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Cheap flights from Iowa to Chicago from $81

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 2/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

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Southwest Logo
3:00 pm - 4:30 pm
OMA
-
MDW
1h 30mnonstop
Southwest Logo
8:20 am - 10:00 am
MDW
-
OMA
1h 40mnonstop
$195Southwest
Sat, Jan 17 - Sat, Jan 24
Southwest Logo
7:20 am - 9:00 am
OMA
-
MDW
1h 40mnonstop
Southwest Logo
1:20 pm - 2:50 pm
MDW
-
OMA
1h 30mnonstop
$197Southwest
Sat, Jan 17 - Sun, Jan 18
Delta Logo
6:30 am - 1:09 pm
CID
-
MDW
6h 39m1 stop
Delta Logo
9:50 am - 3:35 pm
MDW
-
CID
5h 45m1 stop
$199Delta
Mon, Jan 19 - Mon, Jan 26
Delta Logo
6:30 am - 1:09 pm
CID
-
MDW
6h 39m1 stop
Delta Logo
9:33 am - 3:35 pm
MDW
-
CID
6h 02m2 stops
$204Delta
Mon, Jan 19 - Mon, Jan 26
Southwest Logo
7:20 am - 9:00 am
OMA
-
MDW
1h 40mnonstop
Southwest Logo
9:05 am - 2:10 pm
MDW
-
OMA
5h 05m1 stop
$205Southwest
Sat, Jan 17 - Sat, Jan 24
Southwest Logo
5:40 am - 3:20 pm
OMA
-
MDW
9h 40m1 stop
Southwest Logo
8:25 am - 10:05 am
MDW
-
OMA
1h 40mnonstop
$207Southwest
Sat, Jan 17 - Sun, Jan 18
Delta Logo
12:25 pm - 5:55 pm
DSM
-
MDW
5h 30m1 stop
Delta Logo
9:53 am - 3:41 pm
MDW
-
DSM
5h 48m1 stop
$209Delta
Wed, Feb 4 - Wed, Feb 11
Delta Logo
6:30 am - 12:46 pm
CID
-
MDW
6h 16m2 stops
Delta Logo
9:33 am - 3:35 pm
MDW
-
CID
6h 02m2 stops
$209Delta
Mon, Jan 19 - Mon, Jan 26
Southwest Logo
3:20 pm - 7:05 pm
DSM
-
MDW
3h 45m1 stop
Southwest Logo
12:50 pm - 7:15 pm
MDW
-
DSM
6h 25m2 stops
$210Southwest
Wed, Feb 25 - Sat, Feb 28
Southwest Logo
3:00 pm - 4:30 pm
OMA
-
MDW
1h 30mnonstop
Southwest Logo
6:00 am - 3:05 pm
MDW
-
OMA
9h 05m2 stops
$210Southwest
Sat, Jan 17 - Sat, Jan 24

Southwest flights from Iowa to Chicago Midway Airport

Our best Southwest deals on Iowa to Chicago Midway Airport flight tickets
Southwest
Jan 17
OMA3:00 pmOmaha Eppley Airfield
1h 30m
MDW4:30 pmChicago Midway
Jan 24
MDW8:20 amChicago Midway
1h 40m
OMA10:00 amOmaha Eppley Airfield
$195
Find similar
Southwest
Jan 17
OMA3:00 pmOmaha Eppley Airfield
1h 30m
MDW4:30 pmChicago Midway
Jan 18
MDW1:20 pmChicago Midway
1h 30m
OMA2:50 pmOmaha Eppley Airfield
$197
Find similar
Southwest
Jan 17
OMA7:20 amOmaha Eppley Airfield
1h 40m
MDW9:00 amChicago Midway
Jan 24
MDW9:05 amChicago Midway
5h 05m
1 stop
OMA2:10 pmOmaha Eppley Airfield
$205
Find similar

Delta flights from Iowa to Chicago Midway Airport

Our best Delta deals on Iowa to Chicago Midway Airport flight tickets
Delta
Feb 4
DSM6:24 amDes Moines
6h 27m
1 stop
MDW12:51 pmChicago Midway
Feb 11
MDW9:53 amChicago Midway
5h 48m
1 stop
DSM3:41 pmDes Moines
$209
Find similar
Delta
Feb 2
DSM6:24 amDes Moines
6h 22m
1 stop
MDW12:46 pmChicago Midway
Feb 9
MDW9:53 amChicago Midway
5h 48m
1 stop
DSM3:41 pmDes Moines
$244
Find similar
Delta
Jan 8
DSM12:04 pmDes Moines
5h 30m
1 stop
MDW5:34 pmChicago Midway
Jan 12
MDW9:50 amChicago Midway
5h 51m
1 stop
DSM3:41 pmDes Moines
$259
Find similar

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 December 23, 2025.
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

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 1/17

3:00 pm-4:30 pm

Nonstop1h 30m

Chicago Midway

Sat 1/24

8:20 am-10:00 am

Nonstop1h 40m

$195

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 1/17

7:20 am-9:00 am

Nonstop1h 40m

Chicago Midway

Sun 1/18

1:20 pm-2:50 pm

Nonstop1h 30m

$197

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Mon 1/19

6:30 am-1:09 pm

1 stop6h 39m

Chicago Midway

Mon 1/26

9:50 am-3:35 pm

1 stop5h 45m

$199

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Mon 1/19

6:30 am-1:09 pm

1 stop6h 39m

Chicago Midway

Mon 1/26

9:33 am-3:35 pm

2 stops6h 02m

$204

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 1/17

7:20 am-9:00 am

Nonstop1h 40m

Chicago Midway

Sat 1/24

9:05 am-2:10 pm

1 stop5h 05m

$205

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 1/17

5:40 am-3:20 pm

1 stop9h 40m

Chicago Midway

Sun 1/18

8:25 am-10:05 am

Nonstop1h 40m

$207

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 2/4

12:25 pm-5:55 pm

1 stop5h 30m

Chicago Midway

Wed 2/11

9:53 am-3:41 pm

1 stop5h 48m

$209

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Mon 1/19

6:30 am-12:46 pm

2 stops6h 16m

Chicago Midway

Mon 1/26

9:33 am-3:35 pm

2 stops6h 02m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 2/25

3:20 pm-7:05 pm

1 stop3h 45m

Chicago Midway

Sat 2/28

12:50 pm-7:15 pm

2 stops6h 25m

$210

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 1/17

3:00 pm-4:30 pm

Nonstop1h 30m

Chicago Midway

Sat 1/24

6:00 am-3:05 pm

2 stops9h 05m

$210

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, Thursday is the cheapest day to fly to Chicago Midway Airport from Iowa. The lowest ticket price found for a Thursday departure recently was $455. 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, Wednesday 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 $925.

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 $518 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $614. 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

$386

Fastest flight time

1h 20m

Direct flights

Every day
The best flight deal from Iowa to Chicago Midway Airport found on momondo in the last 72 hours is $386
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

  • 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
Valparaiso
Schererville
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.

An easier way to manage your Chicago Midway Airport trip

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