$62+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Aug 6 — Aug 131
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 7, 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 7, 2026.
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:25 am
MSP
- MDW
Nonstop1h 30m
Southwest
Wed 7/299:20 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/2![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/283:20 pm
MSP
- ORD
Nonstop1h 39m
Delta
Sat 8/16:30 am
ORD
- MSP
Nonstop1h 34m
Delta
Deal found 7/3![Delta logo]()
$117
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:30 am
MSP
- MDW
Nonstop1h 25m
Southwest
Sat 9/129:05 am
MDW
- MSP
2 stops9h 40m
Southwest
Deal found 7/2![Southwest logo]()
$132
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Wed 8/57:00 am
ORD
- MSP
Nonstop1h 41m
United Airlines
Deal found 7/2![United Airlines logo]()
$132
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:25 am
MSP
- MDW
Nonstop1h 30m
Southwest
Sat 8/86:35 am
MDW
- MSP
1 stop9h 35m
Southwest
Deal found 7/2![Southwest logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/133:40 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Thu 8/205:42 pm
ORD
- MSP
Nonstop1h 36m
Sun Country Air
Deal found 7/5![Sun Country Air logo]()
$136
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:30 am
MSP
- MDW
1 stop5h 55m
Southwest
Tue 10/274:45 pm
MDW
- MSP
1 stop6h 00m
Southwest
Deal found 7/2![Southwest logo]()
$137
This Cheapflightsfares deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 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 7/7![Sun Country Air logo]()
$138
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:00 am
MSP
- MDW
1 stop3h 50m
Southwest
Sat 8/86:35 am
MDW
- MSP
1 stop9h 35m
Southwest
Deal found 7/2![Southwest logo]()
$142
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:05 am
MSP
- MDW
2 stops6h 55m
Southwest
Sat 9/199:05 am
MDW
- MSP
2 stops9h 40m
Southwest
Deal found 7/2![Southwest logo]()
$147
This Super.com deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:30 pm
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Sun 9/278:00 am
ORD
- MSP
Nonstop1h 36m
Sun Country Air
Deal found 7/6![Sun Country Air logo]()
$147
This Cheapflightsfares deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:05 am
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Thu 7/237:25 am
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 7/2![Sun Country Air logo]()
$148
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 7, 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 7, 2026.
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:55 pm
MSP
- ORD
Nonstop1h 45m
United Airlines
Tue 9/18:14 pm
ORD
- MSP
Nonstop1h 38m
United Airlines
Deal found 7/2![United Airlines logo]()
$149
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:40 pm
MSP
- MDW
1 stop5h 15m
Southwest
Sat 8/296:10 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/2![Southwest logo]()
$159
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:04 am
MSP
- ORD
1 stop6h 59m
Delta
Tue 8/48:28 am
ORD
- MSP
Nonstop1h 35m
Delta
Deal found 7/2![Delta logo]()
$187
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/31:18 pm
MKE
- ORD
Nonstop1h 21m
American Airlines
Sun 10/46:56 am
ORD
- MKE
Nonstop1h 05m
American Airlines
Deal found 7/2![American Airlines logo]()
$195
This United Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:35 pm
EAU
- ORD
Nonstop1h 27m
United Airlines
Sun 8/29:55 pm
ORD
- EAU
Nonstop1h 33m
United Airlines
Deal found 7/6![United Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/234:17 pm
ATW
- ORD
2 stops32h 32m
Multiple Airlines
Fri 9/42:41 pm
ORD
- ATW
1 stop8h 29m
Multiple Airlines
Deal found 7/4![Multiple Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:20 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Mon 8/245:50 pm
MDW
- MSP
1 stop4h 35m
Southwest
Deal found 7/3![Southwest logo]()
$191
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:35 pm
EAU
- ORD
Nonstop1h 30m
United Airlines
Sun 8/239:29 pm
ORD
- EAU
Nonstop1h 32m
United Airlines
Deal found 7/2![United Airlines logo]()
$180
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:55 am
MSP
- MDW
1 stop4h 20m
Southwest
Mon 8/2410:00 am
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/3![Southwest logo]()
$191
This United Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:00 am
EAU
- ORD
Nonstop1h 30m
United Airlines
Sun 8/169:29 pm
ORD
- EAU
Nonstop1h 32m
United Airlines
Deal found 7/3![United Airlines logo]()
$180
This American Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 7/5![American Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:04 am
MSP
- ORD
1 stop6h 50m
Delta
Mon 8/248:24 pm
ORD
- MSP
Nonstop1h 51m
Delta
Deal found 7/3![Delta logo]()
$221
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 8/177:55 am
MSP
- MDW
1 stop4h 20m
Southwest
Wed 8/198:30 am
MDW
- MSP
Nonstop1h 40m
Southwest
Deal found 7/7![Southwest logo]()
$199
This American Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/157:19 pm
MKE
- ORD
Nonstop1h 30m
American Airlines
Tue 1/59:34 pm
ORD
- MKE
Nonstop1h 08m
American Airlines
Deal found 7/4![American Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:10 pm
MSP
- ORD
Nonstop1h 37m
Delta
Wed 8/196:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/3![Delta logo]()
$236
This American Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 8/611:32 am
MKE
- ORD
Nonstop1h 11m
