$59+ Cheap flights from Wisconsin to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Apr 18 — Apr 251
Round-trip
1 adult, Economy
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Find cheap flights from Wisconsin to Midway with Cheapflights
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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 March 19, 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 March 19, 2026.
This Southwest deal was found by Cheapflights users on 3/16. 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 4/153:15 pm
MSP
- MDW
Nonstop1h 35m
Southwest
Wed 4/227:55 am
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 3/16![Southwest logo]()
$117
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/83:15 pm
MSP
- MDW
Nonstop1h 35m
Southwest
Mon 4/135:40 pm
MDW
- MSP
1 stop5h 40m
Southwest
Deal found 3/18![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 3/17. 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.
Sat 4/117:00 am
MSP
- MDW
Nonstop1h 50m
Delta
Tue 4/219:29 am
MDW
- MSP
Nonstop1h 41m
Delta
Deal found 3/17![Delta logo]()
$167
This KAYAK deal was found by Cheapflights users on 3/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/273:40 pm
MSP
- MDW
1 stop8h 00m
Southwest
Tue 4/287:50 am
MDW
- MSP
2 stops6h 45m
Southwest
Deal found 3/17![Southwest logo]()
$172
This KAYAK deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/214:57 pm
MSP
- MDW
Nonstop1h 39m
Delta
Wed 4/229:29 am
MDW
- MSP
Nonstop1h 41m
Delta
Deal found 3/19![Delta logo]()
$174
This Southwest deal was found by Cheapflights users on 3/16. 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.
Thu 4/162:25 pm
MSP
- MDW
Nonstop1h 25m
Southwest
Thu 4/231:30 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 3/16![Southwest logo]()
$177
This Priceline deal was found by Cheapflights users on 3/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2410:34 am
MSP
- MDW
1 stop7h 20m
Frontier
Mon 4/276:20 am
MDW
- MSP
1 stop6h 25m
Frontier
Deal found 3/17![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 3/17. 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 4/145:50 am
MKE
- MDW
Nonstop0h 55m
Southwest
Tue 4/2110:10 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 3/17![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 3/16. 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.
Mon 4/134:50 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Mon 4/2010:10 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 3/16![Southwest logo]()
$201
This Southwest deal was found by Cheapflights users on 3/14. 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 4/147:35 am
MKE
- MDW
2 stops8h 10m
Southwest
Wed 4/2210:10 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 3/14![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 3/14. 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.
Sat 4/115:40 am
MKE
- MDW
Nonstop0h 55m
Southwest
Sat 4/1812:45 pm
MDW
- MKE
1 stop7h 25m
Southwest
Deal found 3/14![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 3/16. 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.
Sun 4/125:50 am
MKE
- MDW
Nonstop0h 55m
Southwest
Sun 4/1910:00 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 3/16![Southwest logo]()
$219
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 March 19, 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 March 19, 2026.
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/510:05 am
MSP
- MDW
Nonstop1h 30m
Southwest
Wed 5/206:20 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 3/19![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 3/17. 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.
Tue 5/1911:40 am
MSP
- MDW
Nonstop1h 39m
Delta
Sat 5/231:59 pm
MDW
- MSP
Nonstop1h 41m
Delta
Deal found 3/17![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 3/16. 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.
Thu 5/145:20 am
MSP
- MDW
Nonstop1h 30m
Southwest
Tue 5/1910:45 am
MDW
- MSP
Nonstop1h 35m
Southwest
Deal found 3/16![Southwest logo]()
$147
This Delta deal was found by Cheapflights users on 3/17. 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.
Sat 5/234:20 pm
MSP
- MDW
Nonstop1h 36m
Delta
Wed 6/39:23 am
MDW
- MSP
Nonstop1h 37m
Delta
Deal found 3/17![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 3/17. 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.
Thu 4/165:20 am
MSP
- MDW
Nonstop1h 30m
Southwest
Mon 4/208:05 am
MDW
- MSP
Nonstop1h 35m
Southwest
Deal found 3/17![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:36 pm
MSN
- MDW
1 stop13h 28m
Multiple Airlines
Wed 4/226:15 am
MDW
- MSN
2 stops11h 41m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$428
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/48:20 am
MSP
- MDW
Nonstop1h 30m
Southwest
Mon 5/115:55 pm
MDW
- MSP
1 stop6h 25m
Southwest
Deal found 3/19![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 3/16. 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.
