$130+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Dec 11 — Dec 181
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 November 11, 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 November 11, 2026.
This Southwest deal was found by Cheapflights users on 11/8. 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 12/309:55 am -
Nonstop1h 20m
Deal found 11/8![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 11/9. 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 12/27:00 am -
1 stop5h 15m
Wed 12/28:40 pm -
Nonstop1h 25m
Deal found 11/9![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 11/9. 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 12/512:45 pm -
Nonstop1h 25m
Mon 12/78:40 pm -
Nonstop1h 25m
Deal found 11/9![Southwest logo]()
$274
This Delta deal was found by Cheapflights users on 11/8. 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 12/56:41 am -
1 stop5h 18m
Sat 12/125:30 pm -
1 stop4h 01m
Deal found 11/8![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 11/11. 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 12/96:00 am -
Nonstop1h 25m
Wed 12/1610:15 am -
2 stops10h 35m
Deal found 11/11![Southwest logo]()
$290
This Delta deal was found by Cheapflights users on 11/7. 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 12/1011:01 am -
1 stop5h 49m
Tue 12/1510:24 am -
1 stop5h 47m
Deal found 11/7![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 11/10. 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 12/115:25 am -
Nonstop1h 30m
Wed 12/168:40 pm -
Nonstop1h 25m
Deal found 11/10![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 11/10. 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 12/36:00 am -
Nonstop1h 25m
Mon 12/78:40 pm -
Nonstop1h 25m
Deal found 11/10![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 11/10. 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 12/811:00 am -
1 stop5h 50m
Tue 12/155:30 pm -
1 stop5h 39m
Deal found 11/10![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 11/11. 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 12/226:10 am -
1 stop4h 51m
Sun 12/276:30 pm -
1 stop4h 38m
Deal found 11/11![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/8. 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 12/1811:00 am -
1 stop5h 50m
Sun 1/36:30 pm -
1 stop4h 38m
Deal found 11/8![Delta logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Mon 12/75:46 pm -
2 stops17h 47m
Sun 12/136:10 pm -
1 stop14h 11m
Deal found 11/11![Multiple Airlines logo]()
$358
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 November 11, 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 November 11, 2026.
This Southwest deal was found by Cheapflights users on 11/8. 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 12/309:55 am -
Nonstop1h 20m
Deal found 11/8![Southwest logo]()
$259
This Delta deal was found by Cheapflights users on 11/10. 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 12/512:38 pm -
1 stop4h 12m
Sat 12/1210:24 am -
1 stop5h 47m
Deal found 11/10![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 11/6. 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 12/83:25 pm -
Nonstop1h 30m
Wed 12/98:05 am -
1 stop6h 10m
Deal found 11/6![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 11/6. 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 12/1212:45 pm -
Nonstop1h 25m
Mon 12/148:40 pm -
Nonstop1h 25m
Deal found 11/6![Southwest logo]()
$274
This Delta deal was found by Cheapflights users on 11/10. 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 1/410:54 am -
1 stop5h 59m
Sat 1/99:56 am -
1 stop6h 17m
Deal found 11/10![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 11/7. 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 12/297:15 pm -
Nonstop1h 20m
Tue 12/2910:05 pm -
Nonstop1h 30m
Deal found 11/7![Southwest logo]()
$274
This Delta deal was found by Cheapflights users on 11/9. 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 12/266:10 am -
1 stop4h 53m
Sun 12/276:30 pm -
1 stop4h 38m
Deal found 11/9![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 11/10. 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 12/307:15 pm -
Nonstop1h 20m
Mon 1/412:45 pm -
2 stops9h 20m
Deal found 11/10![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 11/11. 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 11/256:15 am -
1 stop5h 35m
Fri 11/2711:05 am -
1 stop5h 03m
Deal found 11/11![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 11/10. 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 12/87:00 am -
2 stops10h 05m
Tue 12/1510:15 am -
2 stops10h 35m
Deal found 11/10![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 11/7. 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.
Sun 11/226:15 am -
1 stop5h 35m
Fri 11/2711:05 am -
1 stop5h 03m
Deal found 11/7![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 11/10. 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 12/33:30 pm -
Nonstop1h 30m
Mon 12/78:05 am -
1 stop6h 10m
Deal found 11/10![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 11/9. 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 12/247:00 am -
1 stop5h 15m
Thu 12/318:40 pm -
Nonstop1h 25m
Deal found 11/9![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 11/10. 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 4/1511:00 am -
1 stop5h 50m
Mon 4/199:30 am -
2 stops6h 22m
Deal found 11/10![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 11/11. 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 11/266:15 am -
1 stop4h 10m
Sat 11/2810:34 am -
1 stop5h 34m
Deal found 11/11![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 11/9. 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 12/1411:00 am -
1 stop5h 50m
Thu 12/1712:39 pm -
1 stop3h 42m
Deal found 11/9![Delta logo]()
$567
This Delta deal was found by Cheapflights users on 11/7. 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 12/46:15 am -
1 stop5h 44m
Sun 12/65:30 pm -
1 stop5h 39m
Deal found 11/7![Delta logo]()
$579
Last-minute flights from Iowa to MidwayDiscover last-minute flight deals from Iowa to Midway. Data last updated November 11, 2026 and is based on user searches.
