$119+ Cheap flights from Iowa to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Oct 28 — Nov 41
Round-trip
1 adult, Economy
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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
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Cheapest flights from Iowa to MidwayExplore 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 September 28, 2026.
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 September 28, 2026.
This Southwest deal was found by Cheapflights users on 9/25. 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 10/171:20 pm -
Nonstop1h 20m
Mon 10/199:50 pm -
Nonstop1h 25m
Deal found 9/25![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 9/24. 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.
Mon 10/267:10 pm -
1 stop5h 10m
Wed 10/2810:05 am -
Nonstop1h 25m
Deal found 9/24![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 9/24. 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.
Mon 10/265:10 am -
Nonstop1h 20m
Tue 10/271:05 pm -
2 stops7h 35m
Deal found 9/24![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 9/28. 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 10/216:55 am -
1 stop4h 52m
Sat 10/2410:12 am -
1 stop4h 13m
Deal found 9/28![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 9/24. 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 10/203:00 pm -
Nonstop1h 20m
Thu 10/226:05 am -
1 stop7h 15m
Deal found 9/24![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 9/27. 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 10/205:35 am -
Nonstop1h 20m
Tue 10/201:05 pm -
2 stops7h 35m
Deal found 9/27![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 9/25. 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 11/107:00 am -
2 stops10h 05m
Tue 11/1710:15 am -
2 stops10h 35m
Deal found 9/25![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 9/24. 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 10/224:30 pm -
Nonstop1h 20m
Fri 10/239:50 pm -
Nonstop1h 25m
Deal found 9/24![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 9/24. 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.
Mon 11/95:25 am -
Nonstop1h 30m
Tue 11/1010:15 am -
2 stops10h 35m
Deal found 9/24![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 9/24. 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 11/183:30 pm -
Nonstop1h 30m
Sat 11/219:30 pm -
Nonstop1h 30m
Deal found 9/24![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 9/24. 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 10/237:10 pm -
1 stop5h 10m
Fri 10/309:45 am -
Nonstop1h 25m
Deal found 9/24![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 9/28. 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 11/711:00 am -
1 stop5h 47m
Mon 11/95:29 pm -
1 stop5h 37m
Deal found 9/28![Delta logo]()
$309
Best flights from Iowa to MidwayDiscover carefully curated flight deals from Iowa to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 28, 2026.
Discover carefully curated flight deals from Iowa to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 28, 2026.
This Delta deal was found by Cheapflights users on 9/25. 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 12/36:41 am -
1 stop5h 18m
Mon 12/75:30 pm -
1 stop4h 01m
Deal found 9/25![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 9/28. 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 2/255:10 am -
Nonstop1h 20m
Sat 2/278:55 pm -
Nonstop1h 25m
Deal found 9/28![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 9/28. 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 2/257:00 am -
1 stop4h 51m
Sat 2/279:55 am -
1 stop6h 02m
Deal found 9/28![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 9/25. 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 12/37:00 am -
1 stop5h 15m
Mon 12/710:05 am -
Nonstop1h 20m
Deal found 9/25![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 9/24. 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 11/186:00 am -
Nonstop1h 25m
Sat 11/212:20 pm -
1 stop7h 30m
Deal found 9/24![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 9/27. 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.
Sun 10/185:30 am -
Nonstop1h 20m
Tue 10/2010:05 am -
Nonstop1h 25m
Deal found 9/27![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 9/28. 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 11/135:25 am -
Nonstop1h 30m
Sun 11/1510:05 am -
Nonstop1h 25m
Deal found 9/28![Southwest logo]()
$328
This Delta deal was found by Cheapflights users on 9/28. 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 12/311:00 am -
1 stop5h 50m
Sun 12/610:24 am -
1 stop5h 57m
Deal found 9/28![Delta logo]()
$404
This Southwest deal was found by Cheapflights users on 9/24. 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 12/57:00 am -
2 stops10h 05m
Sun 12/62:35 pm -
1 stop7h 25m
Deal found 9/24![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 9/27. 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 12/411:00 am -
1 stop5h 50m
Sun 12/610:24 am -
1 stop5h 57m
Deal found 9/27![Delta logo]()
$404
This Southwest deal was found by Cheapflights users on 9/24. 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 12/114:25 pm -
Nonstop1h 20m
Sun 12/132:35 pm -
1 stop7h 25m
Deal found 9/24![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 9/27. 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 10/276:20 am -
2 stops6h 27m
Sat 10/315:31 pm -
1 stop5h 29m
Deal found 9/27![Delta logo]()
$454
This Southwest deal was found by Cheapflights users on 9/26. 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 12/47:00 am -
2 stops10h 05m
Sun 12/69:35 pm -
Nonstop1h 25m
Deal found 9/26![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 9/25. 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.
Sun 11/84:25 pm -
Nonstop1h 20m
Mon 11/1610:15 am -
2 stops10h 35m
Deal found 9/25![Southwest logo]()
$375
Last-minute flights from Iowa to MidwayDiscover last-minute flight deals from Iowa to Midway. Data last updated September 28, 2026 and is based on user searches.
