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$101+ 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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Mar 30 — Apr 61
Sun 3/30
Sun 4/6
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 March 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(Delta)

One-way from

$101
(Booking.com)

Popular in

June

Cheapest in

February

Average price

$274
Provider with most accurate pricing for Des Moines-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Des Moines-Chicago Midway flights.
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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. 11% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 25, 2025.

This Delta deal was found by Cheapflights users on 3/23. 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 4/1511:59 amDSM - MDW
1 stop5h 20mDelta
Wed 4/163:02 pmMDW - DSM
1 stop5h 43mDelta
Deal found 3/23$209
This Southwest deal was found by Cheapflights users on 3/23. 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 4/115:30 pmDSM - MDW
1 stop4h 30mSouthwest
Mon 4/144:35 pmMDW - DSM
1 stop5h 35mSouthwest
Deal found 3/23$214
This Mytrip deal was found by Cheapflights users on 3/22. 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.
Sun 4/207:00 amDSM - MDW
2 stops27h 09mAllegiant Air
Sun 4/2710:08 amMDW - DSM
1 stop28h 55mAllegiant Air
Deal found 3/22$415

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 March 25, 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

Tue 4/15

11:59 am-5:19 pm

1 stop5h 20m

Chicago Midway

Wed 4/16

3:02 pm-8:45 pm

1 stop5h 43m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 4/11

5:30 pm-10:00 pm

1 stop4h 30m

Chicago Midway

Mon 4/14

4:35 pm-10:10 pm

1 stop5h 35m

$214

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sun 4/20

7:00 am-10:09 am

2 stops27h 09m

Chicago Midway

Sun 4/27

10:08 am-3:03 pm

1 stop28h 55m

$415

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 4/23

7:27 pm-7:06 pm

1 stop23h 39m

$101

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 5/8

6:30 am-12:28 pm

1 stop5h 58m

$105

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Mon 4/7

6:45 pm-9:45 pm

1 stop3h 00m

$110

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 6/5

12:39 pm-2:03 pm

2 stops25h 24m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 March 25, 2025.
Read through reviews of airlines operating flights from Des Moines to Chicago, such as Southwest, Delta and Allegiant Air. 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
4,272 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,890 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
730 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,273 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 Delta is currently your cheapest option to Chicago Midway Airport, with prices starting at $209. Additional round-trip tickets that might be worth considering are offered by Southwest and Allegiant Air, with the lowest prices starting at $214 and $415, respectively.

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

    $101 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Delta and Southwest, with prices starting from $105 and $110, 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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