$74+ 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
jul. 6 — jul. 131
Round-trip
1 adult, Economy
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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 junio 6, 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 junio 6, 2026.
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
sáb. 8/295:30 am
MSP
- MDW
Nonstop1h 25m
Southwest
mié. 9/25:10 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 6/1![Southwest logo]()
$130
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
mar. 8/114:24 pm
MSP
- MDW
Nonstop1h 37m
Delta
mar. 8/189:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Deal found 6/2![Delta logo]()
$137
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
mar. 7/147:05 am
MSP
- MDW
1 stop7h 25m
Southwest
mar. 7/217:40 am
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 6/2![Southwest logo]()
$147
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
mié. 7/155:25 am
MSP
- MDW
Nonstop1h 30m
Southwest
mié. 7/152:35 pm
MDW
- MSP
1 stop8h 15m
Southwest
Deal found 6/2![Southwest logo]()
$153
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
mar. 7/77:05 am
MSP
- MDW
1 stop7h 25m
Southwest
mar. 7/75:10 pm
MDW
- MSP
1 stop5h 40m
Southwest
Deal found 6/2![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
mar. 8/114:24 pm
MSP
- MDW
Nonstop1h 37m
Delta
lun. 8/177:25 pm
MDW
- MSP
Nonstop1h 45m
Delta
Deal found 6/2![Delta logo]()
$159
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
mar. 7/147:05 am
MSP
- MDW
2 stops6h 30m
Southwest
mié. 7/152:35 pm
MDW
- MSP
1 stop8h 15m
Southwest
Deal found 6/3![Southwest logo]()
$168
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
mar. 8/116:15 am
MSP
- MDW
Nonstop1h 25m
Southwest
lun. 8/315:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Deal found 6/2![Southwest logo]()
$169
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
mié. 7/16:00 am
MKE
- MDW
Nonstop0h 50m
Southwest
mié. 7/89:00 pm
MDW
- MKE
Nonstop0h 55m
Southwest
Deal found 6/4![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
mié. 9/306:40 am
MKE
- MDW
Nonstop0h 50m
Southwest
vie. 10/210:05 pm
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 6/4![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
jue. 8/274:20 pm
MKE
- MDW
Nonstop0h 50m
Southwest
vie. 8/288:40 pm
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 6/3![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
vie. 7/35:40 am
MKE
- MDW
Nonstop0h 50m
Southwest
lun. 7/610:20 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 6/2![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 junio 6, 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 junio 6, 2026.
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
sáb. 8/156:57 am
MSP
- MDW
Nonstop1h 42m
Delta
sáb. 8/157:25 pm
MDW
- MSP
Nonstop1h 45m
Delta
Deal found 6/1![Delta logo]()
$143
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
sáb. 8/295:30 am
MSP
- MDW
Nonstop1h 25m
Southwest
mié. 9/25:20 pm
MDW
- MSP
1 stop5h 30m
Southwest
Deal found 6/3![Southwest logo]()
$169
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
mié. 8/58:00 am
MSP
- MDW
1 stop5h 55m
Southwest
lun. 8/103:20 pm
MDW
- MSP
1 stop6h 00m
Southwest
Deal found 6/1![Southwest logo]()
$179
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
jue. 10/223:10 pm
MSP
- MDW
Nonstop1h 40m
Delta
lun. 10/2612:30 pm
MDW
- MSP
Nonstop1h 39m
Delta
Deal found 6/5![Delta logo]()
$191
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
mié. 7/156:00 am
MKE
- MDW
Nonstop0h 50m
Southwest
mié. 7/2910:10 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 6/2![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
mié. 7/16:00 am
MKE
- MDW
Nonstop0h 50m
Southwest
mié. 7/89:00 pm
MDW
- MKE
Nonstop0h 55m
Southwest
Deal found 6/4![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
mar. 8/2511:29 am
MSP
- MDW
Nonstop1h 41m
Delta
sáb. 8/299:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Deal found 6/5![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
sáb. 8/159:00 am
MSP
- MDW
1 stop3h 39m
Delta
lun. 8/171:51 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 6/2![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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.
