$59+ Cheap flights from Midway (MDW) to Wisconsin
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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Sep 15 — Sep 221
Round-trip
1 adult, Economy
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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 Midway to WisconsinExplore the most affordable flight options available from Midway to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 16, 2026.
Explore the most affordable flight options available from Midway to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 16, 2026.
This Southwest deal was found by Cheapflights users on 8/11. 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 9/59:05 am -
2 stops9h 45m
Sun 9/66:30 am -
Nonstop1h 25m
Deal found 8/11![Southwest logo]()
$124
This Southwest deal was found by Cheapflights users on 8/15. 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 9/295:10 pm -
Nonstop1h 35m
Tue 10/67:30 am -
1 stop5h 55m
Deal found 8/15![Southwest logo]()
$127
This Expedia deal was found by Cheapflights users on 8/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:26 pm -
1 stop11h 37m
Sat 9/52:38 pm -
1 stop8h 09m
Deal found 8/14![Frontier logo]()
$130
This Southwest deal was found by Cheapflights users on 8/15. 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.
Sat 9/198:00 am -
Nonstop1h 45m
Tue 9/229:05 am -
2 stops6h 55m
Deal found 8/15![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 8/14. 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 9/232:20 pm -
Nonstop1h 30m
Fri 9/255:45 am -
Nonstop1h 25m
Deal found 8/14![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 8/12. 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 9/25:10 pm -
Nonstop1h 30m
Sat 9/55:30 am -
Nonstop1h 25m
Deal found 8/12![Southwest logo]()
$142
This Southwest deal was found by Cheapflights users on 8/14. 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.
Fri 10/95:50 pm -
1 stop5h 30m
Mon 10/125:25 am -
Nonstop1h 30m
Deal found 8/14![Southwest logo]()
$144
This Southwest deal was found by Cheapflights users on 8/15. 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 10/295:50 pm -
1 stop5h 30m
Thu 11/127:55 am -
2 stops9h 50m
Deal found 8/15![Southwest logo]()
$148
This Southwest deal was found by Cheapflights users on 8/12. 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 9/910:15 am -
Nonstop0h 50m
Tue 9/153:10 pm -
Nonstop0h 50m
Deal found 8/12![Southwest logo]()
$149
This Priceline deal was found by Cheapflights users on 8/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:05 am -
1 stop7h 38m
Fri 9/119:28 am -
1 stop8h 23m
Deal found 8/13![Frontier logo]()
$149
This Southwest deal was found by Cheapflights users on 8/11. 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.
Thu 9/35:55 am -
1 stop4h 15m
Mon 9/75:45 am -
Nonstop0h 45m
Deal found 8/11![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 8/13. 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.
Thu 9/245:55 am -
1 stop4h 15m
Wed 9/306:40 am -
Nonstop0h 50m
Deal found 8/13![Southwest logo]()
$165
Best flights from Midway to WisconsinDiscover carefully curated flight deals from Midway to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 16, 2026.
Discover carefully curated flight deals from Midway to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 16, 2026.
This Southwest deal was found by Cheapflights users on 8/15. 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 10/142:45 pm -
2 stops8h 00m
Wed 10/214:20 pm -
1 stop5h 35m
Deal found 8/15![Southwest logo]()
$142
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:51 pm -
Nonstop1h 44m
Sat 9/52:20 pm -
Nonstop1h 37m
Deal found 8/11![Delta logo]()
$152
This Southwest deal was found by Cheapflights users on 8/12. 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 9/2610:15 am -
Nonstop0h 50m
Sat 10/36:00 am -
Nonstop0h 50m
Deal found 8/12![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 8/11. 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 9/56:10 pm -
Nonstop0h 55m
Mon 9/75:45 am -
Nonstop0h 45m
Deal found 8/11![Southwest logo]()
$149
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/810:01 am -
Nonstop1h 41m
Sat 10/103:08 pm -
Nonstop1h 39m
Deal found 8/11![Delta logo]()
$183
This Southwest deal was found by Cheapflights users on 8/12. 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 9/59:05 am -
2 stops9h 45m
Sun 9/66:30 am -
Nonstop1h 25m
Deal found 8/12![Southwest logo]()
$154
This Delta deal was found by Cheapflights users on 8/15. 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 10/179:29 am -
1 stop4h 09m
Tue 10/203:08 pm -
Nonstop1h 39m
Deal found 8/15![Delta logo]()
$188
This Southwest deal was found by Cheapflights users on 8/15. 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.
