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Cheap flights from Iowa to Chicago from $107

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 5/11. 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.
Delta Logo
12:34 pm - 6:36 pm
CID
-
MDW
6h 02m
1 stop
Delta Logo
7:13 pm - 11:07 pm
MDW
-
CID
3h 54m
1 stop
$259Delta
Sat, May 2 - Sat, May 23
Delta Logo
6:45 am - 12:43 pm
CID
-
MDW
5h 58m
2 stops
Delta Logo
7:13 pm - 11:07 pm
MDW
-
CID
3h 54m
1 stop
$264Delta
Sat, May 2 - Sat, May 23
Southwest Logo
5:15 am - 6:40 am
OMA
-
MDW
1h 25mnonstop
Southwest Logo
11:50 am - 1:20 pm
MDW
-
OMA
1h 30mnonstop
$265Southwest
Sat, May 2 - Mon, May 4
Southwest Logo
5:30 am - 6:55 am
DSM
-
MDW
1h 25mnonstop
Southwest Logo
8:50 pm - 10:10 pm
MDW
-
DSM
1h 20mnonstop
$269Southwest
Wed, May 27 - Wed, Jun 3
Delta Logo
6:45 am - 12:43 pm
CID
-
MDW
5h 58m
2 stops
Delta Logo
9:22 am - 3:31 pm
MDW
-
CID
6h 09m
2 stops
$269Delta
Sat, May 2 - Sat, May 23
Delta Logo
12:34 pm - 6:36 pm
CID
-
MDW
6h 02m
1 stop
Delta Logo
7:16 pm - 10:52 pm
MDW
-
CID
3h 36m
1 stop
$274Delta
Thu, Apr 30 - Mon, May 4
Southwest Logo
5:30 am - 6:55 am
OMA
-
MDW
1h 25mnonstop
Southwest Logo
10:15 am - 11:45 am
MDW
-
OMA
1h 30mnonstop
$275Southwest
Tue, May 5 - Wed, May 6
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
$279Southwest
Wed, May 27 - Wed, Jun 3
Delta Logo
12:34 pm - 6:36 pm
CID
-
MDW
6h 02m
1 stop
Delta Logo
7:13 pm - 11:07 pm
MDW
-
CID
3h 54m
1 stop
$279Delta
Wed, May 6 - Tue, May 12
Multiple Airlines Logo
12:43 pm - 4:13 pm
LSE
-
MDW
27h 30m
2 stops
Multiple Airlines Logo
6:20 am - 11:53 am
MDW
-
LSE
29h 33m
1 stop
$442Multiple Airlines
Fri, Apr 24 - Sun, Apr 26

Frontier flights from Iowa to Chicago Midway Airport

Our best Frontier deals on Iowa to Chicago Midway Airport flight tickets
Frontier
Apr 27
DSM2:04 pmDes Moines
29h 27m
2 stops
MDW7:31 pmChicago Midway
Apr 30
MDW2:15 pmChicago Midway
22h 54m
2 stops
DSM1:09 pmDes Moines
$312
Frontier
Apr 24
OMA4:04 pmOmaha Eppley Airfield
6h 22m
1 stop
MDW10:26 pmChicago Midway
Apr 27
MDW6:00 amChicago Midway
9h 24m
1 stop
OMA3:24 pmOmaha Eppley Airfield
$361

Southwest flights from Iowa to Chicago Midway Airport

Our best Southwest deals on Iowa to Chicago Midway Airport flight tickets
Southwest
May 2
OMA5:15 amOmaha Eppley Airfield
1h 25m
MDW6:40 amChicago Midway
May 4
MDW11:50 amChicago Midway
1h 30m
OMA1:20 pmOmaha Eppley Airfield
$265
Southwest
May 27
DSM5:30 amDes Moines
1h 25m
MDW6:55 amChicago Midway
Jun 3
MDW8:50 pmChicago Midway
1h 20m
DSM10:10 pmDes Moines
$269
Southwest
May 5
OMA5:30 amOmaha Eppley Airfield
1h 25m
MDW6:55 amChicago Midway
May 6
MDW10:15 amChicago Midway
1h 30m
OMA11:45 amOmaha Eppley Airfield
$275

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 April 15, 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

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Sat 5/2

12:34 pm-6:36 pm

1 stop6h 02m

Chicago Midway

Sat 5/23

7:13 pm-11:07 pm

1 stop3h 54m

$259

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Sat 5/2

6:45 am-12:43 pm

2 stops5h 58m

Chicago Midway

Sat 5/23

7:13 pm-11:07 pm

1 stop3h 54m

$264

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 5/2

5:15 am-6:40 am

Nonstop1h 25m

Chicago Midway

Mon 5/4

11:50 am-1:20 pm

Nonstop1h 30m

$265
Quickest round-trip

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 5/27

5:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Wed 6/3

8:50 pm-10:10 pm

Nonstop1h 20m

$269

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Sat 5/2

6:45 am-12:43 pm

2 stops5h 58m

Chicago Midway

Sat 5/23

9:22 am-3:31 pm

2 stops6h 09m

$269

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Thu 4/30

12:34 pm-6:36 pm

1 stop6h 02m

Chicago Midway

Mon 5/4

7:16 pm-10:52 pm

1 stop3h 36m

$274

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Tue 5/5

5:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Wed 5/6

10:15 am-11:45 am

Nonstop1h 30m

$275

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 5/27

5:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Wed 6/3

6:30 am-2:05 pm

1 stop7h 35m

$279

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Wed 5/6

12:34 pm-6:36 pm

1 stop6h 02m

Chicago Midway

Tue 5/12

7:13 pm-11:07 pm

1 stop3h 54m

$279

La CrosseChicago

LSE - MDW

LSEMDW

La Crosse

Fri 4/24

12:43 pm-4:13 pm

2 stops27h 30m

Chicago Midway

Sun 4/26

6:20 am-11:53 am

1 stop29h 33m

$442

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 $415. 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 $492.

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 $432 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $454. 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.

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

No. A direct flight is the cheapest option for a flight between Iowa to Chicago Midway Airport.

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

$239

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 $239. The best round-trip flight deal from Iowa to Chicago Midway Airport found on momondo in the last 72 hours is $344.
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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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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