$50+ Cheap flights from Wisconsin to Illinois
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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — ORD
Aug 12 — Aug 191
Round-trip
1 adult, Economy
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Cheapest flights from Wisconsin to IllinoisExplore the most affordable flight options available from Wisconsin to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 13, 2026.
Explore the most affordable flight options available from Wisconsin to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 13, 2026.
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:24 pm
MSP
- MDW
Nonstop1h 37m
Delta
Tue 8/257:25 pm
MDW
- MSP
Nonstop1h 45m
Delta
Deal found 7/13![Delta logo]()
$117
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:55 am
MSP
- ORD
Nonstop1h 35m
Delta
Mon 9/218:25 pm
ORD
- MSP
Nonstop1h 43m
Delta
Deal found 7/13![Delta logo]()
$117
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:02 am
MSP
- ORD
Nonstop1h 52m
American Airlines
Wed 9/210:40 pm
ORD
- MSP
Nonstop1h 44m
American Airlines
Deal found 7/12![American Airlines logo]()
$118
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:45 am
MSP
- MDW
Nonstop1h 25m
Southwest
Mon 8/105:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Deal found 7/11![Southwest logo]()
$127
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/223:05 pm
MSP
- MDW
Nonstop1h 25m
Southwest
Tue 10/67:55 am
MDW
- MSP
2 stops6h 55m
Southwest
Deal found 7/10![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
MSP
- MDW
2 stops7h 20m
Southwest
Wed 8/268:30 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/12![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:55 am
MSP
- MDW
1 stop7h 30m
Southwest
Sat 8/88:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/13![Southwest logo]()
$133
This United Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:34 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Thu 8/69:28 pm
ORD
- MSP
Nonstop1h 42m
United Airlines
Deal found 7/12![United Airlines logo]()
$133
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:05 pm
MSP
- MDW
1 stop6h 05m
Southwest
Mon 9/145:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Deal found 7/12![Southwest logo]()
$137
This Super.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:45 am
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Sun 11/17:30 am
ORD
- MSP
Nonstop1h 41m
Sun Country Air
Deal found 7/11![Sun Country Air logo]()
$137
This Sun Country Air deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:55 am
MSP
- ORD
Nonstop1h 41m
Sun Country Air
Mon 11/308:05 pm
ORD
- MSP
Nonstop1h 41m
Sun Country Air
Deal found 7/8![Sun Country Air logo]()
$138
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:55 am
MSP
- MDW
1 stop7h 30m
Southwest
Mon 8/315:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Deal found 7/11![Southwest logo]()
$142
Best flights from Wisconsin to IllinoisDiscover carefully curated flight deals from Wisconsin to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 13, 2026.
Discover carefully curated flight deals from Wisconsin to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 13, 2026.
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:00 pm
MSP
- ORD
Nonstop1h 33m
Delta
Sat 9/266:00 am
ORD
- MSP
Nonstop1h 36m
Delta
Deal found 7/12![Delta logo]()
$117
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:00 am
MSP
- MDW
1 stop5h 55m
Southwest
Tue 10/67:55 am
MDW
- MSP
2 stops6h 55m
Southwest
Deal found 7/10![Southwest logo]()
$138
This United Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:50 am
MKE
- ORD
Nonstop1h 10m
United Airlines
Wed 8/125:59 am
ORD
- MKE
Nonstop1h 08m
United Airlines
Deal found 7/10![United Airlines logo]()
$143
This American Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:17 pm
MKE
- ORD
Nonstop1h 19m
American Airlines
Mon 8/105:15 pm
ORD
- MKE
Nonstop1h 03m
American Airlines
Deal found 7/10![American Airlines logo]()
$144
This Sun Country Air deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:05 pm
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Mon 10/1211:41 am
ORD
- MSP
Nonstop1h 36m
Sun Country Air
Deal found 7/11![Sun Country Air logo]()
$178
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:00 am
MSP
- ORD
Nonstop1h 30m
Delta
Thu 8/138:24 pm
ORD
- MSP
Nonstop1h 51m
Delta
Deal found 7/12![Delta logo]()
$117
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:00 am
MSP
- MDW
2 stops9h 00m
Southwest
Wed 9/24:40 pm
MDW
- MSP
1 stop5h 45m
Southwest
Deal found 7/12![Southwest logo]()
$142
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:00 am
MKE
- ORD
Nonstop0h 59m
United Airlines
Mon 8/107:45 pm
ORD
- MKE
Nonstop1h 11m
United Airlines
Deal found 7/8![United Airlines logo]()
$143
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:20 am
MKE
- ORD
Nonstop1h 10m
United Airlines
Thu 8/134:05 pm
ORD
- MKE
Nonstop1h 10m
United Airlines
Deal found 7/9![United Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:26 pm
MSP
- RFD
1 stop13h 01m
Multiple Airlines
Sun 10/258:53 pm
RFD
- MSP
1 stop15h 19m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/65:45 am
MSP
- MDW
Nonstop1h 25m
Southwest
Thu 8/138:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/8![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/248:10 pm
MSP
- ORD
Nonstop1h 37m
Delta
Mon 8/316:44 pm
ORD
- MSP
Nonstop1h 51m
Delta
Deal found 7/10![Delta logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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.
