$69+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Jul 29 — Aug 51
Round-trip
1 adult, Economy
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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 June 29, 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 June 29, 2026.
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/221:51 pm
MDW
- MSP
Nonstop1h 44m
Delta
Mon 8/244:24 pm
MSP
- MDW
Nonstop1h 37m
Delta
Deal found 6/29![Delta logo]()
$141
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:54 am
MDW
- MSP
Nonstop1h 43m
Delta
Tue 7/216:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Deal found 6/25![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/88:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Mon 8/105:45 am
MSP
- MDW
Nonstop1h 25m
Southwest
Deal found 6/29![Southwest logo]()
$149
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Mon 8/1011:29 am
MSP
- MDW
Nonstop1h 41m
Delta
Deal found 6/25![Delta logo]()
$150
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/44:40 pm
MDW
- MSP
1 stop5h 45m
Southwest
Thu 8/65:45 am
MSP
- MDW
Nonstop1h 25m
Southwest
Deal found 6/28![Southwest logo]()
$151
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:55 am
MDW
- MSP
2 stops12h 10m
Southwest
Sat 8/297:05 am
MSP
- MDW
2 stops9h 50m
Southwest
Deal found 6/28![Southwest logo]()
$153
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Wed 9/99:05 am
MSP
- MDW
2 stops6h 55m
Southwest
Deal found 6/28![Southwest logo]()
$156
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:35 am
MDW
- MSP
1 stop9h 35m
Southwest
Mon 8/176:20 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Deal found 6/28![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Tue 8/118:00 am
MSP
- MDW
1 stop5h 55m
Southwest
Deal found 6/26![Southwest logo]()
$161
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:55 am
MDW
- MSP
2 stops12h 10m
Southwest
Mon 8/243:45 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Deal found 6/29![Southwest logo]()
$162
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:55 pm
MDW
- MKE
Nonstop0h 55m
Southwest
Tue 7/286:00 am
MKE
- MDW
Nonstop0h 50m
Southwest
Deal found 6/25![Southwest logo]()
$171
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/810:15 am
MDW
- MKE
Nonstop0h 50m
Southwest
Mon 8/104:20 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Deal found 6/29![Southwest logo]()
$173
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 June 29, 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 June 29, 2026.
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:55 am
MDW
- MSP
2 stops12h 10m
Southwest
Sat 8/297:05 am
MSP
- MDW
2 stops9h 50m
Southwest
Deal found 6/26![Southwest logo]()
$153
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:19 am
MDW
- MSP
1 stop3h 51m
Delta
Sat 8/14:15 pm
MSP
- MDW
Nonstop1h 37m
Delta
Deal found 6/24![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:15 am
MDW
- MKE
Nonstop0h 50m
Southwest
Tue 9/13:10 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Deal found 6/28![Southwest logo]()
$171
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/810:15 am
MDW
- MKE
Nonstop0h 50m
Southwest
Mon 8/104:20 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Deal found 6/27![Southwest logo]()
$173
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:10 am
MDW
- MKE
Nonstop0h 50m
Southwest
Thu 8/208:00 am
MKE
- MDW
1 stop4h 15m
Southwest
Deal found 6/29![Southwest logo]()
$185
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Sun 8/306:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Deal found 6/24![Delta logo]()
$248
This Lucky2Go deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/236:05 am
MDW
- MSN
2 stops13h 05m
Frontier
Sun 7/267:55 pm
MSN
- MDW
2 stops15h 12m
Frontier
Deal found 6/29![Frontier logo]()
$506
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/79:59 am
MDW
- DLH
1 stop5h 32m
Delta
Sun 8/95:15 am
DLH
- MDW
1 stop3h 24m
Delta
Deal found 6/24![Delta logo]()
$258
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/173:10 pm
MDW
- MKE
1 stop5h 05m
Southwest
Sat 9/196:15 am
MKE
- MDW
1 stop3h 15m
Southwest
Deal found 6/26![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/214:30 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Fri 7/2412:20 pm
MSP
- MDW
Nonstop1h 25m
Southwest
Deal found 6/24![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/249:55 pm
MDW
- MKE
Nonstop0h 55m
Southwest
Fri 7/315:15 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Deal found 6/26![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:51 pm
MDW
- MSP
Nonstop1h 44m
Delta
Sun 9/66:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Deal found 6/24![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/179:55 pm
MDW
- MKE
Nonstop0h 55m
Southwest
Mon 7/205:15 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Deal found 6/24![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:59 am
MDW
- CWA
1 stop5h 41m
Delta
Sun 9/276:51 am
CWA
- MDW
1 stop6h 29m
Delta
