$115+ 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 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Jun 15 — Jun 221
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 May 16, 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 May 16, 2026.
This Southwest deal was found by Cheapflights users on 5/13. 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 6/103:45 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Wed 6/179:20 pm
MDW
- DSM
Nonstop1h 25m
Southwest
Deal found 5/13![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 5/13. 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 6/33:15 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Thu 6/410:10 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 5/13![Southwest logo]()
$263
This Southwest deal was found by Cheapflights users on 5/12. 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 10/105:40 am
DSM
- MDW
Nonstop1h 20m
Southwest
Sat 10/2410:50 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 5/12![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 5/15. 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 9/282:25 pm
DSM
- MDW
1 stop7h 35m
Southwest
Wed 9/308:35 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 5/15![Southwest logo]()
$273
This Delta deal was found by Cheapflights users on 5/11. 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 6/106:08 am
DSM
- MDW
1 stop6h 38m
Delta
Wed 6/179:54 am
MDW
- DSM
1 stop4h 11m
Delta
Deal found 5/11![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 5/13. 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 8/117:15 am
DSM
- MDW
2 stops9h 45m
Southwest
Thu 8/138:50 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 5/13![Southwest logo]()
$278
This Delta deal was found by Cheapflights users on 5/13. 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 8/126:55 am
DSM
- MDW
1 stop6h 13m
Delta
Sat 8/159:59 am
MDW
- DSM
1 stop4h 05m
Delta
Deal found 5/13![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 5/14. 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 7/73:50 pm
OMA
- MDW
Nonstop1h 25m
Southwest
Tue 7/145:50 pm
MDW
- OMA
Nonstop1h 25m
Southwest
Deal found 5/14![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 5/15. 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 8/812:19 pm
DSM
- MDW
1 stop6h 14m
Delta
Sat 8/151:27 pm
MDW
- DSM
1 stop3h 51m
Delta
Deal found 5/15![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 5/14. 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 6/103:45 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Sun 6/1410:25 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 5/14![Southwest logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 6/13:57 pm
DSM
- MDW
2 stops19h 15m
Multiple Airlines
Fri 6/59:23 pm
MDW
- DSM
1 stop26h 05m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 5/12. 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 9/3010:30 am
OMA
- MDW
Nonstop1h 25m
Southwest
Sat 10/310:30 am
MDW
- OMA
Nonstop1h 30m
Southwest
Deal found 5/12![Southwest logo]()
$303
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 May 16, 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 May 16, 2026.
This Southwest deal was found by Cheapflights users on 5/15. 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 6/305:20 am
DSM
- MDW
Nonstop1h 20m
Southwest
Tue 7/79:20 pm
MDW
- DSM
Nonstop1h 25m
Southwest
Deal found 5/15![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 5/11. 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 6/38:42 am
OMA
- MDW
1 stop4h 37m
Delta
Sat 6/61:59 pm
MDW
- OMA
1 stop5h 33m
Delta
Deal found 5/11![Delta logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 6/16:11 pm
CID
- MDW
2 stops17h 01m
Multiple Airlines
Thu 6/189:11 am
MDW
- CID
1 stop25h 47m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 5/15. 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 7/71:10 pm
OMA
- MDW
Nonstop1h 25m
Southwest
Tue 7/141:00 pm
MDW
- OMA
1 stop5h 20m
Southwest
Deal found 5/15![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 5/12. 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 6/91:15 pm
OMA
- MDW
1 stop5h 03m
Delta
Sat 6/136:55 pm
MDW
- OMA
1 stop4h 05m
Delta
Deal found 5/12![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 5/15. 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 9/3010:30 am
OMA
- MDW
Nonstop1h 25m
Southwest
Sat 10/310:30 am
MDW
- OMA
Nonstop1h 30m
Southwest
Deal found 5/15![Southwest logo]()
$303
This Delta deal was found by Cheapflights users on 5/11. 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.
