$49+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — ORD
Aug 22 — Aug 291
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 23, 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 23, 2026.
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/186:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Tue 8/259:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Deal found 7/23![Delta logo]()
$117
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/187:00 am
MSP
- ORD
Nonstop1h 30m
Delta
Wed 8/268:28 am
ORD
- MSP
Nonstop1h 35m
Delta
Deal found 7/23![Delta logo]()
$117
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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.
Mon 11/28:00 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Mon 11/96:00 pm
ORD
- MSP
Nonstop1h 39m
United Airlines
Deal found 7/21![United Airlines logo]()
$119
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/56:00 am
MSP
- MDW
2 stops7h 20m
Southwest
Sat 9/129:05 am
MDW
- MSP
1 stop5h 20m
Southwest
Deal found 7/22![Southwest logo]()
$122
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/32:05 pm
MSP
- MDW
1 stop8h 15m
Southwest
Sun 9/68:40 am
MDW
- MSP
Nonstop1h 40m
Southwest
Deal found 7/21![Southwest logo]()
$123
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/84:40 pm
MSP
- MDW
Nonstop1h 39m
Delta
Fri 9/119:59 am
MDW
- MSP
Nonstop1h 41m
Delta
Deal found 7/22![Delta logo]()
$127
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/86:55 am
MSP
- ORD
Nonstop1h 35m
Delta
Thu 9/108:25 am
ORD
- MSP
Nonstop1h 39m
Delta
Deal found 7/22![Delta logo]()
$127
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/247:55 am
MSP
- MDW
1 stop7h 30m
Southwest
Mon 9/282:35 pm
MDW
- MSP
2 stops7h 30m
Southwest
Deal found 7/21![Southwest logo]()
$128
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/139:45 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Mon 8/176:59 am
ORD
- MSP
Nonstop1h 40m
United Airlines
Deal found 7/21![United Airlines logo]()
$131
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 9/56:00 am
MSP
- MDW
2 stops7h 20m
Southwest
Sun 9/68:40 am
MDW
- MSP
Nonstop1h 40m
Southwest
Deal found 7/20![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:45 am
MSP
- MDW
Nonstop1h 25m
Southwest
Mon 8/178:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/22![Southwest logo]()
$137
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/173:20 pm
MSP
- ORD
Nonstop1h 39m
Delta
Thu 8/206:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/23![Delta logo]()
$137
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 23, 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 23, 2026.
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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
Wed 8/269:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Deal found 7/23![Delta logo]()
$117
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 7/22![Southwest logo]()
$117
This Sun Country Air deal was found by Cheapflights users on 7/18. 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 Sun Country Air 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
Sun 8/238:30 am
ORD
- MSP
Nonstop1h 36m
Sun Country Air
Deal found 7/18![Sun Country Air logo]()
$158
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/2011:18 am
MKE
- ORD
Nonstop1h 11m
United Airlines
Thu 8/2711:41 am
ORD
- MKE
Nonstop0h 57m
United Airlines
Deal found 7/23![United Airlines logo]()
$171
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/205:00 am
MKE
- ORD
Nonstop1h 14m
American Airlines
Mon 8/247:58 pm
ORD
- MKE
Nonstop1h 02m
American Airlines
Deal found 7/22![American Airlines logo]()
$171
This Delta deal was found by Cheapflights users on 7/18. 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 9/58:10 pm
MSP
- ORD
Nonstop1h 37m
Delta
Sun 9/66:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/18![Delta logo]()
$117
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/159:05 am
MSP
- MDW
2 stops6h 55m
Southwest
Thu 9/175:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Deal found 7/21![Southwest logo]()
$122
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/56:00 am
