$83+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Jun 16 — Jun 231
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Wisconsin to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Wisconsin to Chicago
Cheapest
Best
Last-minute
One-way
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 May 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 May 17, 2026.
This Delta deal was found by Cheapflights users on 5/16. 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.
Tue 6/96:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Tue 6/161:49 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 5/16![Delta logo]()
$137
This Delta deal was found by Cheapflights users on 5/16. 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.
Tue 6/93:20 pm
MSP
- ORD
Nonstop1h 42m
Delta
Tue 6/166:30 am
ORD
- MSP
Nonstop1h 36m
Delta
Deal found 5/16![Delta logo]()
$137
This Cheapflightsfares deal was found by Cheapflights users on 5/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/43:30 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Tue 7/711:55 am
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 5/12![Sun Country Air logo]()
$138
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:50 am
MSP
- MDW
1 stop7h 05m
Southwest
Tue 6/24:40 pm
MDW
- MSP
1 stop5h 50m
Southwest
Deal found 5/12![Southwest logo]()
$142
This United Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Tue 6/1610:25 am
ORD
- MSP
Nonstop1h 47m
United Airlines
Deal found 5/11![United Airlines logo]()
$143
This Super.com deal was found by Cheapflights users on 5/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/293:35 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Wed 7/16:24 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 5/12![Sun Country Air logo]()
$146
This Delta deal was found by Cheapflights users on 5/13. 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 10/277:00 am
MSP
- MDW
Nonstop1h 49m
Delta
Mon 11/212:30 pm
MDW
- MSP
Nonstop1h 39m
Delta
Deal found 5/13![Delta logo]()
$147
This Delta deal was found by Cheapflights users on 5/13. 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 6/93:20 pm
MSP
- ORD
Nonstop1h 42m
Delta
Mon 6/158:21 pm
ORD
- MSP
Nonstop1h 47m
Delta
Deal found 5/13![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 5/13. 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 6/37:50 am
MSP
- MDW
1 stop7h 05m
Southwest
Tue 6/92:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/13![Southwest logo]()
$148
This Cheapflightsfares deal was found by Cheapflights users on 5/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:35 am
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Sun 11/17:30 am
ORD
- MSP
Nonstop1h 41m
Sun Country Air
Deal found 5/13![Sun Country Air logo]()
$148
This American Airlines deal was found by Cheapflights users on 5/12. 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 9/96:03 pm
MSP
- ORD
Nonstop1h 42m
American Airlines
Thu 9/106:40 am
ORD
- MSP
Nonstop1h 34m
American Airlines
Deal found 5/12![American Airlines logo]()
$150
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/24:38 pm
MSP
- MDW
Nonstop1h 40m
Delta
Tue 7/79:49 am
MDW
- MSP
Nonstop1h 43m
Delta
Deal found 5/12![Delta logo]()
$152
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 May 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 May 17, 2026.
This Southwest deal was found by Cheapflights users on 5/13. 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 6/45:40 pm
MSP
- MDW
1 stop5h 20m
Southwest
Tue 6/99:20 pm
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 5/13![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 5/13. 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.
Wed 6/35:38 pm
MSP
- ORD
Nonstop1h 42m
Delta
Tue 6/92:07 pm
ORD
- MSP
1 stop5h 01m
Delta
Deal found 5/13![Delta logo]()
$192
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Thu 6/1110:00 am
MKE
- ORD
Nonstop1h 12m
American Airlines
Sun 6/148:00 pm
ORD
- MKE
Nonstop1h 05m
American Airlines
Deal found 5/12![American Airlines logo]()
$219
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Tue 8/1110:45 am
MKE
- ORD
Nonstop1h 11m
United Airlines
Fri 8/213:00 pm
ORD
- MKE
Nonstop1h 10m
United Airlines
Deal found 5/13![United Airlines logo]()
$278
This Southwest deal was found by Cheapflights users on 5/16. 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.
