$84+ 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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Jun 17 — Jun 241
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 May 18, 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 May 18, 2026.
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/93:50 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Wed 6/109:20 pm
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 5/17![Southwest logo]()
$137
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:55 am
MSP
- MDW
1 stop4h 30m
Southwest
Tue 6/92:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/14![Southwest logo]()
$142
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:00 am
MSP
- MDW
Nonstop1h 49m
Delta
Mon 11/212:30 pm
MDW
- MSP
Nonstop1h 39m
Delta
Deal found 5/13![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:50 am
MSP
- MDW
1 stop7h 05m
Southwest
Tue 6/92:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/13![Southwest logo]()
$148
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Wed 7/87:06 pm
MDW
- MSP
Nonstop1h 45m
Delta
Deal found 5/12![Delta logo]()
$152
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:40 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Wed 6/242:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/15![Southwest logo]()
$153
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/304:38 pm
MSP
- MDW
Nonstop1h 40m
Delta
Thu 8/139:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Deal found 5/16![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:55 am
MSP
- MDW
1 stop4h 30m
Southwest
Wed 6/242:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/15![Southwest logo]()
$162
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/61:40 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Tue 6/92:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/12![Southwest logo]()
$163
This Southwest deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:35 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Sat 8/82:25 pm
MDW
- MSP
1 stop5h 40m
Southwest
Deal found 5/16![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 10/712:05 pm
MSP
- MDW
2 stops7h 20m
Southwest
Wed 10/1411:45 am
MDW
- MSP
1 stop11h 15m
Southwest
Deal found 5/17![Southwest logo]()
$168
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:45 am
MSP
- MDW
1 stop6h 00m
Southwest
Tue 6/92:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/13![Southwest logo]()
$172
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 May 18, 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 May 18, 2026.
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:40 pm
MSP
- MDW
1 stop5h 20m
Southwest
Tue 6/99:20 pm
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 5/13![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Thu 7/309:19 am
MDW
- MSP
1 stop3h 51m
Delta
Deal found 5/14![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:00 am
MSP
- MDW
Nonstop1h 30m
Southwest
Mon 6/89:50 pm
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 5/13![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:00 am
MKE
- MDW
Nonstop0h 50m
Southwest
Wed 6/2410:10 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 5/13![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/136:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Sat 6/209:17 am
MDW
- MSP
1 stop3h 58m
Delta
Deal found 5/14![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/234:10 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Tue 6/309:10 pm
MDW
- MKE
Nonstop0h 50m
Southwest
Deal found 5/17![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:10 am
MSP
- MDW
1 stop6h 32m
Delta
Sat 6/67:13 pm
MDW
- MSP
Nonstop1h 42m
Delta
Deal found 5/13![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/113:40 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Tue 8/188:40 pm
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 5/13![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Fri 6/121:26 pm
MDW
- MSP
1 stop5h 42m
Delta
Deal found 5/12![Delta logo]()
$226
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/154:10 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Wed 7/159:10 pm
MDW
- MKE
Nonstop0h 50m
Southwest
Deal found 5/14![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/262:07 pm
ATW
- MDW
1 stop4h 24m
Delta
Sat 7/45:50 pm
MDW
- ATW
1 stop3h 50m
Delta
Deal found 5/13![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:45 am
MKE
- MDW
Nonstop0h 45m
Southwest
Mon 8/1710:10 am
MDW
- MKE
Nonstop0h 50m
Southwest
Deal found 5/15![Southwest logo]()
$218
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:00 am
ATW
- MDW
1 stop5h 46m
Delta
Sat 7/46:55 pm
MDW
- ATW
1 stop4h 03m
Delta
Deal found 5/13![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:40 am
MKE
- MDW
Nonstop0h 50m
Southwest
Thu 6/189:55 pm
MDW
- MKE
Nonstop0h 50m
Southwest
Deal found 5/13![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/252:07 pm
ATW
- MDW
1 stop4h 24m
Delta
Sun 7/59:17 am
MDW
- ATW
