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Cheap flights from Des Moines to Chicago from $66

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Des Moines to Chicago departing on 4/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Des Moines to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:30 am - 6:50 am
DSM
-
MDW
1h 20mnonstop
Southwest Logo
8:40 pm - 10:05 pm
MDW
-
DSM
1h 25mnonstop
$157Southwest
Tue, Mar 31 - Wed, Apr 1
Southwest Logo
5:30 am - 6:50 am
DSM
-
MDW
1h 20mnonstop
Southwest Logo
5:55 am - 1:15 pm
MDW
-
DSM
7h 20m
1 stop
$167Southwest
Tue, Mar 31 - Wed, Apr 1
Southwest Logo
6:40 am - 4:10 pm
DSM
-
MDW
9h 30m
2 stops
Southwest Logo
8:40 pm - 10:05 pm
MDW
-
DSM
1h 25mnonstop
$172Southwest
Tue, Mar 31 - Wed, Apr 1
Delta Logo
6:15 am - 12:29 pm
DSM
-
MDW
6h 14m
1 stop
Delta Logo
9:30 am - 3:42 pm
MDW
-
DSM
6h 12m
1 stop
$177Delta
Wed, Apr 1 - Tue, Apr 7
Southwest Logo
3:40 pm - 4:55 pm
DSM
-
MDW
1h 15mnonstop
Southwest Logo
8:50 pm - 10:10 pm
MDW
-
DSM
1h 20mnonstop
$181Southwest
Tue, Mar 31 - Tue, Apr 7
Southwest Logo
6:40 am - 4:10 pm
DSM
-
MDW
9h 30m
2 stops
Southwest Logo
5:55 am - 1:15 pm
MDW
-
DSM
7h 20m
1 stop
$182Southwest
Tue, Mar 31 - Wed, Apr 1
Delta Logo
6:15 am - 12:29 pm
DSM
-
MDW
6h 14m
1 stop
Delta Logo
9:30 am - 3:42 pm
MDW
-
DSM
6h 12m
1 stop
$184Delta
Wed, Apr 1 - Sat, Apr 4
Southwest Logo
6:40 am - 4:10 pm
DSM
-
MDW
9h 30m
2 stops
Southwest Logo
8:50 pm - 10:10 pm
MDW
-
DSM
1h 20mnonstop
$186Southwest
Tue, Mar 31 - Tue, Apr 7
Southwest Logo
5:30 am - 6:55 am
DSM
-
MDW
1h 25mnonstop
Southwest Logo
10:20 am - 11:45 am
MDW
-
DSM
1h 25mnonstop
$187Southwest
Tue, Apr 7 - Fri, Apr 10
Southwest Logo
3:40 pm - 4:55 pm
DSM
-
MDW
1h 15mnonstop
Southwest Logo
6:30 am - 2:05 pm
MDW
-
DSM
7h 35m
1 stop
$191Southwest
Tue, Mar 31 - Tue, Apr 7

Southwest flights from Des Moines to Chicago Midway Airport

Our best Southwest deals on Des Moines to Chicago Midway Airport flight tickets
Southwest
Mar 31
DSM5:30 amDes Moines
1h 20m
MDW6:50 amChicago Midway
Apr 1
MDW8:40 pmChicago Midway
1h 25m
DSM10:05 pmDes Moines
$157
Southwest
Mar 31
DSM5:30 amDes Moines
1h 20m
MDW6:50 amChicago Midway
Apr 1
MDW5:55 amChicago Midway
7h 20m
1 stop
DSM1:15 pmDes Moines
$167
Southwest
Mar 31
DSM6:40 amDes Moines
9h 30m
2 stops
MDW4:10 pmChicago Midway
Apr 1
MDW8:40 pmChicago Midway
1h 25m
DSM10:05 pmDes Moines
$172

Delta flights from Des Moines to Chicago Midway Airport

Our best Delta deals on Des Moines to Chicago Midway Airport flight tickets
Delta
Apr 1
DSM6:15 amDes Moines
6h 14m
1 stop
MDW12:29 pmChicago Midway
Apr 7
MDW9:30 amChicago Midway
6h 12m
1 stop
DSM3:42 pmDes Moines
$177
Delta
Apr 1
DSM6:15 amDes Moines
6h 14m
1 stop
MDW12:29 pmChicago Midway
Apr 4
MDW9:30 amChicago Midway
6h 12m
1 stop
DSM3:42 pmDes Moines
$184
Delta
Mar 7
DSM10:57 amDes Moines
5h 17m
1 stop
MDW4:14 pmChicago Midway
Mar 9
MDW1:10 pmChicago Midway
3h 44m
1 stop
DSM4:54 pmDes Moines
$201

momondo Fare Finder

 
Customize your flight search to find flights from Des Moines to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 14, 2026.
Use the filters below to find and compare flights from Des Moines to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 3/31

5:30 am-6:50 am

Nonstop1h 20m

Chicago Midway

Wed 4/1

8:40 pm-10:05 pm

Nonstop1h 25m

$157

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 3/31

5:30 am-6:50 am

Nonstop1h 20m

Chicago Midway

Wed 4/1

5:55 am-1:15 pm

1 stop7h 20m

$167

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 3/31

6:40 am-4:10 pm

2 stops9h 30m

Chicago Midway

Wed 4/1

8:40 pm-10:05 pm

Nonstop1h 25m

$172

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 4/1

6:15 am-12:29 pm

1 stop6h 14m

Chicago Midway

Tue 4/7

9:30 am-3:42 pm

1 stop6h 12m

$177

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 3/31

3:40 pm-4:55 pm

Nonstop1h 15m

Chicago Midway

Tue 4/7

8:50 pm-10:10 pm

Nonstop1h 20m

$181

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 3/31

6:40 am-4:10 pm

2 stops9h 30m

Chicago Midway

Wed 4/1

5:55 am-1:15 pm

1 stop7h 20m

$182

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 4/1

6:15 am-12:29 pm

1 stop6h 14m

Chicago Midway

Sat 4/4

9:30 am-3:42 pm

1 stop6h 12m

$184

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 3/31

6:40 am-4:10 pm

2 stops9h 30m

Chicago Midway

Tue 4/7

8:50 pm-10:10 pm

Nonstop1h 20m

$186

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 4/7

5:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Fri 4/10

10:20 am-11:45 am

Nonstop1h 25m

$187

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 3/31

3:40 pm-4:55 pm

Nonstop1h 15m

Chicago Midway

Tue 4/7

6:30 am-2:05 pm

1 stop7h 35m

$191

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Des Moines to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Monday is the cheapest day to fly to Chicago Midway Airport from Des Moines. The lowest ticket price found for a Monday departure recently was $426. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Tuesday is the most expensive day to depart from Des Moines because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $790.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Des Moines in the morning is the least expensive time of day to depart. momondo users have found prices as low as $462 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $492. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Des Moines to Chicago Midway flight route?

Fly from Des Moines to Chicago Midway for the best Des Moines - Chicago Midway flight prices

What cabin class options are available on Des Moines to Chicago Midway flights?

There is only 1 cabin class available to choose from on Des Moines to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Des Moines to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Des Moines to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Des Moines to Chicago Midway Airport (DSM to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Des Moines to Chicago Midway Airport

Best Price Found

$198

Fastest flight time

1h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Des Moines in the past 72 hours is $198. The best round-trip flight deal from Des Moines to Chicago Midway Airport found on momondo in the last 72 hours is $392.
The fastest flight from Des Moines to Chicago Midway Airport takes 1h 20m
Direct flights go from Des Moines to Chicago Midway Airport every day.
Search flight deals

  • How far is Des Moines to Chicago Midway by plane?

    Chicago Midway is 303.6 mi away from Des Moines. 1h 20m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Des Moines Airport to Chicago Midway Airport?

    Prices for flights from Des Moines Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from Des Moines Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Des Moines Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Des Moines to Chicago Midway Airport?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Des Moines to Chicago?

Finding the right flight to Chicago from Des Moines is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Des Moines to Chicago with flexible booking policies on momondo?

Flights from Des Moines to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Des Moines to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Des Moines to Chicago.

I’m not ready to book a flight from Des Moines to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Des Moines and alert you when they change.

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