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Cheap flights from Des Moines to Chicago from $129

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 6/17. 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
3:45 pm - 5:05 pm
DSM
-
MDW
1h 20mnonstop
Southwest Logo
9:20 pm - 10:45 pm
MDW
-
DSM
1h 25mnonstop
$257Southwest
Tue, Jun 9 - Wed, Jun 10
Southwest Logo
2:10 pm - 3:25 pm
DSM
-
MDW
1h 15mnonstop
Southwest Logo
10:05 am - 11:30 am
MDW
-
DSM
1h 25mnonstop
$263Southwest
Sat, Oct 31 - Tue, Nov 3
Southwest Logo
5:20 am - 6:40 am
DSM
-
MDW
1h 20mnonstop
Southwest Logo
7:00 am - 3:05 pm
MDW
-
DSM
8h 05m
1 stop
$267Southwest
Tue, Jun 16 - Tue, Jun 23
Southwest Logo
2:10 pm - 3:25 pm
DSM
-
MDW
1h 15mnonstop
Southwest Logo
8:05 am - 2:10 pm
MDW
-
DSM
6h 05m
1 stop
$273Southwest
Sat, Oct 31 - Tue, Nov 3
Delta Logo
2:45 pm - 6:18 pm
DSM
-
MDW
3h 33m
1 stop
Delta Logo
9:49 am - 2:05 pm
MDW
-
DSM
4h 16m
1 stop
$277Delta
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
1:50 pm - 7:35 pm
DSM
-
MDW
5h 45m
1 stop
Southwest Logo
8:05 am - 2:10 pm
MDW
-
DSM
6h 05m
1 stop
$283Southwest
Thu, Oct 29 - Tue, Nov 3
Southwest Logo
5:40 am - 7:00 am
DSM
-
MDW
1h 20mnonstop
Southwest Logo
10:15 am - 8:45 pm
MDW
-
DSM
10h 30m
2 stops
$284Southwest
Sat, Oct 31 - Tue, Nov 3
Southwest Logo
3:35 pm - 5:00 pm
DSM
-
MDW
1h 25mnonstop
Southwest Logo
10:10 am - 11:30 am
MDW
-
DSM
1h 20mnonstop
$293Southwest
Sat, Jun 20 - Tue, Jun 23
Southwest Logo
1:50 pm - 7:35 pm
DSM
-
MDW
5h 45m
1 stop
Southwest Logo
10:15 am - 8:45 pm
MDW
-
DSM
10h 30m
2 stops
$294Southwest
Thu, Oct 29 - Tue, Nov 3
Southwest Logo
5:40 am - 7:00 am
DSM
-
MDW
1h 20mnonstop
Southwest Logo
9:15 pm - 10:35 pm
MDW
-
DSM
1h 20mnonstop
$299Southwest
Thu, Aug 6 - Sun, Aug 16

Southwest flights from Des Moines to Chicago Midway Airport

Our best Southwest deals on Des Moines to Chicago Midway Airport flight tickets
Southwest
Jun 9
DSM3:45 pmDes Moines
1h 20m
MDW5:05 pmChicago Midway
Jun 10
MDW9:20 pmChicago Midway
1h 25m
DSM10:45 pmDes Moines
$257
Southwest
Oct 31
DSM2:10 pmDes Moines
1h 15m
MDW3:25 pmChicago Midway
Nov 3
MDW10:05 amChicago Midway
1h 25m
DSM11:30 amDes Moines
$263
Southwest
Jun 16
DSM5:20 amDes Moines
1h 20m
MDW6:40 amChicago Midway
Jun 23
MDW7:00 amChicago Midway
8h 05m
1 stop
DSM3:05 pmDes Moines
$267

Delta flights from Des Moines to Chicago Midway Airport

Our best Delta deals on Des Moines to Chicago Midway Airport flight tickets
Delta
Jul 1
DSM2:45 pmDes Moines
3h 33m
1 stop
MDW6:18 pmChicago Midway
Jul 8
MDW9:49 amChicago Midway
4h 16m
1 stop
DSM2:05 pmDes Moines
$277
Delta
Sep 27
DSM6:20 amDes Moines
6h 10m
1 stop
MDW12:30 pmChicago Midway
Sep 29
MDW9:20 amChicago Midway
4h 47m
1 stop
DSM2:07 pmDes Moines
$313
Delta
Aug 6
DSM6:00 amDes Moines
6h 39m
1 stop
MDW12:39 pmChicago Midway
Aug 16
MDW1:27 pmChicago Midway
3h 44m
1 stop
DSM5:11 pmDes Moines
$319

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 May 22, 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

Cheapest round-trip

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 6/9

3:45 pm-5:05 pm

Nonstop1h 20m

Chicago Midway

Wed 6/10

9:20 pm-10:45 pm

Nonstop1h 25m

$257
Quickest round-trip

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 10/31

2:10 pm-3:25 pm

Nonstop1h 15m

Chicago Midway

Tue 11/3

10:05 am-11:30 am

Nonstop1h 25m

$263

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 6/16

5:20 am-6:40 am

Nonstop1h 20m

Chicago Midway

Tue 6/23

7:00 am-3:05 pm

1 stop8h 05m

$267

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 10/31

2:10 pm-3:25 pm

Nonstop1h 15m

Chicago Midway

Tue 11/3

8:05 am-2:10 pm

1 stop6h 05m

$273

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 7/1

2:45 pm-6:18 pm

1 stop3h 33m

Chicago Midway

Wed 7/8

9:49 am-2:05 pm

1 stop4h 16m

$277

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 10/29

1:50 pm-7:35 pm

1 stop5h 45m

Chicago Midway

Tue 11/3

8:05 am-2:10 pm

1 stop6h 05m

$283

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 10/31

5:40 am-7:00 am

Nonstop1h 20m

Chicago Midway

Tue 11/3

10:15 am-8:45 pm

2 stops10h 30m

$284

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 6/20

3:35 pm-5:00 pm

Nonstop1h 25m

Chicago Midway

Tue 6/23

10:10 am-11:30 am

Nonstop1h 20m

$293

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 10/29

1:50 pm-7:35 pm

1 stop5h 45m

Chicago Midway

Tue 11/3

10:15 am-8:45 pm

2 stops10h 30m

$294

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 8/6

5:40 am-7:00 am

Nonstop1h 20m

Chicago Midway

Sun 8/16

9:15 pm-10:35 pm

Nonstop1h 20m

$299

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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Des Moines. The lowest ticket price found for a Wednesday departure recently was $407. 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, Saturday 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 $462.

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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $431 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $450. 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 Airport flights?

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

Can stopping save me money on Des Moines to Chicago Midway Airport flights?

You could potentially save up to 22% on your flight if you consider stops on a Des Moines to Chicago Midway Airport flight.

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

$213

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 $213. The best round-trip flight deal from Des Moines to Chicago Midway Airport found on momondo in the last 72 hours is $386.
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

Frequently asked questions about flying from Des Moines to Chicago Midway Airport

  • 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?

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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.

An easier way to manage your Chicago Midway Airport trip

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