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$55+ Cheap flights from Midway (MDW) to Iowa

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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — DSM
Dec 1 — Dec 81
Mon 12/1
Mon 12/8
1 adult, Economy
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Cheap flight deals from Midway to Iowa

Keep the following information in mind while searching for Midway to Iowa flight deals. Data was last updated November 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(Trip.com)

One-way from

$55
(Priceline)

Popular in

February

Cheapest in

March

Average price

$274
Provider with most accurate pricing for Chicago (CHI)-Des Moines flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Des Moines flights.
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From Chicago Midway to Iowa
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One-way flight from Chicago Midway to Iowa
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Highest demand for flights based on searches. 12% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Midway to Iowa

Cheapest flights from Midway to Iowa
Explore the most affordable flight options available from Midway to Iowa. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 1, 2025.

This Trip.com deal was found by Cheapflights users on 10/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/712:30 pmMDW - OMA
1 stop7h 36mFrontier
Mon 11/1011:29 amOMA - MDW
1 stop7h 10mFrontier
Deal found 10/28$205
This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1412:30 pmMDW - OMA
1 stop7h 36mFrontier
Sun 11/167:46 pmOMA - MDW
1 stop15h 44mFrontier
Deal found 10/29$209
This Delta deal was found by Cheapflights users on 10/30. 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.
Thu 11/209:34 amMDW - DSM
1 stop6h 45mDelta
Sun 11/236:17 amDSM - MDW
1 stop6h 17mDelta
Deal found 10/30$209
This Priceline deal was found by Cheapflights users on 10/29. 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 10/3112:30 pmMDW - OMA
1 stop7h 36mFrontier
Mon 11/311:29 amOMA - MDW
1 stop7h 10mFrontier
Deal found 10/29$228
This Southwest deal was found by Cheapflights users on 10/29. 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.
Thu 12/43:20 pmMDW - OMA
Nonstop1h 30mSouthwest
Mon 12/86:00 pmOMA - MDW
Nonstop1h 30mSouthwest
Deal found 10/29$237
This Delta deal was found by Cheapflights users on 10/29. 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 11/129:41 amMDW - DSM
1 stop4h 24mDelta
Sat 11/1512:30 pmDSM - MDW
1 stop5h 38mDelta
Deal found 10/29$239
This Southwest deal was found by Cheapflights users on 10/31. 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 12/126:45 amMDW - DSM
1 stop4h 15mSouthwest
Sun 12/148:00 amDSM - MDW
2 stops7h 45mSouthwest
Deal found 10/31$248
This Delta deal was found by Cheapflights users on 10/31. 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 11/227:02 pmMDW - CID
1 stop4h 02mDelta
Sun 11/237:00 amCID - MDW
1 stop6h 07mDelta
Deal found 10/31$249
This Southwest deal was found by Cheapflights users on 10/29. 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.
Thu 11/2712:30 pmMDW - OMA
Nonstop1h 30mSouthwest
Mon 12/14:15 pmOMA - MDW
Nonstop1h 25mSouthwest
Deal found 10/29$273
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1310:12 amMDW - OMA
1 stop30h 37mMultiple Airlines
Mon 11/178:51 pmOMA - MDW
2 stops14h 47mMultiple Airlines
Deal found 10/29$280
This Southwest deal was found by Cheapflights users on 10/29. 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.
Sun 11/2311:10 amMDW - OMA
Nonstop1h 30mSouthwest
Mon 11/2412:40 pmOMA - MDW
Nonstop1h 25mSouthwest
Deal found 10/29$284
This Southwest deal was found by Cheapflights users on 10/29. 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 11/2610:20 pmMDW - OMA
Nonstop1h 30mSouthwest
Mon 12/14:15 pmOMA - MDW
Nonstop1h 25mSouthwest
Deal found 10/29$287

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Iowa 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 November 1, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Iowa that are best for you.

