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DSM - MDW

$129 Find cheap flights from Des Moines to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Des Moines to Midway departing on 7/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/29
Sat 7/6

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Des Moines to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Des Moines to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

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Cheap flight deals from Des Moines to Midway (DSM-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Des Moines to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
2:20 pm - 10:00 pmDSM-MDW
7h 40m1 stop
6:15 am - 12:18 pmMDW-DSM
6h 03m1 stop
$258Frontier
Find Deal
Sat, Jul 20 - Mon, Jul 29
2:20 pm - 10:00 pmDSM-MDW
7h 40m1 stop
6:15 am - 12:44 pmMDW-DSM
6h 29m1 stop
$263Frontier
Find Deal
Sat, Jul 13 - Mon, Jul 15
2:24 pm - 9:45 pmDSM-MDW
7h 21m1 stop
5:55 am - 8:14 pmMDW-DSM
14h 19m1 stop
$268Frontier
Find Deal
Thu, Jun 20 - Mon, Jun 24
10:14 am - 5:05 pmDSM-MDW
6h 51m1 stop
1:24 pm - 5:02 pmMDW-DSM
3h 38m1 stop
$292Delta
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Sun, Jul 7 - Wed, Jul 10
4:10 pm - 10:05 pmDSM-MDW
5h 55m1 stop
7:05 am - 11:00 amMDW-DSM
3h 55m1 stop
$306Southwest
Find Deal
Thu, Jun 20 - Fri, Jun 28
4:10 pm - 10:05 pmDSM-MDW
5h 55m1 stop
5:30 am - 11:00 amMDW-DSM
5h 30m2 stops
$311Southwest
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Thu, Jun 20 - Fri, Jun 28
6:35 am - 12:42 pmDSM-MDW
6h 07m1 stop
1:24 pm - 5:02 pmMDW-DSM
3h 38m1 stop
$358Delta
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Mon, Aug 5 - Fri, Aug 9
7:20 am - 8:18 pmDSM-MDW
12h 58m2 stops
2:14 pm - 10:08 amMDW-DSM
19h 54m2 stops
$480Allegiant Air
Find Deal
Fri, Jun 28 - Fri, Jul 5
7:30 am - 8:17 pmDSM-MDW
12h 47m2 stops
5:15 pm - 2:55 pmMDW-DSM
21h 40m2 stops
Fri, Jul 5 - Sun, Jul 7
7:30 am - 8:17 pmDSM-MDW
12h 47m2 stops
7:19 pm - 8:30 pmMDW-DSM
25h 11m3 stops
$1,083
Find Deal
Fri, Jul 12 - Mon, Jul 15

Flights from Des Moines to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Des Moines to Midway to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Des Moines to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Des Moines to Chicago Midway Airport found on KAYAK was with Frontier for $129. Frontier proposed a round-trip connection from $258 and Delta from $292.

Good to know

Cheapest flight

$129
Flight from Des Moines to Chicago Midway Airport

When to book flights from Des Moines to Midway

Are your dates flexible? Find out the best times to travel from Des Moines to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Des Moines to Chicago Midway Airport flights

  • What is the cheapest flight from Des Moines to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Des Moines to Chicago Midway Airport was $129 for a one-way ticket and $258 for a round-trip.

  • Do I need a passport to fly between Des Moines and Chicago Midway Airport?

    A passport is not required to fly from Des Moines to Chicago Midway Airport.

  • Which airports will I be using when flying from Des Moines to Chicago Midway Airport?

    On your way to Chicago Midway Airport, you’ll fly out from Des Moines. You’ll be landing at Chicago Midway.

  • Which aircraft models fly most regularly from Des Moines to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Des Moines to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Des Moines and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from Des Moines to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Des Moines to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Des Moines to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Des Moines is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Des Moines to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Des Moines with another airline. Booking your flights between Des Moines and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Des Moines to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Des Moines up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Des Moines to Midway

 
See real verified KAYAK customer reviews for airlines flying from Des Moines to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Des Moines to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10457 reviews
8.6Crew
7.9Comfort
7.4Food
8.0Entertainment
8.2Boarding
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

Book cheap flights from Des Moines to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Des Moines to Chicago found on KAYAK in the last 72 hours.
7/4Thu
1 stopFrontier
7h 14mDSM-MDW
$129
6/27Thu
1 stopFrontier
7h 21mDSM-MDW
$130
6/24Mon
1 stopFrontier
15h 53mDSM-MDW
$139
6/20Thu
1 stopSouthwest
5h 05mDSM-MDW
$153
7/7Sun
1 stopDelta
6h 51mDSM-MDW
$154
6/20Thu
2 stopsSouthwest
7h 55mDSM-MDW
$158
6/29Sat
1 stopDelta
4h 27mDSM-MDW
$209
6/24Mon
2 stopsAllegiant Air
12h 58mDSM-MDW
$227
6/28Fri
2 stopsAllegiant Air
12h 58mDSM-MDW
$229
6/6Thu
2 stops
26h 38mDSM-MDW
$310

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Last minute flights from Des Moines to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Des Moines to Chicago that are departing in the next 10 days.
6/4Tue
multi-stopSouthwest
8h 05mDSM-MDW
6/7Fri
multi-stopSouthwest
6h 20mMDW-DSM
$411
6/4Tue
multi-stopSouthwest
9h 10mDSM-MDW
6/7Fri
multi-stopSouthwest
11h 00mMDW-DSM
$416
6/4Tue
multi-stopSouthwest
6h 15mDSM-MDW
6/7Fri
multi-stopSouthwest
11h 00mMDW-DSM
$421
6/1Sat
multi-stopDelta
3h 53mDSM-MDW
6/5Wed
multi-stopDelta
6h 43mMDW-DSM
$444
5/31Fri
multi-stopDelta
5h 02mDSM-MDW
6/5Wed
multi-stopDelta
6h 43mMDW-DSM
$485
5/31Fri
multi-stopDelta
5h 02mDSM-MDW
6/3Mon
multi-stopDelta
6h 43mMDW-DSM
$526
6/2Sun
multi-stopDelta
6h 10mDSM-MDW
6/5Wed
multi-stopDelta
6h 43mMDW-DSM
$541
6/2Sun
multi-stopDelta
6h 10mDSM-MDW
6/7Fri
multi-stopDelta
6h 38mMDW-DSM
$566
6/1Sat
multi-stopDelta
3h 53mDSM-MDW
6/6Thu
multi-stopDelta
3h 39mMDW-DSM
$581
6/4Tue
multi-stopSouthwest
9h 05mDSM-MDW
6/15Sat
multi-stopSouthwest
7h 15mMDW-DSM
$603

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Des Moines - Chicago Midway Airport Flights

Departure:

Des Moines (DSM)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Des Moines

Cabin classes: