$119+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — MDW
Jul 29 — Aug 51
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 June 29, 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 June 29, 2026.
This Southwest deal was found by Cheapflights users on 6/28. 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 8/112:40 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Tue 8/1810:30 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/28![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 6/25. 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 8/103:50 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Tue 8/1110:30 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/25![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 6/28. 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 8/13:35 pm
DSM
- MDW
Nonstop1h 25m
Southwest
Sat 8/86:00 pm
MDW
- DSM
Nonstop1h 25m
Southwest
Deal found 6/28![Southwest logo]()
$250
This Southwest deal was found by Cheapflights users on 6/25. 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 8/812:10 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Sat 8/1510:10 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/25![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 6/24. 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.
Wed 8/196:50 am
CID
- MDW
1 stop6h 20m
Delta
Wed 8/267:25 pm
MDW
- CID
1 stop3h 35m
Delta
Deal found 6/24![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 6/29. 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 8/133:50 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Thu 8/2010:05 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/29![Southwest logo]()
$260
This Southwest deal was found by Cheapflights users on 6/24. 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 9/297:15 am
DSM
- MDW
2 stops9h 45m
Southwest
Wed 9/308:35 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/24![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 6/25. 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 9/195:30 am
DSM
- MDW
Nonstop1h 15m
Southwest
Sat 9/1910:15 am
MDW
- DSM
2 stops10h 30m
Southwest
Deal found 6/25![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 6/28. 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.
Mon 8/103:50 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Mon 8/178:50 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/28![Southwest logo]()
$273
This Delta deal was found by Cheapflights users on 6/25. 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.
Tue 7/146:46 am
CID
- MDW
1 stop6h 23m
Delta
Sat 7/189:54 am
MDW
- CID
1 stop5h 38m
Delta
Deal found 6/25![Delta logo]()
$274
This Delta deal was found by Cheapflights users on 6/24. 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.
Wed 7/812:09 pm
CID
- MDW
1 stop6h 09m
Delta
Sat 7/119:54 am
MDW
- CID
1 stop5h 38m
Delta
Deal found 6/24![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 6/28. 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 10/221:50 pm
OMA
- MDW
Nonstop1h 25m
Southwest
Sun 10/2512:05 pm
MDW
- OMA
1 stop5h 15m
Southwest
Deal found 6/28![Southwest logo]()
$301
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 June 29, 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 June 29, 2026.
This Delta deal was found by Cheapflights users on 6/25. 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.
Tue 12/16:45 am
CID
- MDW
1 stop5h 06m
Delta
Sat 12/512:30 pm
MDW
- CID
1 stop3h 22m
Delta
Deal found 6/25![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 6/28. 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.
Mon 8/103:50 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Mon 8/178:50 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/28![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 6/28. 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 8/65:40 am
DSM
- MDW
Nonstop1h 20m
Southwest
Mon 8/1010:05 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/28![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 6/26. 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.
Mon 12/76:00 am
DSM
- MDW
Nonstop1h 25m
Southwest
Thu 12/106:05 am
MDW
- DSM
1 stop8h 05m
Southwest
Deal found 6/26![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 6/28. 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.
Mon 8/106:00 am
DSM
- MDW
1 stop6h 39m
Delta
Mon 8/171:25 pm
MDW
- DSM
1 stop3h 46m
Delta
Deal found 6/28![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 6/26. 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.
Tue 8/257:15 am
DSM
- MDW
2 stops9h 45m
Southwest
Sun 8/3010:15 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/26![Southwest logo]()
$306
This Delta deal was found by Cheapflights users on 6/27. 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.
Sun 9/612:29 pm
CID
- MDW
1 stop3h 28m
Delta
Sat 9/124:52 pm
MDW
- CID
1 stop6h 07m
Delta
Deal found 6/27![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 6/28. 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 8/282:25 pm
DSM
- MDW
1 stop5h 50m
Southwest
Sat 8/296:50 am
MDW
- DSM
1 stop7h 20m
Southwest
Deal found 6/28![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 6/27. 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.
