Skip to main content
Beginning of main content

Cheap Flights from Des Moines to Chicago $305.5

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Here are your best fares found in the past 7 days

The lowest fare found for this route is $310.82 on Sat, May 20 from DSM to MDW
Flights Fare Calendar Find minimum fare between origin DSM and destination MDW Click this button to get previous 30 days data Click this button to get next 30 days data $799 $685 $571 $457 $342 $228 $114 $0 Apr May 30 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T Price is $ 685.6 on Delta Price is $ 685.6 on Delta Price is $ 633.67 on Delta Price is $ 590.6 on Delta Price is $ 563.6 on Delta Price is $ 532.0 on Delta Price is $ 527.7 on Delta Price is $ 522.66 on Delta Price is $ 522.6 on Delta Price is $ 517.6 on Delta Price is $ 507.6 on Delta Price is $ 497.6 on Delta Price is $ 497.6 on Delta Price is $ 497.6 on Delta Price is $ 472.6 on Delta Price is $ 447.6 on Delta Price is $ 437.6 on Delta Price is $ 437.6 on Delta Price is $ 437.6 on Delta Price is $ 427.66 on Delta Price is $ 417.6 on Delta Price is $ 397.6 on Delta Price is $ 397.6 on Delta Price is $ 397.6 on Delta Price is $ 397.6 on Delta Price is $ 397.6 on Delta Price is $ 377.67 on Delta Price is $ 367.1 on Delta Price is $ 366.6 on Delta Price is $ 363.31 on Delta Price is $ 363.31 on Delta Price is $ 362.6 on Delta Price is $ 354.19 on Delta Price is $ 352.46 on Delta Price is $ 352.15 on Delta Price is $ 347.6 on Delta Price is $ 347.6 on Delta Price is $ 347.6 on Delta Price is $ 347.6 on Delta Price is $ 345.5 on Delta Price is $ 344.28 on Delta Price is $ 344.28 on Delta Price is $ 336.51 on Delta Price is $ 326.41 on Delta Price is $ 326.41 on Delta Price is $ 310.82 on Delta

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 : Do travelers from Des Moines typically stay in Chicago for very long?
Answer : The average time spent in Chicago by travelers from Des Moines is four days.

Question : Who's offering the cheapest round-trip flight to Chicago Midway International Airport (MDW) over the coming months?
Answer : Delta Air Lines is the leader in keeping costs down for their passengers over the next three months. Fares are being booked at just $267, which is quite a deal when compared to the more expensive bookings of $632.

Question : What day in the next four weeks has the best fares?
Answer : As of Apr 24th, the best day for booking to Chicago (MDW) is May 5th. It costs $267, which is 22% below the average price to book the same route.

Question : How does Des Moines to Chicago stack up against the rest of the world in overall promptness?
Answer : Using the combined on-time percentage and average delay breakdown, Des Moines to Chicago currently has a 3 out of a possible 5 star rating. A 3-star rating means you should feel slightly worried about getting to Chicago on time.

Question : Is price more important than specific travel days for you?
Answer : Thursday is your cheapest day to fly in the month of May. Flexibility is paramount when booking travel plans in order to keep travel costs down.

Question : Which airline is struggling to get to Chicago on time?
Answer : Flexjet is delayed on 100% of flights from Des Moines International Airport (DSM) to Chicago Midway International Airport (MDW) at the moment. If you’re on Flexjet, be sure to sign up for the delay notifications to stay up to date with your flight’s status.

Question : What are the chances this flight will be delayed?
Answer : Passengers are currently getting to their destination on schedule 73% of the time, which ranks in the top half of the world. If a flight is delayed, though, expect an average of about half an hour added to your flight time.