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$69+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$198
(Delta)

One-way from

$69
(Southwest)

Popular in

July

Cheapest in

May

Average price

$264
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. 11% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 16, 2025.

This Delta deal was found by Cheapflights users on 6/16. 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 8/192:10 pmOMA - MDW
1 stop4h 27mDelta
Sat 8/236:17 pmMDW - OMA
1 stop4h 10mDelta
Deal found 6/16$198
This Delta deal was found by Cheapflights users on 6/14. 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.
Sat 8/912:02 pmCID - MDW
1 stop5h 08mDelta
Sat 8/169:15 amMDW - CID
1 stop6h 18mDelta
Deal found 6/14$199
This Southwest deal was found by Cheapflights users on 6/16. 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.
Sat 8/166:25 amOMA - MDW
2 stops10h 10mSouthwest
Mon 8/182:35 pmMDW - OMA
1 stop3h 05mSouthwest
Deal found 6/16$199
This Delta deal was found by Cheapflights users on 6/14. 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.
Sat 7/1210:56 amDSM - MDW
1 stop6h 14mDelta
Sat 7/191:09 pmMDW - DSM
1 stop3h 51mDelta
Deal found 6/14$209
This Southwest deal was found by Cheapflights users on 6/13. 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 8/308:35 amDSM - MDW
1 stop6h 15mSouthwest
Sun 8/315:55 amMDW - DSM
1 stop7h 10mSouthwest
Deal found 6/13$210
This Booking.com deal was found by Cheapflights users on 6/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/197:51 pmOMA - MDW
1 stop15h 49mFrontier
Sat 6/219:12 pmMDW - OMA
1 stop13h 08mFrontier
Deal found 6/13$238
This Mytrip deal was found by Cheapflights users on 6/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2611:16 amCID - MDW
1 stop23h 31mAllegiant Air
Sun 8/311:37 amMDW - CID
1 stop29h 40mAllegiant Air
Deal found 6/16$333
This Mytrip deal was found by Cheapflights users on 6/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/317:54 pmDSM - MDW
2 stops18h 02mAllegiant Air
Thu 8/78:14 pmMDW - DSM
2 stops21h 51mAllegiant Air
Deal found 6/16$400
This Mytrip deal was found by Cheapflights users on 6/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2510:17 amOMA - MDW
1 stop24h 38mAllegiant Air
Mon 6/302:53 pmMDW - OMA
2 stops18h 12mAllegiant Air
Deal found 6/14$436

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 June 16, 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

Tue 8/19

2:10 pm-6:37 pm

1 stop4h 27m

Chicago Midway

Sat 8/23

6:17 pm-10:27 pm

1 stop4h 10m

$198

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 8/16

6:25 am-4:35 pm

2 stops10h 10m

Chicago Midway

Mon 8/18

2:35 pm-5:40 pm

1 stop3h 05m

$199

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Sat 8/9

12:02 pm-5:10 pm

1 stop5h 08m

Chicago Midway

Sat 8/16

9:15 am-3:33 pm

1 stop6h 18m

$199

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 7/12

10:56 am-5:10 pm

1 stop6h 14m

Chicago Midway

Sat 7/19

1:09 pm-5:00 pm

1 stop3h 51m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 8/30

8:35 am-2:50 pm

1 stop6h 15m

Chicago Midway

Sun 8/31

5:55 am-1:05 pm

1 stop7h 10m

$210

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 7/12

7:51 pm-8:54 pm

1 stop25h 03m

Chicago Midway

Sat 7/19

9:12 pm-10:16 am

1 stop13h 04m

$252

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Sat 7/26

11:16 am-10:47 am

1 stop23h 31m

Chicago Midway

Sun 8/3

11:37 am-5:17 pm

1 stop29h 40m

$333

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 7/31

7:54 pm-1:56 pm

2 stops18h 02m

Chicago Midway

Thu 8/7

8:14 pm-6:05 pm

2 stops21h 51m

$400

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 7/3

9:56 am-2:04 pm

2 stops28h 08m

Chicago Midway

Mon 7/7

2:54 pm-8:56 am

2 stops18h 02m

$474

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Mon 8/4

4:50 pm-6:15 pm

Nonstop1h 25m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 19 results
1
2

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

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated June 16, 2025.
See what other customers who have flown with Southwest, Delta and Allegiant Air from Iowa to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,963 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
722 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,296 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

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

    $69 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and Frontier, with prices starting from $89 and $105, respectively.

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

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

Book flights to Iowa if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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