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$64+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$168
(Southwest)

One-way from

$64
(Mytrip)

Popular in

August

Cheapest in

May

Average price

$289
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. 5% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/2. 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 8/97:25 amOMA - MDW
Nonstop1h 25mSouthwest
Mon 8/119:00 pmMDW - OMA
Nonstop1h 25mSouthwest
Deal found 7/2$168
This Delta deal was found by Cheapflights users on 7/1. 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.
Thu 8/76:30 amOMA - MDW
1 stop5h 59mDelta
Tue 8/129:31 amMDW - OMA
1 stop3h 57mDelta
Deal found 7/1$177
This Southwest deal was found by Cheapflights users on 7/2. 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 8/163:45 pmDSM - MDW
1 stop5h 15mSouthwest
Wed 8/205:40 pmMDW - DSM
1 stop4h 40mSouthwest
Deal found 7/2$189
This Delta deal was found by Cheapflights users on 7/2. 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 8/136:00 amDSM - MDW
1 stop6h 28mDelta
Mon 8/189:15 amMDW - DSM
1 stop4h 54mDelta
Deal found 7/2$209
This Delta deal was found by Cheapflights users on 7/1. 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.
Fri 7/1112:02 pmCID - MDW
1 stop5h 37mDelta
Sun 7/139:24 amMDW - CID
1 stop6h 15mDelta
Deal found 7/1$229
This Frontier deal was found by Cheapflights users on 7/2. 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.
Thu 7/3111:10 amOMA - MDW
1 stop9h 12mFrontier
Sat 8/29:12 pmMDW - OMA
1 stop13h 04mFrontier
Deal found 7/2$274
This Mytrip deal was found by Cheapflights users on 7/1. 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 7/317:54 pmDSM - MDW
2 stops18h 02mAllegiant Air
Mon 8/42:46 pmMDW - DSM
2 stops22h 45mAllegiant Air
Deal found 7/1$333
This Orbitz deal was found by Cheapflights users on 7/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/77:33 pmDSM - MDW
2 stops15h 07mFrontier
Fri 7/1112:35 pmMDW - DSM
1 stop6h 13mFrontier
Deal found 7/2$341
This Delta deal was found by Cheapflights users on 7/2. 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 7/315:55 amMLI - MDW
1 stop12h 07mDelta
Sat 8/212:43 pmMDW - MLI
1 stop9h 36mDelta
Deal found 7/2$796

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 July 3, 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

Sat 8/9

7:25 am-8:50 am

Nonstop1h 25m

Chicago Midway

Mon 8/11

9:00 pm-10:25 pm

Nonstop1h 25m

$168

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 8/7

6:30 am-12:29 pm

1 stop5h 59m

Chicago Midway

Tue 8/12

9:31 am-1:28 pm

1 stop3h 57m

$177

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 8/16

3:45 pm-9:00 pm

1 stop5h 15m

Chicago Midway

Wed 8/20

5:40 pm-10:20 pm

1 stop4h 40m

$189

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 8/13

6:00 am-12:28 pm

1 stop6h 28m

Chicago Midway

Mon 8/18

9:15 am-2:09 pm

1 stop4h 54m

$209

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Fri 7/11

12:02 pm-5:39 pm

1 stop5h 37m

Chicago Midway

Sun 7/13

9:24 am-3:39 pm

1 stop6h 15m

$229

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 7/31

11:10 am-8:22 pm

1 stop9h 12m

Chicago Midway

Sat 8/2

9:12 pm-10:16 am

1 stop13h 04m

$274

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 7/31

7:54 pm-1:56 pm

2 stops18h 02m

Chicago Midway

Mon 8/4

2:46 pm-1:31 pm

2 stops22h 45m

$333

MolineChicago

MLI - MDW

MLIMDW

Moline Quad-City

Thu 7/31

5:55 am-6:02 pm

1 stop12h 07m

Chicago Midway

Sat 8/2

12:43 pm-10:19 pm

1 stop9h 36m

$796

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Tue 8/5

7:45 am-9:10 am

Nonstop1h 25m

$69

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Sat 8/9

2:03 pm-6:40 pm

1 stop4h 37m

$110

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 17 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
No data available for this route at this time. Please check back soon.

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 July 3, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Allegiant Air from Iowa to Chicago Midway Airport by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,270 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

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
4,270 reviews
Southwest
8.0
Very good
4,270 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

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
7,970 reviews
Southwest
8.0
Very good
4,270 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

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
7.2
Good
709 reviews
Southwest
8.0
Very good
4,270 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

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
3,284 reviews
Southwest
8.0
Very good
4,270 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

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?

    $64 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 $69 and $89, 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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