Wed 8/56:15 am
MSP
- MDW
Nonstop1h 25m
Southwest
Sat 8/88:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 5/16![Southwest logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 5/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/174:40 pm
MSP
- RFD
1 stop15h 49m
Multiple Airlines
Sun 6/219:19 am
RFD
- MSP
1 stop9h 38m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 5/14. 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 6/61:40 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Mon 6/89:50 pm
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 5/14![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 5/14. 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 6/61:40 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Sat 6/68:30 pm
MDW
- MSP
Nonstop1h 35m
Southwest
Deal found 5/14![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 5/16. 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 7/49:00 am
MSP
- ORD
1 stop4h 04m
Delta
Tue 7/76:30 am
ORD
- MSP
Nonstop1h 34m
Delta
Deal found 5/16![Delta logo]()
$216
This American Airlines deal was found by Cheapflights users on 5/12. 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 6/106:54 pm
GRB
- ORD
Nonstop1h 36m
American Airlines
Sat 6/1311:00 pm
ORD
- GRB
Nonstop1h 10m
American Airlines
Deal found 5/12![American Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:10 am
MSP
- MDW
1 stop6h 32m
Delta
Sat 6/67:13 pm
MDW
- MSP
Nonstop1h 42m
Delta
Deal found 5/13![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 5/16. 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.
Thu 8/277:40 am
MSP
- MDW
Nonstop1h 30m
Southwest
Sat 8/299:55 am
MDW
- MSP
1 stop6h 15m
Southwest
Deal found 5/16![Southwest logo]()
$187
This American Airlines deal was found by Cheapflights users on 5/16. 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.
Mon 6/156:04 am
GRB
- ORD
Nonstop1h 26m
American Airlines
Sun 6/2111:00 pm
ORD
- GRB
Nonstop1h 10m
American Airlines
Deal found 5/16![American Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 5/14. 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 7/276:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Thu 7/309:19 am
MDW
- MSP
1 stop3h 51m
Delta
Deal found 5/14![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 5/14. 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 6/47:45 am
MSP
- MDW
1 stop6h 00m
Southwest
Mon 6/89:50 pm
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 5/14![Southwest logo]()
$187
This American Airlines deal was found by Cheapflights users on 5/12. 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 7/291:01 pm
GRB
- ORD
Nonstop1h 20m
American Airlines
Fri 8/711:05 pm
ORD
- GRB
Nonstop1h 11m
American Airlines
Deal found 5/12![American Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:55 am
MSP
- ORD
1 stop4h 01m
Delta
Sat 6/1312:46 pm
ORD
- MSP
Nonstop1h 51m
Delta
Deal found 5/13![Delta logo]()
$222
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Tue 6/210:38 am
MKE
- ORD
Nonstop1h 10m
United Airlines
Wed 6/36:29 pm
ORD
- MKE
Nonstop1h 11m
United Airlines
Deal found 5/13![United Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Sat 6/209:43 am
MSN
- ORD
Nonstop1h 17m
American Airlines
Tue 6/2310:05 pm
ORD
- MSN
Nonstop1h 10m
American Airlines
Deal found 5/12![American Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 5/14. 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 7/273:20 pm
MSP
- ORD
Nonstop1h 39m
Delta
Thu 7/308:52 am
ORD
- MSP
1 stop4h 18m
Delta
Deal found 5/14![Delta logo]()
$222
This United Airlines deal was found by Cheapflights users on 5/15. 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 10/246:30 pm
MSN
- ORD
Nonstop1h 20m
United Airlines
Tue 10/277:40 am
ORD
- MSN
Nonstop1h 13m
United Airlines
Deal found 5/15![United Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 5/13. 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 6/48:22 am
MSN
- ORD
Nonstop1h 23m
American Airlines
Sun 6/76:40 am
ORD
- MSN
Nonstop1h 05m
American Airlines
Deal found 5/13![American Airlines logo]()
$240
This Southwest deal was found by Cheapflights users on 5/15. 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 7/217:05 am
MSP
- MDW
2 stops6h 30m
Southwest
Wed 7/225:10 pm
MDW
- MSP
1 stop5h 35m
Southwest
Deal found 5/15![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 5/16. 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.