Sat 6/136:50 am
DSM
- MDW
1 stop6h 19m
Delta
Tue 6/161:26 pm
MDW
- DSM
1 stop3h 57m
Delta
Deal found 5/11![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 5/15. 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 8/52:30 pm
OMA
- MDW
1 stop5h 15m
Southwest
Mon 8/108:35 pm
MDW
- OMA
Nonstop1h 30m
Southwest
Deal found 5/15![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 5/12. 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 6/152:45 pm
DSM
- MDW
1 stop3h 33m
Delta
Wed 6/179:54 am
MDW
- DSM
1 stop4h 11m
Delta
Deal found 5/12![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 5/15. 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 9/286:20 pm
OMA
- MDW
Nonstop1h 25m
Southwest
Tue 9/298:15 am
MDW
- OMA
2 stops6h 05m
Southwest
Deal found 5/15![Southwest logo]()
$318
This Delta deal was found by Cheapflights users on 5/12. 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 7/246:00 am
DSM
- MDW
1 stop6h 38m
Delta
Tue 7/281:18 pm
MDW
- DSM
1 stop3h 54m
Delta
Deal found 5/12![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 5/15. 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 9/241:10 pm
OMA
- MDW
Nonstop1h 25m
Southwest
Sat 9/2610:15 am
MDW
- OMA
Nonstop1h 30m
Southwest
Deal found 5/15![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 5/15. 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 8/118:20 am
OMA
- MDW
2 stops8h 35m
Southwest
Sat 8/152:25 pm
MDW
- OMA
1 stop5h 20m
Southwest
Deal found 5/15![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 5/12. 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 6/265:10 am
DSM
- MDW
Nonstop1h 20m
Southwest
Fri 7/310:10 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 5/12![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 5/15. 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 6/295:10 am
DSM
- MDW
Nonstop1h 20m
Southwest
Mon 7/610:05 pm
MDW
- DSM
Nonstop1h 25m
Southwest
Deal found 5/15![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 5/14. 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 7/186:46 am
CID
- MDW
1 stop6h 23m
Delta
Sat 7/186:55 pm
MDW
- CID
1 stop3h 55m
Delta
Deal found 5/14![Delta logo]()
$443
This Southwest deal was found by Cheapflights users on 5/11. 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.
Sat 11/76:00 am
OMA
- MDW
2 stops8h 30m
Southwest
Mon 11/95:20 pm
MDW
- OMA
Nonstop1h 35m
Southwest
Deal found 5/11![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 5/15. 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 6/264:25 pm
OMA
- MDW
Nonstop1h 25m
Southwest
Mon 6/299:25 pm
MDW
- OMA
Nonstop1h 30m
Southwest
Deal found 5/15![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 5/12. 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 6/36:57 am
CID
- MDW
1 stop6h 22m
Delta
Mon 6/81:26 pm
MDW
- CID
2 stops9h 23m
Delta
Deal found 5/12![Delta logo]()
$529
This Southwest deal was found by Cheapflights users on 5/14. 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 7/204:25 pm
OMA
- MDW
Nonstop1h 25m
Southwest
Mon 7/279:25 pm
MDW
- OMA
Nonstop1h 30m
Southwest
Deal found 5/14![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 5/11. 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.
Mon 6/111:59 am
CID
- MDW
1 stop5h 57m
Delta
Wed 6/39:23 am
MDW
- CID
1 stop6h 08m
Delta
Deal found 5/11![Delta logo]()
$538
This Southwest deal was found by Cheapflights users on 5/11. 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.
Fri 7/245:10 am
DSM
- MDW
Nonstop1h 20m
Southwest
Tue 7/287:00 am
MDW
- DSM
1 stop8h 05m
Southwest
Deal found 5/11![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 5/11. 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.
