$59+ Cheap flights from Wisconsin 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Sep 28 — Oct 51
Round-trip
1 adult, Economy
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Find cheap flights from Wisconsin 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
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Cheapest flights from Wisconsin to MidwayExplore the most affordable flight options available from Wisconsin to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
Explore the most affordable flight options available from Wisconsin to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
This Delta deal was found by Cheapflights users on 8/25. 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.
Wed 10/77:00 am -
Nonstop1h 44m
Thu 10/1510:01 am -
Nonstop1h 41m
Deal found 8/25![Delta logo]()
$117
This Frontier deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:01 pm -
1 stop8h 46m
Tue 11/36:16 am -
1 stop7h 50m
Deal found 8/27![Frontier logo]()
$118
This Southwest deal was found by Cheapflights users on 8/27. 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.
Mon 9/215:45 am -
Nonstop1h 25m
Wed 9/234:40 pm -
1 stop5h 50m
Deal found 8/27![Southwest logo]()
$127
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:05 am -
2 stops6h 55m
Wed 9/232:20 pm -
Nonstop1h 30m
Deal found 8/27![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 8/25. 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 10/78:05 am -
1 stop7h 25m
Wed 10/1410:10 am -
Nonstop1h 25m
Deal found 8/25![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 8/27. 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.
Wed 10/77:15 am -
Nonstop1h 30m
Fri 10/92:05 pm -
Nonstop1h 25m
Deal found 8/27![Southwest logo]()
$134
This Frontier deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:42 am -
1 stop12h 05m
Tue 11/36:16 am -
1 stop7h 50m
Deal found 8/27![Frontier logo]()
$135
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3112:05 pm -
1 stop6h 35m
Mon 11/26:30 pm -
1 stop6h 10m
Deal found 8/25![Southwest logo]()
$137
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:25 am -
Nonstop1h 30m
Sat 10/311:55 am -
2 stops10h 15m
Deal found 8/25![Southwest logo]()
$138
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:25 am -
Nonstop1h 30m
Tue 10/204:30 pm -
1 stop5h 55m
Deal found 8/27![Southwest logo]()
$144
This Southwest deal was found by Cheapflights users on 8/27. 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 9/195:45 am -
Nonstop0h 45m
Thu 10/19:55 am -
Nonstop0h 50m
Deal found 8/27![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2211:45 am -
1 stop3h 40m
Tue 9/298:35 pm -
Nonstop0h 45m
Deal found 8/25![Southwest logo]()
$189
Best flights from Wisconsin to MidwayDiscover carefully curated flight deals from Wisconsin to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
Discover carefully curated flight deals from Wisconsin to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:55 am -
1 stop5h 15m
Fri 10/309:25 pm -
Nonstop1h 25m
Deal found 8/25![Southwest logo]()
$144
This Delta deal was found by Cheapflights users on 8/27. 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 9/246:05 am -
1 stop6h 34m
Sat 9/269:59 am -
Nonstop1h 41m
Deal found 8/27![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:30 pm -
Nonstop1h 45m
Sat 11/2110:10 pm -
Nonstop1h 30m
Deal found 8/25![Southwest logo]()
$174
This Delta deal was found by Cheapflights users on 8/25. 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.
Fri 9/187:05 am -
Nonstop1h 43m
Sat 9/199:29 am -
1 stop4h 00m
Deal found 8/25![Delta logo]()
$194
This KAYAK deal was found by Cheapflights users on 8/24. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:10 pm -
Nonstop0h 50m
Wed 9/168:35 pm -
Nonstop0h 45m
Deal found 8/24![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:40 am -
Nonstop0h 50m
Tue 9/2910:15 am -
Nonstop0h 50m
Deal found 8/25![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 8/26. 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 9/191:30 pm -
Nonstop0h 50m
Wed 9/238:35 pm -
Nonstop0h 45m
Deal found 8/26![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 8/24. 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 11/106:20 am -
Nonstop1h 00m
Sat 11/1410:15 am -
Nonstop0h 50m
Deal found 8/24![Southwest logo]()
$179
This Delta deal was found by Cheapflights users on 8/29. 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.
