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Cheap flights from Iowa to Chicago from $105

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 8/19. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Iowa to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:10 am - 7:30 am
DSM
-
MDW
1h 20mnonstop
Southwest Logo
10:10 am - 11:30 am
MDW
-
DSM
1h 20mnonstop
$208Southwest
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
12:10 pm - 1:30 pm
DSM
-
MDW
1h 20mnonstop
Southwest Logo
10:10 am - 11:30 am
MDW
-
DSM
1h 20mnonstop
$209Southwest
Sat, Aug 22 - Sat, Aug 29
Southwest Logo
5:40 am - 7:00 am
DSM
-
MDW
1h 20mnonstop
Southwest Logo
10:05 am - 11:25 am
MDW
-
DSM
1h 20mnonstop
$210Southwest
Mon, Aug 24 - Thu, Aug 27
Southwest Logo
2:40 pm - 4:00 pm
DSM
-
MDW
1h 20mnonstop
Southwest Logo
10:30 am - 11:50 am
MDW
-
DSM
1h 20mnonstop
$218Southwest
Tue, Aug 4 - Tue, Aug 11
Southwest Logo
2:25 pm - 10:00 pm
DSM
-
MDW
7h 35m
1 stop
Southwest Logo
10:05 am - 11:25 am
MDW
-
DSM
1h 20mnonstop
$219Southwest
Mon, Aug 24 - Mon, Aug 31
Southwest Logo
3:50 pm - 5:10 pm
DSM
-
MDW
1h 20mnonstop
Southwest Logo
2:15 pm - 9:00 pm
MDW
-
DSM
6h 45m
1 stop
$220Southwest
Thu, Aug 27 - Tue, Sep 1
Delta Logo
6:00 am - 12:39 pm
DSM
-
MDW
6h 39m
1 stop
Delta Logo
1:25 pm - 5:18 pm
MDW
-
DSM
3h 53m
1 stop
$227Delta
Sat, Aug 22 - Sat, Aug 29
Delta Logo
12:29 pm - 6:01 pm
CID
-
MDW
5h 32m
1 stop
Delta Logo
9:59 am - 3:35 pm
MDW
-
CID
5h 36m
1 stop
$259Delta
Mon, Aug 17 - Thu, Aug 27
Delta Logo
6:46 am - 1:09 pm
CID
-
MDW
6h 23m
1 stop
Delta Logo
7:06 pm - 10:50 pm
MDW
-
CID
3h 44m
1 stop
$309Delta
Sat, Jul 25 - Mon, Jul 27
Multiple Airlines Logo
3:01 pm - 9:51 am
CID
-
MDW
18h 50m
2 stops
Multiple Airlines Logo
9:14 am - 8:38 am
MDW
-
CID
23h 24m
1 stop
$454Multiple Airlines
Tue, Aug 4 - Thu, Aug 6

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Southwest flights from Iowa to Chicago Midway Airport

Our best Southwest deals on Iowa to Chicago Midway Airport flight tickets
Southwest
Aug 26
DSM6:10 amDes Moines
1h 20m
MDW7:30 amChicago Midway
Aug 29
MDW10:10 amChicago Midway
1h 20m
DSM11:30 amDes Moines
$208
Southwest
Aug 22
DSM12:10 pmDes Moines
1h 20m
MDW1:30 pmChicago Midway
Aug 29
MDW10:10 amChicago Midway
1h 20m
DSM11:30 amDes Moines
$209
Southwest
Aug 24
DSM5:40 amDes Moines
1h 20m
MDW7:00 amChicago Midway
Aug 27
MDW10:05 amChicago Midway
1h 20m
DSM11:25 amDes Moines
$210

Delta flights from Iowa to Chicago Midway Airport

Our best Delta deals on Iowa to Chicago Midway Airport flight tickets
Delta
Aug 22
DSM6:00 amDes Moines
6h 39m
1 stop
MDW12:39 pmChicago Midway
Aug 29
MDW1:25 pmChicago Midway
3h 53m
1 stop
DSM5:18 pmDes Moines
$227
Delta
Aug 17
CID12:29 pmCedar Rapids
5h 32m
1 stop
MDW6:01 pmChicago Midway
Aug 27
MDW9:59 amChicago Midway
5h 36m
1 stop
CID3:35 pmCedar Rapids
$259
Delta
Aug 6
DSM6:00 amDes Moines
6h 39m
1 stop
MDW12:39 pmChicago Midway
Aug 11
MDW1:25 pmChicago Midway
3h 46m
1 stop
DSM5:11 pmDes Moines
$289

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 July 10, 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

Cheapest round-trip
Quickest round-trip

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 8/26

6:10 am-7:30 am

Nonstop1h 20m

Chicago Midway

Sat 8/29

10:10 am-11:30 am

Nonstop1h 20m

$208

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 8/22

12:10 pm-1:30 pm

Nonstop1h 20m

Chicago Midway

Sat 8/29

10:10 am-11:30 am

Nonstop1h 20m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Mon 8/24

5:40 am-7:00 am

Nonstop1h 20m

Chicago Midway

Thu 8/27

10:05 am-11:25 am

Nonstop1h 20m

$210

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 8/4

2:40 pm-4:00 pm

Nonstop1h 20m

Chicago Midway

Tue 8/11

10:30 am-11:50 am

Nonstop1h 20m

$218

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Mon 8/24

2:25 pm-10:00 pm

1 stop7h 35m

Chicago Midway

Mon 8/31

10:05 am-11:25 am

Nonstop1h 20m

$219

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 8/27

3:50 pm-5:10 pm

Nonstop1h 20m

Chicago Midway

Tue 9/1

2:15 pm-9:00 pm

1 stop6h 45m

$220

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 8/22

6:00 am-12:39 pm

1 stop6h 39m

Chicago Midway

Sat 8/29

1:25 pm-5:18 pm

1 stop3h 53m

$227

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Mon 8/17

12:29 pm-6:01 pm

1 stop5h 32m

Chicago Midway

Thu 8/27

9:59 am-3:35 pm

1 stop5h 36m

$259

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Sat 7/25

6:46 am-1:09 pm

1 stop6h 23m

Chicago Midway

Mon 7/27

7:06 pm-10:50 pm

1 stop3h 44m

$309

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Tue 8/4

3:01 pm-9:51 am

2 stops18h 50m

Chicago Midway

Thu 8/6

9:14 am-8:38 am

1 stop23h 24m

$454

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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Iowa. The lowest ticket price found for a Wednesday departure recently was $387. 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 Iowa 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 Iowa in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $429 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $451. 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 Airport flights?

There is only 1 cabin class available to choose from on Iowa 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.

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

$229

Fastest flight time

1h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Iowa in the past 72 hours is $229. The best round-trip flight deal from Iowa to Chicago Midway Airport found on momondo in the last 72 hours is $391.
The fastest flight from Iowa to Chicago Midway Airport takes 1h 20m
Direct flights go from Iowa to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Iowa to Chicago Midway Airport

  • 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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