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$67+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This Southwest deal was found by Cheapflights users on 12/17. 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 12/3111:05 amOMA - MDW
Nonstop1h 25mSouthwest
Wed 1/712:10 pmMDW - OMA
1 stop6h 30mSouthwest
Deal found 12/17$236
This Delta deal was found by Cheapflights users on 12/16. 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 12/196:50 amDSM - MDW
1 stop6h 20mDelta
Sat 1/105:00 pmMDW - DSM
1 stop4h 24mDelta
Deal found 12/16$309
This Southwest deal was found by Cheapflights users on 12/17. 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 12/196:50 pmDSM - MDW
1 stop2h 55mSouthwest
Sat 1/176:40 amMDW - DSM
1 stop8h 15mSouthwest
Deal found 12/17$314
This Southwest deal was found by Cheapflights users on 12/15. 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 12/316:00 pmOMA - MDW
Nonstop1h 30mSouthwest
Sun 1/47:45 amMDW - OMA
Nonstop1h 30mSouthwest
Deal found 12/15$317
This Southwest deal was found by Cheapflights users on 12/15. 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 12/316:15 amDSM - MDW
1 stop5h 10mSouthwest
Sat 1/37:00 pmMDW - DSM
1 stop6h 20mSouthwest
Deal found 12/15$357
This Southwest deal was found by Cheapflights users on 12/16. 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 12/316:15 amDSM - MDW
1 stop5h 10mSouthwest
Fri 1/24:20 pmMDW - DSM
1 stop7h 45mSouthwest
Deal found 12/16$362
This Trip.com deal was found by Cheapflights users on 12/17. 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.
Tue 12/2311:14 amDSM - MDW
1 stop10h 44mFrontier
Sun 1/410:50 pmMDW - DSM
1 stop20h 54mFrontier
Deal found 12/17$377
This Southwest deal was found by Cheapflights users on 12/17. 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 12/216:50 pmDSM - MDW
1 stop2h 55mSouthwest
Wed 12/318:25 amMDW - DSM
1 stop3h 00mSouthwest
Deal found 12/17$383
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/2410:17 amCID - MDW
1 stop11h 41mMultiple Airlines
Wed 1/75:10 pmMDW - CID
2 stops15h 16mMultiple Airlines
Deal found 12/17$405
This Delta deal was found by Cheapflights users on 12/16. 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 12/166:50 amDSM - MDW
1 stop6h 20mDelta
Wed 12/179:34 amMDW - DSM
1 stop6h 42mDelta
Deal found 12/16$409
This Southwest deal was found by Cheapflights users on 12/16. 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 12/306:50 pmDSM - MDW
1 stop2h 55mSouthwest
Fri 1/23:35 pmMDW - DSM
2 stops8h 30mSouthwest
Deal found 12/16$414
This Southwest deal was found by Cheapflights users on 12/16. 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 12/307:55 pmOMA - MDW
Nonstop1h 30mSouthwest
Mon 1/59:35 pmMDW - OMA
Nonstop1h 30mSouthwest
Deal found 12/16$419

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$152
(Southwest)

One-way from

$67
(Southwest)

Popular in

December

Cheapest in

September

Average price

$290

Good round-trip deal

$387 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. 4% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip 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 December 18, 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

Wed 1/7

10:55 am-12:20 pm

Nonstop1h 25m

Chicago Midway

Sat 1/10

8:20 am-10:00 am

Nonstop1h 40m

$152

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 1/7

9:00 am-1:09 pm

1 stop4h 09m

Chicago Midway

Wed 1/7

7:16 pm-10:54 pm

1 stop3h 38m

$157

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 2/18

1:50 pm-9:50 pm

1 stop8h 00m

Chicago Midway

Sat 2/21

2:05 pm-12:05 am

2 stops10h 00m

$177

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 2/19

6:05 am-12:46 pm

1 stop6h 41m

Chicago Midway

Sat 2/21

11:45 am-4:53 pm

1 stop5h 08m

$191

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 2/19

5:20 am-10:20 am

1 stop5h 00m

Chicago Midway

Sat 2/21

10:15 am-6:45 pm

2 stops8h 30m

$196

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Wed 1/7

12:11 pm-6:32 pm

1 stop6h 21m

Chicago Midway

Sat 1/10

5:00 pm-10:45 pm

1 stop5h 45m

$199

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Mon 1/12

12:11 pm-6:32 pm

1 stop6h 21m

Chicago Midway

Tue 1/20

7:16 pm-10:45 pm

1 stop3h 29m

$199

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Tue 1/13

6:30 am-1:09 pm

1 stop6h 39m

Chicago Midway

Tue 1/20

7:16 pm-10:45 pm

1 stop3h 29m

$199

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Fri 2/13

6:36 am-1:07 pm

1 stop6h 31m

Chicago Midway

Sun 2/15

5:00 pm-10:43 pm

1 stop5h 43m

$199

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 1/8

3:55 pm-10:05 pm

2 stops6h 10m

Chicago Midway

Mon 1/12

2:35 pm-9:40 pm

2 stops7h 05m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 55 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 1h 25m. The time it takes to get you to your destination can typically vary by up to 2h 44m. 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.

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

    While on average a flight from Iowa to Chicago Midway Airport is generally $446, our data shows the cheapest flight currently is $328. When looking at the most popular route, (Omaha Eppley Airfield - Chicago Midway), you can expect to pay $152 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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