$65 Cheap Flights from Chicago (MDW) to Des Moines (DSM)

View $65 flight on Tue, Aug 19, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Des Moines International Airport (DSM)

Cheap Flights from Chicago to Des Moines (MDW-DSM)

Prices were available within the past 7 days and start at $65 for one-way flights and $130 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Aug 20 - Sat, Aug 23
MDW
Chicago
DSM
Des Moines
$130 Roundtrip, found 5 days ago
$130
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Chicago to Des Moines, returning Sat, Aug 23, priced at $130 found 5 days ago
Southwest Airlines
Wed, Aug 20 - Sat, Aug 23
MDW
Chicago
DSM
Des Moines
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Chicago to Des Moines, returning Sat, Aug 23, priced at $140 found 5 days ago
Southwest Airlines
Wed, Aug 20 - Sat, Aug 23
MDW
Chicago
DSM
Des Moines
$160 Roundtrip, found 5 days ago
$160
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Chicago to Des Moines, returning Sat, Aug 23, priced at $160 found 5 days ago
Southwest Airlines
Thu, Aug 21 - Mon, Sep 1
MDW
Chicago
DSM
Des Moines
$167 Roundtrip, found 6 days ago
$167
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 21 from Chicago to Des Moines, returning Mon, Sep 1, priced at $167 found 6 days ago
Southwest Airlines
Fri, Sep 5 - Sun, Sep 7
MDW
Chicago
DSM
Des Moines
$168 Roundtrip, found 4 days ago
$168
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Sep 5 from Chicago to Des Moines, returning Sun, Sep 7, priced at $168 found 4 days ago
Southwest Airlines
Wed, Aug 20 - Sat, Aug 23
MDW
Chicago
DSM
Des Moines
$169 Roundtrip, found 5 days ago
$169
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Chicago to Des Moines, returning Sat, Aug 23, priced at $169 found 5 days ago
Southwest Airlines
Wed, Aug 20 - Sat, Aug 23
MDW
Chicago
DSM
Des Moines
$170 Roundtrip, found 5 days ago
$170
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Chicago to Des Moines, returning Sat, Aug 23, priced at $170 found 5 days ago
Southwest Airlines
Wed, Aug 20 - Sat, Aug 23
MDW
Chicago
DSM
Des Moines
$174 Roundtrip, found 5 days ago
$174
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Chicago to Des Moines, returning Sat, Aug 23, priced at $174 found 5 days ago
Southwest Airlines
Thu, Aug 21 - Mon, Sep 1
MDW
Chicago
DSM
Des Moines
$180 Roundtrip, found 6 days ago
$180
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 21 from Chicago to Des Moines, returning Mon, Sep 1, priced at $180 found 6 days ago
Delta
Tue, Sep 30 - Fri, Oct 17
MDW
Chicago
DSM
Des Moines
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 30 from Chicago to Des Moines, returning Fri, Oct 17, priced at $209 found 2 days ago
Flights from Chicago (MDW) to Des Moines (DSM)
Origin airport
Midway Intl.
Destination airport
Des Moines Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$129
Distance
305 mi

Chicago to Des Moines Flights

The cheapest times to fly from Chicago to Des Moines

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Des Moines are during the month of August. You can find some of the cheapest flights from Chicago to Des Moines with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Des Moines

Sunday is one of the best days to book for cheap flights from Chicago to Des Moines: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Des Moines

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Des Moines in 2025. You can also book with separate airlines for your outbound and return journeys, from $65 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Des Moines flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Des Moines airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Des Moines Intl. Airport (DSM) cost?
Discover the latest flight deals from MDW to DSM by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to DSM?
The cheapest flights from MDW to DSM are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Des Moines Intl. Airport (DSM)?
There's no direct route from Chicago, IL (MDW-Midway Intl.) to Des Moines Intl. Airport (DSM). However, you'll find other airports that have nonstop flights. Begin your journey at O'Hare Intl. Airport (ORD) and head straight to Des Moines without layovers.
What is the cheapest airline that flies from MDW to DSM?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to DSM. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Des Moines Intl. Airport (DSM)?
You'll need to book a flight with a layover if you're traveling from Midway Intl. Airport (MDW) to Des Moines Intl. Airport (DSM). There are no daily direct flights on this route. However, simply filter your search to include one or more stops to discover an option that works for you.
What day of the week has the most flights from MDW to DSM?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Just remember that flight schedules can vary depending on a range of factors, including the season and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Des Moines Intl. Airport (DSM)?
Book a flight from Midway Intl. Airport (MDW) to Des Moines Intl. Airport (DSM) that leaves before 3 PM to reduce the risk of delays and cancellations. Departures after this hour are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Des Moines Intl. Airport (DSM) last-minute?
Waiting until just before your trip to book a ticket from MDW to DSM often results in higher prices. While you may come across some last-minute deals, there's no guarantee. Allow some flexibility in your schedule for a better chance of landing a bargain.
Is it cheaper to book a MDW to DSM flight and hotel package?
You'll typically save money by booking a MDW to DSM flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After choosing your ideal accommodations and flights, consider other add-ons like car rentals, tours and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Des Moines Intl. Airport (DSM)?
You can usually cancel or reschedule your MDW to DSM flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find further details on our Customer Service portal.

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*Available to One Key members.