Sat 9/56:10 pm -
Nonstop1h 35m
Tue 9/83:05 pm -
Nonstop1h 25m
Deal found 8/15![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 8/11. 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 9/218:40 pm -
Nonstop0h 45m
Thu 9/244:50 pm -
1 stop5h 10m
Deal found 8/11![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 8/13. 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.
Thu 9/35:55 am -
1 stop4h 15m
Mon 9/75:45 am -
Nonstop0h 45m
Deal found 8/13![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 8/15. 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 10/299:55 am -
Nonstop0h 50m
Mon 11/25:30 am -
Nonstop1h 05m
Deal found 8/15![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 8/11. 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 9/43:10 pm -
1 stop5h 10m
Mon 9/75:45 am -
Nonstop0h 45m
Deal found 8/11![Southwest logo]()
$179
This Delta deal was found by Cheapflights users on 8/12. 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.
Sat 9/261:19 pm -
1 stop4h 01m
Sat 10/312:02 pm -
1 stop5h 57m
Deal found 8/12![Delta logo]()
$298
This Southwest deal was found by Cheapflights users on 8/15. 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 9/3010:15 am -
Nonstop0h 50m
Wed 10/76:10 am -
Nonstop0h 50m
Deal found 8/15![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 8/15. 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 9/295:20 pm -
1 stop5h 35m
Tue 10/69:55 am -
2 stops6h 25m
Deal found 8/15![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 8/15. 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 9/54:52 pm -
1 stop5h 49m
Sun 9/65:15 am -
1 stop3h 24m
Deal found 8/15![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 8/12. 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 9/2611:45 am -
2 stops7h 05m
Sat 10/37:10 am -
2 stops7h 40m
Deal found 8/12![Southwest logo]()
$213
This Delta deal was found by Cheapflights users on 8/14. 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.
Fri 10/1610:01 am -
1 stop5h 40m
Tue 10/205:14 am -
1 stop3h 30m
Deal found 8/14![Delta logo]()
$398
This Southwest deal was found by Cheapflights users on 8/14. 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.
Thu 10/17:45 am -
Nonstop1h 25m
Sun 10/410:40 am -
Nonstop1h 30m
Deal found 8/14![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 8/11. 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 9/118:40 pm -
Nonstop1h 35m
Mon 9/147:10 am -
1 stop7h 00m
Deal found 8/11![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 8/15. 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 9/54:52 pm -
1 stop4h 15m
Sun 9/611:07 am -
1 stop5h 52m
Deal found 8/15![Delta logo]()
$549
This Delta deal was found by Cheapflights users on 8/12. 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 9/117:13 pm -
1 stop3h 22m
Sun 9/135:15 am -
1 stop3h 33m
Deal found 8/12![Delta logo]()
$643
This Delta deal was found by Cheapflights users on 8/14. 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.
Fri 9/41:25 pm -
1 stop3h 23m
Sun 9/611:07 am -
1 stop5h 52m
Deal found 8/14![Delta logo]()
$649
This Delta deal was found by Cheapflights users on 8/13. 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.
Thu 11/1212:30 pm -
1 stop6h 40m
Mon 11/1612:34 pm -
1 stop4h 05m
Deal found 8/13![Delta logo]()
$652
This Delta deal was found by Cheapflights users on 8/12. 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 10/29:59 am -
1 stop5h 30m
Sun 10/45:15 am -
1 stop3h 33m
Deal found 8/12![Delta logo]()
$673
This Delta deal was found by Cheapflights users on 8/12. 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 1/812:30 pm -
1 stop3h 18m
Sun 1/177:00 am -
2 stops5h 33m
Deal found 8/12![Delta logo]()
$713
This Delta deal was found by Cheapflights users on 8/15. 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.
Fri 9/251:19 pm -
2 stops6h 06m
Sun 9/275:15 am -
1 stop3h 33m
Deal found 8/15![Delta logo]()
$729
This Delta deal was found by Cheapflights users on 8/14. 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.
