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$72+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Sep 1 — Sep 81
Mon 9/1
Mon 9/8
1 adult, Economy
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Cheap flight deals from Iowa to Midway

Keep the following information in mind while searching for Iowa to Midway flight deals. Data was last updated August 27, 2025.

Round-trip from

$182
(Expedia)

One-way from

$72
(Priceline)

Popular in

July

Cheapest in

May

Average price

$276
From Iowa to Chicago Midway
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One-way flight from Iowa to Chicago Midway
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Highest demand for flights based on searches. 8% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 27, 2025.

This Orbitz deal was found by Cheapflights users on 8/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2412:00 pmOMA - MDW
1 stop11h 46mFrontier
Mon 10/2712:11 pmMDW - OMA
1 stop7h 53mFrontier
Deal found 8/26$182
This Priceline deal was found by Cheapflights users on 8/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3111:40 amOMA - MDW
1 stop6h 59mFrontier
Sun 11/212:30 pmMDW - OMA
1 stop6h 21mFrontier
Deal found 8/27$196
This Delta deal was found by Cheapflights users on 8/26. 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.
Tue 9/166:00 amDSM - MDW
1 stop6h 28mDelta
Tue 9/239:20 amMDW - DSM
1 stop4h 43mDelta
Deal found 8/26$197
This Delta deal was found by Cheapflights users on 8/25. 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.
Fri 11/216:17 amDSM - MDW
1 stop6h 17mDelta
Mon 11/249:32 amMDW - DSM
1 stop6h 47mDelta
Deal found 8/25$209
This Priceline deal was found by Cheapflights users on 8/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/711:29 amOMA - MDW
1 stop7h 10mFrontier
Sun 11/912:30 pmMDW - OMA
1 stop6h 21mFrontier
Deal found 8/27$214
This Southwest deal was found by Cheapflights users on 8/26. 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 10/73:35 pmOMA - MDW
Nonstop1h 25mSouthwest
Wed 10/810:20 amMDW - OMA
Nonstop1h 30mSouthwest
Deal found 8/26$217
This FlightHub deal was found by Cheapflights users on 8/26. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:46 pmOMA - MDW
1 stop15h 44mFrontier
Mon 11/312:30 pmMDW - OMA
1 stop7h 36mFrontier
Deal found 8/26$221
This Southwest deal was found by Cheapflights users on 8/24. 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.
Fri 9/261:55 pmDSM - MDW
1 stop10h 10mSouthwest
Mon 9/296:05 pmMDW - DSM
1 stop4h 45mSouthwest
Deal found 8/24$224
This Southwest deal was found by Cheapflights users on 8/25. 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 9/154:20 pmOMA - MDW
Nonstop1h 25mSouthwest
Wed 9/174:00 pmMDW - OMA
Nonstop1h 30mSouthwest
Deal found 8/25$227
This Delta deal was found by Cheapflights users on 8/26. 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 9/246:00 amDSM - MDW
1 stop6h 28mDelta
Wed 10/11:08 pmMDW - DSM
1 stop3h 37mDelta
Deal found 8/26$228
This Delta deal was found by Cheapflights users on 8/27. 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 10/1112:30 pmDSM - MDW
1 stop5h 55mDelta
Sat 10/1811:10 amMDW - DSM
1 stop5h 42mDelta
Deal found 8/27$234
This Delta deal was found by Cheapflights users on 8/26. 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.
Tue 10/76:25 amOMA - MDW
1 stop6h 03mDelta
Wed 10/89:35 amMDW - OMA
1 stop3h 52mDelta
Deal found 8/26$237

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 August 27, 2025.
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

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Fri 10/24

12:00 pm-11:46 pm

1 stop11h 46m

Chicago Midway

Mon 10/27

12:11 pm-8:04 pm

1 stop7h 53m

$182

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Fri 10/31

11:40 am-6:39 pm

1 stop6h 59m

Chicago Midway

Sun 11/2

12:30 pm-6:51 pm

1 stop6h 21m

$196

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 9/16

6:00 am-12:28 pm

1 stop6h 28m

Chicago Midway

Tue 9/23

9:20 am-2:03 pm

1 stop4h 43m

$197

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 11/21

6:17 am-12:34 pm

1 stop6h 17m

Chicago Midway

Mon 11/24

9:32 am-4:19 pm

1 stop6h 47m

$209

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Fri 11/7

11:29 am-6:39 pm

1 stop7h 10m

Chicago Midway

Sun 11/9

12:30 pm-6:51 pm

1 stop6h 21m

$214

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Tue 10/7

5:55 pm-7:25 pm

Nonstop1h 30m

Chicago Midway

Wed 10/8

7:50 am-9:20 am

Nonstop1h 30m

$217

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Tue 9/23

5:40 pm-7:15 pm

Nonstop1h 35m

Chicago Midway

Tue 9/30

8:30 am-10:00 am

Nonstop1h 30m

$217

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 10/30

7:46 pm-11:30 am

1 stop15h 44m

Chicago Midway

Mon 11/3

12:30 pm-8:06 pm

1 stop7h 36m

$221

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 9/26

1:55 pm-12:05 am

1 stop10h 10m

Chicago Midway

Mon 9/29

6:05 pm-10:50 pm

1 stop4h 45m

$224

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Mon 9/15

4:20 pm-5:45 pm

Nonstop1h 25m

Chicago Midway

Wed 9/17

4:00 pm-5:30 pm

Nonstop1h 30m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/25

Showing 1-10 of 53 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 Frontier, Delta, and Southwest fly from Iowa to Chicago Midway Airport in about 1h 30m. The time it takes to get you to your destination can typically vary by up to 10h 16m. Iowa and Chicago Midway Airport are separated by a distance of 422 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.

  • 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.

  • What is the cheapest month to book a flight from Iowa to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Iowa to Chicago Midway Airport (average of $160). Flying from Iowa to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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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