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$119 Cheap Flights from Des Moines (DSM) to Chicago (MDW)

View $119 flight on Wed, Dec 2, 2026Opens 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 $119 for one-way flights and $237 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, Nov 16 - Wed, Nov 18
DSM
Des Moines
MDW
Chicago
$237 Roundtrip, found 6 hours ago
$237
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Mon, Nov 16 from Des Moines to Chicago, returning Wed, Nov 18, priced at $237 found 6 hours ago
Southwest Airlines
Wed, Nov 4 - Thu, Nov 5
DSM
Des Moines
MDW
Chicago
$247 Roundtrip, found 12 hours ago
$247
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Nov 4 from Des Moines to Chicago, returning Thu, Nov 5, priced at $247 found 12 hours ago
Southwest Airlines
Sat, Dec 5 - Mon, Dec 7
DSM
Des Moines
MDW
Chicago
$252 Roundtrip, found 8 hours ago
$252
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Sat, Dec 5 from Des Moines to Chicago, returning Mon, Dec 7, priced at $252 found 8 hours ago
Delta
Sat, Dec 5 - Mon, Dec 7
DSM
Des Moines
MDW
Chicago
$257 Roundtrip, found 8 hours ago
$257
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Dec 5 from Des Moines to Chicago, returning Mon, Dec 7, priced at $257 found 8 hours ago
Southwest Airlines
Thu, Oct 29 - Fri, Oct 30
DSM
Des Moines
MDW
Chicago
$257 Roundtrip, found 2 hours ago
$257
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Thu, Oct 29 from Des Moines to Chicago, returning Fri, Oct 30, priced at $257 found 2 hours ago
Southwest Airlines
Fri, Dec 4 - Mon, Dec 7
DSM
Des Moines
MDW
Chicago
$262 Roundtrip, found 22 hours ago
$262
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Fri, Dec 4 from Des Moines to Chicago, returning Mon, Dec 7, priced at $262 found 22 hours ago
Southwest Airlines
Thu, Oct 29 - Fri, Oct 30
DSM
Des Moines
MDW
Chicago
$267 Roundtrip, found 2 hours ago
$267
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Thu, Oct 29 from Des Moines to Chicago, returning Fri, Oct 30, priced at $267 found 2 hours ago
Delta
Sat, Dec 5 - Mon, Dec 7
DSM
Des Moines
MDW
Chicago
$267 Roundtrip, found 8 hours ago
$267
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Dec 5 from Des Moines to Chicago, returning Mon, Dec 7, priced at $267 found 8 hours ago
Southwest Airlines
Thu, Oct 29 - Fri, Oct 30
DSM
Des Moines
MDW
Chicago
$268 Roundtrip, found 2 hours ago
$268
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Thu, Oct 29 from Des Moines to Chicago, returning Fri, Oct 30, priced at $268 found 2 hours ago
Southwest Airlines
Thu, Nov 5 - Sat, Nov 7
DSM
Des Moines
MDW
Chicago
$272 Roundtrip, found 6 hours ago
$272
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Thu, Nov 5 from Des Moines to Chicago, returning Sat, Nov 7, priced at $272 found 6 hours ago

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 $417
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $417

What you need to know for your flight from Des Moines Intl. to Midway Intl.

Des Moines (DSM) to Chicago (MDW) at a glance

Travel between Des Moines (DSM) and Chicago (MDW) with a selection of airlines catering to this domestic short-haul route. Evaluate options for cheap flights from Des Moines to Chicago, whether you prefer full-service or low-cost carriers, to find the best fit for your budget and schedule. Discover the key details for weekly flights from Des Moines International Airport to Midway International Airport as you plan your exploration of Chicago’s iconic attractions and vibrant neighborhoods.