Sun 9/131:19 pm -
1 stop4h 01m
Sun 9/207:00 am -
1 stop5h 39m
Deal found 8/14![Delta logo]()
$734
This Delta deal was found by Cheapflights users on 8/12. 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 8/289:59 am -
1 stop5h 33m
Sun 8/3012:03 pm -
1 stop5h 58m
Deal found 8/12![Delta logo]()
$734
This Delta deal was found by Cheapflights users on 8/13. 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.
Sun 9/277:13 pm -
1 stop3h 22m
Sun 10/45:15 am -
1 stop3h 33m
Deal found 8/13![Delta logo]()
$763
Last-minute flights from Midway to WisconsinDiscover last-minute flight deals from Midway to Wisconsin. Data last updated August 16, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Wisconsin. Data last updated August 16, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/12. 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 9/19:59 am -
Nonstop1h 43m
Sun 9/66:57 am -
Nonstop1h 42m
Deal found 8/12![Delta logo]()
$150
This Southwest deal was found by Cheapflights users on 8/12. 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 9/25:10 pm -
Nonstop1h 30m
Sat 9/55:30 am -
Nonstop1h 25m
Deal found 8/12![Southwest logo]()
$142
This Southwest deal was found by Cheapflights users on 8/11. 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.
Thu 9/35:55 am -
1 stop4h 15m
Mon 9/75:45 am -
Nonstop0h 45m
Deal found 8/11![Southwest logo]()
$159
This Expedia deal was found by Cheapflights users on 8/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:26 pm -
1 stop11h 37m
Sat 9/52:38 pm -
1 stop8h 09m
Deal found 8/14![Frontier logo]()
$130
This Southwest deal was found by Cheapflights users on 8/11. 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 9/59:05 am -
2 stops9h 45m
Sun 9/66:30 am -
Nonstop1h 25m
Deal found 8/11![Southwest logo]()
$124
This Priceline deal was found by Cheapflights users on 8/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:05 am -
1 stop7h 38m
Fri 9/119:28 am -
1 stop8h 23m
Deal found 8/13![Frontier logo]()
$149
This Southwest deal was found by Cheapflights users on 8/12. 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 9/910:15 am -
Nonstop0h 50m
Tue 9/153:10 pm -
Nonstop0h 50m
Deal found 8/12![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 8/12. 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 9/94:40 pm -
1 stop3h 20m
Wed 9/164:25 pm -
1 stop5h 30m
Deal found 8/12![Southwest logo]()
$169
This Southwest deal was found by Cheapflights users on 8/15. 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.
Sat 9/198:00 am -
Nonstop1h 45m
Tue 9/229:05 am -
2 stops6h 55m
Deal found 8/15![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 8/14. 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 9/232:20 pm -
Nonstop1h 30m
Fri 9/255:45 am -
Nonstop1h 25m
Deal found 8/14![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 8/13. 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.
Thu 9/245:55 am -
1 stop4h 15m
Wed 9/306:40 am -
Nonstop0h 50m
Deal found 8/13![Southwest logo]()
$165
This Southwest deal was found by Cheapflights users on 8/15. 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 9/294:40 pm -
1 stop5h 50m
Tue 10/65:30 am -
Nonstop1h 30m
Deal found 8/15![Southwest logo]()
$127
One-way flights from Midway to WisconsinSearch for one-way flight options from Midway to Wisconsin. Find affordable one-way fares based on user searches. Data last updated August 16, 2026.
Search for one-way flight options from Midway to Wisconsin. Find affordable one-way fares based on user searches. Data last updated August 16, 2026.
This Delta deal was found by Cheapflights users on 8/14. 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 10/3110:01 am -
Nonstop1h 41m
Deal found 8/14![Delta logo]()
$59
This Southwest deal was found by Cheapflights users on 8/13. 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.
Fri 10/305:00 am -
1 stop7h 00m
Deal found 8/13![Southwest logo]()
$60
This Southwest deal was found by Cheapflights users on 8/11. 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 9/59:05 am -
2 stops9h 45m
Deal found 8/11![Southwest logo]()
$65
This Southwest deal was found by Cheapflights users on 8/13. 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 10/288:10 am -
1 stop6h 40m
Deal found 8/13![Southwest logo]()
$69
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:05 am -
1 stop7h 38m
Deal found 8/13![Frontier logo]()
$72
This Southwest deal was found by Cheapflights users on 8/13. 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 10/142:45 pm -
2 stops8h 00m
Deal found 8/13![Southwest logo]()
$74
This Southwest deal was found by Cheapflights users on 8/11. 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.