American Airlines
Mon 8/105:15 pm
ORD
- MKE
Nonstop1h 03m
American Airlines
Deal found 7/7![American Airlines logo]()
$220
This United Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:00 am
EAU
- ORD
Nonstop1h 30m
United Airlines
Sat 9/124:50 pm
ORD
- EAU
Nonstop1h 29m
United Airlines
Deal found 7/6![United Airlines logo]()
$200
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:55 am
MSP
- MDW
1 stop4h 20m
Southwest
Mon 8/103:20 pm
MDW
- MSP
1 stop6h 00m
Southwest
Deal found 7/3![Southwest logo]()
$201
This deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:00 am
EAU
- ORD
Nonstop1h 29m
United Airlines
Mon 10/1912:29 pm
ORD
- EAU
Nonstop1h 25m
United Airlines
Deal found 7/4![United Airlines logo]()
$200
This Delta deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:15 am
DLH
- ORD
1 stop3h 15m
Delta
Sun 8/166:00 am
ORD
- DLH
1 stop5h 01m
Delta
Deal found 7/4![Delta logo]()
$258
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:00 am
EAU
- ORD
Nonstop1h 29m
United Airlines
Sun 10/1810:00 pm
ORD
- EAU
Nonstop1h 32m
United Airlines
Deal found 7/2![United Airlines logo]()
$200
This American Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/233:24 pm
GRB
- ORD
Nonstop1h 20m
American Airlines
Thu 8/65:08 pm
ORD
- GRB
Nonstop1h 17m
American Airlines
Deal found 7/4![American Airlines logo]()
$254
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:02 am
GRB
- ORD
1 stop5h 12m
Delta
Sun 9/137:05 am
ORD
- GRB
1 stop3h 17m
Delta
Deal found 7/2![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 10/25:35 pm
MSP
- MDW
1 stop5h 30m
Southwest
Mon 10/57:45 am
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 7/7![Southwest logo]()
$240
This United Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/205:30 am
EAU
- ORD
Nonstop1h 35m
United Airlines
Thu 12/2412:35 pm
ORD
- EAU
Nonstop1h 30m
United Airlines
Deal found 7/5![United Airlines logo]()
$200
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/231:02 pm
MSN
- ORD
Nonstop1h 12m
American Airlines
Sun 7/266:40 am
ORD
- MSN
Nonstop1h 11m
American Airlines
Deal found 7/2![American Airlines logo]()
$255
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:57 am
GRB
- ORD
1 stop6h 11m
Delta
Thu 9/31:59 pm
ORD
- GRB
1 stop6h 41m
Delta
Deal found 7/6![Delta logo]()
$259
This deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/92:35 pm
EAU
- ORD
Nonstop1h 30m
United Airlines
Tue 10/2010:00 pm
ORD
- EAU
Nonstop1h 32m
United Airlines
Deal found 7/4![United Airlines logo]()
$200
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:55 am
MSP
- MDW
1 stop5h 15m
Southwest
Mon 10/197:45 am
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 7/2![Southwest logo]()
$258
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/302:05 pm
ATW
- ORD
1 stop4h 24m
Delta
Sun 8/28:52 am
ORD
- ATW
1 stop4h 33m
Delta
Deal found 7/6![Delta logo]()
$259
Last-minute flights from Wisconsin to ChicagoDiscover last-minute flight deals from Wisconsin to Chicago. Data last updated July 7, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Chicago. Data last updated July 7, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:05 am
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Sat 7/256:05 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 7/2![Sun Country Air logo]()
$147
This Cheapflightsfares deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:05 am
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Thu 7/237:25 am
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 7/2![Sun Country Air logo]()
$148
This Sun Country Air deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:35 am
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Sat 7/256:05 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 7/6![Sun Country Air logo]()
$158
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:25 am
MSP
- MDW
Nonstop1h 30m
Southwest
Wed 7/299:20 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/2![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/283:20 pm
MSP
- ORD
Nonstop1h 39m
Delta
Sat 8/16:30 am
ORD
- MSP
Nonstop1h 34m
Delta
Deal found 7/3![Delta logo]()
$117
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Wed 8/57:00 am
ORD
- MSP
Nonstop1h 41m
United Airlines
Deal found 7/2![United Airlines logo]()
$132
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:25 am
MSP
- MDW
Nonstop1h 30m
Southwest
Sat 8/86:35 am
MDW
- MSP
1 stop9h 35m
Southwest
Deal found 7/2![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:00 am
MSP
- MDW
1 stop3h 50m
Southwest
Sat 8/86:35 am
MDW
- MSP
1 stop9h 35m
Southwest
Deal found 7/2![Southwest logo]()
$142
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:30 am
MSP
- MDW
Nonstop1h 25m
Southwest
Mon 8/108:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/2![Southwest logo]()
$149
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Thu 8/1310:25 am
ORD
- MSP
Nonstop1h 40m
United Airlines
Deal found 7/2![United Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/133:40 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Thu 8/205:42 pm
ORD
- MSP
Nonstop1h 36m
Sun Country Air
Deal found 7/5![Sun Country Air logo]()
$136
This Cheapflightsfares deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares 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
Thu 8/275:12 pm
ORD
- MSP
Nonstop1h 36m
Sun Country Air
Deal found 7/4![Sun Country Air logo]()
$138
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 7, 2026.
Search for one-way flight options from Wisconsin to Chicago. Find affordable one-way fares based on user searches. Data last updated July 7, 2026.
This eDestinos deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:30 pm
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Deal found 7/6![Sun Country Air logo]()
$62
This Kiwi.com deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 7/7![Sun Country Air logo]()
$68
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/64:20 pm
MSP
- MDW
1 stop5h 35m
Southwest
Deal found 7/2![Southwest logo]()
$69
This Cheapflightsfares deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:10 am
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Deal found 7/3![Sun Country Air logo]()
$69
This Flightnetwork deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/103:50 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Deal found 7/5![Sun Country Air logo]()
$70
This eDestinos deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2110:35 am
MSP
- ORD
Nonstop1h 47m
Sun Country Air
Deal found 7/2![Sun Country Air logo]()
$72
This Trip.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3011:40 am
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Deal found 7/2![Sun Country Air logo]()
$73
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:00 am
MSP
- MDW
2 stops7h 20m
Southwest
Deal found 7/3![Southwest logo]()
$74
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Deal found 7/2![United Airlines logo]()
$74
This Sun Country Air deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/284:55 pm
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Deal found 7/3![Sun Country Air logo]()
$77
This Kiwi.com deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/253:15 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Deal found 7/7![Sun Country Air logo]()
$80
This Trip.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:35 am
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Deal found 7/2![Sun Country Air logo]()
$82
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 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (Southwest) |
One-way from | $62 (eDestinos) |
Good round-trip deal | $346 or less |
Good one-way deal | $164 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 7, 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 - ORD
MSPORD
Minneapolis St Paul
Thu 8/20
6:55 pm-8:40 pm
Nonstop1h 45m
Chicago O'Hare Intl
Tue 9/1
8:14 pm-9:52 pm
Nonstop1h 38m
$149
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Thu 8/27
4:40 pm-9:55 pm
1 stop5h 15m
Chicago Midway
Sat 8/29
6:10 pm-7:40 pm
Nonstop1h 30m
$159
Eau ClaireChicago
EAU - ORD
EAUORD
Eau Claire
Fri 7/31
2:35 pm-4:02 pm
Nonstop1h 27m
Chicago O'Hare Intl
Sun 8/2
9:55 pm-11:28 pm
Nonstop1h 33m
$180
Eau ClaireChicago
EAU - ORD
EAUORD
Eau Claire
Fri 8/21
2:35 pm-4:05 pm
Nonstop1h 30m
Chicago O'Hare Intl
Sun 8/23
9:29 pm-11:01 pm
Nonstop1h 32m
$180
Eau ClaireChicago
EAU - ORD
EAUORD
Eau Claire
Fri 8/14
5:00 am-6:30 am
Nonstop1h 30m
Chicago O'Hare Intl
Sun 8/16
9:29 pm-11:01 pm
Nonstop1h 32m
$180
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Wed 7/29
6:04 am-1:03 pm
1 stop6h 59m
Chicago O'Hare Intl
Tue 8/4
8:28 am-10:03 am
Nonstop1h 35m
$187
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Thu 8/20
6:20 pm-7:50 pm
Nonstop1h 30m
Chicago Midway
Mon 8/24
5:50 pm-10:25 pm
1 stop4h 35m
$191
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Mon 8/17
7:55 am-12:15 pm
1 stop4h 20m
Chicago Midway
Mon 8/24
10:00 am-11:30 am
Nonstop1h 30m
$191
MilwaukeeChicago
MKE - ORD
MKEORD
Milwaukee-Mitchell
Sat 10/3
1:18 pm-2:39 pm
Nonstop1h 21m
Chicago O'Hare Intl
Sun 10/4
6:56 am-8:01 am
Nonstop1h 05m
$195
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Mon 8/17
7:55 am-12:15 pm
1 stop4h 20m
Chicago Midway
Wed 8/19
8:30 am-10:10 am
Nonstop1h 40m
$199
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-ORD
MSP-MDW
MKE-ORD
EAU-ORD
ATW-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-ORD
MSP-MDW
MKE-ORD
EAU-ORD
What is the cheapest month to book a flight from Wisconsin to Chicago?
Currently, January is the cheapest month in which you can book a flight from Wisconsin to Chicago (average of $179). Flying from Wisconsin to Chicago in July is currently the most expensive (average of $180). 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 7, 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 33% 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 7, 2026.
The most flights from USWI to CHI are scheduled on a Tuesday (59 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 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 4, 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
Hammond
Lansing
Merrillville
Valparaiso
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.
Alternative routes
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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 7, 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 7, 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 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$168 | Average$297 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$272 | FlexibilityNo cancel fee | On-time69% |