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$105+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$209
(Delta)

One-way from

$105
(Southwest)

Popular in

July

Cheapest in

May

Average price

$264
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 ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junio 12, 2025.

This Delta deal was found by Cheapflights users on 6/10. 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.
mié. 8/136:00 amDSM - MDW
1 stop6h 28mDelta
lun. 8/181:43 pmMDW - DSM
1 stop3h 29mDelta
Deal found 6/10$209
This Southwest deal was found by Cheapflights users on 6/10. 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.
mar. 7/295:35 pmDSM - MDW
1 stop4h 05mSouthwest
vie. 8/18:00 pmMDW - DSM
1 stop3h 50mSouthwest
Deal found 6/10$214
This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/208:38 pmDSM - MDW
1 stop24h 15mFrontier
lun. 6/2312:35 pmMDW - DSM
1 stop7h 18mFrontier
Deal found 6/10$405
This Mytrip deal was found by Cheapflights users on 6/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 7/2710:40 amDSM - MDW
2 stops27h 24mAllegiant Air
dom. 8/38:14 pmMDW - DSM
2 stops25h 50mAllegiant Air
Deal found 6/12$411

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 junio 12, 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

mié. 8/13

6:00 am-12:28 pm

1 stop6h 28m

Chicago Midway

lun. 8/18

1:43 pm-5:12 pm

1 stop3h 29m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

mar. 7/29

5:35 pm-9:40 pm

1 stop4h 05m

Chicago Midway

vie. 8/1

8:00 pm-11:50 pm

1 stop3h 50m

$214

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

dom. 7/27

10:40 am-2:04 pm

2 stops27h 24m

Chicago Midway

dom. 8/3

8:14 pm-10:04 pm

2 stops25h 50m

$411

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

vie. 7/11

7:33 pm-1:50 pm

2 stops18h 17m

Chicago Midway

lun. 7/14

12:35 pm-6:48 pm

1 stop6h 13m

$416

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

sáb. 10/4

3:50 pm-7:05 pm

1 stop3h 15m

$105

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

sáb. 7/12

2:21 pm-10:47 am

1 stop20h 26m

$123

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

vie. 8/22

6:20 pm-12:24 am

1 stop6h 04m

$183

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

sáb. 9/6

6:00 am-12:28 pm

1 stop6h 28m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 junio 12, 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
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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
725 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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 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 $411, respectively.

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

    $105 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 Frontier, with prices starting from $123 and $183, 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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