Wed 10/77:00 am -
Nonstop1h 44m
Sun 10/1110:12 am -
Nonstop1h 41m
Deal found 8/29![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:05 am -
Nonstop1h 30m
Tue 10/274:45 pm -
1 stop6h 00m
Deal found 8/25![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 8/28. 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 9/226:05 am -
1 stop6h 34m
Wed 9/239:59 am -
Nonstop1h 41m
Deal found 8/28![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 8/25. 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 9/267:05 am -
2 stops9h 50m
Wed 9/302:20 pm -
Nonstop1h 30m
Deal found 8/25![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1012:35 pm -
1 stop4h 12m
Tue 10/1312:27 pm -
1 stop6h 45m
Deal found 8/24![Delta logo]()
$268
This Southwest deal was found by Cheapflights users on 8/27. 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 9/196:15 am -
1 stop3h 15m
Thu 10/19:55 am -
Nonstop0h 50m
Deal found 8/27![Southwest logo]()
$189
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:08 pm -
Nonstop1h 39m
Sun 10/1110:01 am -
Nonstop1h 41m
Deal found 8/28![Delta logo]()
$282
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/102:50 pm -
1 stop2h 55m
Sat 10/1711:25 am -
1 stop3h 35m
Deal found 8/25![Southwest logo]()
$199
This Delta deal was found by Cheapflights users on 8/25. 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.
Wed 10/285:14 am -
1 stop6h 33m
Sat 10/3110:01 am -
1 stop5h 40m
Deal found 8/25![Delta logo]()
$288
This KAYAK deal was found by Cheapflights users on 8/24. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/224:25 pm -
1 stop5h 30m
Fri 9/2510:10 am -
Nonstop0h 50m
Deal found 8/24![Southwest logo]()
$199
This Delta deal was found by Cheapflights users on 8/25. 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.
Wed 9/911:09 am -
1 stop5h 48m
Sun 9/137:13 pm -
1 stop3h 49m
Deal found 8/25![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:02 pm -
1 stop6h 17m
Sat 9/129:59 am -
1 stop5h 37m
Deal found 8/26![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 8/28. 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 9/266:00 am -
2 stops7h 20m
Mon 9/288:00 am -
Nonstop1h 45m
Deal found 8/28![Southwest logo]()
$263
This Delta deal was found by Cheapflights users on 8/28. 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 9/1811:43 am -
1 stop6h 36m
Tue 9/227:13 pm -
1 stop3h 22m
Deal found 8/28![Delta logo]()
$322
This Southwest deal was found by Cheapflights users on 8/25. 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 10/2312:45 pm -
2 stops8h 10m
Sun 10/257:45 am -
Nonstop1h 25m
Deal found 8/25![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 8/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:09 am -
1 stop5h 48m
Sat 9/129:59 am -
1 stop5h 38m
Deal found 8/26![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 8/25. 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.
Fri 9/42:06 pm -
1 stop4h 27m
Fri 9/119:29 am -
1 stop3h 49m
Deal found 8/25![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 8/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:09 am -
1 stop5h 50m
Sun 9/64:52 pm -
1 stop6h 04m
Deal found 8/26![Delta logo]()
$337
This Delta deal was found by Cheapflights users on 8/27. 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 11/126:13 am -
1 stop4h 29m
Sat 11/146:44 pm -
1 stop3h 16m
Deal found 8/27![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:15 am -
1 stop3h 33m
Sat 9/129:29 am -
2 stops6h 00m
Deal found 8/25![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 8/24. 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 9/98:10 am -
1 stop5h 10m
Sat 9/129:29 am -
2 stops6h 00m
Deal found 8/24![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 8/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:13 am -
1 stop3h 54m
Mon 9/149:59 am -
1 stop5h 26m
Deal found 8/26![Delta logo]()
$437
Last-minute flights from Wisconsin to MidwayDiscover last-minute flight deals from Wisconsin to Midway. Data last updated August 29, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Midway. Data last updated August 29, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/26. 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.