Tue 5/195:50 am
MKE
- MDW
Nonstop0h 55m
Southwest
Sat 5/236:10 pm
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 3/16![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 3/15. 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.
Tue 4/147:00 am
ATW
- MDW
1 stop5h 43m
Delta
Tue 4/219:29 am
MDW
- ATW
1 stop6h 09m
Delta
Deal found 3/15![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 3/14. 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.
Mon 4/134:50 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Mon 4/209:30 pm
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 3/14![Southwest logo]()
$201
This Delta deal was found by Cheapflights users on 3/17. 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 5/612:00 pm
GRB
- MDW
1 stop6h 36m
Delta
Sat 5/99:23 am
MDW
- GRB
1 stop6h 16m
Delta
Deal found 3/17![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 3/14. 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.
Sat 4/115:40 am
MKE
- MDW
Nonstop0h 55m
Southwest
Sat 4/1810:30 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 3/14![Southwest logo]()
$201
This Delta deal was found by Cheapflights users on 3/15. 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.
Tue 4/284:57 pm
MSP
- MDW
Nonstop1h 39m
Delta
Thu 4/309:29 am
MDW
- MSP
Nonstop1h 41m
Delta
Deal found 3/15![Delta logo]()
$266
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/164:50 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Thu 4/2310:10 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 3/19![Southwest logo]()
$201
This Southwest deal was found by Cheapflights users on 3/14. 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 4/144:05 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Wed 4/2212:20 pm
MDW
- MKE
1 stop4h 55m
Southwest
Deal found 3/14![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/17:00 am
ATW
- MDW
1 stop5h 29m
Delta
Sun 4/51:10 pm
MDW
- ATW
1 stop4h 32m
Delta
Deal found 3/19![Delta logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:30 am
ATW
- MDW
2 stops37h 37m
Multiple Airlines
Sun 4/199:04 am
MDW
- ATW
1 stop13h 13m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$453
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/174:50 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Fri 4/249:30 pm
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 3/18![Southwest logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:36 pm
MSN
- MDW
1 stop26h 16m
Multiple Airlines
Wed 4/296:10 am
MDW
- MSN
2 stops11h 46m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/37:00 am
GRB
- MDW
1 stop5h 29m
Delta
Tue 4/79:30 am
MDW
- GRB
1 stop6h 08m
Delta
Deal found 3/19![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 3/15. 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.
Thu 4/912:37 pm
DLH
- MDW
1 stop6h 03m
Delta
Mon 4/137:16 pm
MDW
- DLH
1 stop3h 30m
Delta
Deal found 3/15![Delta logo]()
$318
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/165:20 am
MSP
- MDW
Nonstop1h 30m
Southwest
Sun 4/197:35 am
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 3/19![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 3/15. 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.
Thu 5/215:15 am
DLH
- MDW
1 stop3h 27m
Delta
Sat 5/231:59 pm
MDW
- DLH
1 stop5h 32m
Delta
Deal found 3/15![Delta logo]()
$318
This Southwest deal was found by Cheapflights users on 3/15. 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 4/2410:20 am
MSP
- MDW
Nonstop1h 30m
Southwest
Mon 4/278:05 am
MDW
- MSP
Nonstop1h 35m
Southwest
Deal found 3/15![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/1812:05 pm
ATW
- MDW
1 stop6h 31m
Delta
Wed 4/221:24 pm
MDW
- ATW
1 stop4h 14m
Delta
Deal found 3/18![Delta logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:36 pm
MSN
- MDW
1 stop29h 21m
Multiple Airlines
Wed 4/86:00 am
MDW
- MSN
2 stops11h 56m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$614
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/174:15 pm
MSP
- MDW
1 stop5h 20m
Southwest
Mon 5/185:40 pm
MDW
- MSP
1 stop5h 40m
Southwest
Deal found 3/19![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/155:00 am
DLH
- MDW
1 stop3h 46m
Delta
Sat 4/187:16 pm
MDW
- DLH
1 stop3h 30m
Delta
Deal found 3/18![Delta logo]()
$330
This Southwest deal was found by Cheapflights users on 3/14. 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.