  • Fastest flight duration: around 1h 15m non-stop
  • Route distance: roughly 300 miles (485 km)
  • Flights per week: around 7 departures on average
  • Typical fares (one-way): economy tickets often range from $85–$335, depending on seasonality and how far ahead you book

Flights from Des Moines International Airport (DSM) to Midway International Airport (MDW)

Based on recent traveler bookings, here are the top airlines favored for flights from Des Moines to Chicago, typically offering both one-stop and non-stop options. Popular layover points include Lambert-St. Louis International Airport (STL) with about a 45-minute layover, Detroit Metropolitan Wayne County Airport (DTW) with around a 2-hour layover, and Minneapolis - St. Paul International Airport (MSP) with approximately a 2-hour and 30-minute layover. This variety allows you to balance price, total travel time, and cabin class to find your ideal itinerary.

  • Southwest Airlines: Known for its budget-friendly rates, this low-cost airline provides both non-stop and one-stop flights, with one-way prices generally ranging from $85 to $325. Southwest operates around 82% of the flights on this route, featuring an average in-flight duration of 2 hours and 15 minutes, leading to a total travel time of about 3 hours and 45 minutes.
  • Delta: As a full-service airline, Delta offers one-stop services with one-way fares typically priced between $115 and $595. It makes up approximately 18% of the departures for this route, with an in-flight time of 2 hours and 15 minutes, and a total travel time of around 3 hours and 45 minutes, including the layover.

Alternative route from Des Moines (DSM) to Chicago (MDW)

  • Des Moines to Chicago (DSM-ORD): O'Hare International Airport (ORD) is located approximately 16 miles from Midway International Airport (MDW). One-way economy fares on this route generally fall between $95 and $315, influenced by the time of year and how early you book your tickets. Travelers can find both non-stop and one-stop flights available. Major airlines operating on this route include United and American Airlines. Additionally, first class service is offered for this journey.

How to find the best prices for flights from Des Moines (DSM) to Chicago (MDW)

Getting some of the best deals on flights from Des Moines to Chicago is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually available when booking 2-8 weeks in advance, although most travelers tend to book within 2 weeks. Afternoon departures (12pm-6pm) are often less expensive and are the most popular times to fly. Additionally, flying on Wednesday typically offers lower prices, while Monday remains the most favored travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Midway International Airport from Des Moines International Airport

Chicago welcomes travelers from Des Moines with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
  • Car rental: Renting a car from Midway International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Midway International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Midway International Airport, travelers will find Midway Station, a metro station, just about 0.2 miles away on foot, while Chicago Ashburn Station, a train station, is located approximately 4.1 miles from the airport and is best accessed by car. Additionally, Lyons Seaport, a seaport, is around 7.2 miles away by car.

Frequently asked questions

How much does a flight from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $119 and cheap return flights from $237 Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights typically cost between $189 and $687, and return flights often range between $211 and $749. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from DSM to MDW is November when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter DSM to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.)?
Frontier Airlines is one of the cheapest airlines offering connecting flights from Des Moines (DSM) to Chicago (MDW), with round-trip tickets starting from around $194. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are approximately 1 nonstop flights per day from Des Moines Intl. (DSM) to Midway Intl. (MDW). For more options, look at flights that include layovers.
What is the earliest flight from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Des Moines International Airport (DSM) to Midway International Airport (MDW) typically departs at around 5:25 AM, operated by Southwest Airlines. An early departure like this can help you maximize your time in Chicago. This service operates seasonally in July and August. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Des Moines (DSM) to Chicago (MDW) are in the early morning, from 6am to 9am. About 64% of passengers prefer this time window. Many major carriers, including Southwest Airlines and Delta Air Lines, offer flights during this window. This timing is favored as it allows you to arrive in Chicago with a full day ahead.
How long does it take to fly from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.)?
A nonstop flight from DSM to MDW typically takes around 1 hour 20 minutes, covering approximately 305 miles. Connecting flights on this route usually add 5 hours to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the DSM to MDW route with Delta Air Lines.
How do I earn miles on a Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Des Moines Intl. (DSM)?
When traveling from Des Moines Intl. (DSM) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Dallas-Fort Worth Intl. (DFW), Charlotte-Douglas Intl. (CLT), Lambert-St. Louis Intl. (STL) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Des Moines, IA (DSM-Des Moines Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Des Moines Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$237
Distance
305 mi
Average flight time
1 hour 19 mins

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 November. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $119 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

*Flight schedules are subject to change.

*Available to One Key members.

 

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