$87 Cheap Flights from Des Moines (DSM) to Chicago (MDW)

View $87 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 $87 for one-way flights and $159 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Dec 17 - Sat, Jan 3
DSM
Des Moines
MDW
Chicago
$159 Roundtrip, found 9 hours ago
$159
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Dec 17 from Des Moines to Chicago, returning Sat, Jan 3, priced at $159 found 9 hours ago
Delta
Tue, Nov 18 - Sat, Nov 22
DSM
Des Moines
MDW
Chicago
$169 Roundtrip, found 20 hours ago
$169
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Nov 18 from Des Moines to Chicago, returning Sat, Nov 22, priced at $169 found 20 hours ago
Delta
Tue, Jan 6 - Tue, Jan 13
DSM
Des Moines
MDW
Chicago
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jan 6 from Des Moines to Chicago, returning Tue, Jan 13, priced at $177 found 6 days ago
Southwest Airlines
Tue, Nov 11 - Wed, Nov 12
DSM
Des Moines
MDW
Chicago
$180 Roundtrip, found 4 days ago
$180
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Nov 11 from Des Moines to Chicago, returning Wed, Nov 12, priced at $180 found 4 days ago
Southwest Airlines
Tue, Nov 11 - Wed, Nov 12
DSM
Des Moines
MDW
Chicago
$185 Roundtrip, found 4 days ago
$185
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Nov 11 from Des Moines to Chicago, returning Wed, Nov 12, priced at $185 found 4 days ago
Southwest Airlines
Tue, Nov 4 - Sat, Nov 8
DSM
Des Moines
MDW
Chicago
$186 Roundtrip, found 3 days ago
$186
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Des Moines to Chicago, returning Sat, Nov 8, priced at $186 found 3 days ago
Delta
Sat, Dec 27 - Mon, Jan 5
DSM
Des Moines
MDW
Chicago
$189 Roundtrip, found 4 hours ago
$189
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Dec 27 from Des Moines to Chicago, returning Mon, Jan 5, priced at $189 found 4 hours ago
Southwest Airlines
Tue, Nov 4 - Sat, Nov 8
DSM
Des Moines
MDW
Chicago
$192 Roundtrip, found 3 days ago
$192
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Des Moines to Chicago, returning Sat, Nov 8, priced at $192 found 3 days ago
Delta
Sat, Aug 30 - Sat, Sep 6
DSM
Des Moines
MDW
Chicago
$194 Roundtrip, found 4 hours ago
$194
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Aug 30 from Des Moines to Chicago, returning Sat, Sep 6, priced at $194 found 4 hours ago
Frontier Airlines
Mon, Oct 20 - Sun, Oct 26
DSM
Des Moines
MDW
Chicago
$208 Roundtrip, found 2 days ago
$208
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Des Moines to Chicago, returning Sun, Oct 26, priced at $208 found 2 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.

Graph displaying average flight prices per month

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 $169
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $169
Flights from Des Moines (DSM) to Chicago (MDW)
Origin airport
Des Moines Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$158
Distance
305 mi

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 December. 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 $87 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.

 

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 $87 or cheap return flight from $159 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)?
December 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.

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*Available to One Key members.