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Cheap flights from Iowa to Chicago from $53

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 10/4. 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

Southwest Logo
3:15 pm - 4:45 pmOMA-MDW
1h 30mnonstop
Southwest Logo
10:20 am - 11:50 amMDW-OMA
1h 30mnonstop
$105Southwest
Find Deal
Sat, Oct 11 - Tue, Oct 14
Southwest Logo
11:40 am - 8:00 pmOMA-MDW
8h 20m1 stop
Southwest Logo
8:20 am - 10:00 amMDW-OMA
1h 40mnonstop
$114Southwest
Find Deal
Wed, Dec 17 - Sat, Jan 10
Southwest Logo
5:40 pm - 7:15 pmOMA-MDW
1h 35mnonstop
Southwest Logo
8:10 am - 9:40 amMDW-OMA
1h 30mnonstop
$122Southwest
Find Deal
Wed, Sep 17 - Thu, Sep 18
Southwest Logo
6:25 pm - 7:50 pmOMA-MDW
1h 25mnonstop
Southwest Logo
10:25 pm - 11:50 pmMDW-OMA
1h 25mnonstop
$139Southwest
Find Deal
Fri, Sep 5 - Sun, Sep 7
Southwest Logo
10:20 am - 7:05 pmOMA-MDW
8h 45m2 stops
Southwest Logo
8:20 pm - 9:50 pmMDW-OMA
1h 30mnonstop
$145Southwest
Find Deal
Sat, Oct 25 - Wed, Oct 29
Southwest Logo
11:40 am - 8:00 pmOMA-MDW
8h 20m1 stop
Southwest Logo
9:05 am - 2:10 pmMDW-OMA
5h 05m1 stop
$149Southwest
Find Deal
Wed, Dec 17 - Sat, Jan 10
Delta Logo
2:10 pm - 6:37 pmOMA-MDW
4h 27m1 stop
Delta Logo
9:30 am - 1:28 pmMDW-OMA
3h 58m1 stop
$193Delta
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Tue, Sep 2 - Tue, Sep 9
Delta Logo
2:08 pm - 6:35 pmOMA-MDW
4h 27m1 stop
Delta Logo
9:35 am - 1:28 pmMDW-OMA
3h 53m1 stop
$197Delta
Find Deal
Wed, Sep 17 - Wed, Sep 24
Delta Logo
12:20 pm - 5:35 pmCID-MDW
5h 15m1 stop
Delta Logo
7:10 pm - 10:41 pmMDW-CID
3h 31m1 stop
$214Delta
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Sat, Oct 4 - Tue, Oct 14
Frontier Logo
7:33 pm - 8:54 pmDSM-MDW
25h 21m1 stop
Frontier Logo
2:44 pm - 6:48 pmMDW-DSM
28h 04m1 stop
$230Frontier
Find Deal
Fri, Aug 15 - Sun, Aug 17

Delta flights from Iowa to Chicago Midway Airport

Our best Delta deals on Iowa to Chicago Midway Airport flight tickets
Delta
Sep 2
OMA2:10 pmOmaha Eppley Airfield
4h 27m
1 stop
MDW6:37 pmChicago Midway
Sep 9
MDW9:30 amChicago Midway
3h 58m
1 stop
OMA1:28 pmOmaha Eppley Airfield
$193
Find similar
Delta
Sep 17
OMA2:08 pmOmaha Eppley Airfield
4h 27m
1 stop
MDW6:35 pmChicago Midway
Sep 24
MDW9:35 amChicago Midway
3h 53m
1 stop
OMA1:28 pmOmaha Eppley Airfield
$197
Find similar
Delta
Oct 4
CID12:20 pmCedar Rapids
5h 15m
1 stop
MDW5:35 pmChicago Midway
Oct 14
MDW7:10 pmChicago Midway
3h 31m
1 stop
CID10:41 pmCedar Rapids
$214
Find similar

Southwest flights from Iowa to Chicago Midway Airport

Our best Southwest deals on Iowa to Chicago Midway Airport flight tickets
Southwest
Oct 11
OMA3:15 pmOmaha Eppley Airfield
1h 30m
MDW4:45 pmChicago Midway
Oct 14
MDW10:20 amChicago Midway
1h 30m
OMA11:50 amOmaha Eppley Airfield
$105
Find similar
Southwest
Dec 17
OMA11:40 amOmaha Eppley Airfield
8h 20m
1 stop
MDW8:00 pmChicago Midway
Jan 10
MDW8:20 amChicago Midway
1h 40m
OMA10:00 amOmaha Eppley Airfield
$114
Find similar
Southwest
Sep 17
OMA5:40 pmOmaha Eppley Airfield
1h 35m
MDW7:15 pmChicago Midway
Sep 18
MDW8:10 amChicago Midway
1h 30m
OMA9:40 amOmaha Eppley Airfield
$122
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 August 5, 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 10/11

3:15 pm-4:45 pm

Nonstop1h 30m

Chicago Midway

Tue 10/14

10:20 am-11:50 am

Nonstop1h 30m

$105

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 12/17

11:40 am-8:00 pm

1 stop8h 20m

Chicago Midway

Sat 1/10

8:20 am-10:00 am

Nonstop1h 40m

$114

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 9/17

5:40 pm-7:15 pm

Nonstop1h 35m

Chicago Midway

Thu 9/18

8:10 am-9:40 am

Nonstop1h 30m

$122

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Fri 9/5

6:25 pm-7:50 pm

Nonstop1h 25m

Chicago Midway

Sun 9/7

10:25 pm-11:50 pm

Nonstop1h 25m

$139

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 10/25

10:20 am-7:05 pm

2 stops8h 45m

Chicago Midway

Wed 10/29

8:20 pm-9:50 pm

Nonstop1h 30m

$145

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 12/17

11:40 am-8:00 pm

1 stop8h 20m

Chicago Midway

Sat 1/10

9:05 am-2:10 pm

1 stop5h 05m

$149

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Tue 9/2

2:10 pm-6:37 pm

1 stop4h 27m

Chicago Midway

Tue 9/9

9:30 am-1:28 pm

1 stop3h 58m

$193

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 9/17

2:08 pm-6:35 pm

1 stop4h 27m

Chicago Midway

Wed 9/24

9:35 am-1:28 pm

1 stop3h 53m

$197

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Sat 10/4

12:20 pm-5:35 pm

1 stop5h 15m

Chicago Midway

Tue 10/14

7:10 pm-10:41 pm

1 stop3h 31m

$214

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 8/15

7:33 pm-8:54 pm

1 stop25h 21m

Chicago Midway

Sun 8/17

2:44 pm-6:48 pm

1 stop28h 04m

$230

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 airline that flies from Iowa to Chicago Midway?

Southwest, Delta, and Frontier are the most popular carriers operating from Iowa to Chicago Midway

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

$53

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 $53. The best round-trip flight deal from Iowa to Chicago Midway Airport found on momondo in the last 72 hours is $105.
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.

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
Lansing
Portage
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.

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