Sun 6/286:04 am
MSP
- ORD
1 stop4h 46m
Delta
Wed 7/16:30 am
ORD
- MSP
Nonstop1h 36m
Delta
Deal found 5/16![Delta logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 5/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:30 pm
MSP
- RFD
1 stop13h 29m
Multiple Airlines
Wed 10/289:34 am
RFD
- MSP
1 stop11h 39m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$386
This United Airlines deal was found by Cheapflights users on 5/15. 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 5/307:03 am
DLH
- ORD
Nonstop1h 54m
United Airlines
Sat 6/139:30 pm
ORD
- DLH
Nonstop1h 53m
United Airlines
Deal found 5/15![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 5/16. 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.
Wed 6/1011:30 am
MSP
- MDW
Nonstop1h 39m
Delta
Sat 6/136:55 pm
MDW
- MSP
Nonstop1h 46m
Delta
Deal found 5/16![Delta logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 5/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:55 pm
MSP
- RFD
1 stop16h 57m
Multiple Airlines
Sun 9/133:53 pm
RFD
- MSP
1 stop5h 56m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$389
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 7/12:40 pm
ATW
- ORD
Nonstop1h 20m
United Airlines
Sun 7/58:45 am
ORD
- ATW
Nonstop1h 16m
United Airlines
Deal found 5/13![United Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 5/13. 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.
Fri 7/105:00 am
MSP
- MDW
Nonstop1h 30m
Southwest
Sat 7/118:30 pm
MDW
- MSP
Nonstop1h 35m
Southwest
Deal found 5/13![Southwest logo]()
$246
Last-minute flights from Wisconsin to ChicagoDiscover last-minute flight deals from Wisconsin to Chicago. Data last updated May 17, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Chicago. Data last updated May 17, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:50 am
MSP
- MDW
1 stop7h 05m
Southwest
Tue 6/24:40 pm
MDW
- MSP
1 stop5h 50m
Southwest
Deal found 5/12![Southwest logo]()
$142
This Southwest deal was found by Cheapflights users on 5/13. 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 6/37:50 am
MSP
- MDW
1 stop7h 05m
Southwest
Tue 6/92:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/13![Southwest logo]()
$148
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/311:40 am
MSP
- MDW
Nonstop1h 39m
Delta
Mon 6/81:49 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 5/12![Delta logo]()
$152
This Super.com deal was found by Cheapflights users on 5/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/43:35 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Mon 6/87:09 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 5/14![Sun Country Air logo]()
$156
This Southwest deal was found by Cheapflights users on 5/12. 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 6/61:40 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Tue 6/99:20 pm
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 5/12![Southwest logo]()
$147
This Delta deal was found by Cheapflights users on 5/16. 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.
Tue 6/96:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Tue 6/161:49 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 5/16![Delta logo]()
$137
This Delta deal was found by Cheapflights users on 5/16. 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.
Tue 6/93:20 pm
MSP
- ORD
Nonstop1h 42m
Delta
Tue 6/166:30 am
ORD
- MSP
Nonstop1h 36m
Delta
Deal found 5/16![Delta logo]()
$137
This Delta deal was found by Cheapflights users on 5/13. 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 6/93:20 pm
MSP
- ORD
Nonstop1h 42m
Delta
Mon 6/158:21 pm
ORD
- MSP
Nonstop1h 47m
Delta
Deal found 5/13![Delta logo]()
$147
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/187:00 am
MSP
- ORD
Nonstop1h 35m
Delta
Tue 6/233:55 pm
ORD
- MSP
Nonstop1h 45m
Delta
Deal found 5/12![Delta logo]()
$152
This Southwest deal was found by Cheapflights users on 5/15. 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 6/236:40 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Wed 6/242:35 pm
MDW
- MSP
1 stop8h 10m
Southwest
Deal found 5/15![Southwest logo]()
$153
This Super.com deal was found by Cheapflights users on 5/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/293:35 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Wed 7/16:24 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 5/12![Sun Country Air logo]()
$146
This Cheapflightsfares deal was found by Cheapflights users on 5/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/293:35 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Fri 7/36:19 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 5/16![Sun Country Air logo]()
$148
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 May 17, 2026.
