$131+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Sep 20 — Sep 271
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
Last-minute
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 August 21, 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 August 21, 2026.
This Southwest deal was found by Cheapflights users on 8/16. 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 9/105:40 am -
Nonstop1h 20m
Sat 9/1210:10 am -
Nonstop1h 20m
Deal found 8/16![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 8/17. 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 9/103:50 pm -
Nonstop1h 20m
Mon 9/147:00 am -
1 stop6h 45m
Deal found 8/17![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 8/17. 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 11/55:25 am -
Nonstop1h 30m
Fri 11/610:05 am -
Nonstop1h 25m
Deal found 8/17![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 8/18. 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 9/157:15 am -
2 stops9h 45m
Tue 9/2210:30 am -
Nonstop1h 20m
Deal found 8/18![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 8/18. 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 9/1010:20 am -
1 stop6h 37m
Sat 9/124:48 pm -
1 stop4h 23m
Deal found 8/18![Delta logo]()
$281
This Southwest deal was found by Cheapflights users on 8/17. 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 9/103:50 pm -
Nonstop1h 20m
Fri 9/112:05 pm -
1 stop7h 15m
Deal found 8/17![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 8/17. 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 10/24:30 pm -
Nonstop1h 20m
Fri 10/99:35 pm -
Nonstop1h 20m
Deal found 8/17![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 8/16. 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
Wed 10/71:05 pm -
2 stops7h 30m
Deal found 8/16![Southwest logo]()
$291
This Delta deal was found by Cheapflights users on 8/16. 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 10/22:46 pm -
1 stop3h 33m
Tue 10/612:27 pm -
1 stop6h 44m
Deal found 8/16![Delta logo]()
$292
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 August 21, 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 August 21, 2026.
This Southwest deal was found by Cheapflights users on 8/19. 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 9/162:40 pm -
Nonstop1h 25m
Thu 9/178:50 pm -
Nonstop1h 25m
Deal found 8/19![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 8/19. 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 9/195:30 am -
Nonstop1h 15m
Sat 9/2610:10 am -
Nonstop1h 20m
Deal found 8/19![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 8/16. 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 9/306:10 am -
Nonstop1h 20m
Wed 10/710:05 am -
Nonstop1h 25m
Deal found 8/16![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 8/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:30 pm -
Nonstop1h 20m
Mon 10/2611:50 am -
2 stops10h 05m
Deal found 8/20![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 8/16. 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 10/17:10 pm -
1 stop5h 05m
Sat 10/36:15 am -
1 stop7h 25m
Deal found 8/16![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/17. 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 9/103:50 pm -
Nonstop1h 20m
Fri 9/112:05 pm -
1 stop7h 15m
Deal found 8/17![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 8/18. 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 9/102:25 pm -
1 stop7h 35m
Sat 9/1210:15 am -
2 stops10h 35m
Deal found 8/18![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 8/17. 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 9/512:10 pm -
Nonstop1h 20m
Sat 9/196:00 pm -
Nonstop1h 30m
Deal found 8/17![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 8/17. 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 9/512:10 pm -
Nonstop1h 20m
Mon 9/78:50 pm -
Nonstop1h 25m
Deal found 8/17![Southwest logo]()
$344
Last-minute flights from Des Moines to MidwayDiscover last-minute flight deals from Des Moines to Midway. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Des Moines to Midway. Data last updated August 21, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/18. 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 9/105:40 am -
Nonstop1h 20m
Mon 9/1410:05 am -
Nonstop1h 20m
Deal found 8/18![Southwest logo]()
$261
This Delta deal was found by Cheapflights users on 8/18. 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 9/1010:20 am -
1 stop6h 37m
Sat 9/124:48 pm -
1 stop4h 23m
Deal found 8/18![Delta logo]()
$281
This Southwest deal was found by Cheapflights users on 8/17. 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 9/103:50 pm -
Nonstop1h 20m
Fri 9/112:05 pm -
1 stop7h 15m
Deal found 8/17![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 8/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:50 pm -
Nonstop1h 20m
Mon 9/148:50 pm -
Nonstop1h 25m
Deal found 8/20![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 8/18. 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 9/157:15 am -
2 stops9h 45m
Tue 9/222:15 pm -
1 stop6h 50m
Deal found 8/18![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 8/17. 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 9/195:30 am -
Nonstop1h 15m
Sun 9/209:30 pm -
Nonstop1h 25m
Deal found 8/17![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 8/20. 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 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
Fri 9/258:50 pm -
Nonstop1h 25m
Deal found 8/20![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 8/16. 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
Wed 10/78:35 pm -
Nonstop1h 20m
Deal found 8/16![Southwest logo]()
$276
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 August 21, 2026.
