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$74+ Cheap flights from Iowa to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Iowa to Midway

Cheapest flights from Iowa to Midway
Explore the most affordable flight options available from Iowa to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Southwest deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/94:20 pm
DSM
-
MDW
Nonstop1h 20m
Southwest
Tue 3/1010:15 am
MDW
-
DSM
Nonstop1h 25m
Southwest
Deal found 1/27$164
This Southwest deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:20 pm
DSM
-
MDW
1 stop3h 45m
Southwest
Tue 3/1710:15 am
MDW
-
DSM
Nonstop1h 25m
Southwest
Deal found 1/27$167
This Southwest deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/74:35 pm
DSM
-
MDW
Nonstop1h 20m
Southwest
Mon 3/99:50 pm
MDW
-
DSM
Nonstop1h 25m
Southwest
Deal found 1/28$171
This Southwest deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:10 am
DSM
-
MDW
1 stop3h 20m
Southwest
Mon 3/169:50 pm
MDW
-
DSM
Nonstop1h 25m
Southwest
Deal found 1/27$174
This Southwest deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:35 am
DSM
-
MDW
1 stop8h 10m
Southwest
Tue 3/36:10 am
MDW
-
DSM
1 stop5h 15m
Southwest
Deal found 1/27$177
This Delta deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:55 am
DSM
-
MDW
1 stop6h 30m
Delta
Sat 4/49:30 am
MDW
-
DSM
1 stop6h 12m
Delta
Deal found 1/28$184
This Delta deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:36 am
CID
-
MDW
1 stop4h 27m
Delta
Sat 2/285:00 pm
MDW
-
CID
1 stop5h 43m
Delta
Deal found 1/28$199
This Frontier deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/201:59 pm
OMA
-
MDW
1 stop8h 26m
Frontier
Mon 2/236:00 am
MDW
-
OMA
1 stop7h 04m
Frontier
Deal found 1/27$199
This Delta deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/46:30 am
CID
-
MDW
1 stop6h 36m
Delta
Fri 3/277:20 pm
MDW
-
CID
1 stop3h 32m
Delta
Deal found 1/28$229
This Delta deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/76:30 am
CID
-
MDW
2 stops6h 16m
Delta
Fri 5/296:45 pm
MDW
-
CID
1 stop3h 34m
Delta
Deal found 1/27$234
This Delta deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/46:30 am
CID
-
MDW
1 stop6h 36m
Delta
Fri 2/277:20 pm
MDW
-
CID
1 stop3h 23m
Delta
Deal found 1/28$244
This Southwest deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/243:10 pm
OMA
-
MDW
Nonstop1h 25m
Southwest
Wed 3/48:25 am
MDW
-
OMA
Nonstop1h 40m
Southwest
Deal found 1/28$245

Find flight deals from Iowa to Midway

Keep the following information in mind while searching for Iowa to Midway flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$164
(Southwest)

One-way from

$74
(Priceline)

Popular in

January

Cheapest in

September

Average price

$291

Good round-trip deal

$386 or less

Good one-way deal

$188 or less
Provider with most accurate pricing for Des Moines-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Des Moines-Chicago (CHI) flights.
Search Deals
From Iowa to Chicago Midway
Search Deals
One-way flight from Iowa to Chicago Midway
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Iowa to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Iowa to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Iowa to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Iowa to Chicago Midway Airport that are best for you.

Fly from

Iowa

Fly to

Midway

Route

Depart

Return

Price

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 2/25

3:20 pm-7:05 pm

1 stop3h 45m

Chicago Midway

Tue 3/17

10:15 am-11:40 am

Nonstop1h 25m

$167

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 5/7

4:20 pm-5:40 pm

Nonstop1h 20m

Chicago Midway

Mon 5/11

9:45 pm-11:05 pm

Nonstop1h 20m

$171

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 4/21

5:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Fri 4/24

9:45 pm-11:05 pm

Nonstop1h 20m

$172

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 3/3

6:10 am-9:30 am

1 stop3h 20m

Chicago Midway

Mon 3/16

9:50 pm-11:15 pm

Nonstop1h 25m

$174

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 2/25

6:50 am-1:05 pm

1 stop6h 15m

Chicago Midway

Wed 3/4

9:50 am-3:40 pm

1 stop5h 50m

$177

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 2/25

3:20 pm-7:05 pm

1 stop3h 45m

Chicago Midway

Wed 3/4

2:20 pm-9:10 pm

2 stops6h 50m

$182

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 4/1

6:55 am-1:25 pm

1 stop6h 30m

Chicago Midway

Sat 4/4

9:30 am-3:42 pm

1 stop6h 12m

$184

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 3/7

4:35 pm-5:55 pm

Nonstop1h 20m

Chicago Midway

Mon 3/9

12:50 pm-10:20 pm

2 stops9h 30m

$186

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 5/6

3:15 pm-4:35 pm

Nonstop1h 20m

Chicago Midway

Sat 5/9

10:05 am-11:30 am

Nonstop1h 25m

$187

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Sat 2/21

6:36 am-11:03 am

1 stop4h 27m

Chicago Midway

Sat 2/28

5:00 pm-10:43 pm

1 stop5h 43m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 52 results
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Best time to book a flight from Iowa to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Iowa with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Iowa to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Iowa to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Iowa to Chicago Midway Airport?

    Airlines like Southwest and Delta fly from Iowa to Chicago Midway Airport in about 3h 45m. The time it takes to get you to your destination can typically vary by up to 42m. Iowa and Chicago Midway Airport are separated by a distance of 305 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Iowa to Chicago Midway Airport?

    The most popular route from Iowa to Chicago Midway Airport is Omaha Eppley Airfield - Chicago Midway. You may also consider Des Moines - Chicago Midway or Cedar Rapids - Chicago Midway.

  • What are the cheapest flights from Iowa to Chicago Midway Airport?

    While on average a flight from Iowa to Chicago Midway Airport is generally $314, our data shows the cheapest flight currently is $163. When looking at the most popular route, (Omaha Eppley Airfield - Chicago Midway), you can expect to pay $219 for that flight.

  • Can I find deals for flights from Iowa to Midway that include hotel bookings?

    Yes. In addition to deals on Iowa to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Iowa to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Iowa to Midway.

  • Can I find deals for business class flights from Iowa to Midway?

    Yes. Cheapflights offers flight deals from Iowa to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Iowa to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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