Sat 6/136:10 am
DSM
- MDW
2 stops8h 35m
Southwest
Tue 6/1610:10 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 5/11![Southwest logo]()
$344
This Delta deal was found by Cheapflights users on 5/14. 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 5/286:57 am
CID
- MDW
1 stop6h 22m
Delta
Sun 5/319:22 am
MDW
- CID
2 stops6h 09m
Delta
Deal found 5/14![Delta logo]()
$624
This Delta deal was found by Cheapflights users on 5/12. 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 6/111:59 am
CID
- MDW
1 stop5h 57m
Delta
Thu 6/187:16 pm
MDW
- CID
1 stop3h 33m
Delta
Deal found 5/12![Delta logo]()
$699
This Delta deal was found by Cheapflights users on 5/15. 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 8/612:29 pm
CID
- MDW
1 stop5h 32m
Delta
Sun 8/99:24 am
MDW
- CID
2 stops6h 11m
Delta
Deal found 5/15![Delta logo]()
$724
Last-minute flights from Iowa to MidwayDiscover last-minute flight deals from Iowa to Midway. Data last updated May 16, 2026 and is based on user searches.
Discover last-minute flight deals from Iowa to Midway. Data last updated May 16, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 6/13:57 pm
DSM
- MDW
2 stops19h 15m
Multiple Airlines
Fri 6/59:23 pm
MDW
- DSM
1 stop26h 05m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 5/13. 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 6/33:15 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Thu 6/410:10 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 5/13![Southwest logo]()
$263
This Southwest deal was found by Cheapflights users on 5/11. 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.
Sun 6/74:15 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Tue 6/910:10 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 5/11![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 5/11. 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.
Mon 6/84:40 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Mon 6/155:15 am
MDW
- DSM
1 stop7h 35m
Southwest
Deal found 5/11![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 5/13. 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 6/103:45 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Wed 6/179:20 pm
MDW
- DSM
Nonstop1h 25m
Southwest
Deal found 5/13![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 5/13. 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 6/106:08 am
DSM
- MDW
1 stop6h 38m
Delta
Wed 6/179:54 am
MDW
- DSM
1 stop4h 11m
Delta
Deal found 5/13![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 5/11. 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 6/101:10 pm
OMA
- MDW
Nonstop1h 25m
Southwest
Wed 6/109:00 pm
MDW
- OMA
Nonstop1h 30m
Southwest
Deal found 5/11![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 5/14. 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 6/103:45 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Sun 6/1410:25 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 5/14![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 5/13. 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 6/108:00 am
OMA
- MDW
1 stop5h 09m
Delta
Wed 6/177:16 pm
MDW
- OMA
1 stop3h 44m
Delta
Deal found 5/13![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 5/13. 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 6/105:20 am
OMA
- MDW
Nonstop1h 25m
Southwest
Wed 6/175:50 pm
MDW
- OMA
Nonstop1h 25m
Southwest
Deal found 5/13![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 5/11. 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.
Sun 6/146:08 am
DSM
- MDW
1 stop6h 38m
Delta
Wed 6/179:54 am
MDW
- DSM
1 stop4h 11m
Delta
Deal found 5/11![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 5/11. 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 6/245:20 am
DSM
- MDW
Nonstop1h 20m
Southwest
Fri 6/264:15 pm
MDW
- DSM
1 stop6h 05m
Southwest
Deal found 5/11![Southwest logo]()
$303
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 May 16, 2026.
