DSM - MDW

$119 Find Cheap Flights from Des Moines to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$237
Typical prices: $273-$481
Southwest
Sat 12/15Sat 12/22
DSM - MDW • Non-stop
Cheapest one-way
$119
Typical prices: $178-$292
Southwest
Sun 12/23
DSM - MDW • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 1h 24m
Direct flights
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Direct flights
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When to travel
Cheapest • 23% price drop
Most popular
Good to know
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Good to know
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Booking Insights
Flight Deals

Cheap Flights from Des Moines to Midway (DSM-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Des Moines to Midway

Tue, Dec 15 - Tue, Dec 22
Southwest Logo
6:00 am - 7:25 amDSM  Des Moines-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
9:55 am - 11:15 amMDW  Chicago Midway-DSM Des Moines
1h 20mnonstop
$237Southwest
Fri, Dec 18 - Fri, Dec 25
Southwest Logo
7:15 pm - 8:35 pmDSM  Des Moines-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
10:05 am - 11:25 amMDW  Chicago Midway-DSM Des Moines
1h 20mnonstop
$237Southwest
Sat, Feb 13 - Thu, Feb 25
Southwest Logo
3:25 pm - 4:40 pmDSM  Des Moines-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
9:45 pm - 11:05 pmMDW  Chicago Midway-DSM Des Moines
1h 20mnonstop
$237Southwest
Wed, Dec 23 - Wed, Dec 23
Southwest Logo
5:10 am - 6:30 amDSM  Des Moines-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
10:05 pm - 11:35 pmMDW  Chicago Midway-DSM Des Moines
1h 30mnonstop
$237Southwest
Sat, Dec 5 - Mon, Dec 7
Southwest Logo
12:45 pm - 2:10 pmDSM  Des Moines-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
8:40 pm - 10:05 pmMDW  Chicago Midway-DSM Des Moines
1h 25mnonstop
$237Southwest
Thu, Dec 3 - Mon, Dec 7
Southwest Logo
6:00 am - 7:25 amDSM  Des Moines-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
8:40 pm - 10:05 pmMDW  Chicago Midway-DSM Des Moines
1h 25mnonstop
$237Southwest
Thu, Dec 3 - Thu, Dec 10
Delta Logo
11:01 am - 4:50 pmDSM  Des Moines-MDW Chicago Midway
5h 49m1 stop Minneapolis St Paul
Delta Logo
10:24 am - 4:11 pmMDW  Chicago Midway-DSM Des Moines
5h 47m1 stop Minneapolis St Paul
$257Delta
Wed, Nov 25 - Tue, Dec 1
Delta Logo
11:00 am - 4:39 pmDSM  Des Moines-MDW Chicago Midway
5h 39m1 stop Minneapolis St Paul
Delta Logo
5:30 pm - 9:31 pmMDW  Chicago Midway-DSM Des Moines
4h 01m1 stop Minneapolis St Paul
$257Delta
Wed, Nov 25 - Wed, Dec 2
Delta Logo
11:00 am - 4:39 pmDSM  Des Moines-MDW Chicago Midway
5h 39m1 stop Minneapolis St Paul
Delta Logo
10:24 am - 4:11 pmMDW  Chicago Midway-DSM Des Moines
5h 47m1 stop Minneapolis St Paul
$257Delta
Tue, Nov 24 - Tue, Dec 1
Delta Logo
11:00 am - 4:39 pmDSM  Des Moines-MDW Chicago Midway
5h 39m1 stop Minneapolis St Paul
Delta Logo
5:30 pm - 9:31 pmMDW  Chicago Midway-DSM Des Moines
4h 01m1 stop Minneapolis St Paul
$257Delta
Booking Insights

Price, demand and travel trends for Des Moines to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Des Moines to Chicago Midway Airport?

Round-trip flights from Des Moines to Chicago Midway Airport typically range from $273 to $481. The lowest price found in the past 5 days was $237, on Southwest.

What's the cheapest day of the week to fly from Des Moines to Chicago Midway Airport?

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Des Moines to Chicago Midway Airport. It’s 24% cheaper than the average day, while Friday is the most expensive, with prices 25% higher.

Key details for Des Moines to Chicago Midway Airport flights

Cheapest flight

$119
The most popular month to fly with an average 26% increase in travelers.
One-way 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

Your Des Moines to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Des Moines to Chicago Midway Airport?

    These are the earliest and latest flight times available from Des Moines to Chicago Midway Airport:

    • Earliest: departs at 5:10 am and lands at 6:34 am
    • Latest: departs at 7:15 pm and lands at 8:39 pm.

    The flight takes about 1h 24m.

  • What cabin classes can I book on flights from Des Moines to Chicago Midway Airport?

    Only Economy Class is available on flights from Des Moines to Chicago Midway Airport.

  • How long is a flight from Des Moines to Chicago Midway Airport?

    A nonstop flight from Des Moines to Chicago Midway Airport takes 1h 24m, covering 305 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Des Moines to Chicago Midway Airport flight?

    Round-trip flights from Des Moines to Chicago Midway Airport range from $273 to $481, with an average of $339 over the past 12 months. Anything below $273 counts as a good deal.

  • How much can I save by taking a layover when flying from Des Moines to Chicago Midway Airport?

    On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $329 round-trip, compared to $401 via a layover through Detroit Metropolitan Wayne County (DTW).

  • What is the standard checked-bag allowance on flights from Des Moines to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Des Moines to Chicago Midway Airport?

    The Canadair (Bombardier) Regional Jet 700 family is used most often on this route, operated mainly by American Airlines. Other aircraft seen on the route include Embraer 175 variants.

  • How are flight departures from Des Moines to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on Des Moines to Chicago Midway Airport flights, with 50% of flights leaving in that window. Afternoon departures account for 50%, evening flights for 0%, and night flights for 0%.

  • Have flight prices from Des Moines to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $237 to $1,568. That means the highest observed fare was about 7x higher than the lowest one.

  • How are flight prices from Des Moines to Chicago Midway Airport looking right now?

    One-way fares from Des Moines to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $121, which is 55% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Des Moines to Chicago Midway Airport?

    Flights from Des Moines to Chicago Midway Airport usually depart from Des Moines (DSM) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from Des Moines to Chicago Midway Airport pass through?

    Most connecting flights from Des Moines to Chicago Midway Airport pass through Detroit Metropolitan Wayne County (DTW), which handles 100% of one-stop traffic on this route.

  • Can I save money by using flexible dates for flights from Des Moines to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 39% on flights from Des Moines to Chicago Midway Airport. Tuesday is the cheapest departure day at $261 round-trip on average, while Friday is the most expensive at $427, a difference of $166.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Des Moines to Chicago Midway Airport?

    Only Southwest operates flights between Des Moines and Chicago Midway Airport.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Des Moines to Chicago Midway Airport flights?

    Among airlines operating Des Moines to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Des Moines to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Des Moines to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Tuesday departure and avoid flying on Friday. On this route, Tuesday flights average $261, about $166 less than Friday fares (39% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Des Moines to Chicago Midway Airport trip for September. Fares historically average $261 round-trip in that month - typically $326 less than the most expensive month, which is October (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

Prefer to fly direct from Des Moines to Chicago Midway Airport?

 
Find which airlines fly direct from Des Moines Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Des Moines to Chicago Midway

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

Direct returns

Chicago Midway to Des Moines

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

More options for your flight from Des Moines to Midway

Complete your trip to Chicago with a hotel stay or car rental