Search for one-way flight options from Des Moines to Midway. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Southwest deal was found by Cheapflights users on 8/17. 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 9/175:40 am -
Nonstop1h 20m
Deal found 8/17![Southwest logo]()
$131
This Delta deal was found by Cheapflights users on 8/18. 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 9/152:46 pm -
1 stop3h 33m
Deal found 8/18![Delta logo]()
$141
This Southwest deal was found by Cheapflights users on 8/16. 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
Deal found 8/16![Southwest logo]()
$142
This Southwest deal was found by Cheapflights users on 8/17. 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 9/227:15 am -
2 stops9h 45m
Deal found 8/17![Southwest logo]()
$146
This Delta deal was found by Cheapflights users on 8/16. 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 10/1610:51 am -
1 stop5h 56m
Deal found 8/16![Delta logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Mon 10/198:25 pm -
2 stops39h 52m
Deal found 8/16![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Mon 11/166:45 am -
3 stops52h 13m
Deal found 8/16![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Mon 9/219:31 pm -
2 stops20h 15m
Deal found 8/19![Multiple Airlines logo]()
$162
This Southwest deal was found by Cheapflights users on 8/18. 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 9/205:40 am -
Nonstop1h 20m
Deal found 8/18![Southwest logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Mon 9/149:31 pm -
2 stops20h 15m
Deal found 8/16![Multiple Airlines logo]()
$172
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 August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $261 (Southwest) |
One-way from | $131 (Southwest) |
Popular in | July |
Cheapest in | September |
Average price | $353 |
Good round-trip deal | $348 or less |
Good one-way deal | $209 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 August 21, 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
Wed 9/16
2:40 pm-4:05 pm
Nonstop1h 25m
Chicago Midway
Thu 9/17
8:50 pm-10:15 pm
Nonstop1h 25m
$261
Quickest round-trip
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Sat 9/19
5:30 am-6:45 am
Nonstop1h 15m
Chicago Midway
Sat 9/26
10:10 am-11:30 am
Nonstop1h 20m
$261
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Wed 9/30
6:10 am-7:30 am
Nonstop1h 20m
Chicago Midway
Wed 10/7
10:05 am-11:30 am
Nonstop1h 25m
$261
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Thu 10/22
4:30 pm-5:50 pm
Nonstop1h 20m
Chicago Midway
Mon 10/26
11:50 am-9:55 pm
2 stops10h 05m
$276
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
Sat 10/3
6:15 am-1:40 pm
1 stop7h 25m
$281
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Thu 9/10
3:50 pm-5:10 pm
Nonstop1h 20m
Chicago Midway
Fri 9/11
2:05 pm-9:20 pm
1 stop7h 15m
$282
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Thu 9/10
2:25 pm-10:00 pm
1 stop7h 35m
Chicago Midway
Sat 9/12
10:15 am-8:50 pm
2 stops10h 35m
$314
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Sat 9/5
12:10 pm-1:30 pm
Nonstop1h 20m
Chicago Midway
Sat 9/19
6:00 pm-7:30 pm
Nonstop1h 30m
$344
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Sat 9/5
12:10 pm-1:30 pm
Nonstop1h 20m
Chicago Midway
Mon 9/7
8:50 pm-10:15 pm
Nonstop1h 25m
$344
Cheapest one-way
Quickest one-way
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Thu 9/17
5:40 am-7:00 am
Nonstop1h 20m
$131
Showing 1-10 of 20 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 August.
| 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?
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Porter
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