Deal found 6/24![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:40 pm
MDW
- MKE
Nonstop0h 45m
Southwest
Sun 8/235:45 am
MKE
- MDW
Nonstop0h 45m
Southwest
Deal found 6/28![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/279:55 pm
MDW
- MKE
Nonstop0h 55m
Southwest
Mon 8/35:15 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Deal found 6/27![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:13 pm
MDW
- DLH
1 stop3h 22m
Delta
Sun 9/1311:43 am
DLH
- MDW
1 stop6h 36m
Delta
Deal found 6/28![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:10 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Wed 9/308:00 am
MSP
- MDW
1 stop5h 55m
Southwest
Deal found 6/25![Southwest logo]()
$226
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/31:26 pm
MDW
- DLH
2 stops9h 24m
Delta
Sun 7/55:00 am
DLH
- MDW
1 stop3h 37m
Delta
Deal found 6/26![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:00 pm
MDW
- GRB
1 stop3h 28m
Delta
Tue 12/157:00 am
GRB
- MDW
1 stop5h 33m
Delta
Deal found 6/26![Delta logo]()
$356
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Sun 8/96:15 am
MSP
- MDW
Nonstop1h 25m
Southwest
Deal found 6/27![Southwest logo]()
$248
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:54 am
MDW
- GRB
1 stop5h 37m
Delta
Sat 8/16:50 am
GRB
- MDW
1 stop5h 48m
Delta
Deal found 6/25![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:55 am
MDW
- MSP
2 stops12h 10m
Southwest
Mon 8/107:10 am
MSP
- MDW
1 stop7h 00m
Southwest
Deal found 6/27![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:25 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Sun 9/205:15 pm
MSP
- MDW
1 stop5h 40m
Southwest
Deal found 6/27![Southwest logo]()
$258
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:25 pm
MDW
- DLH
1 stop3h 16m
Delta
Sun 8/235:15 am
DLH
- MDW
1 stop3h 24m
Delta
Deal found 6/27![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Sun 8/307:55 am
MSP
- MDW
1 stop6h 10m
Southwest
Deal found 6/28![Southwest logo]()
$268
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/101:18 pm
MDW
- GRB
1 stop3h 49m
Delta
Tue 7/1412:05 pm
GRB
- MDW
1 stop6h 13m
Delta
Deal found 6/25![Delta logo]()
$399
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/285:10 pm
MDW
- MSP
1 stop5h 40m
Southwest
Fri 7/315:50 am
MSP
- MDW
2 stops6h 30m
Southwest
Deal found 6/26![Southwest logo]()
$273
This deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:25 pm
MDW
- DLH
1 stop3h 16m
Delta
Mon 8/178:18 am
DLH
- MDW
1 stop4h 52m
Delta
Deal found 6/26![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:54 am
MDW
- GRB
1 stop5h 37m
Delta
Sun 7/196:50 am
GRB
- MDW
1 stop5h 48m
Delta
Deal found 6/27![Delta logo]()
$416
Last-minute flights from Midway to WisconsinDiscover last-minute flight deals from Midway to Wisconsin. Data last updated June 29, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Wisconsin. Data last updated June 29, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/151:49 pm
MDW
- MSP
Nonstop1h 44m
Delta
Sat 7/186:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Deal found 6/24![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:54 am
MDW
- MSP
Nonstop1h 43m
Delta
Tue 7/216:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Deal found 6/25![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:10 am
MDW
- MSP
Nonstop1h 30m
Southwest
Wed 7/227:05 am
MSP
- MDW
2 stops6h 30m
Southwest
Deal found 6/25![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:20 pm
MDW
- MSP
1 stop6h 35m
Southwest
Sat 7/2512:35 pm
MSP
- MDW
1 stop4h 30m
Southwest
Deal found 6/26![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:20 pm
MDW
- MSP
1 stop6h 35m
Southwest
Wed 7/297:05 am
MSP
- MDW
2 stops6h 30m
Southwest
Deal found 6/24![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/235:05 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Wed 7/295:25 am
MSP
- MDW
Nonstop1h 30m
Southwest
Deal found 6/26![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:55 pm
MDW
- MKE
Nonstop0h 55m
Southwest
Tue 7/286:00 am
MKE
- MDW
Nonstop0h 50m
Southwest
Deal found 6/25![Southwest logo]()
$171
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:55 pm
MDW
- MSP
Nonstop1h 47m
Delta
Wed 7/296:04 am
MSP
- MDW
1 stop6h 34m
Delta
Deal found 6/26![Delta logo]()
$206
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/279:55 pm
MDW
- MKE
Nonstop0h 55m
Southwest
Mon 8/35:40 am
MKE
- MDW
Nonstop0h 50m
Southwest
Deal found 6/28![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/281:49 pm
MDW
- MSP
Nonstop1h 44m
Delta
Thu 7/304:40 pm
MSP
- MDW
Nonstop1h 38m
Delta
Deal found 6/26![Delta logo]()
$216
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:19 am
MDW
- MSP
1 stop3h 51m
Delta
Sat 8/14:15 pm
MSP
- MDW
Nonstop1h 37m
Delta
Deal found 6/24![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:00 pm
MDW
- MSP
1 stop5h 20m
Southwest
Wed 8/56:15 am
MSP
- MDW
Nonstop1h 25m
Southwest
Deal found 6/29![Southwest logo]()
$226
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 June 29, 2026.
