Skip to main content
Beginning of main content

Cheap Flights from Des Moines to Chicago $231.63

Search over 282,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Best Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheapest Flights from Des Moines to Chicago (DSM to MDW)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Des Moines to Chicago (DSM to MDW)

Question : How many days should you spend in Chicago if you're flying in from Des Moines?
Answer : Travelers from DSM to MDW stay six days on average.

Question : Which airline is struggling to get to Chicago on time?
Answer : Flights on Flexjet to Chicago from Des Moines during the last month were late 100% of the time. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.

Question : In the next four weeks, what day should you book your trip?
Answer : December 17th offers bookings (as of November 28th) that are 19% below the average price for this route. Saving on booking fees means you'll have more money to spend on your trip.

Question : How often are flights on time from Des Moines International Airport (DSM) to Chicago Midway International Airport (MDW)?
Answer : Passengers are currently getting to their destination on schedule 67% of the time, which ranks in the bottom half across all routes. When there is a delay, it averages between 20-30 minutes.

Question : How many departure times from Des Moines International Airport (DSM) to Chicago Midway International Airport (MDW) are there on a daily basis?
Answer : On average, there are three options. The average route has 31 different flight times per day, so expect fewer choices than you're used to.

Question : Looking for the shortest flight from DSM to MDW?
Answer : The quickest direct flight is 1 hour and 5 minutes via Southwest Airlines. If you catch the 6:25 PM CST departure, you'll arrive at 7:30 PM CST.

Question : Would you be willing to change your travel days if it saved you money?
Answer : For the month of December, the cheapest day to fly is Sunday. Having flexibility in your travel plans means you can save, so be sure to plan ahead when possible.