$77 Cheap Flights from Des Moines (DSM) to Chicago (MDW)

View $77 flight on Thu, Nov 6, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $77 for one-way flights and $181 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, Oct 20 - Wed, Oct 22
DSM
Des Moines
MDW
Chicago
$181 Roundtrip, found 4 days ago
$181
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, Oct 20 from Des Moines to Chicago, returning Wed, Oct 22, priced at $181 found 4 days ago
Southwest Airlines
Tue, Nov 4 - Wed, Nov 5
DSM
Des Moines
MDW
Chicago
$183 Roundtrip, found 12 hours ago
$183
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Des Moines to Chicago, returning Wed, Nov 5, priced at $183 found 12 hours ago
Southwest Airlines
Wed, Nov 12 - Mon, Nov 17
DSM
Des Moines
MDW
Chicago
$196 Roundtrip, found 8 hours ago
$196
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Des Moines to Chicago, returning Mon, Nov 17, priced at $196 found 8 hours ago
Southwest Airlines
Wed, Nov 12 - Mon, Nov 17
DSM
Des Moines
MDW
Chicago
$201 Roundtrip, found 8 hours ago
$201
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Des Moines to Chicago, returning Mon, Nov 17, priced at $201 found 8 hours ago
Southwest Airlines
Mon, Oct 20 - Wed, Oct 22
DSM
Des Moines
MDW
Chicago
$206 Roundtrip, found 4 days ago
$206
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, Oct 20 from Des Moines to Chicago, returning Wed, Oct 22, priced at $206 found 4 days ago
Delta
Wed, Nov 12 - Mon, Nov 17
DSM
Des Moines
MDW
Chicago
$209 Roundtrip, found 8 hours ago
$209
Roundtrip
found 8 hours ago
Select Delta flight, departing Wed, Nov 12 from Des Moines to Chicago, returning Mon, Nov 17, priced at $209 found 8 hours ago
Delta
Wed, Feb 25 - Thu, Mar 5
DSM
Des Moines
MDW
Chicago
$209 Roundtrip, found 3 hours ago
$209
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Feb 25 from Des Moines to Chicago, returning Thu, Mar 5, priced at $209 found 3 hours ago
Southwest Airlines
Sun, May 3 - Wed, May 6
DSM
Des Moines
MDW
Chicago
$209 Roundtrip, found 3 days ago
$209
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sun, May 3 from Des Moines to Chicago, returning Wed, May 6, priced at $209 found 3 days ago
Delta
Sat, Oct 18 - Sat, Oct 25
DSM
Des Moines
MDW
Chicago
$214 Roundtrip, found 23 hours ago
$214
Roundtrip
found 23 hours ago
Select Delta flight, departing Sat, Oct 18 from Des Moines to Chicago, returning Sat, Oct 25, priced at $214 found 23 hours ago
Frontier Airlines
Fri, Oct 17 - Thu, Oct 23
DSM
Des Moines
MDW
Chicago
$317 Roundtrip, found 3 days ago
$317
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Oct 17 from Des Moines to Chicago, returning Thu, Oct 23, priced at $317 found 3 days ago

Find the cheapest month to fly from Des Moines (DSM) to Chicago (MDW)

November is typically the cheapest month to fly

From $148 - $673 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $214
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $214

Frequently asked questions

How much does a flight from Des Moines Intl. Airport (DSM) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $77 or cheap return flight from $181 from Des Moines Intl. Airport (DSM) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Des Moines Intl. Airport (DSM) to Midway Intl. Airport (MDW)?
October is the most affordable month to fly from DSM to MDW. Avoiding peak travel times is often the key to finding a great deal.
What is the cheapest airline that flies from Des Moines Intl. Airport (DSM) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest DSM to MDW flight.
How many flights per day from Des Moines Intl. Airport (DSM) to Midway Intl. Airport (MDW)?
You'll need to catch a flight with a layover when traveling from Des Moines Intl. Airport (DSM) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, just filter your search to include one or two stops to find the best option for your trip.
What day of the week has the most flights from DSM to MDW?
Generally you'll find the largest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can change based on the season, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Des Moines Intl. Airport (DSM) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Des Moines Intl. Airport (DSM) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Departures after this time have a 22% higher chance of cancellation.**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.
What airports do you fly into for Chicago from Des Moines Intl. Airport (DSM)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Des Moines Intl. Airport (DSM). Check out the options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Des Moines Intl. Airport (DSM) to Midway Intl. Airport (MDW) last-minute?
Holding off until right before your break to book a ticket from DSM to MDW often results in higher prices. While you might find some last-minute deals, they aren't always guaranteed. Be flexible with your itinerary for the best chance of getting a bargain.
Is it cheaper to book a DSM to MDW flight and hotel package?
You can save money by booking a DSM to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. Once you've chosen your ideal flights and accommodations, consider adding extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from Des Moines Intl. Airport (DSM) to Midway Intl. Airport (MDW)?
If you booked your DSM to MDW flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you'd like more information.

Travel information

Travel information

Origin airport
Des Moines Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$180
Distance
305 mi

Book with confidence

Book with confidence

Des Moines to Chicago Flights

The cheapest times to fly from Des Moines to Chicago

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 Des Moines to Chicago are during the month of October. You can find some of the cheapest flights from Des Moines to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from Des Moines to Chicago: 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 Des Moines to Chicago

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 Des Moines to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $77 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 Des Moines to Chicago 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 Des Moines to Chicago 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.

 

Des Moines to Chicago Flights

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