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$88+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(Delta)

One-way from

$88
(Mytrip)

Popular in

June

Cheapest in

February

Average price

$278
Provider with most accurate pricing for Des Moines-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Des Moines-Chicago (CHI) flights.
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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. 10% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 1, 2025.

This Delta deal was found by Cheapflights users on 4/1. 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 5/311:59 amDSM - MDW
1 stop5h 20mDelta
Tue 5/63:02 pmMDW - DSM
1 stop5h 43mDelta
Deal found 4/1$209
This Southwest deal was found by Cheapflights users on 3/31. 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 4/256:00 amDSM - MDW
1 stop5h 55mSouthwest
Tue 4/296:25 amMDW - DSM
1 stop5h 10mSouthwest
Deal found 3/31$214
This Southwest deal was found by Cheapflights users on 3/31. 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.
Wed 4/2310:45 amOMA - MDW
Nonstop1h 25mSouthwest
Wed 4/232:25 pmMDW - OMA
Nonstop1h 30mSouthwest
Deal found 3/31$217
This Delta deal was found by Cheapflights users on 3/31. 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.
Wed 5/711:57 amCID - MDW
1 stop5h 48mDelta
Sat 5/106:30 pmMDW - CID
1 stop4h 31mDelta
Deal found 3/31$219
This Frontier deal was found by Cheapflights users on 4/1. 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.
Sun 7/1311:10 amOMA - MDW
1 stop9h 11mFrontier
Mon 7/219:12 pmMDW - OMA
1 stop13h 04mFrontier
Deal found 4/1$290
This Delta deal was found by Cheapflights users on 3/31. 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 6/286:15 amOMA - MDW
1 stop6h 16mDelta
Tue 7/19:23 amMDW - OMA
1 stop3h 57mDelta
Deal found 3/31$297
This Mytrip deal was found by Cheapflights users on 4/1. 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 5/17:30 amDSM - MDW
2 stops26h 39mAllegiant Air
Thu 5/810:58 amMDW - DSM
1 stop28h 05mAllegiant Air
Deal found 4/1$303

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 April 1, 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

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 5/3

11:59 am-5:19 pm

1 stop5h 20m

Chicago Midway

Tue 5/6

3:02 pm-8:45 pm

1 stop5h 43m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 4/25

6:00 am-11:55 am

1 stop5h 55m

Chicago Midway

Tue 4/29

6:25 am-11:35 am

1 stop5h 10m

$214

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 4/23

10:45 am-12:10 pm

Nonstop1h 25m

Chicago Midway

Wed 4/23

2:25 pm-3:55 pm

Nonstop1h 30m

$217

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Wed 5/7

11:57 am-5:45 pm

1 stop5h 48m

Chicago Midway

Tue 5/13

7:25 pm-11:01 pm

1 stop3h 36m

$219

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sun 7/13

11:10 am-8:21 pm

1 stop9h 11m

Chicago Midway

Mon 7/21

9:12 pm-10:16 am

1 stop13h 04m

$290

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 6/28

6:15 am-12:31 pm

1 stop6h 16m

Chicago Midway

Tue 7/1

9:23 am-1:20 pm

1 stop3h 57m

$297

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 5/1

7:30 am-10:09 am

2 stops26h 39m

Chicago Midway

Thu 5/8

10:58 am-3:03 pm

1 stop28h 05m

$303

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sun 5/11

9:02 pm-7:08 pm

1 stop22h 06m

$88

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 4/30

7:27 pm-7:08 pm

1 stop23h 41m

$89

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 5/8

6:00 am-9:55 am

1 stop3h 55m

$105

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 16 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 April 1, 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
4,275 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,277 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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?

    $88 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $105 and $129, 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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