Wed 9/912:10 pm
CID
- MDW
1 stop6h 09m
Delta
Mon 9/147:13 pm
MDW
- CID
1 stop3h 46m
Delta
Deal found 6/27![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 6/24. 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 9/85:25 pm
OMA
- MDW
1 stop5h 45m
Southwest
Fri 9/117:55 am
MDW
- OMA
2 stops6h 45m
Southwest
Deal found 6/24![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 6/29. 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 7/3112:09 pm
CID
- MDW
1 stop6h 09m
Delta
Fri 8/77:25 pm
MDW
- CID
1 stop3h 35m
Delta
Deal found 6/29![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 6/28. 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 8/2111:10 am
OMA
- MDW
2 stops9h 00m
Southwest
Tue 8/2510:10 am
MDW
- OMA
2 stops9h 10m
Southwest
Deal found 6/28![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 6/25. 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.
Mon 8/36:50 am
CID
- MDW
1 stop6h 20m
Delta
Mon 8/177:25 pm
MDW
- CID
1 stop3h 35m
Delta
Deal found 6/25![Delta logo]()
$374
This Southwest deal was found by Cheapflights users on 6/27. 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.
Sat 8/157:05 am
OMA
- MDW
2 stops6h 15m
Southwest
Tue 8/1810:10 am
MDW
- OMA
2 stops9h 10m
Southwest
Deal found 6/27![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 6/24. 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 7/256:46 am
CID
- MDW
1 stop6h 23m
Delta
Fri 7/319:54 am
MDW
- CID
1 stop5h 44m
Delta
Deal found 6/24![Delta logo]()
$379
This Southwest deal was found by Cheapflights users on 6/24. 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 11/55:30 am
OMA
- MDW
Nonstop1h 35m
Southwest
Sun 11/82:35 pm
MDW
- OMA
2 stops9h 05m
Southwest
Deal found 6/24![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 6/24. 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 8/215:40 am
DSM
- MDW
Nonstop1h 20m
Southwest
Sun 8/239:30 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/24![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 6/27. 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 12/2511:00 am
OMA
- MDW
Nonstop1h 25m
Southwest
Tue 1/58:55 pm
MDW
- OMA
Nonstop1h 35m
Southwest
Deal found 6/27![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 6/27. 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.
Thu 7/912:09 pm
CID
- MDW
1 stop6h 09m
Delta
Sat 7/116:55 pm
MDW
- CID
1 stop3h 55m
Delta
Deal found 6/27![Delta logo]()
$464
This Southwest deal was found by Cheapflights users on 6/29. 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 9/276:15 am
OMA
- MDW
1 stop6h 35m
Southwest
Sun 10/1112:35 pm
MDW
- OMA
Nonstop1h 30m
Southwest
Deal found 6/29![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 6/25. 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.
Fri 9/182:05 pm
OMA
- MDW
2 stops9h 40m
Southwest
Sun 9/207:55 am
MDW
- OMA
1 stop5h 40m
Southwest
Deal found 6/25![Southwest logo]()
$362
This Delta deal was found by Cheapflights users on 6/27. 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.
Sat 7/116:46 am
CID
- MDW
1 stop6h 23m
Delta
Sat 7/116:55 pm
MDW
- CID
1 stop16h 31m
Delta
Deal found 6/27![Delta logo]()
$536
This Southwest deal was found by Cheapflights users on 6/26. 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 7/177:30 pm
OMA
- MDW
1 stop4h 45m
Southwest
Mon 7/2711:20 am
MDW
- OMA
2 stops11h 45m
Southwest
Deal found 6/26![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 6/28. 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.
Sun 8/166:50 am
CID
- MDW
2 stops5h 49m
Delta
Mon 8/177:25 pm
MDW
- CID
1 stop3h 35m
Delta
Deal found 6/28![Delta logo]()
$558
This Southwest deal was found by Cheapflights users on 6/27. 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 7/244:25 pm
OMA
- MDW
Nonstop1h 25m
Southwest
Sun 7/269:55 am
MDW
- OMA
Nonstop1h 30m
Southwest
Deal found 6/27![Southwest logo]()
$412
This Delta deal was found by Cheapflights users on 6/28. 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.
Fri 7/1012:09 pm
CID
- MDW
1 stop6h 09m
Delta
Sat 7/119:54 am
MDW
- CID
1 stop5h 38m
Delta
Deal found 6/28![Delta logo]()
$604
This Southwest deal was found by Cheapflights users on 6/26. 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.