1 stop4h 10m
Delta
Deal found 5/13![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/146:00 am
MKE
- MDW
Nonstop0h 50m
Southwest
Sun 6/2110:25 pm
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 5/15![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:00 am
CWA
- MDW
1 stop4h 51m
Delta
Mon 10/1912:30 pm
MDW
- CWA
1 stop3h 18m
Delta
Deal found 5/13![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:45 am
MKE
- MDW
Nonstop0h 45m
Southwest
Thu 8/2010:10 am
MDW
- MKE
1 stop5h 30m
Southwest
Deal found 5/13![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:10 am
DLH
- MDW
1 stop6h 41m
Delta
Sat 10/319:30 am
MDW
- DLH
2 stops6h 14m
Delta
Deal found 5/14![Delta logo]()
$264
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:05 am
MSP
- MDW
2 stops6h 30m
Southwest
Wed 7/225:10 pm
MDW
- MSP
1 stop5h 35m
Southwest
Deal found 5/15![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Fri 6/121:26 pm
MDW
- MSP
1 stop5h 42m
Delta
Deal found 5/14![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/97:35 am
MSP
- MDW
2 stops6h 15m
Southwest
Wed 8/124:40 pm
MDW
- MSP
1 stop5h 40m
Southwest
Deal found 5/12![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2711:09 am
ATW
- MDW
1 stop5h 56m
Delta
Sat 7/45:50 pm
MDW
- ATW
1 stop3h 50m
Delta
Deal found 5/13![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/64:40 pm
MSP
- MDW
1 stop5h 15m
Southwest
Sun 8/910:10 am
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 5/15![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/102:07 pm
ATW
- MDW
1 stop4h 24m
Delta
Wed 6/177:16 pm
MDW
- ATW
1 stop3h 42m
Delta
Deal found 5/13![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:45 am
MSP
- MDW
1 stop6h 00m
Southwest
Sun 6/73:10 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 5/13![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 5/317:00 am
ATW
- MDW
1 stop5h 42m
Delta
Sat 6/276:55 pm
MDW
- ATW
1 stop4h 03m
Delta
Deal found 5/17![Delta logo]()
$298
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:32 pm
ATW
- MDW
1 stop5h 24m
Delta
Sat 6/276:55 pm
MDW
- ATW
1 stop4h 03m
Delta
Deal found 5/17![Delta logo]()
$298
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/47:00 am
ATW
- MDW
1 stop5h 42m
Delta
Sat 6/276:55 pm
MDW
- ATW
1 stop4h 03m
Delta
Deal found 5/17![Delta logo]()
$298
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Mon 8/39:24 am
MDW
- MSP
1 stop3h 56m
Delta
Deal found 5/15![Delta logo]()
$307
Last-minute flights from Wisconsin to MidwayDiscover last-minute flight deals from Wisconsin to Midway. Data last updated May 18, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Midway. Data last updated May 18, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:50 am
MSP
- MDW
1 stop7h 05m
Southwest
Tue 6/92:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/13![Southwest logo]()
$148
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:45 am
MSP
- MDW
1 stop6h 00m
Southwest
Tue 6/92:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/13![Southwest logo]()
$172
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:00 am
MSP
- MDW
Nonstop1h 30m
Southwest
Mon 6/89:50 pm
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 5/12![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/64:20 pm
MSP
- MDW
Nonstop1h 36m
Delta
Tue 6/91:49 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 5/12![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/61:40 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Tue 6/92:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/12![Southwest logo]()
$163
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/93:50 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Wed 6/109:20 pm
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 5/17![Southwest logo]()
$137
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:55 am
MSP
- MDW
1 stop4h 30m
Southwest
Tue 6/92:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/14![Southwest logo]()
$142
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:05 am
MSP
- MDW
2 stops6h 30m
Southwest
Tue 6/232:50 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 5/17![Southwest logo]()
$152
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:55 am
MSP
- MDW
1 stop4h 30m
Southwest
Wed 6/242:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/15![Southwest logo]()
$162
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/226:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Wed 6/241:49 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 5/13![Delta logo]()
$182
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:40 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Wed 6/242:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/15![Southwest logo]()
$153
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/304:38 pm
MSP
- MDW
Nonstop1h 40m
Delta
Thu 8/139:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Deal found 5/16![Delta logo]()
$157
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 May 18, 2026.
