 9/3![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 8/30. 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 10/143:00 pm -
Nonstop1h 20m
Wed 10/219:20 am -
1 stop5h 00m
Deal found 8/30![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 9/4. 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 10/237:10 pm -
1 stop5h 10m
Tue 11/36:05 am -
1 stop8h 10m
Deal found 9/4![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 9/3. 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 10/207:05 am -
2 stops9h 00m
Fri 10/239:45 am -
Nonstop1h 25m
Deal found 9/3![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 9/4. 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 10/37:00 am -
2 stops11h 00m
Tue 10/63:35 pm -
1 stop5h 05m
Deal found 9/4![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 8/30. 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.
Sat 10/37:00 am -
2 stops11h 00m
Sun 10/49:55 am -
Nonstop1h 25m
Deal found 8/30![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 8/30. 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.
Thu 9/242:25 pm -
1 stop7h 40m
Mon 9/282:05 pm -
1 stop7h 15m
Deal found 8/30![Southwest logo]()
$369
Last-minute flights from Des Moines to MidwayDiscover last-minute flight deals from Des Moines to Midway. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from Des Moines to Midway. Data last updated September 5, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/31. 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 -
Nonstop1h 20m
Fri 9/258:50 pm -
Nonstop1h 25m
Deal found 8/31![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 9/3. 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 9/245:40 am -
Nonstop1h 20m
Sat 9/266:00 pm -
Nonstop1h 30m
Deal found 9/3![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 9/2. 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.
Tue 9/297:15 am -
2 stops9h 45m
Thu 10/19:50 pm -
Nonstop1h 20m
Deal found 9/2![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 9/2. 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.
Mon 10/127:10 pm -
1 stop5h 10m
Tue 10/1310:05 am -
Nonstop1h 25m
Deal found 9/2![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 8/31. 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 10/157:10 pm -
1 stop5h 10m
Thu 10/224:50 pm -
1 stop5h 20m
Deal found 8/31![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 9/1. 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.
Fri 10/164:30 pm -
Nonstop1h 20m
Fri 10/239:50 pm -
Nonstop1h 25m
Deal found 9/1![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 9/1. 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 10/177:00 am -
2 stops11h 00m
Sat 10/2410:40 am -
Nonstop1h 20m
Deal found 9/1![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 9/3. 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 10/197:10 pm -
1 stop5h 10m
Wed 10/211:05 pm -
2 stops7h 35m
Deal found 9/3![Southwest logo]()
$262
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 September 5, 2026.
Search for one-way flight options from Des Moines to Midway. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
This Southwest deal was found by Cheapflights users on 9/3. 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 9/302:40 pm -
Nonstop1h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$119
This Delta deal was found by Cheapflights users on 9/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:46 pm -
1 stop3h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Delta logo]()
$129
This Southwest deal was found by Cheapflights users on 9/2. 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.
Fri 10/164:30 pm -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Southwest logo]()
$131
This Southwest deal was found by Cheapflights users on 9/1. 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.
Wed 9/237:15 am -
2 stops9h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 9/2. 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.
Sat 10/177:00 am -
2 stops11h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Southwest logo]()
$152
This Southwest deal was found by Cheapflights users on 9/1. 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 10/15:10 am -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Southwest logo]()
$154
This Southwest deal was found by Cheapflights users on 9/4. 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 10/35:50 am -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Southwest logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 10/46:40 am -
2 stops41h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$162
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 September 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $237 (Southwest) |
One-way from | $119 (Southwest) |
Popular in | July |
Cheapest in | October |
Average price | $261 |
Good round-trip deal | $364 or less |
Good one-way deal | $208 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 7,457,451 searches. Data last updated September 5, 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
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Thu 10/1
7:10 pm-12:15 am
1 stop5h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Tue 11/3
7:00 am-12:15 pm
1 stop5h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$165
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Tue 9/29
2:46 pm-6:19 pm
1 stop3h 33m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$166
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Sat 10/31
6:55 am-11:47 am
1 stop4h 52m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Sun 11/1
6:40 am-12:00 pm
1 stop5h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$190
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Sun 11/1
10:57 am-4:47 pm
1 stop5h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$200
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Thu 9/17
2:25 pm-10:05 pm
1 stop7h 40m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Fri 10/2
6:20 am-3:10 pm
2 stops8h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$249
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Wed 9/30
7:15 am-5:00 pm
2 stops9h 45m
Chicago Midway
Thu 10/8
9:45 am-11:10 am
Nonstop1h 25m
$264
Quickest round-trip
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Sun 9/13
3:50 pm-5:10 pm
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$274
Showing 1-10 of 18 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 September.
| 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
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Valparaiso
Hammond
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Porter
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