Discover last-minute flight deals from Iowa to Midway. Data last updated September 28, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/24. 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 10/312:10 pm -
1 stop5h 49m
Tue 10/610:12 am -
1 stop6h 11m
Deal found 9/24![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 9/24. 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 10/157:10 pm -
1 stop5h 10m
Sat 10/177:25 pm -
Nonstop1h 25m
Deal found 9/24![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 9/25. 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 10/171:20 pm -
Nonstop1h 20m
Mon 10/199:50 pm -
Nonstop1h 25m
Deal found 9/25![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 9/25. 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.
Mon 10/194:30 pm -
Nonstop1h 20m
Wed 10/211:05 pm -
2 stops7h 35m
Deal found 9/25![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 9/24. 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 10/203:00 pm -
Nonstop1h 20m
Thu 10/226:05 am -
1 stop7h 15m
Deal found 9/24![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 9/27. 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 10/205:35 am -
Nonstop1h 20m
Tue 10/201:05 pm -
2 stops7h 35m
Deal found 9/27![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 9/28. 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 10/216:55 am -
1 stop4h 52m
Sat 10/2410:12 am -
1 stop4h 13m
Deal found 9/28![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 9/24. 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 10/224:30 pm -
Nonstop1h 20m
Fri 10/239:50 pm -
Nonstop1h 25m
Deal found 9/24![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 9/24. 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 10/237:10 pm -
1 stop5h 10m
Fri 10/309:45 am -
Nonstop1h 25m
Deal found 9/24![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 9/24. 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.
Mon 10/267:10 pm -
1 stop5h 10m
Wed 10/2810:05 am -
Nonstop1h 25m
Deal found 9/24![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 9/24. 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.
Mon 10/265:10 am -
Nonstop1h 20m
Tue 10/271:05 pm -
2 stops7h 35m
Deal found 9/24![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 9/27. 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 10/2711:00 am -
1 stop5h 47m
Sat 10/315:31 pm -
1 stop5h 29m
Deal found 9/27![Delta logo]()
$324
One-way flights from Iowa to MidwaySearch for one-way flight options from Iowa to Midway. Find affordable one-way fares based on user searches. Data last updated September 28, 2026.
Search for one-way flight options from Iowa to Midway. Find affordable one-way fares based on user searches. Data last updated September 28, 2026.
This Southwest deal was found by Cheapflights users on 9/28. 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 10/241:20 pm -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Southwest logo]()
$119
This Delta deal was found by Cheapflights users on 9/28. 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 10/2410:57 am -
1 stop5h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Delta logo]()
$129
This Southwest deal was found by Cheapflights users on 9/28. 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 11/47:00 am -
2 stops10h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 9/27. 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 11/65:25 am -
Nonstop1h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Southwest logo]()
$139
This Southwest deal was found by Cheapflights users on 9/27. 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 10/237:10 pm -
1 stop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Southwest logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/258:00 am -
2 stops39h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$164
This Southwest deal was found by Cheapflights users on 9/24. 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 12/235:10 am -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Southwest logo]()
$165
This Frontier deal was found by Cheapflights users on 9/27. 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.
Tue 3/239:35 am -
1 stop10h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$171
This Southwest deal was found by Cheapflights users on 9/28. 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 10/277:05 am -
2 stops9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 9/24. 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 12/307:10 pm -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Southwest logo]()
$190
This Delta deal was found by Cheapflights users on 9/28. 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 12/166:15 am -
1 stop5h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Delta logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/166:09 pm -
1 stop21h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Allegiant Air logo]()
$297
Find flight deals from Iowa to Midway
Keep the following information in mind while searching for Iowa to Midway flight deals. Data was last updated September 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $237 (Southwest) |
One-way from | $119 (Southwest) |
Popular in | July |
Cheapest in | October |
Average price | $311 |
Good round-trip deal | $419 or less |
Good one-way deal | $208 or less |
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 7,457,451 searches. Data last updated September 28, 2026.
Use the filters below to find and compare flights from Iowa to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Tue 12/15
3:30 pm-4:55 pm
Nonstop1h 25m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$119
Quickest round-trip
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Tue 12/22
7:10 pm-8:30 pm
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$119
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Mon 11/23
6:45 am-11:50 am
1 stop5h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Sat 12/12
6:41 am-11:59 am
1 stop5h 18m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Fri 10/23
4:30 pm-5:50 pm
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$165
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Wed 12/23
5:10 am-6:30 am
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$165
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Tue 10/27
7:05 am-4:05 pm
2 stops9h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$180
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Tue 11/24
5:10 am-6:30 am
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$190
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Fri 11/27
5:25 am-6:55 am
Nonstop1h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$190
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Sat 11/21
11:00 am-4:39 pm
1 stop5h 39m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$200
Showing 1-10 of 36 resultsSorted by cheapest first
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.
DSM-MDW
CID-MDW
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
USIA-MDW
DSM-MDW
CID-MDW
What is the cheapest time of day to fly from IA to MDW?
Find hourly flight availability from Iowa to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 28, 2026.
A simple way to save on the total cost of your ticket is to fly from Iowa to Chicago Midway Airport in the afternoon. If you’re flexible enough to do this you can expect to save up to 35% on your trip compared to booking a flight in the evening.
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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