HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$89+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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 13, 2025.

Round-trip from

$197
(Southwest)

One-way from

$89
(Delta)

Popular in

July

Cheapest in

May

Average price

$276
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. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 13, 2025.

This Southwest deal was found by Cheapflights users on 8/11. 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 9/85:30 pmDSM - MDW
1 stop2h 55mSouthwest
Tue 9/93:50 pmMDW - DSM
1 stop5h 35mSouthwest
Deal found 8/11$197
This Delta deal was found by Cheapflights users on 8/12. 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 9/226:00 amDSM - MDW
1 stop6h 28mDelta
Wed 9/249:20 amMDW - DSM
1 stop4h 43mDelta
Deal found 8/12$202
This Southwest deal was found by Cheapflights users on 8/11. 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 9/108:25 amDSM - MDW
2 stops8h 40mSouthwest
Wed 9/173:10 pmMDW - DSM
2 stops7h 10mSouthwest
Deal found 8/11$207
This Southwest deal was found by Cheapflights users on 8/11. 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 9/41:55 pmDSM - MDW
1 stop10h 10mSouthwest
Sat 9/69:45 amMDW - DSM
2 stops10h 35mSouthwest
Deal found 8/11$208
This Southwest deal was found by Cheapflights users on 8/11. 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 9/238:25 amDSM - MDW
2 stops9h 00mSouthwest
Tue 9/303:10 pmMDW - DSM
2 stops7h 10mSouthwest
Deal found 8/11$213
This Southwest deal was found by Cheapflights users on 8/12. 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 11/145:45 amDSM - MDW
1 stop4h 10mSouthwest
Sun 11/166:45 amMDW - DSM
1 stop4h 15mSouthwest
Deal found 8/12$214
This Delta deal was found by Cheapflights users on 8/11. 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 10/146:05 amDSM - MDW
1 stop6h 23mDelta
Thu 10/169:20 amMDW - DSM
1 stop4h 39mDelta
Deal found 8/11$218
This Delta deal was found by Cheapflights users on 8/12. 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 9/97:00 amDSM - MDW
1 stop6h 03mDelta
Tue 9/169:20 amMDW - DSM
1 stop4h 43mDelta
Deal found 8/12$223
This Southwest deal was found by Cheapflights users on 8/12. 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 9/108:25 amDSM - MDW
1 stop4h 15mSouthwest
Fri 9/125:25 amMDW - DSM
1 stop7h 35mSouthwest
Deal found 8/12$233
This Southwest deal was found by Cheapflights users on 8/12. 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 10/26:35 amDSM - MDW
1 stop6h 05mSouthwest
Sat 10/115:15 amMDW - DSM
1 stop6h 55mSouthwest
Deal found 8/12$273

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 August 13, 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

Mon 9/8

5:30 pm-8:25 pm

1 stop2h 55m

Chicago Midway

Tue 9/9

3:50 pm-9:25 pm

1 stop5h 35m

$197

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 11/13

2:37 pm-6:07 pm

1 stop3h 30m

Chicago Midway

Sat 11/15

9:20 am-2:08 pm

1 stop4h 48m

$197

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Mon 9/22

5:30 pm-8:25 pm

1 stop2h 55m

Chicago Midway

Wed 9/24

6:25 am-11:25 am

1 stop5h 00m

$197

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 9/27

10:55 am-5:35 pm

1 stop6h 40m

Chicago Midway

Sat 10/4

9:20 am-2:03 pm

1 stop4h 43m

$197

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 9/9

8:25 am-12:40 pm

1 stop4h 15m

Chicago Midway

Tue 9/16

6:25 am-11:25 am

1 stop5h 00m

$197

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 9/10

8:25 am-12:40 pm

1 stop4h 15m

Chicago Midway

Wed 9/17

5:40 pm-10:20 pm

1 stop4h 40m

$197

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 9/23

6:30 am-11:55 am

1 stop5h 25m

Chicago Midway

Tue 9/30

5:40 pm-10:20 pm

1 stop4h 40m

$197

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Mon 9/22

6:00 am-12:28 pm

1 stop6h 28m

Chicago Midway

Wed 9/24

9:20 am-2:03 pm

1 stop4h 43m

$202

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 9/23

7:00 am-1:03 pm

1 stop6h 03m

$89

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 9/13

6:00 am-12:28 pm

1 stop6h 28m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 18 results
1
2

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.

  • What is the cheapest airline to fly from Des Moines to Chicago Midway Airport round-trip?

    Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $197.

  • 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.

  • What is the cheapest month to book a flight from Des Moines to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Des Moines to Chicago Midway Airport (average of $160). Flying from Des Moines to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Benton Harbor
Porter
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.