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$67+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — DSM
Jan 16 — Jan 231
Fri 1/16
Fri 1/23
1 adult, Economy
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Cheap 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 December 17, 2025.

This Delta deal was found by Cheapflights users on 12/14. 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 12/305:59 pmMDW - CID
1 stop4h 55mDelta
Sat 1/36:25 amCID - MDW
1 stop4h 41mDelta
Deal found 12/14$229
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:12 amMDW - OMA
1 stop9h 23mFrontier
Mon 1/511:11 amOMA - MDW
1 stop10h 47mFrontier
Deal found 12/15$298
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 12/318:25 amMDW - DSM
1 stop3h 00mSouthwest
Sun 1/46:50 pmDSM - MDW
1 stop2h 55mSouthwest
Deal found 12/16$328
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 12/304:20 pmMDW - DSM
1 stop7h 45mSouthwest
Sat 1/36:45 pmDSM - MDW
1 stop5h 10mSouthwest
Deal found 12/16$384
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/232:01 pmMDW - OMA
1 stop5h 46mFrontier
Mon 12/294:35 pmOMA - MDW
1 stop5h 37mFrontier
Deal found 12/15$393
This Southwest deal was found by Cheapflights users on 12/14. 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 12/187:20 pmMDW - DSM
1 stop4h 15mSouthwest
Fri 12/195:30 amDSM - MDW
1 stop4h 35mSouthwest
Deal found 12/14$409
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.
Tue 12/234:20 pmMDW - DSM
1 stop7h 45mSouthwest
Wed 12/246:15 amDSM - MDW
1 stop5h 10mSouthwest
Deal found 12/15$414
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:15 amMDW - OMA
1 stop7h 20mFrontier
Mon 12/294:35 pmOMA - MDW
1 stop5h 37mFrontier
Deal found 12/16$427
This Southwest deal was found by Cheapflights users on 12/14. 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 12/243:20 pmMDW - OMA
Nonstop1h 30mSouthwest
Fri 12/2612:40 pmOMA - MDW
Nonstop1h 25mSouthwest
Deal found 12/14$443
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.
Tue 12/166:20 amMDW - DSM
1 stop5h 05mSouthwest
Tue 12/235:30 amDSM - MDW
1 stop4h 35mSouthwest
Deal found 12/15$444
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 12/245:15 pmMDW - DSM
1 stop4h 20mSouthwest
Sat 12/275:40 amDSM - MDW
1 stop8h 40mSouthwest
Deal found 12/17$468
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.
Tue 12/234:20 pmMDW - DSM
1 stop7h 45mSouthwest
Sat 12/275:40 amDSM - MDW
1 stop8h 40mSouthwest
Deal found 12/17$474

Find flight deals from Midway to Iowa

Keep the following information in mind while searching for Midway to Iowa flight deals. Data was last updated December 17, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$171
(Southwest)

One-way from

$67
(Southwest)

Popular in

February

Cheapest in

March

Average price

$389
Provider with most accurate pricing for Chicago (CHI)-Des Moines flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Des Moines flights.
Search Deals
From Chicago Midway to Iowa
Search Deals
One-way flight from Chicago Midway to Iowa
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 17, 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

ChicagoOmaha

MDW - OMA

MDWOMA

Chicago Midway

Wed 1/14

2:20 pm-9:40 pm

2 stops7h 20m

Omaha Eppley Airfield

Wed 1/21

3:55 pm-7:05 pm

1 stop3h 10m

$158

ChicagoOmaha

MDW - OMA

MDWOMA

Chicago Midway

Sat 1/24

8:20 am-10:00 am

Nonstop1h 40m

Omaha Eppley Airfield

Mon 1/26

5:50 am-7:20 am

Nonstop1h 30m

$171

ChicagoOmaha

MDW - OMA

MDWOMA

Chicago Midway

Thu 1/22

8:25 am-10:05 am

Nonstop1h 40m

Omaha Eppley Airfield

Mon 1/26

10:55 am-12:20 pm

Nonstop1h 25m

$171

ChicagoOmaha

MDW - OMA

MDWOMA

Chicago Midway

Tue 1/13

1:49 pm-7:53 pm

1 stop6h 04m

Omaha Eppley Airfield

Tue 1/20

9:00 am-1:09 pm

1 stop4h 09m

$191

ChicagoOmaha

MDW - OMA

MDWOMA

Chicago Midway

Tue 1/20

8:30 am-10:15 am

Nonstop1h 45m

Omaha Eppley Airfield

Wed 1/21

10:55 am-12:20 pm

Nonstop1h 25m

$193

ChicagoDes Moines

MDW - DSM

MDWDSM

Chicago Midway

Thu 2/5

9:53 am-3:41 pm

1 stop5h 48m

Des Moines

Sat 2/7

6:54 am-11:05 am

1 stop4h 11m

$209

ChicagoDes Moines

MDW - DSM

MDWDSM

Chicago Midway

Tue 1/6

9:50 am-3:41 pm

1 stop5h 51m

Des Moines

Thu 1/8

12:04 pm-5:34 pm

1 stop5h 30m

$209

ChicagoDes Moines

MDW - DSM

MDWDSM

Chicago Midway

Tue 1/6

9:50 am-3:41 pm

1 stop5h 51m

Des Moines

Sun 1/11

6:24 am-12:48 pm

1 stop6h 24m

$209

ChicagoDes Moines

MDW - DSM

MDWDSM

Chicago Midway

Wed 1/7

6:10 am-11:25 am

1 stop5h 15m

Des Moines

Wed 1/7

3:20 pm-7:05 pm

1 stop3h 45m

$209

ChicagoDes Moines

MDW - DSM

MDWDSM

Chicago Midway

Wed 1/7

9:50 am-3:41 pm

1 stop5h 51m

Des Moines

Sat 1/10

6:24 am-12:48 pm

1 stop6h 24m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 43 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 December 17, 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 5h 48m. 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 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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