MSP
- MDW
2 stops7h 20m
Southwest
Sat 9/1211:45 am
MDW
- MSP
2 stops7h 00m
Southwest
Deal found 7/22![Southwest logo]()
$127
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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
Thu 8/278:28 am
ORD
- MSP
Nonstop1h 35m
Delta
Deal found 7/21![Delta logo]()
$127
This Kissandfly.com deal was found by Cheapflights users on 7/18. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:00 am
ORD
- STL
1 stop16h 03m
Frontier
Sun 9/66:17 pm
STL
- ORD
1 stop13h 36m
Frontier
Deal found 7/18![Frontier logo]()
$313
This United Airlines deal was found by Cheapflights users on 7/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:55 pm
MSP
- ORD
Nonstop1h 45m
United Airlines
Thu 8/278:45 am
ORD
- MSP
Nonstop1h 40m
United Airlines
Deal found 7/18![United Airlines logo]()
$181
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/213:45 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Wed 9/238:30 am
MDW
- MSP
Nonstop1h 40m
Southwest
Deal found 7/21![Southwest logo]()
$167
This American Airlines deal was found by Cheapflights users on 7/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:48 pm
MKE
- ORD
Nonstop1h 33m
American Airlines
Sun 8/910:05 am
ORD
- MKE
Nonstop0h 57m
American Airlines
Deal found 7/18![American Airlines logo]()
$205
This United Airlines deal was found by Cheapflights users on 7/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:30 am
MKE
- ORD
Nonstop1h 11m
United Airlines
Sat 8/225:45 pm
ORD
- MKE
Nonstop1h 10m
United Airlines
Deal found 7/18![United Airlines logo]()
$191
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 10/216:00 am
MSP
- MDW
1 stop6h 48m
Delta
Sat 10/2412:28 pm
MDW
- MSP
Nonstop1h 42m
Delta
Deal found 7/23![Delta logo]()
$177
This United Airlines deal was found by Cheapflights users on 7/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/241:19 pm
MKE
- ORD
Nonstop1h 11m
United Airlines
Sat 8/292:40 pm
ORD
- MKE
Nonstop1h 07m
United Airlines
Deal found 7/19![United Airlines logo]()
$191
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:04 am
MSP
- ORD
1 stop7h 04m
Delta
Mon 8/178:24 pm
ORD
- MSP
Nonstop1h 51m
Delta
Deal found 7/23![Delta logo]()
$182
This Southwest deal was found by Cheapflights users on 7/19. 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 10/195:55 am
MSP
- MDW
1 stop5h 15m
Southwest
Thu 10/222:05 pm
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 7/19![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/147:02 pm
GRB
- ORD
Nonstop1h 38m
American Airlines
Sun 8/1611:05 pm
ORD
- GRB
Nonstop1h 11m
American Airlines
Deal found 7/20![American Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/196:04 am
MSP
- ORD
1 stop7h 04m
Delta
Sat 8/226:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/22![Delta logo]()
$192
This American Airlines deal was found by Cheapflights users on 7/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:14 pm
ATW
- ORD
Nonstop1h 34m
American Airlines
Sun 10/1811:00 pm
ORD
- ATW
Nonstop1h 12m
American Airlines
Deal found 7/18![American Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 7/18. 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 8/193:05 pm
MSP
- STL
2 stops7h 05m
Southwest
Thu 8/208:55 pm
STL
- MSP
Nonstop1h 30m
Southwest
Deal found 7/18![Southwest logo]()
$210
This Delta deal was found by Cheapflights users on 7/19. 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 8/126:55 am
MSP
- STL
Nonstop1h 42m
Delta
Sat 8/155:34 pm
STL
- MSP
Nonstop1h 41m
Delta
Deal found 7/19![Delta logo]()
$195
This United Airlines deal was found by Cheapflights users on 7/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:23 pm
DLH
- ORD
Nonstop1h 56m
United Airlines
Tue 8/189:30 pm
ORD
- DLH
Nonstop1h 52m
United Airlines
Deal found 7/19![United Airlines logo]()
$239
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/176:53 pm
MSN
- ORD
Nonstop1h 37m
American Airlines
Mon 8/248:10 am
ORD
- MSN
Nonstop1h 07m
American Airlines
Deal found 7/20![American Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 7/19. 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.
