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Cheap flights from Iowa to Chicago from $72

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Iowa to Chicago departing on 5/16. 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 Iowa to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:30 am - 6:55 am
DSM
-
MDW
1h 25mnonstop
Southwest Logo
8:50 pm - 10:10 pm
MDW
-
DSM
1h 20mnonstop
$157Southwest
Wed, Apr 8 - Wed, Apr 15
Southwest Logo
4:20 pm - 5:40 pm
DSM
-
MDW
1h 20mnonstop
Southwest Logo
1:55 pm - 8:55 pm
MDW
-
DSM
7h 00m
1 stop
$160Southwest
Fri, May 1 - Sat, May 2
Frontier Logo
4:04 pm - 10:26 pm
OMA
-
MDW
6h 22m
1 stop
Frontier Logo
6:00 am - 3:24 pm
MDW
-
OMA
9h 24m
1 stop
$160Frontier
Fri, Apr 24 - Mon, Apr 27
Southwest Logo
5:25 am - 6:45 am
DSM
-
MDW
1h 20mnonstop
Southwest Logo
10:20 am - 11:45 am
MDW
-
DSM
1h 25mnonstop
$168Southwest
Thu, Apr 9 - Mon, Apr 13
Southwest Logo
3:40 pm - 4:55 pm
DSM
-
MDW
1h 15mnonstop
Southwest Logo
8:40 pm - 10:05 pm
MDW
-
DSM
1h 25mnonstop
$169Southwest
Tue, Mar 24 - Tue, Mar 31
Delta Logo
6:15 am - 12:29 pm
DSM
-
MDW
6h 14m
1 stop
Delta Logo
1:10 pm - 4:54 pm
MDW
-
DSM
3h 44m
1 stop
$177Delta
Wed, Apr 1 - Sat, Apr 4
Southwest Logo
5:30 am - 6:55 am
DSM
-
MDW
1h 25mnonstop
Southwest Logo
6:30 am - 2:05 pm
MDW
-
DSM
7h 35m
1 stop
$179Southwest
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
5:25 am - 6:45 am
DSM
-
MDW
1h 20mnonstop
Southwest Logo
9:45 pm - 11:05 pm
MDW
-
DSM
1h 20mnonstop
$180Southwest
Thu, Apr 9 - Thu, Apr 16
Delta Logo
6:45 am - 1:25 pm
CID
-
MDW
6h 40m
1 stop
Delta Logo
7:20 pm - 10:52 pm
MDW
-
CID
3h 32m
1 stop
$199Delta
Tue, Mar 17 - Tue, Mar 24
Allegiant Air Logo
5:23 pm - 8:34 am
MLI
-
MDW
15h 11m
1 stop
Allegiant Air Logo
9:16 am - 9:09 am
MDW
-
MLI
23h 53m
1 stop
$564Allegiant Air
Wed, Mar 25 - Thu, Apr 2

Delta flights from Iowa to Chicago Midway Airport

Our best Delta deals on Iowa to Chicago Midway Airport flight tickets
Delta
Apr 1
DSM6:15 amDes Moines
6h 14m
1 stop
MDW12:29 pmChicago Midway
Apr 4
MDW1:10 pmChicago Midway
3h 44m
1 stop
DSM4:54 pmDes Moines
$177
Delta
Mar 17
CID6:45 amCedar Rapids
6h 40m
1 stop
MDW1:25 pmChicago Midway
Mar 24
MDW7:20 pmChicago Midway
3h 32m
1 stop
CID10:52 pmCedar Rapids
$199
Delta
Apr 7
CID6:45 amCedar Rapids
5h 44m
2 stops
MDW12:29 pmChicago Midway
Apr 14
MDW7:16 pmChicago Midway
3h 36m
1 stop
CID10:52 pmCedar Rapids
$204

Southwest flights from Iowa to Chicago Midway Airport

Our best Southwest deals on Iowa to Chicago Midway Airport flight tickets
Southwest
Apr 8
DSM5:30 amDes Moines
1h 25m
MDW6:55 amChicago Midway
Apr 15
MDW8:50 pmChicago Midway
1h 20m
DSM10:10 pmDes Moines
$157
Southwest
May 1
DSM4:20 pmDes Moines
1h 20m
MDW5:40 pmChicago Midway
May 2
MDW1:55 pmChicago Midway
7h 00m
1 stop
DSM8:55 pmDes Moines
$160
Southwest
Apr 2
DSM5:35 amDes Moines
1h 20m
MDW6:55 amChicago Midway
Apr 8
MDW6:30 amChicago Midway
7h 35m
1 stop
DSM2:05 pmDes Moines
$167

momondo Fare Finder

 
Customize your flight search to find flights from Iowa 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 24, 2026.
Use the filters below to find and compare flights from Iowa to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 4/8

5:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Wed 4/15

8:50 pm-10:10 pm

Nonstop1h 20m

$157

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 5/1

4:20 pm-5:40 pm

Nonstop1h 20m

Chicago Midway

Sat 5/2

1:55 pm-8:55 pm

1 stop7h 00m

$160

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Fri 4/24

4:04 pm-10:26 pm

1 stop6h 22m

Chicago Midway

Mon 4/27

6:00 am-3:24 pm

1 stop9h 24m

$160

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 4/9

5:25 am-6:45 am

Nonstop1h 20m

Chicago Midway

Mon 4/13

10:20 am-11:45 am

Nonstop1h 25m

$168

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 3/24

3:40 pm-4:55 pm

Nonstop1h 15m

Chicago Midway

Tue 3/31

8:40 pm-10:05 pm

Nonstop1h 25m

$169

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 4/1

6:15 am-12:29 pm

1 stop6h 14m

Chicago Midway

Sat 4/4

1:10 pm-4:54 pm

1 stop3h 44m

$177

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 4/7

5:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Tue 4/14

6:30 am-2:05 pm

1 stop7h 35m

$179

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 4/9

5:25 am-6:45 am

Nonstop1h 20m

Chicago Midway

Thu 4/16

9:45 pm-11:05 pm

Nonstop1h 20m

$180

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Tue 3/17

6:45 am-1:25 pm

1 stop6h 40m

Chicago Midway

Tue 3/24

7:20 pm-10:52 pm

1 stop3h 32m

$199

MolineChicago

MLI - MDW

MLIMDW

Moline Quad-City

Wed 3/25

5:23 pm-8:34 am

1 stop15h 11m

Chicago Midway

Thu 4/2

9:16 am-9:09 am

1 stop23h 53m

$564

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 Iowa 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 Iowa. 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 Iowa because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $527.

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

Flying to Chicago Midway Airport from Iowa in the morning is the least expensive time of day to depart. momondo users have found prices as low as $458 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $469. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Iowa to Chicago Midway flight route?

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

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

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

Cheap Iowa to Chicago Midway Airport flight deals and tips

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

Best Price Found

$185

Fastest flight time

1h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Iowa in the past 72 hours is $185. The best round-trip flight deal from Iowa to Chicago Midway Airport found on momondo in the last 72 hours is $392.
The fastest flight from Iowa to Chicago Midway Airport takes 1h 15m
Direct flights go from Iowa to Chicago Midway Airport every day.
Search flight deals

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

    Prices for flights from Iowa to Chicago Midway Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Iowa to Chicago Midway Airport?

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Iowa to Chicago Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

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
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Iowa to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo enables you to select and highlight flights to Chicago from Iowa with this policy.

How can momondo help me find flights from Iowa to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Iowa.

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

Of course. momondo tracks the price of Iowa to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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