Search for one-way flight options from Wisconsin to Midway. Find affordable one-way fares based on user searches. Data last updated May 18, 2026.
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:55 am
MSP
- MDW
1 stop9h 10m
Southwest
Deal found 5/15![Southwest logo]()
$84
This KAYAK deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/34:20 pm
MSP
- MDW
Nonstop1h 36m
Delta
Deal found 5/13![Delta logo]()
$86
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/135:25 am
MSP
- MDW
Nonstop1h 30m
Southwest
Deal found 5/13![Southwest logo]()
$89
This Frontier deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:24 pm
MSP
- MDW
1 stop7h 44m
Frontier
Deal found 5/13![Frontier logo]()
$95
This Trip.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/82:24 pm
MSP
- MDW
1 stop7h 44m
Frontier
Deal found 5/13![Frontier logo]()
$96
This Trip.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/142:24 pm
MSP
- MDW
1 stop7h 44m
Frontier
Deal found 5/14![Frontier logo]()
$97
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/64:40 pm
MSP
- MDW
1 stop5h 15m
Southwest
Deal found 5/12![Southwest logo]()
$99
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MKE
- MDW
Nonstop0h 50m
Southwest
Deal found 5/14![Southwest logo]()
$99
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/88:05 am
MSP
- MDW
1 stop8h 00m
Southwest
Deal found 5/13![Southwest logo]()
$104
This Expedia deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/182:24 pm
MSP
- MDW
1 stop7h 44m
Frontier
Deal found 5/13![Frontier logo]()
$105
This Trip.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/42:24 pm
MSP
- MDW
1 stop7h 47m
Frontier
Deal found 5/13![Frontier logo]()
$107
This Super.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/62:22 pm
MSP
- MDW
1 stop7h 40m
Frontier
Deal found 5/14![Frontier logo]()
$108
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 May 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $137 (Southwest) |
One-way from | $84 (Southwest) |
Good round-trip deal | $344 or less |
Good one-way deal | $211 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 2,558,603 searches. Data last updated May 18, 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 - MDW
MSPMDW
Minneapolis St Paul
Thu 6/4
5:40 pm-11:00 pm
1 stop5h 20m
Chicago Midway
Tue 6/9
9:20 pm-10:45 pm
Nonstop1h 25m
$157
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Thu 6/4
5:00 am-6:30 am
Nonstop1h 30m
Chicago Midway
Mon 6/8
9:50 pm-11:15 pm
Nonstop1h 25m
$177
Quickest round-trip
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Wed 6/17
6:00 am-6:50 am
Nonstop0h 50m
Chicago Midway
Wed 6/24
10:10 am-10:55 am
Nonstop0h 45m
$197
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Tue 6/23
4:10 pm-5:00 pm
Nonstop0h 50m
Chicago Midway
Tue 6/30
9:10 pm-10:00 pm
Nonstop0h 50m
$197
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Tue 8/11
3:40 pm-4:30 pm
Nonstop0h 50m
Chicago Midway
Tue 8/18
8:40 pm-9:25 pm
Nonstop0h 45m
$197
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Wed 7/15
4:10 pm-5:00 pm
Nonstop0h 50m
Chicago Midway
Wed 7/15
9:10 pm-10:00 pm
Nonstop0h 50m
$197
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Fri 8/14
5:45 am-6:30 am
Nonstop0h 45m
Chicago Midway
Mon 8/17
10:10 am-11:00 am
Nonstop0h 50m
$218
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Thu 6/11
5:40 am-6:30 am
Nonstop0h 50m
Chicago Midway
Thu 6/18
9:55 pm-10:45 pm
Nonstop0h 50m
$219
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Sun 6/14
6:00 am-6:50 am
Nonstop0h 50m
Chicago Midway
Sun 6/21
10:25 pm-11:10 pm
Nonstop0h 45m
$219
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Mon 7/27
6:55 am-8:37 am
Nonstop1h 42m
Chicago Midway
Thu 7/30
9:19 am-1:10 pm
1 stop3h 51m
$222
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
CWA-MDW
DLH-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
CWA-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 May 18, 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
Hammond
Porter
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