Discover last-minute flight deals from Iowa to Midway. Data last updated November 11, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 11/9. 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 12/27:00 am -
1 stop5h 15m
Wed 12/28:40 pm -
Nonstop1h 25m
Deal found 11/9![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 11/10. 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 12/36:00 am -
Nonstop1h 25m
Mon 12/78:40 pm -
Nonstop1h 25m
Deal found 11/10![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 11/9. 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 12/512:45 pm -
Nonstop1h 25m
Mon 12/78:40 pm -
Nonstop1h 25m
Deal found 11/9![Southwest logo]()
$274
This Delta deal was found by Cheapflights users on 11/8. 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 12/56:41 am -
1 stop5h 18m
Sat 12/125:30 pm -
1 stop4h 01m
Deal found 11/8![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 11/10. 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 12/55:20 am -
Nonstop1h 25m
Sat 12/1210:35 am -
Nonstop1h 25m
Deal found 11/10![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 11/10. 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 12/811:00 am -
1 stop5h 50m
Tue 12/155:30 pm -
1 stop5h 39m
Deal found 11/10![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 11/11. 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 12/96:00 am -
Nonstop1h 25m
Wed 12/1610:15 am -
2 stops10h 35m
Deal found 11/11![Southwest logo]()
$290
This Delta deal was found by Cheapflights users on 11/7. 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 12/1011:01 am -
1 stop5h 49m
Tue 12/1510:24 am -
1 stop5h 47m
Deal found 11/7![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 11/10. 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 12/115:25 am -
Nonstop1h 30m
Wed 12/168:40 pm -
Nonstop1h 25m
Deal found 11/10![Southwest logo]()
$304
This Delta deal was found by Cheapflights users on 11/8. 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 12/1811:00 am -
1 stop5h 50m
Sun 1/36:30 pm -
1 stop4h 38m
Deal found 11/8![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 11/11. 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 12/226:10 am -
1 stop4h 51m
Sun 12/276:30 pm -
1 stop4h 38m
Deal found 11/11![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 11/8. 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 12/309:55 am -
Nonstop1h 20m
Deal found 11/8![Southwest logo]()
$259
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 November 11, 2026.
Search for one-way flight options from Iowa to Midway. Find affordable one-way fares based on user searches. Data last updated November 11, 2026.
This Southwest deal was found by Cheapflights users on 11/8. 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 12/512:45 pm -
Nonstop1h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Southwest logo]()
$130
This Southwest deal was found by Cheapflights users on 11/10. 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 12/26:00 am -
Nonstop1h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Southwest logo]()
$135
This Delta deal was found by Cheapflights users on 11/8. 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 12/512:38 pm -
1 stop4h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Delta logo]()
$140
This Delta deal was found by Cheapflights users on 11/10. 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 12/211:01 am -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Delta logo]()
$145
This Delta deal was found by Cheapflights users on 11/9. 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 12/1011:01 am -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$155
This KAYAK deal was found by Cheapflights users on 11/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:01 am -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$168
This Southwest deal was found by Cheapflights users on 11/10. 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 12/115:25 am -
Nonstop1h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Southwest logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 12/67:15 am -
1 stop10h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Allegiant Air logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 11/236:06 pm -
2 stops18h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 11/256:06 pm -
2 stops18h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 11/237:08 pm -
1 stop13h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Allegiant Air logo]()
$326
This Delta deal was found by Cheapflights users on 11/10. 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.
Sun 1/36:10 am -
1 stop4h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Delta logo]()
$334
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 November 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $259 (Southwest) |
One-way from | $130 (Southwest) |
Popular in | July |
Cheapest in | December |
Average price | $378 |
Good round-trip deal | $335 or less |
Good one-way deal | $238 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 November 11, 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
Sat 12/5
12:45 pm-2:10 pm
Nonstop1h 25m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$130
Quickest round-trip
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Sat 2/6
1:10 pm-2:30 pm
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Tue 12/8
3:25 pm-4:55 pm
Nonstop1h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Tue 12/8
11:01 am-4:50 pm
1 stop5h 49m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Thu 12/10
6:00 am-7:25 am
Nonstop1h 25m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Fri 12/11
5:25 am-6:55 am
Nonstop1h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Sun 12/6
4:25 pm-5:45 pm
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$219
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Thu 12/24
7:00 am-5:05 pm
2 stops10h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$220
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 12/30
9:55 am-11:15 am
Nonstop1h 20m
$259
Des MoinesChicago
DSM Des Moines - MDW Chicago Midway
DSMMDW
Des Moines
Tue 12/8
3:25 pm-4:55 pm
Nonstop1h 30m
Chicago Midway
Wed 12/9
8:05 am-2:15 pm
1 stop6h 10m
$269
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 November 11, 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 31% 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Iowa to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Iowa to Midway by cabin class
Find flights from Iowa to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 11, 2026.
Iowa and Midway flights
Browse other Iowa and Midway flight options. Last updated on November 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Iowa to Midway flights
Consider these flights traveling from Iowa to Midway.
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 7,457,451 searches. Data last updated November 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$283 | Average$329 | FlexibilityNo cancel fee | On-time63% |