sáb. 8/221:30 pm
MKE
- MDW
Nonstop0h 50m
Southwest
mar. 8/258:40 pm
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 6/6![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
vie. 7/35:15 pm
MKE
- MDW
Nonstop0h 50m
Southwest
vie. 7/1010:20 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 6/5![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
mié. 7/17:00 am
ATW
- MDW
1 stop5h 46m
Delta
mié. 7/89:19 am
MDW
- ATW
1 stop4h 06m
Delta
Deal found 6/1![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
mar. 7/2111:15 am
MSP
- MDW
Nonstop1h 30m
Southwest
jue. 7/235:05 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 6/5![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
mié. 7/13:50 pm
MSP
- MDW
Nonstop1h 30m
Southwest
lun. 7/69:50 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 6/3![Southwest logo]()
$226
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
mié. 7/811:27 am
ATW
- MDW
1 stop6h 51m
Delta
sáb. 7/116:55 pm
MDW
- ATW
1 stop4h 01m
Delta
Deal found 6/3![Delta logo]()
$274
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
vie. 7/102:05 pm
ATW
- MDW
1 stop4h 20m
Delta
dom. 7/129:19 am
MDW
- ATW
1 stop4h 06m
Delta
Deal found 6/4![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
mié. 9/306:40 am
MKE
- MDW
Nonstop0h 50m
Southwest
vie. 10/25:40 pm
MDW
- MKE
1 stop5h 25m
Southwest
Deal found 6/4![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
vie. 6/262:07 pm
ATW
- MDW
1 stop4h 24m
Delta
lun. 6/297:16 pm
MDW
- ATW
1 stop3h 42m
Delta
Deal found 6/2![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
jue. 8/274:50 pm
MKE
- MDW
1 stop5h 05m
Southwest
vie. 8/288:40 pm
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 6/3![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
mié. 7/17:00 am
ATW
- MDW
1 stop5h 46m
Delta
mar. 7/79:19 am
MDW
- ATW
1 stop4h 06m
Delta
Deal found 6/4![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
mar. 8/119:05 am
MSP
- MDW
2 stops6h 55m
Southwest
jue. 8/135:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Deal found 6/1![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
vie. 8/282:06 pm
ATW
- MDW
1 stop4h 27m
Delta
sáb. 8/291:27 pm
MDW
- ATW
1 stop4h 14m
Delta
Deal found 6/4![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
sáb. 7/45:55 am
MSP
- MDW
1 stop5h 25m
Southwest
lun. 7/69:50 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 6/4![Southwest logo]()
$236
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
vie. 7/106:50 am
GRB
- MDW
1 stop5h 48m
Delta
lun. 7/131:18 pm
MDW
- GRB
1 stop3h 49m
Delta
Deal found 6/4![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
lun. 6/294:15 pm
MSP
- MDW
Nonstop1h 30m
Southwest
mar. 6/309:20 pm
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 6/3![Southwest logo]()
$239
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
dom. 8/237:00 am
ATW
- MDW
1 stop5h 39m
Delta
vie. 9/47:25 pm
MDW
- ATW
1 stop3h 31m
Delta
Deal found 6/4![Delta logo]()
$284
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
lun. 7/137:05 am
MSP
- MDW
2 stops6h 30m
Southwest
mar. 7/144:30 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 6/2![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
vie. 10/21:56 pm
ATW
- MDW
1 stop4h 37m
Delta
jue. 10/89:30 am
MDW
- ATW
1 stop3h 16m
Delta
Deal found 6/2![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
sáb. 7/118:00 am
DLH
- MDW
1 stop5h 09m
Delta
lun. 7/137:06 pm
MDW
- DLH
1 stop3h 43m
Delta
Deal found 6/3![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
vie. 9/251:56 pm
ATW
- MDW
1 stop4h 37m
Delta
sáb. 10/101:00 pm
MDW
- ATW
1 stop3h 37m
Delta
Deal found 6/3![Delta logo]()
$304
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
vie. 9/1112:00 pm
DLH
- MDW
1 stop6h 05m
Delta
dom. 9/139:30 am
MDW
- DLH
2 stops5h 49m
Delta
Deal found 6/3![Delta logo]()
$309
Last-minute flights from Wisconsin to MidwayDiscover last-minute flight deals from Wisconsin to Midway. Data last updated junio 6, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Midway. Data last updated junio 6, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
mar. 6/236:40 pm
MSP
- MDW
Nonstop1h 30m
Southwest
mar. 6/239:20 pm
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 6/2![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
mié. 7/16:00 am
MKE
- MDW
Nonstop0h 50m
Southwest
mié. 7/89:00 pm
MDW
- MKE
Nonstop0h 55m
Southwest
Deal found 6/4![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
mié. 7/17:00 am
ATW
- MDW
1 stop5h 46m
Delta
mié. 7/89:19 am
MDW
- ATW
1 stop4h 06m
Delta
Deal found 6/1![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
vie. 7/311:30 am
MSP
- MDW
Nonstop1h 39m
Delta
mié. 7/89:19 am
MDW
- MSP
1 stop3h 51m
Delta
Deal found 6/4![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
vie. 7/35:50 am
MSP
- MDW
2 stops6h 30m
Southwest
sáb. 7/46:05 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 6/5![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
vie. 7/35:40 am
MKE
- MDW
Nonstop0h 50m
Southwest
lun. 7/610:20 am
MDW
- MKE
Nonstop0h 45m
Southwest
Deal found 6/2![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
vie. 7/37:20 am
MKE
- MDW
1 stop6h 25m
Southwest
vie. 7/106:00 pm
MDW
- MKE
1 stop5h 00m
Southwest
Deal found 6/3![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
mar. 7/77:05 am
MSP
- MDW
1 stop7h 25m
Southwest
mar. 7/75:10 pm
MDW
- MSP
1 stop5h 40m
Southwest
Deal found 6/2![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
mar. 7/147:05 am
MSP
- MDW
1 stop7h 25m
Southwest
mar. 7/217:40 am
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 6/2![Southwest logo]()
$147
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
mar. 7/147:05 am
MSP
- MDW
2 stops6h 30m
Southwest
mié. 7/152:35 pm
MDW
- MSP
1 stop8h 15m
Southwest
Deal found 6/3![Southwest logo]()
$168
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
mar. 7/146:55 am
MSP
- MDW
Nonstop1h 42m
Delta
mar. 7/219:19 am
MDW
- MSP
1 stop3h 51m
Delta
Deal found 6/4![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
mié. 7/155:25 am
MSP
- MDW
Nonstop1h 30m
Southwest
mié. 7/1510:15 am
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 6/2![Southwest logo]()
$137
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 junio 6, 2026.