Search for one-way flight options from Iowa to Midway. Find affordable one-way fares based on user searches. Data last updated May 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/15. 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 6/74:01 pm
DSM
- MDW
2 stops43h 11m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 6/16:11 pm
CID
- MDW
2 stops27h 51m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 5/14. 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 6/87:56 pm
OMA
- MDW
2 stops39h 13m
Frontier
Deal found 5/14![Frontier logo]()
$128
This Southwest deal was found by Cheapflights users on 5/13. 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 6/105:20 am
DSM
- MDW
Nonstop1h 20m
Southwest
Deal found 5/13![Southwest logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Tue 6/98:25 pm
OMA
- MDW
2 stops25h 46m
Frontier
Deal found 5/13![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 5/15. 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 8/1211:11 am
OMA
- MDW
1 stop21h 13m
Allegiant Air
Deal found 5/15![Allegiant Air logo]()
$134
This Southwest deal was found by Cheapflights users on 5/13. 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 6/84:40 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Deal found 5/13![Southwest logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Sat 8/86:42 pm
OMA
- MDW
1 stop13h 42m
Allegiant Air
Deal found 5/12![Allegiant Air logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 6/108:15 pm
OMA
- MDW
2 stops25h 56m
Frontier
Deal found 5/13![Frontier logo]()
$138
This Delta deal was found by Cheapflights users on 5/13. 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 6/106:08 am
DSM
- MDW
1 stop6h 38m
Delta
Deal found 5/13![Delta logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Tue 8/48:15 pm
OMA
- MDW
2 stops38h 52m
Frontier
Deal found 5/12![Frontier logo]()
$140
This Southwest deal was found by Cheapflights users on 5/15. 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 8/117:15 am
DSM
- MDW
2 stops9h 45m
Southwest
Deal found 5/15![Southwest logo]()
$144
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 May 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $257 (Southwest) |
One-way from | $115 (Kiwi.com) |
Popular in | April |
Cheapest in | September |
Average price | $224 |
Good round-trip deal | $386 or less |
Good one-way deal | $223 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 2,558,603 searches. Data last updated May 16, 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 - MDW
DSMMDW
Des Moines
Tue 6/30
5:20 am-6:40 am
Nonstop1h 20m
Chicago Midway
Tue 7/7
9:20 pm-10:45 pm
Nonstop1h 25m
$257
OmahaChicago
OMA - MDW
OMAMDW
Omaha Eppley Airfield
Tue 7/7
1:10 pm-2:35 pm
Nonstop1h 25m
Chicago Midway
Tue 7/14
1:00 pm-6:20 pm
1 stop5h 20m
$297
OmahaChicago
OMA - MDW
OMAMDW
Omaha Eppley Airfield
Wed 9/30
10:30 am-11:55 am
Nonstop1h 25m
Chicago Midway
Sat 10/3
10:30 am-12:00 pm
Nonstop1h 30m
$303
OmahaChicago
OMA - MDW
OMAMDW
Omaha Eppley Airfield
Wed 8/5
2:30 pm-7:45 pm
1 stop5h 15m
Chicago Midway
Mon 8/10
8:35 pm-10:05 pm
Nonstop1h 30m
$313
OmahaChicago
OMA - MDW
OMAMDW
Omaha Eppley Airfield
Mon 9/28
6:20 pm-7:45 pm
Nonstop1h 25m
Chicago Midway
Tue 9/29
8:15 am-2:20 pm
2 stops6h 05m
$318
OmahaChicago
OMA - MDW
OMAMDW
Omaha Eppley Airfield
Thu 9/24
1:10 pm-2:35 pm
Nonstop1h 25m
Chicago Midway
Sat 9/26
10:15 am-11:45 am
Nonstop1h 30m
$319
OmahaChicago
OMA - MDW
OMAMDW
Omaha Eppley Airfield
Wed 6/3
8:42 am-1:19 pm
1 stop4h 37m
Chicago Midway
Sat 6/6
1:59 pm-7:32 pm
1 stop5h 33m
$323
Cedar RapidsChicago
CID - MDW
CIDMDW
Cedar Rapids
Mon 6/1
6:11 pm-11:12 am
2 stops17h 01m
Chicago Midway
Thu 6/18
9:11 am-10:58 am
1 stop25h 47m
$327
OmahaChicago
OMA - MDW
OMAMDW
Omaha Eppley Airfield
Tue 8/11
8:20 am-4:55 pm
2 stops8h 35m
Chicago Midway
Sat 8/15
2:25 pm-7:45 pm
1 stop5h 20m
$328
Quickest round-trip
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Fri 6/26
5:10 am-6:30 am
Nonstop1h 20m
Chicago Midway
Fri 7/3
10:10 am-11:30 am
Nonstop1h 20m
$329
Showing 1-10 of 56 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
OMA-MDW
CID-MDW
LSE-MDW
MLI-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
OMA-MDW
CID-MDW
LSE-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 May 16, 2026.
When flying from Iowa to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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
Hammond
Porter
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