HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$55+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Iowa to Midway with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(Southwest)

One-way from

$55
(Frontier)

Popular in

June

Cheapest in

November

Average price

$295
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. 10% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals

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 February 22, 2025.

This Southwest deal was found by Cheapflights users on 2/20. 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 3/124:05 pmOMA - MDW
Nonstop1h 30mSouthwest
Thu 3/138:25 amMDW - OMA
Nonstop1h 35mSouthwest
Deal found 2/20$207
This Delta deal was found by Cheapflights users on 2/21. 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 4/111:55 amDSM - MDW
1 stop6h 23mDelta
Tue 4/82:57 pmMDW - DSM
1 stop5h 49mDelta
Deal found 2/21$209
This Frontier deal was found by Cheapflights users on 2/20. 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.
Mon 3/243:58 pmOMA - MDW
1 stop8h 19mFrontier
Fri 3/286:40 amMDW - OMA
1 stop8h 18mFrontier
Deal found 2/20$210
This Delta deal was found by Cheapflights users on 2/22. 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 4/86:28 amOMA - MDW
1 stop6h 07mDelta
Sat 4/1211:22 amMDW - OMA
1 stop5h 12mDelta
Deal found 2/22$212
This Southwest deal was found by Cheapflights users on 2/21. 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 4/25:10 pmDSM - MDW
2 stops5h 35mSouthwest
Wed 4/96:25 amMDW - DSM
1 stop5h 10mSouthwest
Deal found 2/21$214
This Booking.com deal was found by Cheapflights users on 2/22. 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.
Fri 3/76:57 pmDSM - MDW
1 stop13h 56mFrontier
Sun 3/96:40 amMDW - DSM
1 stop13h 05mFrontier
Deal found 2/22$230
This Mytrip deal was found by Cheapflights users on 2/21. 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.
Mon 3/106:19 pmCID - MDW
1 stop23h 27mAllegiant Air
Thu 4/36:10 pmMDW - CID
1 stop23h 23mAllegiant Air
Deal found 2/21$244
This Delta deal was found by Cheapflights users on 2/21. 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.
Mon 11/246:50 amCID - MDW
1 stop6h 12mDelta
Tue 12/29:20 amMDW - CID
1 stop6h 23mDelta
Deal found 2/21$258
This Mytrip deal was found by Cheapflights users on 2/21. 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.
Tue 3/189:19 amOMA - MDW
1 stop8h 27mAllegiant Air
Mon 3/2410:54 amMDW - OMA
2 stops32h 08mAllegiant Air
Deal found 2/21$437
This Mytrip deal was found by Cheapflights users on 2/22. 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.
Fri 6/66:30 amDSM - MDW
2 stops13h 16mAllegiant Air
Sun 6/158:09 pmMDW - DSM
2 stops24h 18mAllegiant Air
Deal found 2/22$501
This Mytrip deal was found by Cheapflights users on 2/21. 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.
Mon 3/107:03 pmMLI - MDW
1 stop22h 43mAllegiant Air
Thu 3/206:26 pmMDW - MLI
1 stop23h 47mAllegiant Air
Deal found 2/21$871

Find flights from Iowa to Midway within your budget

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 February 22, 2025.

Fly from

Iowa

Fly to

Midway

Route

Depart

Return

Price

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 3/12

4:05 pm-5:35 pm

Nonstop1h 30m

Chicago Midway

Thu 3/13

8:25 am-10:00 am

Nonstop1h 35m

$207

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 4/1

11:55 am-6:18 pm

1 stop6h 23m

Chicago Midway

Tue 4/8

2:57 pm-8:46 pm

1 stop5h 49m

$209

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Mon 3/24

3:58 pm-12:17 am

1 stop8h 19m

Chicago Midway

Fri 3/28

6:40 am-2:58 pm

1 stop8h 18m

$210

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Tue 4/8

6:28 am-12:35 pm

1 stop6h 07m

Chicago Midway

Sat 4/12

11:22 am-4:34 pm

1 stop5h 12m

$212

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 4/2

5:10 pm-10:45 pm

2 stops5h 35m

Chicago Midway

Wed 4/9

6:25 am-11:35 am

1 stop5h 10m

$214

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 3/7

6:57 pm-8:53 am

1 stop13h 56m

Chicago Midway

Sun 3/9

6:40 am-7:45 pm

1 stop13h 05m

$230

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Mon 3/10

6:19 pm-5:46 pm

1 stop23h 27m

Chicago Midway

Thu 4/3

6:10 pm-5:33 pm

1 stop23h 23m

$244

Cedar RapidsChicago

CID - MDW

CIDMDW

Cedar Rapids

Wed 7/16

6:50 am-1:02 pm

1 stop6h 12m

Chicago Midway

Sat 7/19

6:45 pm-10:18 pm

1 stop3h 33m

$262

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Tue 3/18

9:19 am-5:46 pm

1 stop8h 27m

Chicago Midway

Mon 3/24

10:54 am-7:02 pm

2 stops32h 08m

$437

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 6/6

6:30 am-7:46 pm

2 stops13h 16m

Chicago Midway

Sun 6/15

8:09 pm-8:27 pm

2 stops24h 18m

$501

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 20 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.

Travel insights for flights from Iowa to Midway

Get recent, data-driven insights about flights from Iowa to Midway including ideal travel times, pricing trends, and more.

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 February 22, 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
8.1
Very good
4,395 reviews

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
764 reviews
Southwest
8.1
Very good
4,395 reviews

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,352 reviews
Southwest
8.1
Very good
4,395 reviews

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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?

    $55 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 $89 and $99, respectively.

  • 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.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Iowa to Midway

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Boston to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Seattle to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Denver to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Newark to Midway flights
Philadelphia to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Ontario to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Los Angeles to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Hobby to O'Hare Intl flights
Burbank to O'Hare Intl flights
LaGuardia to Midway flights
Austin to O'Hare Intl flights
San Diego to O'Hare Intl flights
Dulles Intl to Midway flights
Orlando to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Seattle to Midway flights
Charlotte to O'Hare Intl flights
Atlanta to Midway flights
Dallas/Fort Worth to Midway flights
Hobby to Midway flights
Tampa to O'Hare Intl flights
San Francisco to Midway flights
Miami to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hartford to O'Hare Intl flights
Portland to O'Hare Intl flights
Minneapolis to Midway flights
Baltimore to Midway flights
Boston to Midway flights
Cleveland to O'Hare Intl flights
Detroit to O'Hare Intl flights
Reagan-National to Midway flights
San Diego to Midway flights
Richmond to O'Hare Intl flights

Top airline flying from Iowa to Midway

Discover the top airline that operate flights from Iowa to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$195Average$562FlexibilityNo cancel feeOn-timeN/A
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.