Wed 9/96:40 am -
Nonstop0h 50m
Wed 9/168:35 pm -
Nonstop0h 45m
Deal found 8/26![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 8/25. 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 9/1610:35 am -
Nonstop1h 25m
Fri 9/188:00 am -
Nonstop1h 45m
Deal found 8/25![Southwest logo]()
$151
This Delta deal was found by Cheapflights users on 8/25. 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.
Fri 9/187:05 am -
Nonstop1h 43m
Tue 9/229:59 am -
Nonstop1h 41m
Deal found 8/25![Delta logo]()
$134
This Southwest deal was found by Cheapflights users on 8/27. 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 9/195:45 am -
Nonstop0h 45m
Thu 10/19:55 am -
Nonstop0h 50m
Deal found 8/27![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 8/28. 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 9/196:15 am -
1 stop3h 15m
Wed 9/234:40 pm -
1 stop3h 20m
Deal found 8/28![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 8/27. 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.
Mon 9/217:40 am -
Nonstop1h 30m
Wed 9/232:20 pm -
Nonstop1h 30m
Deal found 8/27![Southwest logo]()
$117
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:05 am -
2 stops6h 55m
Wed 9/232:20 pm -
Nonstop1h 30m
Deal found 8/27![Southwest logo]()
$132
This Delta deal was found by Cheapflights users on 8/27. 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 9/2411:41 am -
Nonstop1h 39m
Mon 9/287:13 pm -
Nonstop1h 47m
Deal found 8/27![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 8/26. 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 9/254:50 pm -
1 stop5h 10m
Sun 9/276:15 pm -
Nonstop0h 55m
Deal found 8/26![Southwest logo]()
$234
This Southwest deal was found by Cheapflights users on 8/26. 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 9/299:05 am -
2 stops6h 55m
Tue 10/62:45 pm -
2 stops8h 00m
Deal found 8/26![Southwest logo]()
$147
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:05 am -
2 stops6h 55m
Fri 10/25:50 pm -
1 stop5h 30m
Deal found 8/25![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 8/25. 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 9/3010:35 am -
Nonstop1h 25m
Fri 10/25:50 pm -
1 stop5h 30m
Deal found 8/25![Southwest logo]()
$144
One-way flights from Wisconsin to MidwaySearch for one-way flight options from Wisconsin to Midway. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
Search for one-way flight options from Wisconsin to Midway. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
This Delta deal was found by Cheapflights users on 8/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:41 am -
Nonstop1h 39m
Deal found 8/26![Delta logo]()
$59
This CheapOair deal was found by Cheapflights users on 8/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:30 am -
1 stop8h 21m
Deal found 8/25![Frontier logo]()
$60
This Super.com deal was found by Cheapflights users on 8/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:43 am -
1 stop9h 03m
Deal found 8/28![Frontier logo]()
$64
This Priceline deal was found by Cheapflights users on 8/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/273:01 pm -
1 stop8h 46m
Deal found 8/26![Frontier logo]()
$65
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:55 pm -
1 stop6h 15m
Deal found 8/27![Southwest logo]()
$69
This Southwest deal was found by Cheapflights users on 8/28. 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 10/165:25 am -
Nonstop1h 30m
Deal found 8/28![Southwest logo]()
$76
This Southwest deal was found by Cheapflights users on 8/28. 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 11/27:55 am -
2 stops9h 50m
Deal found 8/28![Southwest logo]()
$80
This Super.com deal was found by Cheapflights users on 8/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:01 pm -
1 stop8h 46m
Deal found 8/27![Frontier logo]()
$81
This Priceline deal was found by Cheapflights users on 8/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:01 pm -
1 stop8h 46m
Deal found 8/28![Frontier logo]()
$82
This Southwest deal was found by Cheapflights users on 8/27. 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.
Thu 10/15:55 am -
Nonstop0h 50m
Deal found 8/27![Southwest logo]()
$90
This Southwest deal was found by Cheapflights users on 8/27. 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 9/266:15 am -
1 stop3h 15m
Deal found 8/27![Southwest logo]()
$100
This Southwest deal was found by Cheapflights users on 8/26. 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 9/254:50 pm -
1 stop5h 10m
Deal found 8/26![Southwest logo]()
$110
Find flight deals from Wisconsin to Midway
Keep the following information in mind while searching for Wisconsin to Midway flight deals. Data was last updated August 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (Delta) |
One-way from | $59 (Delta) |
Good round-trip deal | $318 or less |
Good one-way deal | $204 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Wisconsin 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 August 29, 2026.
Use the filters below to find and compare flights from Wisconsin to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MinneapolisChicago
MSP Minneapolis St Paul - MDW Chicago Midway
MSPMDW
Minneapolis St Paul
Thu 10/29
5:55 am-11:10 am
1 stop5h 15m
Chicago Midway
Fri 10/30
9:25 pm-10:50 pm
Nonstop1h 25m
$144
MinneapolisChicago
MSP Minneapolis St Paul - MDW Chicago Midway
MSPMDW
Minneapolis St Paul
Thu 11/19
3:30 pm-5:15 pm
Nonstop1h 45m
Chicago Midway
Sat 11/21
10:10 pm-11:40 pm
Nonstop1h 30m
$174
MinneapolisChicago
MSP Minneapolis St Paul - MDW Chicago Midway
MSPMDW
Minneapolis St Paul
Thu 9/24
6:05 am-12:39 pm
1 stop6h 34m
Chicago Midway
Sat 9/26
9:59 am-11:40 am
Nonstop1h 41m
$177
Quickest round-trip
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Tue 9/15
3:10 pm-4:00 pm
Nonstop0h 50m
Chicago Midway
Wed 9/16
8:35 pm-9:20 pm
Nonstop0h 45m
$179
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Tue 9/22
6:40 am-7:30 am
Nonstop0h 50m
Chicago Midway
Tue 9/29
10:15 am-11:05 am
Nonstop0h 50m
$179
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Sat 9/19
1:30 pm-2:20 pm
Nonstop0h 50m
Chicago Midway
Wed 9/23
8:35 pm-9:20 pm
Nonstop0h 45m
$179
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Tue 11/10
6:20 am-7:20 am
Nonstop1h 00m
Chicago Midway
Sat 11/14
10:15 am-11:05 am
Nonstop0h 50m
$179
MinneapolisChicago
MSP Minneapolis St Paul - MDW Chicago Midway
MSPMDW
Minneapolis St Paul
Sun 10/25
5:05 am-6:35 am
Nonstop1h 30m
Chicago Midway
Tue 10/27
4:45 pm-10:45 pm
1 stop6h 00m
$182
MinneapolisChicago
MSP Minneapolis St Paul - MDW Chicago Midway
MSPMDW
Minneapolis St Paul
Sat 9/26
7:05 am-4:55 pm
2 stops9h 50m
Chicago Midway
Wed 9/30
2:20 pm-3:50 pm
Nonstop1h 30m
$187
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Sat 9/19
6:15 am-9:30 am
1 stop3h 15m
Chicago Midway
Thu 10/1
9:55 am-10:45 am
Nonstop0h 50m
$189
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Wisconsin to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Wisconsin with our price prediction graph.
MSP-MDW
MKE-MDW
ATW-MDW
MSN-MDW
GRB-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 Wisconsin to Chicago Midway Airport
USWI-MDW
MSP-MDW
MKE-MDW
ATW-MDW
MSN-MDW
What is the cheapest time of day to fly from WI to MDW?
Find hourly flight availability from Wisconsin 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 August 29, 2026.
When flying from Wisconsin 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 Wisconsin to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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