Sun 4/127:15 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Tue 4/144:50 pm
MDW
- MSP
1 stop6h 15m
Southwest
Deal found 3/14![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 3/15. 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.
Tue 4/1412:47 pm
DLH
- MDW
1 stop5h 49m
Delta
Tue 4/219:29 am
MDW
- DLH
1 stop6h 19m
Delta
Deal found 3/15![Delta logo]()
$333
Last-minute flights from Wisconsin to MidwayDiscover last-minute flight deals from Wisconsin to Midway. Data last updated March 19, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Midway. Data last updated March 19, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/83:15 pm
MSP
- MDW
Nonstop1h 35m
Southwest
Mon 4/135:40 pm
MDW
- MSP
1 stop5h 40m
Southwest
Deal found 3/18![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 3/17. 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.
Thu 4/95:50 am
MKE
- MDW
Nonstop0h 55m
Southwest
Mon 4/1310:10 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 3/17![Southwest logo]()
$201
This Delta deal was found by Cheapflights users on 3/17. 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.
Sat 4/117:00 am
MSP
- MDW
Nonstop1h 50m
Delta
Tue 4/219:29 am
MDW
- MSP
Nonstop1h 41m
Delta
Deal found 3/17![Delta logo]()
$167
This Southwest deal was found by Cheapflights users on 3/16. 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.
Sun 4/125:50 am
MKE
- MDW
Nonstop0h 55m
Southwest
Sun 4/1910:00 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 3/16![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 3/17. 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 4/145:50 am
MKE
- MDW
Nonstop0h 55m
Southwest
Tue 4/2110:10 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 3/17![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 3/16. 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 4/153:15 pm
MSP
- MDW
Nonstop1h 35m
Southwest
Wed 4/227:55 am
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 3/16![Southwest logo]()
$117
This Southwest deal was found by Cheapflights users on 3/16. 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.
Thu 4/162:25 pm
MSP
- MDW
Nonstop1h 25m
Southwest
Thu 4/231:30 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 3/16![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/174:50 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Fri 4/245:50 pm
MDW
- MKE
1 stop5h 20m
Southwest
Deal found 3/18![Southwest logo]()
$229
This KAYAK deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/214:57 pm
MSP
- MDW
Nonstop1h 39m
Delta
Wed 4/229:29 am
MDW
- MSP
Nonstop1h 41m
Delta
Deal found 3/19![Delta logo]()
$174
This Priceline deal was found by Cheapflights users on 3/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2410:34 am
MSP
- MDW
1 stop7h 20m
Frontier
Mon 4/276:20 am
MDW
- MSP
1 stop6h 25m
Frontier
Deal found 3/17![Frontier logo]()
$180
This KAYAK deal was found by Cheapflights users on 3/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:20 pm
MSP
- MDW
1 stop5h 25m
Southwest
Tue 4/287:50 am
MDW
- MSP
2 stops6h 45m
Southwest
Deal found 3/17![Southwest logo]()
$172
This Southwest deal was found by Cheapflights users on 3/15. 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 4/304:50 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Sun 5/34:05 pm
MDW
- MKE
1 stop7h 05m
Southwest
Deal found 3/15![Southwest logo]()
$255
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 March 19, 2026.
Search for one-way flight options from Wisconsin to Midway. Find affordable one-way fares based on user searches. Data last updated March 19, 2026.
This Southwest deal was found by Cheapflights users on 3/17. 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 4/83:15 pm
MSP
- MDW
Nonstop1h 35m
Southwest
Deal found 3/17![Southwest logo]()
$59
This KAYAK deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:00 am
MSP
- MDW
Nonstop1h 46m
Delta
Deal found 3/19![Delta logo]()
$87
This Delta deal was found by Cheapflights users on 3/16. 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.