Thu 8/68:43 am
MKE
- ORD
2 stops11h 10m
Frontier
Mon 8/1010:16 am
ORD
- MKE
1 stop21h 42m
Frontier
Deal found 7/10![Frontier logo]()
$396
This Sun Country Air deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/185:00 pm
MSP
- ORD
Nonstop1h 40m
Sun Country Air
Mon 12/2110:45 am
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 7/9![Sun Country Air logo]()
$208
This United Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:00 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Sat 9/58:14 pm
ORD
- MSP
Nonstop1h 38m
United Airlines
Deal found 7/10![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/244:24 pm
MSP
- MDW
Nonstop1h 37m
Delta
Sat 8/299:24 am
MDW
- MSP
1 stop3h 57m
Delta
Deal found 7/12![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 9/106:20 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Thu 9/175:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Deal found 7/10![Southwest logo]()
$187
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:45 pm
MSN
- ORD
Nonstop1h 15m
American Airlines
Sun 8/309:30 pm
ORD
- MSN
Nonstop1h 09m
American Airlines
Deal found 7/9![American Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:00 pm
MSP
- ORD
Nonstop1h 41m
Delta
Sat 8/296:59 am
ORD
- MSP
1 stop6h 22m
Delta
Deal found 7/12![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:05 am
MSP
- MDW
2 stops6h 55m
Southwest
Sat 9/56:10 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/10![Southwest logo]()
$193
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:00 am
MSN
- ORD
Nonstop1h 12m
American Airlines
Thu 8/135:06 pm
ORD
- MSN
Nonstop1h 13m
American Airlines
Deal found 7/9![American Airlines logo]()
$239
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:15 am
MKE
- ORD
Nonstop1h 11m
United Airlines
Sun 8/237:50 pm
ORD
- MKE
Nonstop1h 10m
United Airlines
Deal found 7/9![United Airlines logo]()
$200
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:00 am
MSP
- ORD
1 stop6h 59m
Delta
Mon 9/218:25 pm
ORD
- MSP
Nonstop1h 43m
Delta
Deal found 7/12![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:30 am
MSP
- MDW
Nonstop1h 25m
Southwest
Sat 8/87:55 am
MDW
- MSP
2 stops12h 10m
Southwest
Deal found 7/11![Southwest logo]()
$200
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/38:38 am
MKE
- ORD
Nonstop1h 22m
American Airlines
Tue 8/115:15 pm
ORD
- MKE
Nonstop1h 03m
American Airlines
Deal found 7/8![American Airlines logo]()
$251
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/103:56 pm
MSP
- ORD
1 stop4h 34m
Delta
Mon 8/176:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/11![Delta logo]()
$189
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/184:00 pm
MSP
- ORD
Nonstop1h 41m
Delta
Thu 8/201:44 pm
ORD
- MSP
1 stop7h 02m
Delta
Deal found 7/11![Delta logo]()
$189
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:00 pm
MKE
- STL
1 stop4h 40m
Southwest
Tue 9/155:55 am
STL
- MKE
1 stop6h 05m
Southwest
Deal found 7/9![Southwest logo]()
$215
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:23 pm
DLH
- ORD
Nonstop1h 56m
United Airlines
Mon 8/249:30 pm
ORD
- DLH
Nonstop1h 52m
United Airlines
Deal found 7/13![United Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:05 pm
MKE
- STL
1 stop6h 05m
Southwest
Thu 10/16:10 pm
STL
- MKE
1 stop4h 20m
Southwest
Deal found 7/10![Southwest logo]()
$215
Last-minute flights from Wisconsin to IllinoisDiscover last-minute flight deals from Wisconsin to Illinois. Data last updated July 13, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Illinois. Data last updated July 13, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Tue 8/119:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Deal found 7/13![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:45 am
MSP
- MDW
Nonstop1h 25m
Southwest
Mon 8/105:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Deal found 7/13![Southwest logo]()
$127
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:55 am
MSP
- MDW
1 stop7h 30m
Southwest
Sat 8/88:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/13![Southwest logo]()
$133
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:00 am
MKE
- ORD
Nonstop0h 59m
United Airlines