Tue 7/146:20 am
OMA
- MDW
2 stops6h 05m
Southwest
Fri 7/179:25 pm
MDW
- OMA
Nonstop1h 35m
Southwest
Deal found 6/26![Southwest logo]()
$414
This Southwest deal was found by Cheapflights users on 6/28. 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 9/411:05 am
OMA
- MDW
Nonstop1h 25m
Southwest
Sun 9/68:45 am
MDW
- OMA
Nonstop1h 35m
Southwest
Deal found 6/28![Southwest logo]()
$418
Last-minute flights from Iowa to MidwayDiscover last-minute flight deals from Iowa to Midway. Data last updated June 29, 2026 and is based on user searches.
Discover last-minute flight deals from Iowa to Midway. Data last updated June 29, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/24. 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.
Wed 7/812:09 pm
CID
- MDW
1 stop6h 09m
Delta
Sat 7/119:54 am
MDW
- CID
1 stop5h 38m
Delta
Deal found 6/24![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 6/25. 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.
Tue 7/146:46 am
CID
- MDW
1 stop6h 23m
Delta
Sat 7/259:54 am
MDW
- CID
1 stop5h 38m
Delta
Deal found 6/25![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 6/24. 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 7/1511:00 am
OMA
- MDW
2 stops6h 00m
Southwest
Sat 7/1810:15 am
MDW
- OMA
Nonstop1h 25m
Southwest
Deal found 6/24![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 6/24. 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 7/186:00 am
DSM
- MDW
1 stop6h 38m
Delta
Sat 7/251:18 pm
MDW
- DSM
1 stop3h 52m
Delta
Deal found 6/24![Delta logo]()
$273
This Southwest deal was found by Cheapflights users on 6/28. 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.
Mon 7/205:10 am
DSM
- MDW
Nonstop1h 20m
Southwest
Wed 7/2210:10 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/28![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 6/28. 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 7/213:45 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Fri 7/246:50 am
MDW
- DSM
1 stop6h 00m
Southwest
Deal found 6/28![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 6/24. 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 7/225:20 am
DSM
- MDW
Nonstop1h 20m
Southwest
Wed 7/299:20 pm
MDW
- DSM
Nonstop1h 30m
Southwest
Deal found 6/24![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 6/24. 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 7/223:45 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Mon 7/2710:10 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 6/24![Southwest logo]()
$291
This Delta deal was found by Cheapflights users on 6/24. 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.
Wed 7/222:45 pm
DSM
- MDW
1 stop3h 33m
Delta
Mon 7/271:18 pm
MDW
- DSM
1 stop3h 54m
Delta
Deal found 6/24![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 6/25. 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.
Fri 7/245:15 pm
OMA
- MDW
1 stop5h 50m
Southwest
Tue 7/2812:20 pm
MDW
- OMA
Nonstop1h 25m
Southwest
Deal found 6/25![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 6/26. 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.
Tue 7/281:10 pm
OMA
- MDW
Nonstop1h 25m
Southwest
Mon 8/311:00 am
MDW
- OMA
2 stops10h 25m
Southwest
Deal found 6/26![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 6/25. 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.
Wed 7/295:10 pm
OMA
- MDW
1 stop5h 30m
Southwest
Fri 7/319:55 am
MDW
- OMA
1 stop5h 10m
Southwest
Deal found 6/25![Southwest logo]()
$307
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 June 29, 2026.
Search for one-way flight options from Iowa to Midway. Find affordable one-way fares based on user searches. Data last updated June 29, 2026.
This Southwest deal was found by Cheapflights users on 6/28. 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 7/211:10 pm
OMA
- MDW
Nonstop1h 25m
Southwest
Deal found 6/28![Southwest logo]()
$119
This Southwest deal was found by Cheapflights users on 6/26. 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.
Mon 8/246:20 pm
OMA
- MDW
Nonstop1h 25m
Southwest
Deal found 6/26![Southwest logo]()
$123
This Southwest deal was found by Cheapflights users on 6/28. 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 8/256:10 am
DSM
- MDW
Nonstop1h 20m
Southwest
Deal found 6/28![Southwest logo]()
$124
This Southwest deal was found by Cheapflights users on 6/26. 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.
Sat 8/85:30 am
DSM
- MDW
Nonstop1h 15m
Southwest
Deal found 6/26![Southwest logo]()
$125
This Southwest deal was found by Cheapflights users on 6/24. 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 7/225:20 am
DSM
- MDW
Nonstop1h 20m
Southwest
Deal found 6/24![Southwest logo]()
$127
This Delta deal was found by Cheapflights users on 6/24. 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.
Tue 8/251:47 pm
OMA
- MDW
1 stop4h 14m
Delta
Deal found 6/24![Delta logo]()
$129
This Delta deal was found by Cheapflights users on 6/28. 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.
Mon 8/2411:11 am
OMA
- MDW
1 stop6h 50m
Delta
Deal found 6/28![Delta logo]()
$133
This Delta deal was found by Cheapflights users on 6/28. 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.
Tue 8/256:00 am
DSM
- MDW
1 stop6h 39m
Delta
Deal found 6/28![Delta logo]()
$134
This Southwest deal was found by Cheapflights users on 6/25. 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 7/181:30 pm
OMA
- MDW
2 stops7h 30m
Southwest
Deal found 6/25![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 6/25. 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.
Wed 9/237:15 am
DSM
- MDW
1 stop7h 05m
Southwest
Deal found 6/25![Southwest logo]()
$135
This Delta deal was found by Cheapflights users on 6/29. 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 7/282:45 pm
DSM
- MDW
1 stop3h 33m
Delta
Deal found 6/29![Delta logo]()
$137
This Southwest deal was found by Cheapflights users on 6/25. 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 9/147:55 am
OMA
- MDW
Nonstop1h 25m
Southwest
Deal found 6/25![Southwest logo]()
$137
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 June 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $247 (Southwest) |
One-way from | $119 (Southwest) |
Popular in | May |
Cheapest in | September |
Average price | $359 |
Good round-trip deal | $416 or less |
Good one-way deal | $229 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 June 29, 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
Cedar RapidsChicago
CID - MDW
CIDMDW
Cedar Rapids
Tue 12/1
6:45 am-11:51 am
1 stop5h 06m
Chicago Midway
Sat 12/5
12:30 pm-3:52 pm
1 stop3h 22m
$259
Quickest round-trip
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Mon 8/10
3:50 pm-5:10 pm
Nonstop1h 20m
Chicago Midway
Mon 8/17
8:50 pm-10:10 pm
Nonstop1h 20m
$273
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Thu 8/6
5:40 am-7:00 am
Nonstop1h 20m
Chicago Midway
Mon 8/10
10:05 am-11:25 am
Nonstop1h 20m
$273
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Mon 12/7
6:00 am-7:25 am
Nonstop1h 25m
Chicago Midway
Thu 12/10
6:05 am-2:10 pm
1 stop8h 05m
$283
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Tue 8/25
7:15 am-5:00 pm
2 stops9h 45m
Chicago Midway
Sun 8/30
10:15 am-11:35 am
Nonstop1h 20m
$306
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Fri 8/28
2:25 pm-8:15 pm
1 stop5h 50m
Chicago Midway
Sat 8/29
6:50 am-2:10 pm
1 stop7h 20m
$308
OmahaChicago
OMA - MDW
OMAMDW
Omaha Eppley Airfield
Tue 9/8
5:25 pm-11:10 pm
1 stop5h 45m
Chicago Midway
Fri 9/11
7:55 am-2:40 pm
2 stops6h 45m
$312
OmahaChicago
OMA - MDW
OMAMDW
Omaha Eppley Airfield
Fri 8/21
11:10 am-8:10 pm
2 stops9h 00m
Chicago Midway
Tue 8/25
10:10 am-7:20 pm
2 stops9h 10m
$317
OmahaChicago
OMA - MDW
OMAMDW
Omaha Eppley Airfield
Sat 8/15
7:05 am-1:20 pm
2 stops6h 15m
Chicago Midway
Tue 8/18
10:10 am-7:20 pm
2 stops9h 10m
$317
OmahaChicago
OMA - MDW
OMAMDW
Omaha Eppley Airfield
Thu 11/5
5:30 am-7:05 am
Nonstop1h 35m
Chicago Midway
Sun 11/8
2:35 pm-11:40 pm
2 stops9h 05m
$320
Showing 1-10 of 58 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.
CID-MDW
DSM-MDW
OMA-MDW
MLI-MDW
LSE-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
CID-MDW
DSM-MDW
OMA-MDW
MLI-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 June 29, 2026.
A simple way to save on the total cost of your ticket is to fly from Iowa to Chicago Midway Airport at noon. If you’re flexible enough to do this you can expect to save up to 58% 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
Hammond
Lansing
Merrillville
Valparaiso
Porter
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