Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Des Moines to Chicago from $91

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 10/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Des Moines to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:30 pm - 6:08 pmDSM-MDW
5h 38m1 stop
Delta Logo
9:41 am - 2:08 pmMDW-DSM
4h 27m1 stop
$209Delta
Find Deal
Sat, Nov 15 - Sat, Nov 22
Delta Logo
6:05 am - 12:28 pmDSM-MDW
6h 23m1 stop
Delta Logo
3:00 pm - 9:03 pmMDW-DSM
6h 03m1 stop
$214Delta
Find Deal
Mon, Oct 20 - Sat, Oct 25
Delta Logo
6:05 am - 12:28 pmDSM-MDW
6h 23m1 stop
Delta Logo
1:48 pm - 5:16 pmMDW-DSM
3h 28m1 stop
$217Delta
Find Deal
Tue, Nov 4 - Wed, Nov 5
Southwest Logo
4:45 pm - 10:05 pmDSM-MDW
5h 20m1 stop
Southwest Logo
5:55 pm - 9:50 pmMDW-DSM
3h 55m1 stop
$219Southwest
Find Deal
Tue, Oct 14 - Wed, Oct 15
Southwest Logo
5:35 am - 3:15 pmDSM-MDW
9h 40m1 stop
Southwest Logo
3:00 pm - 9:50 pmMDW-DSM
6h 50m2 stops
$220Southwest
Find Deal
Mon, Oct 27 - Tue, Oct 28
Southwest Logo
4:45 pm - 10:25 pmDSM-MDW
5h 40m2 stops
Southwest Logo
7:40 am - 11:00 amMDW-DSM
3h 20m1 stop
$224Southwest
Find Deal
Tue, Oct 14 - Thu, Oct 16
Southwest Logo
5:35 am - 3:15 pmDSM-MDW
9h 40m1 stop
Southwest Logo
3:00 pm - 9:50 pmMDW-DSM
6h 50m2 stops
$225Southwest
Find Deal
Mon, Oct 20 - Tue, Oct 21
Multiple Airlines Logo
2:37 pm - 12:36 amDSM-MDW
9h 59m1 stop
Multiple Airlines Logo
5:28 pm - 6:00 pmMDW-DSM
24h 32m1 stop
$226Multiple Airlines
Find Deal
Thu, Oct 23 - Fri, Oct 24
Multiple Airlines Logo
7:30 am - 10:03 pmDSM-MDW
14h 33m2 stops
Multiple Airlines Logo
6:26 pm - 2:55 pmMDW-DSM
20h 29m1 stop
$250Multiple Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
Frontier Logo
2:37 pm - 12:24 amDSM-MDW
9h 47m1 stop
Frontier Logo
8:05 am - 1:52 pmMDW-DSM
29h 47m2 stops
$305Frontier
Find Deal
Fri, Oct 17 - Tue, Oct 21

Delta flights from Des Moines to Chicago Midway Airport

Our best Delta deals on Des Moines to Chicago Midway Airport flight tickets
Delta
Nov 15
DSM12:30 pmDes Moines
5h 38m
1 stop
MDW6:08 pmChicago Midway
Nov 22
MDW9:41 amChicago Midway
4h 27m
1 stop
DSM2:08 pmDes Moines
$209
Find similar
Delta
Oct 20
DSM6:05 amDes Moines
6h 23m
1 stop
MDW12:28 pmChicago Midway
Oct 25
MDW3:00 pmChicago Midway
6h 03m
1 stop
DSM9:03 pmDes Moines
$214
Find similar
Delta
Nov 4
DSM6:05 amDes Moines
6h 23m
1 stop
MDW12:28 pmChicago Midway
Nov 5
MDW1:48 pmChicago Midway
3h 28m
1 stop
DSM5:16 pmDes Moines
$217
Find similar

Southwest flights from Des Moines to Chicago Midway Airport

Our best Southwest deals on Des Moines to Chicago Midway Airport flight tickets
Southwest
Oct 14
DSM4:45 pmDes Moines
5h 20m
1 stop
MDW10:05 pmChicago Midway
Oct 15
MDW5:55 pmChicago Midway
3h 55m
1 stop
DSM9:50 pmDes Moines
$219
Find similar
Southwest
Oct 27
DSM5:35 amDes Moines
9h 40m
1 stop
MDW3:15 pmChicago Midway
Oct 28
MDW3:00 pmChicago Midway
6h 50m
2 stops
DSM9:50 pmDes Moines
$220
Find similar
Southwest
Oct 14
DSM4:45 pmDes Moines
5h 40m
2 stops
MDW10:25 pmChicago Midway
Oct 16
MDW7:40 amChicago Midway
3h 20m
1 stop
DSM11:00 amDes Moines
$224
Find similar

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 October 2, 2025.
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

Sat 11/15

12:30 pm-6:08 pm

1 stop5h 38m

Chicago Midway

Sat 11/22

9:41 am-2:08 pm

1 stop4h 27m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Mon 10/20

6:05 am-12:28 pm

1 stop6h 23m

Chicago Midway

Sat 10/25

3:00 pm-9:03 pm

1 stop6h 03m

$214

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 11/4

6:05 am-12:28 pm

1 stop6h 23m

Chicago Midway

Wed 11/5

1:48 pm-5:16 pm

1 stop3h 28m

$217

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 10/14

4:45 pm-10:05 pm

1 stop5h 20m

Chicago Midway

Wed 10/15

5:55 pm-9:50 pm

1 stop3h 55m

$219

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Mon 10/27

5:35 am-3:15 pm

1 stop9h 40m

Chicago Midway

Tue 10/28

3:00 pm-9:50 pm

2 stops6h 50m

$220

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 10/14

4:45 pm-10:25 pm

2 stops5h 40m

Chicago Midway

Thu 10/16

7:40 am-11:00 am

1 stop3h 20m

$224

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Mon 10/20

5:35 am-3:15 pm

1 stop9h 40m

Chicago Midway

Tue 10/21

3:00 pm-9:50 pm

2 stops6h 50m

$225

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 10/23

2:37 pm-12:36 am

1 stop9h 59m

Chicago Midway

Fri 10/24

5:28 pm-6:00 pm

1 stop24h 32m

$226

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 10/30

7:30 am-10:03 pm

2 stops14h 33m

Chicago Midway

Thu 11/6

6:26 pm-2:55 pm

1 stop20h 29m

$250

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 10/17

2:37 pm-12:24 am

1 stop9h 47m

Chicago Midway

Tue 10/21

8:05 am-1:52 pm

2 stops29h 47m

$305

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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

Fastest flight time

1h 20m

Direct flights

Mon and Tue
The fastest flight from Des Moines to Chicago Midway Airport takes 1h 20m
Direct flights go from Des Moines to Chicago Midway Airport on Monday and Tuesday. There are no airlines offering direct flights.
Search flight deals

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

    Chicago Midway is 303.6 mi away from Des Moines. 3h 15m 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 11/1
Sat 11/8
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago