$59+ Cheap flights from Wisconsin to Chicago (CHI)
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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Aug 16 — Aug 231
Round-trip
1 adult, Economy
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Cheapest flights from Wisconsin to ChicagoExplore the most affordable flight options available from Wisconsin to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 17, 2026.
Explore the most affordable flight options available from Wisconsin to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 17, 2026.
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 8/85:30 am
MSP
- MDW
Nonstop1h 25m
Southwest
Tue 8/118:30 am
MDW
- MSP
Nonstop1h 40m
Southwest
Deal found 7/12![Southwest logo]()
$117
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 9/59:42 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Mon 9/78:45 am
ORD
- MSP
Nonstop1h 40m
United Airlines
Deal found 7/13![United Airlines logo]()
$117
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:02 am
MSP
- ORD
Nonstop1h 52m
American Airlines
Mon 8/1010:40 pm
ORD
- MSP
Nonstop1h 44m
American Airlines
Deal found 7/13![American Airlines logo]()
$118
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 9/512:30 pm
MSP
- MDW
1 stop8h 15m
Southwest
Mon 9/72:25 pm
MDW
- MSP
Nonstop1h 30m
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.
Sat 10/2410:35 am
MSP
- MDW
Nonstop1h 30m
Southwest
Tue 10/277:55 am
MDW
- MSP
2 stops6h 55m
Southwest
Deal found 7/13![Southwest logo]()
$128
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 9/56:00 am
MSP
- MDW
2 stops7h 20m
Southwest
Sat 9/126:10 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/13![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:05 am
MSP
- MDW
1 stop8h 00m
Southwest
Sat 8/228:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/15![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 7/13. 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.
Mon 8/247:10 am
MSP
- MDW
1 stop7h 00m
Southwest
Mon 8/315:50 pm
MDW
- MSP
1 stop4h 35m
Southwest
Deal found 7/13![Southwest logo]()
$137
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:00 am
MSP
- ORD
Nonstop1h 30m
Delta
Thu 8/208:24 pm
ORD
- MSP
Nonstop1h 51m
Delta
Deal found 7/15![Delta logo]()
$137
This Cheapflightsfares deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/59:00 am
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Fri 10/96:39 pm
ORD
- MSP
Nonstop1h 50m
Sun Country Air
Deal found 7/17![Sun Country Air logo]()
$138
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 10/177:10 am
MSP
- MDW
2 stops7h 40m
Southwest
Tue 10/207:55 am
MDW
- MSP
2 stops6h 55m
Southwest
Deal found 7/13![Southwest logo]()
$143
Best flights from Wisconsin to ChicagoDiscover carefully curated flight deals from Wisconsin to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 17, 2026.
Discover carefully curated flight deals from Wisconsin to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 17, 2026.
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:35 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Wed 9/910:15 am
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/15![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Sat 8/221:51 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 7/15![Delta logo]()
$117
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 8/206:00 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Sat 8/226:59 am
ORD
- MSP
Nonstop1h 40m
United Airlines
Deal found 7/13![United Airlines logo]()
$117
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:00 pm
MKE
- ORD
Nonstop1h 29m
American Airlines
Sun 9/67:58 pm
ORD
- MKE
Nonstop1h 02m
American Airlines
Deal found 7/17![American Airlines logo]()
$171
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.
Mon 8/244:24 pm
MSP
- MDW
Nonstop1h 37m
Delta
Tue 8/257:25 pm
MDW
- MSP
Nonstop1h 45m
Delta
Deal found 7/13![Delta logo]()
$117
This 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 8/225:30 am
MSP
- MDW
Nonstop1h 25m
Southwest
Tue 8/252:20 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/13![Southwest logo]()
$117
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.
Mon 9/76:55 pm
MSP
- ORD
Nonstop1h 45m
United Airlines
Thu 9/1010:25 am
ORD
- MSP
Nonstop1h 38m
United Airlines
Deal found 7/13![United Airlines 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 8/2610:35 am
MSP
- MDW
Nonstop1h 25m
Southwest
Wed 9/28:30 am
MDW
- MSP
Nonstop1h 40m
Southwest
Deal found 7/12![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:00 am
MSP
- MDW
Nonstop1h 49m
Delta
Tue 12/85:35 pm
MDW
- MSP
Nonstop1h 40m
Delta
Deal found 7/15![Delta 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.
Wed 9/2312:25 pm
MSP
- MDW
Nonstop1h 25m
Southwest
Sat 9/266:10 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/13![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:10 pm
MSP
- ORD
Nonstop1h 37m
Delta
Tue 8/186:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/15![Delta 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.
Thu 8/207:40 am
MSP
- MDW
Nonstop1h 30m
Southwest
Mon 8/244:10 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/13![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:10 pm
MSP
- ORD
Nonstop1h 37m
Delta
Sun 9/66:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/17![Delta logo]()
$117
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:00 pm
MSP
- ORD
Nonstop1h 33m
Delta
Wed 9/1612:29 pm
ORD
- MSP
Nonstop1h 42m
Delta
Deal found 7/14![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 8/2611:32 am
MKE
- ORD
Nonstop1h 11m
American Airlines
Wed 9/26:50 am
ORD
- MKE
Nonstop0h 59m
American Airlines
Deal found 7/12![American Airlines logo]()
$173
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:30 am
MKE
- ORD
Nonstop1h 11m
United Airlines
Tue 8/185:59 am
ORD
- MKE
Nonstop1h 08m
United Airlines
Deal found 7/14![United Airlines logo]()
$171
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:05 pm
MSP
- MDW
1 stop6h 05m
Southwest
Mon 8/315:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Deal found 7/14![Southwest logo]()
$137
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/88:50 am
MKE
- ORD
Nonstop1h 10m
United Airlines
Sat 8/159:30 pm
ORD
- MKE
Nonstop1h 06m
United Airlines
Deal found 7/15![United Airlines logo]()
$171
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:50 am
MSP
- MDW
1 stop9h 30m
Southwest
Tue 12/15:15 pm
MDW
- MSP
1 stop5h 35m
Southwest
Deal found 7/14![Southwest logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:17 pm
MSP
- RFD
1 stop12h 45m
Multiple Airlines
Sun 9/69:29 pm
RFD
- MSP
2 stops15h 37m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$464
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:00 am
EAU
- ORD
Nonstop1h 27m
United Airlines
Wed 8/512:30 pm
ORD
- EAU
Nonstop1h 30m
United Airlines
Deal found 7/15![United Airlines logo]()
$180
This American Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/77:45 am
MKE
- ORD
Nonstop1h 20m
American Airlines
Sun 1/175:29 pm
ORD
- MKE
Nonstop1h 07m
American Airlines
Deal found 7/16![American Airlines logo]()
$219
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:35 pm
EAU
- ORD
Nonstop1h 30m
United Airlines
Sat 9/2610:00 pm
ORD
- EAU
Nonstop1h 32m
United Airlines
Deal found 7/15![United Airlines logo]()
$180
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/83:56 pm
MSP
- ORD
1 stop4h 34m
Delta
Mon 8/106:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/16![Delta logo]()
$177
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:27 pm
GRB
- ORD
Nonstop1h 33m
American Airlines
Mon 10/58:10 am
ORD
- GRB
Nonstop1h 12m
American Airlines
Deal found 7/17![American Airlines logo]()
$239
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:00 am
EAU
- ORD
Nonstop1h 30m
United Airlines
Thu 8/2012:29 pm
ORD
- EAU
Nonstop1h 25m
United Airlines
Deal found 7/14![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:00 am
EAU
- ORD
Nonstop1h 29m
United Airlines
Mon 10/1912:29 pm
ORD
- EAU
Nonstop1h 25m
United Airlines
Deal found 7/15![United Airlines logo]()
$180
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:05 pm
MSP
- ORD
Nonstop1h 33m
Delta
Mon 9/288:25 am
ORD
- MSP
Nonstop1h 39m
Delta
Deal found 7/17![Delta logo]()
$181
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/52:35 pm
EAU
- ORD
Nonstop1h 27m
United Airlines
Wed 8/1912:29 pm
ORD
- EAU
Nonstop1h 25m
United Airlines
Deal found 7/15![United Airlines logo]()
$180
This American Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/112:46 pm
GRB
- ORD
Nonstop1h 20m
American Airlines
Sun 8/211:00 pm
ORD
- GRB
Nonstop1h 12m
American Airlines
Deal found 7/15![American Airlines logo]()
$269
Last-minute flights from Wisconsin to ChicagoDiscover last-minute flight deals from Wisconsin to Chicago. Data last updated July 17, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Chicago. Data last updated July 17, 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 8/47:00 am
MSP
- ORD
Nonstop1h 30m
Delta
Sat 8/86:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/13![Delta logo]()
$147
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:02 am
MSP
- ORD
Nonstop1h 52m
American Airlines
Mon 8/1010:40 pm
ORD
- MSP
Nonstop1h 44m
American Airlines
Deal found 7/13![American Airlines logo]()
$118
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 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.
Sat 8/85:30 am
MSP
- MDW
Nonstop1h 25m
Southwest
Tue 8/118:30 am
MDW
- MSP
Nonstop1h 40m
Southwest
Deal found 7/12![Southwest logo]()
$117
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.
Mon 8/105:13 pm
MSP
- ORD
Nonstop1h 47m
United Airlines
Thu 8/134:00 pm
ORD
- MSP
Nonstop1h 59m
United Airlines
Deal found 7/13![United Airlines 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.
Tue 8/116:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Sat 8/227:25 pm
MDW
- MSP
Nonstop1h 45m
Delta
Deal found 7/13![Delta logo]()
$147
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 8/176:55 pm
ORD
- MSP
Nonstop1h 38m
United Airlines
Deal found 7/15![United Airlines logo]()
$151
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:05 am
MSP
- MDW
1 stop8h 00m
Southwest
Sat 8/228:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/15![Southwest logo]()
$133
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:20 pm
MSP
- ORD
Nonstop1h 39m
Delta
Mon 8/248:24 pm
ORD
- MSP
Nonstop1h 51m
Delta
Deal found 7/15![Delta logo]()
$137
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.
Mon 8/247:10 am
MSP
- MDW
1 stop7h 00m
Southwest
Mon 8/315:50 pm
MDW
- MSP
1 stop4h 35m
Southwest
Deal found 7/13![Southwest logo]()
$137
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:00 am
MSP
- MDW
2 stops7h 20m
Southwest
Mon 8/318:40 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/14![Southwest logo]()
$132
One-way flights from Wisconsin to ChicagoSearch for one-way flight options from Wisconsin to Chicago. Find affordable one-way fares based on user searches. Data last updated July 17, 2026.
Search for one-way flight options from Wisconsin to Chicago. Find affordable one-way fares based on user searches. Data last updated July 17, 2026.
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:15 am
MSP
- MDW
Nonstop1h 25m
Southwest
Deal found 7/14![Southwest logo]()
$59
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:10 pm
MSP
- ORD
Nonstop1h 37m
Delta
Deal found 7/14![Delta logo]()
$59
This Kiwi.com deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 7/17![Sun Country Air logo]()
$68
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 10/32:35 pm
MSP
- MDW
1 stop3h 10m
Southwest
Deal found 7/12![Southwest logo]()
$69
This Sun Country Air deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:05 am
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Deal found 7/17![Sun Country Air logo]()
$69
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am
MSP
- ORD
Nonstop1h 43m
United Airlines
Deal found 7/16![United Airlines logo]()
$71
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 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 8/298:05 am
MSP
- MDW
1 stop8h 00m
Southwest
Deal found 7/12![Southwest logo]()
$74
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/164:40 pm
MSP
- MDW
Nonstop1h 39m
Delta
Deal found 7/15![Delta logo]()
$79
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/203:35 pm
MSP
- ORD
Nonstop1h 39m
Sun Country Air
Deal found 7/13![Sun Country Air logo]()
$79
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:20 am
MSP
- MDW
2 stops11h 00m
Southwest
Deal found 7/16![Southwest logo]()
$80
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:30 pm
MSP
- ORD
1 stop11h 31m
Frontier
Deal found 7/12![Frontier logo]()
$84
Find flight deals from Wisconsin to Chicago
Keep the following information in mind while searching for Wisconsin to Chicago flight deals. Data was last updated July 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (Southwest) |
One-way from | $59 (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 Chicago 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 17, 2026.
Use the filters below to find and compare flights from Wisconsin to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Tue 9/8
5:35 pm-7:05 pm
Nonstop1h 30m
Chicago Midway
Wed 9/9
10:15 am-11:45 am
Nonstop1h 30m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 8/15
6:57 am-8:39 am
Nonstop1h 42m
Chicago Midway
Sat 8/22
1:51 pm-3:35 pm
Nonstop1h 44m
$117
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Thu 8/20
6:00 am-7:44 am
Nonstop1h 44m
Chicago O'Hare Intl
Sat 8/22
6:59 am-8:39 am
Nonstop1h 40m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Mon 8/24
4:24 pm-6:01 pm
Nonstop1h 37m
Chicago Midway
Tue 8/25
7:25 pm-9:10 pm
Nonstop1h 45m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 8/22
5:30 am-6:55 am
Nonstop1h 25m
Chicago Midway
Tue 8/25
2:20 pm-3:50 pm
Nonstop1h 30m
$117
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Mon 9/7
6:55 pm-8:40 pm
Nonstop1h 45m
Chicago O'Hare Intl
Thu 9/10
10:25 am-12:03 pm
Nonstop1h 38m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Wed 8/26
10:35 am-12:00 pm
Nonstop1h 25m
Chicago Midway
Wed 9/2
8:30 am-10:10 am
Nonstop1h 40m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 12/5
7:00 am-8:49 am
Nonstop1h 49m
Chicago Midway
Tue 12/8
5:35 pm-7:15 pm
Nonstop1h 40m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Wed 9/23
12:25 pm-1:50 pm
Nonstop1h 25m
Chicago Midway
Sat 9/26
6:10 pm-7:40 pm
Nonstop1h 30m
$117
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Wed 8/12
8:10 pm-9:47 pm
Nonstop1h 37m
Chicago O'Hare Intl
Tue 8/18
6:00 am-7:30 am
Nonstop1h 30m
$117
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Wisconsin to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Wisconsin with our price prediction graph.
MSP-MDW
MSP-ORD
MKE-ORD
MSP-RFD
EAU-ORD
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
USWI-CHI
MSP-MDW
MSP-ORD
MKE-ORD
MSP-RFD
What is the cheapest month to book a flight from Wisconsin to Chicago?
Currently, November is the cheapest month in which you can book a flight from Wisconsin to Chicago (average of $224). Flying from Wisconsin to Chicago 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 CHI?
Find hourly flight availability from Wisconsin to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 17, 2026.
One of the essential ways to save on airfare from Wisconsin to Chicago 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 Chicago
Explore weekly flight availability from Wisconsin to Chicago. 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 17, 2026.
The most flights from USWI to CHI are scheduled on a Wednesday (59 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).
What is the cheapest day to fly from Wisconsin to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Chicago. Price data was last updated on July 11, 2026.
Travelers seeking maximum savings on their Wisconsin to Chicago 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.
Related info for your journey
Find useful and relevant information for your journey from Wisconsin to Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Wisconsin to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 17, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Wisconsin to Chicago by cabin class
Find flights from Wisconsin to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Wisconsin and Chicago flights
Browse other Wisconsin and Chicago flight options. Last updated on July 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Wisconsin to Chicago flights
Consider these flights traveling from Wisconsin to Chicago.
Top 2 airlines flying from Wisconsin to Chicago
Discover the top 2 airlines that operate flights from Wisconsin to Chicago. 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 17, 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% |