Search for one-way flight options from Midway to Wisconsin. Find affordable one-way fares based on user searches. Data last updated June 29, 2026.
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/285:10 pm
MDW
- MSP
1 stop5h 40m
Southwest
Deal found 6/28![Southwest logo]()
$69
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:35 am
MDW
- MSP
1 stop9h 35m
Southwest
Deal found 6/28![Southwest logo]()
$74
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:55 am
MDW
- MSP
2 stops12h 10m
Southwest
Deal found 6/28![Southwest logo]()
$80
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 6/28![Southwest logo]()
$83
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:00 pm
MDW
- MKE
Nonstop0h 55m
Southwest
Deal found 6/24![Southwest logo]()
$86
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:10 am
MDW
- MKE
Nonstop0h 50m
Southwest
Deal found 6/29![Southwest logo]()
$88
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/211:49 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 6/25![Delta logo]()
$89
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Deal found 6/24![Delta logo]()
$91
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Deal found 6/25![Southwest logo]()
$93
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2810:05 am
MDW
- MKE
1 stop5h 30m
Southwest
Deal found 6/28![Southwest logo]()
$96
This Super.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:05 am
MDW
- MSP
1 stop7h 34m
Frontier
Deal found 6/29![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:25 am
MDW
- MSP
1 stop7h 53m
Frontier
Deal found 6/25![Frontier logo]()
$105
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 June 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $147 (Delta) |
One-way from | $69 (Southwest) |
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 June 29, 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 - MSP
MDWMSP
Chicago Midway
Sat 8/22
7:55 am-8:05 pm
2 stops12h 10m
Minneapolis St Paul
Sat 8/29
7:05 am-4:55 pm
2 stops9h 50m
$153
ChicagoMilwaukee
MDW - MKE
MDWMKE
Chicago Midway
Wed 8/26
10:15 am-11:05 am
Nonstop0h 50m
Milwaukee-Mitchell
Tue 9/1
3:10 pm-4:00 pm
Nonstop0h 50m
$171
ChicagoMilwaukee
MDW - MKE
MDWMKE
Chicago Midway
Sat 8/8
10:15 am-11:05 am
Nonstop0h 50m
Milwaukee-Mitchell
Mon 8/10
4:20 pm-5:10 pm
Nonstop0h 50m
$173
ChicagoMilwaukee
MDW - MKE
MDWMKE
Chicago Midway
Thu 8/13
10:10 am-11:00 am
Nonstop0h 50m
Milwaukee-Mitchell
Thu 8/20
8:00 am-12:15 pm
1 stop4h 15m
$185
ChicagoMinneapolis
MDW - MSP
MDWMSP
Chicago Midway
Wed 7/29
9:19 am-1:10 pm
1 stop3h 51m
Minneapolis St Paul
Sat 8/1
4:15 pm-5:52 pm
Nonstop1h 37m
$187
ChicagoMilwaukee
MDW - MKE
MDWMKE
Chicago Midway
Thu 9/17
3:10 pm-8:15 pm
1 stop5h 05m
Milwaukee-Mitchell
Sat 9/19
6:15 am-9:30 am
1 stop3h 15m
$215
ChicagoMinneapolis
MDW - MSP
MDWMSP
Chicago Midway
Tue 7/21
4:30 pm-6:00 pm
Nonstop1h 30m
Minneapolis St Paul
Fri 7/24
12:20 pm-1:45 pm
Nonstop1h 25m
$216
ChicagoMilwaukee
MDW - MKE
MDWMKE
Chicago Midway
Fri 7/24
9:55 pm-10:50 pm
Nonstop0h 55m
Milwaukee-Mitchell
Fri 7/31
5:15 pm-6:05 pm
Nonstop0h 50m
$219
ChicagoMilwaukee
MDW - MKE
MDWMKE
Chicago Midway
Fri 7/17
9:55 pm-10:50 pm
Nonstop0h 55m
Milwaukee-Mitchell
Mon 7/20
5:15 pm-6:05 pm
Nonstop0h 50m
$219
Quickest round-trip
ChicagoMilwaukee
MDW - MKE
MDWMKE
Chicago Midway
Fri 8/21
8:40 pm-9:25 pm
Nonstop0h 45m
Milwaukee-Mitchell
Sun 8/23
5:45 am-6:30 am
Nonstop0h 45m
$219
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-MSN
MDW-LSE
MDW-CWA
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-MSN
MDW-LSE
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 June 29, 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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