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$135+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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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 July 3, 2025.

Round-trip from

$189
(Southwest)

One-way from

$135
(Southwest)

Popular in

August

Cheapest in

May

Average price

$289
From Des Moines to Chicago Midway
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One-way flight from Des Moines to Chicago Midway
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Highest demand for flights based on searches. 5% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 July 3, 2025.

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.
Sat 8/163:45 pmDSM - MDW
1 stop5h 15mSouthwest
Wed 8/205:40 pmMDW - DSM
1 stop4h 40mSouthwest
Deal found 7/2$189
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/136:00 amDSM - MDW
1 stop6h 28mDelta
Mon 8/189:15 amMDW - DSM
1 stop4h 54mDelta
Deal found 7/2$209
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/317:54 pmDSM - MDW
2 stops18h 02mAllegiant Air
Mon 8/42:46 pmMDW - DSM
2 stops22h 45mAllegiant Air
Deal found 7/1$333
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/77:33 pmDSM - MDW
2 stops15h 07mFrontier
Fri 7/1112:35 pmMDW - DSM
1 stop6h 13mFrontier
Deal found 7/2$341

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 3, 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

Sat 8/16

3:45 pm-9:00 pm

1 stop5h 15m

Chicago Midway

Wed 8/20

5:40 pm-10:20 pm

1 stop4h 40m

$189

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 8/13

6:00 am-12:28 pm

1 stop6h 28m

Chicago Midway

Mon 8/18

9:15 am-2:09 pm

1 stop4h 54m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 7/31

7:54 pm-1:56 pm

2 stops18h 02m

Chicago Midway

Mon 8/4

2:46 pm-1:31 pm

2 stops22h 45m

$333

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 7/29

5:35 pm-9:40 pm

1 stop4h 05m

$135

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sun 7/20

3:45 pm-9:41 am

2 stops17h 56m

$171

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 8/15

10:59 am-5:37 pm

1 stop6h 38m

$224

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 8/1

7:33 pm-8:54 pm

1 stop25h 21m

$261

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 3, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Allegiant Air from Des Moines to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
708 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 are the cheapest airlines flying 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 $189. Additional round-trip tickets that might be worth considering are offered by Delta and Allegiant Air, with the lowest prices starting at $209 and $333, respectively.

  • What are the cheapest airlines to fly from Des Moines to Chicago Midway Airport one-way?

    $135 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Allegiant Air and Delta, with prices starting from $171 and $224, respectively.

  • 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 Des Moines?

Book flights to Des Moines if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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