Sat 8/223:15 pm
MSP
- STL
Nonstop1h 29m
Delta
Mon 8/245:34 pm
STL
- MSP
Nonstop1h 41m
Delta
Deal found 7/19![Delta logo]()
$195
This United Airlines deal was found by Cheapflights users on 7/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:23 pm
DLH
- ORD
Nonstop1h 56m
United Airlines
Mon 8/319:30 pm
ORD
- DLH
Nonstop1h 52m
United Airlines
Deal found 7/19![United Airlines logo]()
$239
This American Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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.
Tue 8/115:00 am
MSN
- ORD
Nonstop1h 12m
American Airlines
Tue 8/1811:00 pm
ORD
- MSN
Nonstop1h 10m
American Airlines
Deal found 7/21![American Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 10/98:00 am
MSP
- STL
Nonstop1h 30m
Southwest
Sat 10/101:45 pm
STL
- MSP
Nonstop1h 30m
Southwest
Deal found 7/21![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 7/19. 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.
Thu 8/279:54 pm
MSP
- STL
Nonstop1h 32m
Delta
Mon 8/3111:13 am
STL
- MSP
Nonstop1h 37m
Delta
Deal found 7/19![Delta logo]()
$195
Last-minute flights from Wisconsin to IllinoisDiscover last-minute flight deals from Wisconsin to Illinois. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Illinois. Data last updated July 23, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/126:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Wed 8/199:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Deal found 7/21![Delta logo]()
$127
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/124:00 pm
MSP
- ORD
Nonstop1h 41m
Delta
Wed 8/198:28 am
ORD
- MSP
Nonstop1h 35m
Delta
Deal found 7/21![Delta logo]()
$127
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/139:45 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Mon 8/176:59 am
ORD
- MSP
Nonstop1h 40m
United Airlines
Deal found 7/21![United Airlines logo]()
$131
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:45 am
MSP
- MDW
Nonstop1h 25m
Southwest
Mon 8/178:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/22![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:05 pm
MSP
- MDW
1 stop8h 15m
Southwest
Wed 8/194:40 pm
MDW
- MSP
1 stop5h 45m
Southwest
Deal found 7/20![Southwest logo]()
$122
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/173:20 pm
MSP
- ORD
Nonstop1h 39m
Delta
Mon 8/245:57 pm
ORD
- MSP
Nonstop1h 37m
Delta
Deal found 7/22![Delta logo]()
$137
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/181:55 pm
MSP
- MDW
1 stop6h 15m
Southwest
Thu 8/205:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Deal found 7/22![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/188:10 pm
MSP
- ORD
Nonstop1h 37m
Delta
Thu 8/206:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/22![Delta logo]()
$117
This Sun Country Air deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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.
Tue 8/1810:30 am
MSP
- ORD
Nonstop1h 47m
Sun Country Air
Thu 8/205:42 pm
ORD
- MSP
Nonstop1h 36m
Sun Country Air
Deal found 7/20![Sun Country Air logo]()
$138
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/207:40 am
MSP
- MDW
Nonstop1h 30m
Southwest
Thu 8/278:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/21![Southwest logo]()
$144
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:10 am
MSP
- MDW
1 stop7h 00m
Southwest
Thu 8/278:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/23![Southwest logo]()
$142
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:35 am
MSP
- MDW
Nonstop1h 25m
Southwest
Sat 8/296:10 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/20![Southwest logo]()
$139
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 23, 2026.
