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Cheap flights from Iowa to Chicago from $55

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 12/15. 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

Enter your travel dates to find the best prices.
Southwest Logo
6:25 am - 3:20 pmDSM-MDW
8h 55m1 stop
Southwest Logo
6:20 am - 11:25 amMDW-DSM
5h 05m1 stop
$207Southwest
Find Deal
sáb., dic. 13 - lun., dic. 15
Delta Logo
6:17 am - 12:34 pmDSM-MDW
6h 17m1 stop
Delta Logo
9:59 am - 2:19 pmMDW-DSM
4h 20m1 stop
$209Delta
Find Deal
mié., dic. 3 - mié., dic. 10
Southwest Logo
4:15 pm - 10:35 pmDSM-MDW
6h 20m2 stops
Southwest Logo
6:20 am - 11:25 amMDW-DSM
5h 05m1 stop
$214Southwest
Find Deal
mié., dic. 3 - vie., dic. 5
Southwest Logo
6:25 am - 1:00 pmOMA-MDW
6h 35m1 stop
Southwest Logo
8:20 am - 9:55 amMDW-OMA
1h 35mnonstop
$223Southwest
Find Deal
mar., dic. 9 - sáb., dic. 13
Southwest Logo
4:15 pm - 8:45 pmDSM-MDW
4h 30m1 stop
Southwest Logo
6:45 am - 11:00 amMDW-DSM
4h 15m1 stop
$224Southwest
Find Deal
vie., dic. 5 - dom., dic. 7
Frontier Logo
7:58 pm - 1:59 pmDSM-MDW
18h 01m2 stops
Frontier Logo
12:18 pm - 7:03 pmMDW-DSM
6h 45m1 stop
$226Frontier
Find Deal
vie., dic. 5 - vie., dic. 12
Southwest Logo
6:00 am - 1:05 pmOMA-MDW
7h 05m2 stops
Southwest Logo
12:30 pm - 2:00 pmMDW-OMA
1h 30mnonstop
$228Southwest
Find Deal
mar., dic. 9 - sáb., dic. 13
Frontier Logo
4:28 pm - 10:12 pmOMA-MDW
5h 44m1 stop
Frontier Logo
8:15 am - 3:40 pmMDW-OMA
7h 25m1 stop
$230Frontier
Find Deal
lun., dic. 15 - lun., dic. 29
Multiple Airlines Logo
7:58 pm - 1:59 pmDSM-MDW
18h 01m2 stops
Multiple Airlines Logo
10:13 am - 10:46 pmMDW-DSM
12h 33m1 stop
$234Multiple Airlines
Find Deal
vie., dic. 5 - dom., dic. 7
Multiple Airlines Logo
7:58 pm - 1:59 pmDSM-MDW
18h 01m2 stops
Multiple Airlines Logo
10:13 am - 10:46 pmMDW-DSM
12h 33m1 stop
$251Multiple Airlines
Find Deal
vie., dic. 5 - dom., dic. 7

Delta flights from Iowa to Chicago Midway Airport

Our best Delta deals on Iowa to Chicago Midway Airport flight tickets
Delta
Dec 3
DSM6:17 amDes Moines
6h 17m
1 stop
MDW12:34 pmChicago Midway
Dec 10
MDW9:59 amChicago Midway
4h 20m
1 stop
DSM2:19 pmDes Moines
$209
Find similar
Delta
Dec 3
OMA12:24 pmOmaha Eppley Airfield
5h 54m
1 stop
MDW6:18 pmChicago Midway
Dec 6
MDW9:59 amChicago Midway
6h 50m
1 stop
OMA4:49 pmOmaha Eppley Airfield
$233
Find similar
Delta
Nov 20
DSM6:17 amDes Moines
6h 17m
1 stop
MDW12:34 pmChicago Midway
Nov 23
MDW9:34 amChicago Midway
6h 45m
1 stop
DSM4:19 pmDes Moines
$239
Find similar

Southwest flights from Iowa to Chicago Midway Airport

Our best Southwest deals on Iowa to Chicago Midway Airport flight tickets
Southwest
Dec 13
DSM6:25 amDes Moines
8h 55m
1 stop
MDW3:20 pmChicago Midway
Dec 15
MDW6:20 amChicago Midway
5h 05m
1 stop
DSM11:25 amDes Moines
$207
Find similar
Southwest
Dec 3
DSM4:15 pmDes Moines
6h 20m
2 stops
MDW10:35 pmChicago Midway
Dec 5
MDW6:20 amChicago Midway
5h 05m
1 stop
DSM11:25 amDes Moines
$214
Find similar
Southwest
Dec 9
OMA6:25 amOmaha Eppley Airfield
6h 35m
1 stop
MDW1:00 pmChicago Midway
Dec 13
MDW8:20 amChicago Midway
1h 35m
OMA9:55 amOmaha Eppley Airfield
$223
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 noviembre 6, 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

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

sáb. 12/13

6:25 am-3:20 pm

1 stop8h 55m

Chicago Midway

lun. 12/15

6:20 am-11:25 am

1 stop5h 05m

$207

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

mié. 12/3

6:17 am-12:34 pm

1 stop6h 17m

Chicago Midway

mié. 12/10

9:59 am-2:19 pm

1 stop4h 20m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

mié. 12/3

4:15 pm-10:35 pm

2 stops6h 20m

Chicago Midway

vie. 12/5

6:20 am-11:25 am

1 stop5h 05m

$214

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

mar. 12/9

6:25 am-1:00 pm

1 stop6h 35m

Chicago Midway

sáb. 12/13

8:20 am-9:55 am

Nonstop1h 35m

$223

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

vie. 12/5

4:15 pm-8:45 pm

1 stop4h 30m

Chicago Midway

dom. 12/7

6:45 am-11:00 am

1 stop4h 15m

$224

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

vie. 12/5

7:58 pm-1:59 pm

2 stops18h 01m

Chicago Midway

vie. 12/12

12:18 pm-7:03 pm

1 stop6h 45m

$226

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

mar. 12/9

6:00 am-1:05 pm

2 stops7h 05m

Chicago Midway

sáb. 12/13

12:30 pm-2:00 pm

Nonstop1h 30m

$228

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

lun. 12/15

4:28 pm-10:12 pm

1 stop5h 44m

Chicago Midway

lun. 12/29

8:15 am-3:40 pm

1 stop7h 25m

$230

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

vie. 12/5

7:58 pm-1:59 pm

2 stops18h 01m

Chicago Midway

dom. 12/7

10:13 am-10:46 pm

1 stop12h 33m

$234

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

vie. 12/5

7:58 pm-1:59 pm

2 stops18h 01m

Chicago Midway

dom. 12/7

10:13 am-10:46 pm

1 stop12h 33m

$251

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, Saturday is the cheapest day to fly to Chicago Midway Airport from Iowa. The lowest ticket price found for a Saturday departure recently was $677. 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, Friday 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 $744.

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 $651 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $677. 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

$244

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 $244. The best round-trip flight deal from Iowa to Chicago Midway Airport found on momondo in the last 72 hours is $518.
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
Crown Point
Munster
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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