Search for one-way flight options from Wisconsin to Midway. Find affordable one-way fares based on user searches. Data last updated junio 6, 2026.
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
mié. 7/86:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Deal found 6/5![Delta logo]()
$74
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
mar. 7/77:55 am
MSP
- MDW
1 stop4h 30m
Southwest
Deal found 6/1![Southwest logo]()
$79
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
mié. 7/297:05 am
MSP
- MDW
2 stops6h 30m
Southwest
Deal found 6/2![Southwest logo]()
$84
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
sáb. 8/86:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Deal found 6/1![Delta logo]()
$91
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
sáb. 8/294:24 pm
MSP
- MDW
Nonstop1h 37m
Delta
Deal found 6/5![Delta logo]()
$96
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
mar. 6/306:00 am
MKE
- MDW
Nonstop0h 50m
Southwest
Deal found 6/3![Southwest logo]()
$99
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
jue. 8/62:05 pm
MSP
- MDW
1 stop6h 05m
Southwest
Deal found 6/1![Southwest logo]()
$101
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
sáb. 8/297:05 am
MSP
- MDW
2 stops9h 50m
Southwest
Deal found 6/2![Southwest logo]()
$106
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
lun. 6/295:15 pm
MKE
- MDW
Nonstop0h 50m
Southwest
Deal found 6/1![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
mié. 8/269:05 am
MSP
- MDW
2 stops6h 55m
Southwest
Deal found 6/4![Southwest logo]()
$111
This Frontier deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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.
mié. 8/122:24 pm
MSP
- MDW
1 stop7h 39m
Frontier
Deal found 6/6![Frontier logo]()
$115
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
mié. 7/16:04 am
MSP
- MDW
1 stop6h 42m
Delta
Deal found 6/3![Delta logo]()
$119
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 junio 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $130 (Delta) |
One-way from | $74 (Delta) |
Good round-trip deal | $318 or less |
Good one-way deal | $184 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 junio 6, 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
sáb. 8/15
6:57 am-8:39 am
Nonstop1h 42m
Chicago Midway
sáb. 8/15
7:25 pm-9:10 pm
Nonstop1h 45m
$143
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
sáb. 8/29
5:30 am-6:55 am
Nonstop1h 25m
Chicago Midway
mié. 9/2
5:20 pm-10:50 pm
1 stop5h 30m
$169
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
mié. 8/5
8:00 am-1:55 pm
1 stop5h 55m
Chicago Midway
lun. 8/10
3:20 pm-9:20 pm
1 stop6h 00m
$179
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
jue. 10/22
3:10 pm-4:50 pm
Nonstop1h 40m
Chicago Midway
lun. 10/26
12:30 pm-2:09 pm
Nonstop1h 39m
$191
Quickest round-trip
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
mié. 7/15
6:00 am-6:50 am
Nonstop0h 50m
Chicago Midway
mié. 7/29
10:10 am-10:55 am
Nonstop0h 45m
$197
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
mié. 7/1
6:00 am-6:50 am
Nonstop0h 50m
Chicago Midway
mié. 7/8
9:00 pm-9:55 pm
Nonstop0h 55m
$197
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
mar. 8/25
11:29 am-1:10 pm
Nonstop1h 41m
Chicago Midway
sáb. 8/29
9:59 am-11:42 am
Nonstop1h 43m
$217
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
sáb. 8/15
9:00 am-12:39 pm
1 stop3h 39m
Chicago Midway
lun. 8/17
1:51 pm-3:35 pm
Nonstop1h 44m
$219
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
sáb. 8/22
1:30 pm-2:20 pm
Nonstop0h 50m
Chicago Midway
mar. 8/25
8:40 pm-9:25 pm
Nonstop0h 45m
$219
MilwaukeeChicago
MKE - MDW
MKEMDW
Milwaukee-Mitchell
vie. 7/3
5:15 pm-6:05 pm
Nonstop0h 50m
Chicago Midway
vie. 7/10
10:20 am-11:05 am
Nonstop0h 45m
$219
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
GRB-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
GRB-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 junio 6, 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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