Tue 9/228:35 pm -
Nonstop0h 45m
Deal found 8/11![Southwest logo]()
$75
This Jetabroad deal was found by Cheapflights users on 8/12. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:05 am -
1 stop7h 38m
Deal found 8/12![Frontier logo]()
$75
This Southwest deal was found by Cheapflights users on 8/13. 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.
Fri 10/167:45 am -
Nonstop1h 25m
Deal found 8/13![Southwest logo]()
$76
This Priceline deal was found by Cheapflights users on 8/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:40 am -
1 stop8h 38m
Deal found 8/11![Frontier logo]()
$77
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sat 10/311:55 am -
2 stops10h 15m
Deal found 8/13![Southwest logo]()
$80
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:25 am -
1 stop7h 23m
Deal found 8/13![Frontier logo]()
$81
Find flight deals from Midway to Wisconsin
Keep the following information in mind while searching for Midway to Wisconsin flight deals. Data was last updated August 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $124 (Southwest) |
One-way from | $59 (Delta) |
Good round-trip deal | $199 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Wisconsin 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 August 16, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Wisconsin that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMinneapolis
MDW Chicago Midway - MSP Minneapolis St Paul
MDWMSP
Chicago Midway
Wed 10/14
2:45 pm-10:45 pm
2 stops8h 00m
Minneapolis St Paul
Wed 10/21
4:20 pm-9:55 pm
1 stop5h 35m
$142
Quickest round-trip
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Sat 9/26
10:15 am-11:05 am
Nonstop0h 50m
Milwaukee-Mitchell
Sat 10/3
6:00 am-6:50 am
Nonstop0h 50m
$149
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Sat 9/5
6:10 pm-7:05 pm
Nonstop0h 55m
Milwaukee-Mitchell
Mon 9/7
5:45 am-6:30 am
Nonstop0h 45m
$149
ChicagoMinneapolis
MDW Chicago Midway - MSP Minneapolis St Paul
MDWMSP
Chicago Midway
Thu 9/3
1:51 pm-3:35 pm
Nonstop1h 44m
Minneapolis St Paul
Sat 9/5
2:20 pm-3:57 pm
Nonstop1h 37m
$152
ChicagoMinneapolis
MDW Chicago Midway - MSP Minneapolis St Paul
MDWMSP
Chicago Midway
Sat 9/5
9:05 am-6:50 pm
2 stops9h 45m
Minneapolis St Paul
Sun 9/6
6:30 am-7:55 am
Nonstop1h 25m
$154
ChicagoMinneapolis
MDW Chicago Midway - MSP Minneapolis St Paul
MDWMSP
Chicago Midway
Sat 9/5
6:10 pm-7:45 pm
Nonstop1h 35m
Minneapolis St Paul
Tue 9/8
3:05 pm-4:30 pm
Nonstop1h 25m
$157
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Mon 9/21
8:40 pm-9:25 pm
Nonstop0h 45m
Milwaukee-Mitchell
Thu 9/24
4:50 pm-10:00 pm
1 stop5h 10m
$159
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Thu 9/3
5:55 am-10:10 am
1 stop4h 15m
Milwaukee-Mitchell
Mon 9/7
5:45 am-6:30 am
Nonstop0h 45m
$159
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Thu 10/29
9:55 am-10:45 am
Nonstop0h 50m
Milwaukee-Mitchell
Mon 11/2
5:30 am-6:35 am
Nonstop1h 05m
$179
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Fri 9/4
3:10 pm-8:20 pm
1 stop5h 10m
Milwaukee-Mitchell
Mon 9/7
5:45 am-6:30 am
Nonstop0h 45m
$179
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Midway to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Midway with our price prediction graph.
MDW-MSP
MDW-MKE
MDW-LSE
MDW-MSN
MDW-GRB
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 Chicago Midway Airport to Wisconsin
MDW-USWI
MDW-MSP
MDW-MKE
MDW-LSE
MDW-MSN
What is the cheapest time of day to fly from MDW to WI?
Find hourly flight availability from Midway to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 16, 2026.
When flying from Chicago Midway Airport to Wisconsin, 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 Midway to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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