Mon 8/107:45 pm
ORD
- MKE
Nonstop1h 11m
United Airlines
Deal found 7/8![United Airlines logo]()
$143
This American Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:17 pm
MKE
- ORD
Nonstop1h 19m
American Airlines
Mon 8/105:15 pm
ORD
- MKE
Nonstop1h 03m
American Airlines
Deal found 7/10![American Airlines logo]()
$144
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:30 am
MSP
- MDW
Nonstop1h 25m
Southwest
Sat 8/82:25 pm
MDW
- MSP
1 stop5h 40m
Southwest
Deal found 7/11![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
MSP
- MDW
2 stops7h 20m
Southwest
Mon 8/178:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/12![Southwest logo]()
$162
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:55 am
MSP
- MDW
1 stop4h 20m
Southwest
Mon 8/243:20 pm
MDW
- MSP
1 stop6h 00m
Southwest
Deal found 7/13![Southwest logo]()
$137
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:30 am
MSP
- MDW
Nonstop1h 25m
Southwest
Wed 8/268:30 am
MDW
- MSP
Nonstop1h 40m
Southwest
Deal found 7/12![Southwest logo]()
$117
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
MSP
- MDW
2 stops7h 20m
Southwest
Tue 8/255:10 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/13![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2510:35 am
MSP
- MDW
Nonstop1h 25m
Southwest
Tue 9/18:30 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/11![Southwest logo]()
$152
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:02 am
MSP
- STL
1 stop5h 52m
American Airlines
Mon 8/318:07 pm
STL
- MSP
1 stop4h 17m
American Airlines
Deal found 7/11![American Airlines logo]()
$159
One-way flights from Wisconsin to IllinoisSearch for one-way flight options from Wisconsin to Illinois. Find affordable one-way fares based on user searches. Data last updated July 13, 2026.
Search for one-way flight options from Wisconsin to Illinois. Find affordable one-way fares based on user searches. Data last updated July 13, 2026.
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:05 am
MSP
- STL
Nonstop1h 25m
Southwest
Deal found 7/8![Southwest logo]()
$50
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/114:30 pm
MSP
- STL
Nonstop1h 25m
Southwest
Deal found 7/13![Southwest logo]()
$59
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/269:45 am
MSP
- STL
1 stop5h 56m
United Airlines
Deal found 7/13![United Airlines logo]()
$64
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:20 pm
MSP
- STL
2 stops7h 25m
Southwest
Deal found 7/10![Southwest logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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.
Thu 8/203:00 pm
MSP
- ORD
Nonstop1h 39m
Sun Country Air
Deal found 7/8![Sun Country Air logo]()
$68
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:00 am
MSP
- MDW
1 stop3h 50m
Southwest
Deal found 7/13![Southwest logo]()
$69
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:15 am
MSP
- STL
1 stop6h 40m
Southwest
Deal found 7/12![Southwest logo]()
$69
This Cheapflightsfares deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:45 am
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Deal found 7/9![Sun Country Air logo]()
$69
This eDestinos deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:40 pm
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Deal found 7/12![Sun Country Air logo]()
$72
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:00 am
MKE
- ORD
Nonstop1h 10m
United Airlines
Deal found 7/8![United Airlines logo]()
$72
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
MSP
- MDW
1 stop8h 10m
Southwest
Deal found 7/12![Southwest logo]()
$74
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:05 pm
MSP
- STL
2 stops7h 05m
Southwest
Deal found 7/12![Southwest logo]()
$74
Find flight deals from Wisconsin to Illinois
Keep the following information in mind while searching for Wisconsin to Illinois flight deals. Data was last updated July 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (Delta) |
One-way from | $50 (Southwest) |
Good round-trip deal | $344 or less |
Good one-way deal | $168 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Wisconsin to Illinois 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 July 13, 2026.