Fly from

Midway

Fly to

Iowa

Route

Depart

Return

Price

ChicagoDes Moines

MDW - DSM

MDWDSM

Chicago Midway

Thu 11/20

9:34 am-4:19 pm

1 stop6h 45m

Des Moines

Sun 11/23

6:17 am-12:34 pm

1 stop6h 17m

$209

ChicagoDes Moines

MDW - DSM

MDWDSM

Chicago Midway

Fri 12/12

7:20 pm-11:35 pm

1 stop4h 15m

Des Moines

Sun 12/14

5:45 am-9:55 am

1 stop4h 10m

$209

ChicagoOmaha

MDW - OMA

MDWOMA

Chicago Midway

Thu 12/4

3:20 pm-4:50 pm

Nonstop1h 30m

Omaha Eppley Airfield

Mon 12/8

3:40 pm-5:10 pm

Nonstop1h 30m

$237

ChicagoDes Moines

MDW - DSM

MDWDSM

Chicago Midway

Wed 11/12

9:41 am-2:05 pm

1 stop4h 24m

Des Moines

Sat 11/15

12:30 pm-6:08 pm

1 stop5h 38m

$239

ChicagoCedar Rapids

MDW - CID

MDWCID

Chicago Midway

Sat 11/22

7:02 pm-11:04 pm

1 stop4h 02m

Cedar Rapids

Sun 11/23

7:00 am-1:07 pm

1 stop6h 07m

$249

ChicagoOmaha

MDW - OMA

MDWOMA

Chicago Midway

Sun 12/21

6:20 pm-8:00 pm

Nonstop1h 40m

Omaha Eppley Airfield

Thu 12/25

6:00 pm-7:30 pm

Nonstop1h 30m

$284

ChicagoOmaha

MDW - OMA

MDWOMA

Chicago Midway

Wed 12/24

8:25 pm-9:55 pm

Nonstop1h 30m

Omaha Eppley Airfield

Mon 12/29

6:35 pm-9:45 pm

1 stop3h 10m

$287

ChicagoOmaha

MDW - OMA

MDWOMA

Chicago Midway

Wed 11/26

10:20 pm-11:50 pm

Nonstop1h 30m

Omaha Eppley Airfield

Mon 12/1

4:15 pm-5:40 pm

Nonstop1h 25m

$287

ChicagoOmaha

MDW - OMA

MDWOMA

Chicago Midway

Sun 11/23

11:10 am-12:40 pm

Nonstop1h 30m

Omaha Eppley Airfield

Mon 11/24

5:05 am-9:55 am

1 stop4h 50m

$294

ChicagoDes Moines

MDW - DSM

MDWDSM

Chicago Midway

Sat 3/7

1:00 pm-4:56 pm

1 stop3h 56m

Des Moines

Mon 3/9

6:20 am-12:35 pm

1 stop6h 15m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 42 results
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Best time to book a flight from Midway to Iowa

Have a flexible travel schedule? Discover the best time to fly to Iowa from Midway 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 Chicago Midway Airport to Iowa

What is the cheapest time of day to fly from MDW to IA?

Find hourly flight availability from Midway to Iowa. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 1, 2025.

It’s optimal to fly from Chicago Midway Airport to Iowa in the afternoon. By choosing this option you can save up to 66% on the cost of your flight, compared to a flight at noon.

Related info for your journey

Find useful and relevant information for your journey from Midway to Iowa. 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 Chicago Midway Airport to Iowa?

    Departing from Chicago Midway Airport to Iowa will take you 4h 15m. Airlines will cover a distance of 305 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Iowa one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $105. Users have also found prices from $107 and $129 on Frontier and Southwest, respectively.

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

    When deciding which route to take from Chicago Midway Airport to Iowa consider Chicago Midway - Omaha Eppley Airfield, Chicago Midway - Des Moines or Chicago Midway - Cedar Rapids as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Iowa 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

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Alternative routes for Midway to Iowa

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