Search for one-way flight options from Wisconsin to Illinois. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/224:30 pm
MSP
- STL
Nonstop1h 25m
Southwest
Deal found 7/22![Southwest logo]()
$49
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/196:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Deal found 7/22![Delta logo]()
$59
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/53:05 pm
MSP
- STL
1 stop5h 35m
Southwest
Deal found 7/21![Southwest logo]()
$59
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 9/113:55 pm
MSP
- ORD
Nonstop1h 38m
Delta
Deal found 7/20![Delta logo]()
$59
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/56:00 am
MSP
- MDW
2 stops7h 20m
Southwest
Deal found 7/22![Southwest logo]()
$64
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/198:10 pm
MSP
- ORD
Nonstop1h 37m
Delta
Deal found 7/21![Delta logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Tue 8/1810:30 am
MSP
- ORD
Nonstop1h 47m
Sun Country Air
Deal found 7/19![Sun Country Air logo]()
$68
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:05 pm
MSP
- MDW
1 stop6h 05m
Southwest
Deal found 7/20![Southwest logo]()
$69
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 10/3012:45 pm
MSP
- STL
1 stop7h 00m
Southwest
Deal found 7/21![Southwest logo]()
$69
This Super.com deal was found by Cheapflights users on 7/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:30 pm
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Deal found 7/19![Sun Country Air logo]()
$69
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 10/246:50 am
MSP
- MDW
2 stops11h 10m
Southwest
Deal found 7/20![Southwest logo]()
$70
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 11/167:05 am
MSP
- STL
2 stops12h 25m
Southwest
Deal found 7/22![Southwest logo]()
$70
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 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (Delta) |
One-way from | $49 (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 23, 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 - MDW
MSPMDW
Minneapolis St Paul
Sat 8/22
4:24 pm-6:01 pm
Nonstop1h 37m
Chicago Midway
Wed 8/26
9:59 am-11:42 am
Nonstop1h 43m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Thu 8/20
7:55 am-12:15 pm
1 stop4h 20m
Chicago Midway
Mon 8/24
3:20 pm-9:20 pm
1 stop6h 00m
$117
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Sat 9/5
8:10 pm-9:47 pm
Nonstop1h 37m
Chicago O'Hare Intl
Sun 9/6
6:00 am-7:30 am
Nonstop1h 30m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Tue 9/15
9:05 am-4:00 pm
2 stops6h 55m
Chicago Midway
Thu 9/17
5:55 am-10:15 am
1 stop4h 20m
$122
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 9/5
6:00 am-1:20 pm
2 stops7h 20m
Chicago Midway
Sat 9/12
11:45 am-6:45 pm
2 stops7h 00m
$127
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Mon 8/24
8:10 pm-9:47 pm
Nonstop1h 37m
Chicago O'Hare Intl
Thu 8/27
8:28 am-10:03 am
Nonstop1h 35m
$127
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Thu 8/20
3:00 pm-4:39 pm
Nonstop1h 39m
Chicago O'Hare Intl
Sun 8/23
8:30 am-10:06 am
Nonstop1h 36m
$158
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Mon 9/21
3:45 pm-5:15 pm
Nonstop1h 30m
Chicago Midway
Wed 9/23
8:30 am-10:10 am
Nonstop1h 40m
$167
Quickest round-trip
MilwaukeeChicago
MKE - ORD
MKEORD
Milwaukee-Mitchell
Thu 8/20
11:18 am-12:29 pm
Nonstop1h 11m
Chicago O'Hare Intl
Thu 8/27
11:41 am-12:38 pm
Nonstop0h 57m
$171
MilwaukeeChicago
MKE - ORD
MKEORD
Milwaukee-Mitchell
Thu 8/20
5:00 am-6:14 am
Nonstop1h 14m
Chicago O'Hare Intl
Mon 8/24
7:58 pm-9:00 pm
Nonstop1h 02m
$171
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-MDW
MSP-ORD
MSP-STL
MKE-ORD
ORD-STL
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-MDW
MSP-ORD
MSP-STL
MKE-ORD
What is the cheapest month to book a flight from Wisconsin to Illinois?
Currently, November is the cheapest month in which you can book a flight from Wisconsin to Illinois (average of $224). Flying from Wisconsin to Illinois in July is currently the most expensive (average of $307). 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 23, 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 23, 2026.
The most flights from USWI to USIL are scheduled on a Tuesday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 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 18, 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 23, 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.
Boarding
7.7
Food
6.6
Comfort
7.3
Crew
8.1
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - ORD
Boarding
7.7
Food
6.6
Comfort
7.3
Crew
8.1
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - ORD
Boarding
7.7
Food
6.6
Comfort
7.3
Crew
8.1
Entertainment
7.1
Overall
7.4
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.
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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 23, 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 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$168 | Average$296 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$274 | FlexibilityNo cancel fee | On-time69% |