Use the filters below to find and compare flights from Wisconsin to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Tue 9/15
8:00 pm-9:33 pm
Nonstop1h 33m
Chicago O'Hare Intl
Sat 9/26
6:00 am-7:36 am
Nonstop1h 36m
$117
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Sat 8/8
7:00 am-8:30 am
Nonstop1h 30m
Chicago O'Hare Intl
Thu 8/13
8:24 pm-10:15 pm
Nonstop1h 51m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Tue 9/22
8:00 am-1:55 pm
1 stop5h 55m
Chicago Midway
Tue 10/6
7:55 am-2:50 pm
2 stops6h 55m
$138
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Wed 8/26
7:00 am-4:00 pm
2 stops9h 00m
Chicago Midway
Wed 9/2
4:40 pm-10:25 pm
1 stop5h 45m
$142
MilwaukeeChicago
MKE - ORD
MKEORD
Milwaukee-Mitchell
Wed 8/5
7:50 am-9:00 am
Nonstop1h 10m
Chicago O'Hare Intl
Wed 8/12
5:59 am-7:07 am
Nonstop1h 08m
$143
Quickest round-trip
MilwaukeeChicago
MKE - ORD
MKEORD
Milwaukee-Mitchell
Thu 8/6
5:00 am-5:59 am
Nonstop0h 59m
Chicago O'Hare Intl
Mon 8/10
7:45 pm-8:56 pm
Nonstop1h 11m
$143
MilwaukeeChicago
MKE - ORD
MKEORD
Milwaukee-Mitchell
Thu 8/6
6:20 am-7:30 am
Nonstop1h 10m
Chicago O'Hare Intl
Thu 8/13
4:05 pm-5:15 pm
Nonstop1h 10m
$143
MilwaukeeChicago
MKE - ORD
MKEORD
Milwaukee-Mitchell
Thu 8/6
1:17 pm-2:36 pm
Nonstop1h 19m
Chicago O'Hare Intl
Mon 8/10
5:15 pm-6:18 pm
Nonstop1h 03m
$144
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Thu 8/6
5:45 am-7:10 am
Nonstop1h 25m
Chicago Midway
Thu 8/13
8:00 am-9:45 am
Nonstop1h 45m
$177
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Mon 8/24
8:10 pm-9:47 pm
Nonstop1h 37m
Chicago O'Hare Intl
Mon 8/31
6:44 pm-8:35 pm
Nonstop1h 51m
$177
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Wisconsin to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Wisconsin with our price prediction graph.
MSP-STL
MSP-ORD
MSP-MDW
MKE-ORD
MSP-RFD
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 Illinois
USWI-USIL
MSP-STL
MSP-ORD
MSP-MDW
MKE-ORD
What is the cheapest month to book a flight from Wisconsin to Illinois?
Currently, January is the cheapest month in which you can book a flight from Wisconsin to Illinois (average of $179). Flying from Wisconsin to Illinois in August is currently the most expensive (average of $191). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from WI to IL?
Find hourly flight availability from Wisconsin to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 13, 2026.
One of the essential ways to save on airfare from Wisconsin to Illinois is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 34% on airfare.
Weekly flight availability from Wisconsin to Illinois
Explore weekly flight availability from Wisconsin to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 13, 2026.
The most flights from USWI to USIL are scheduled on a Sunday (58 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (43 on average).
What is the cheapest day to fly from Wisconsin to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Illinois. Price data was last updated on July 11, 2026.
Travelers seeking maximum savings on their Wisconsin to Illinois flight should consider departing on Thursday afternoons when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated July 13, 2026.
See what other customers who have flown with United Airlines and American Airlines from Wisconsin to Illinois have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.4
Boarding
7.7
Entertainment
7.1
Food
6.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - ORD
Overall
7.4
Boarding
7.7
Entertainment
7.1
Food
6.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - ORD
Overall
7.4
Boarding
7.7
Entertainment
7.1
Food
6.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - ORD
Related info for your journey
Find useful and relevant information for your journey from Wisconsin to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Wisconsin to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Wisconsin to Illinois by cabin class
Find flights from Wisconsin to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Wisconsin and Illinois flights
Browse other Wisconsin and Illinois flight options. Last updated on July 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Wisconsin after your stay in Illinois
Wisconsin to Illinois flights
Consider these flights traveling from Wisconsin to Illinois.
Top 2 airlines flying from Wisconsin to Illinois
Discover the top 2 airlines that operate flights from Wisconsin to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$168 | Average$296 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$273 | FlexibilityNo cancel fee | On-time69% |