Sat 4/184:57 pm
MSP
- MDW
Nonstop1h 39m
Delta
Deal found 3/16![Delta logo]()
$89
This Frontier deal was found by Cheapflights users on 3/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2011:30 am
MSP
- MDW
1 stop8h 01m
Frontier
Deal found 3/17![Frontier logo]()
$91
This Super.com deal was found by Cheapflights users on 3/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:58 am
MSP
- MDW
1 stop10h 21m
Frontier
Deal found 3/15![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 3/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2410:34 am
MSP
- MDW
1 stop29h 39m
Frontier
Deal found 3/15![Frontier logo]()
$95
This Frontier deal was found by Cheapflights users on 3/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1711:47 am
MSP
- MDW
1 stop9h 50m
Frontier
Deal found 3/16![Frontier logo]()
$96
This Trip.com deal was found by Cheapflights users on 3/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2711:30 am
MSP
- MDW
1 stop10h 49m
Frontier
Deal found 3/17![Frontier logo]()
$98
This Delta deal was found by Cheapflights users on 3/16. 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.
Mon 4/67:00 am
MSP
- MDW
Nonstop1h 50m
Delta
Deal found 3/16![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 3/17. 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.
Thu 4/165:50 am
MKE
- MDW
Nonstop0h 55m
Southwest
Deal found 3/17![Southwest logo]()
$101
This Southwest deal was found by Cheapflights users on 3/16. 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.
Tue 4/77:10 am
MSP
- MDW
2 stops8h 35m
Southwest
Deal found 3/16![Southwest logo]()
$104
This Southwest deal was found by Cheapflights users on 3/17. 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.
Fri 5/14:50 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Deal found 3/17![Southwest logo]()
$110
Find flight deals from Wisconsin to Midway
Keep the following information in mind while searching for Wisconsin to Midway flight deals. Data was last updated March 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (Southwest) |
One-way from | $59 (Southwest) |
Popular in | April |
Cheapest in | January |
Average price | $199 |
Good round-trip deal | $358 or less |
Good one-way deal | $178 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 March 19, 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
Tue 5/5
10:05 am-11:35 am
Nonstop1h 30m
Chicago Midway
Wed 5/20
6:20 pm-7:50 pm
Nonstop1h 30m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Tue 5/19
11:40 am-1:19 pm
Nonstop1h 39m
Chicago Midway
Sat 5/23
1:59 pm-3:40 pm
Nonstop1h 41m
$147
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Thu 5/14
5:20 am-6:50 am
Nonstop1h 30m
Chicago Midway
Tue 5/19
10:45 am-12:20 pm
Nonstop1h 35m
$147
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 5/23
4:20 pm-5:56 pm
Nonstop1h 36m
Chicago Midway
Wed 6/3
9:23 am-11:00 am
Nonstop1h 37m
$147
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Thu 4/16
5:20 am-6:50 am
Nonstop1h 30m
Chicago Midway
Mon 4/20
8:05 am-9:40 am
Nonstop1h 35m
$177
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Mon 5/4
8:20 am-9:50 am
Nonstop1h 30m
Chicago Midway
Mon 5/11
5:55 pm-12:20 am
1 stop6h 25m
$187
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Tue 5/19
5:50 am-6:45 am
Nonstop0h 55m
Chicago Midway
Sat 5/23
6:10 pm-6:55 pm
Nonstop0h 45m
$191
Quickest round-trip
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Mon 4/13
4:50 pm-5:40 pm
Nonstop0h 50m
Chicago Midway
Mon 4/20
9:30 pm-10:15 pm
Nonstop0h 45m
$201
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Sat 4/11
5:40 am-6:35 am
Nonstop0h 55m
Chicago Midway
Sat 4/18
10:30 am-11:15 am
Nonstop0h 45m
$201
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Thu 4/16
4:50 pm-5:40 pm
Nonstop0h 50m
Chicago Midway
Thu 4/23
10:10 am-10:55 am
Nonstop0h 45m
$201
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
MSN-MDW
MKE-MDW
ATW-MDW
GRB-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Wisconsin to Chicago Midway Airport
USWI-MDW
MSP-MDW
MSN-MDW
MKE-MDW
ATW-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 March 19, 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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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