Search for one-way flight options from Wisconsin to Chicago. Find affordable one-way fares based on user searches. Data last updated May 17, 2026.
This Trip.com deal was found by Cheapflights users on 5/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/113:05 pm
MSP
- ORD
Nonstop1h 39m
Sun Country Air
Deal found 5/12![Sun Country Air logo]()
$83
This Southwest deal was found by Cheapflights users on 5/15. 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.
Wed 6/107:55 am
MSP
- MDW
1 stop9h 10m
Southwest
Deal found 5/15![Southwest logo]()
$84
This KAYAK deal was found by Cheapflights users on 5/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/34:20 pm
MSP
- MDW
Nonstop1h 36m
Delta
Deal found 5/13![Delta logo]()
$86
This Super.com deal was found by Cheapflights users on 5/13. 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.
Thu 6/255:55 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Deal found 5/13![Sun Country Air logo]()
$88
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/136:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Deal found 5/13![Delta logo]()
$89
This Delta deal was found by Cheapflights users on 5/14. 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.
Sat 8/810:05 am
MSP
- ORD
Nonstop1h 32m
Delta
Deal found 5/14![Delta logo]()
$89
This KAYAK deal was found by Cheapflights users on 5/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/93:20 pm
MSP
- ORD
Nonstop1h 42m
Delta
Deal found 5/14![Delta logo]()
$90
This Southwest deal was found by Cheapflights users on 5/12. 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.
Mon 7/277:15 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Deal found 5/12![Southwest logo]()
$94
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/208:15 pm
MSP
- ORD
Nonstop1h 37m
Delta
Deal found 5/12![Delta logo]()
$94
This Frontier deal was found by Cheapflights users on 5/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:24 pm
MSP
- MDW
1 stop7h 44m
Frontier
Deal found 5/13![Frontier logo]()
$95
This Frontier deal was found by Cheapflights users on 5/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:57 pm
MSP
- ORD
1 stop6h 27m
Frontier
Deal found 5/12![Frontier logo]()
$95
This Trip.com deal was found by Cheapflights users on 5/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/82:24 pm
MSP
- MDW
1 stop7h 44m
Frontier
Deal found 5/13![Frontier logo]()
$96
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 May 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $137 (Southwest) |
One-way from | $83 (Trip.com) |
Good round-trip deal | $344 or less |
Good one-way deal | $194 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 May 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
Thu 6/4
5:40 pm-11:00 pm
1 stop5h 20m
Chicago Midway
Tue 6/9
9:20 pm-10:45 pm
Nonstop1h 25m
$157
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Wed 8/5
6:15 am-7:40 am
Nonstop1h 25m
Chicago Midway
Sat 8/8
8:00 am-9:45 am
Nonstop1h 45m
$157
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 6/6
1:40 pm-3:10 pm
Nonstop1h 30m
Chicago Midway
Mon 6/8
9:50 pm-11:15 pm
Nonstop1h 25m
$177
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 6/6
1:40 pm-3:10 pm
Nonstop1h 30m
Chicago Midway
Sat 6/6
8:30 pm-10:05 pm
Nonstop1h 35m
$177
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Thu 8/27
7:40 am-9:10 am
Nonstop1h 30m
Chicago Midway
Sat 8/29
9:55 am-4:10 pm
1 stop6h 15m
$187
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Thu 6/4
7:45 am-1:45 pm
1 stop6h 00m
Chicago Midway
Mon 6/8
9:50 pm-11:15 pm
Nonstop1h 25m
$187
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Wed 6/3
5:38 pm-7:20 pm
Nonstop1h 42m
Chicago O'Hare Intl
Tue 6/9
2:07 pm-7:08 pm
1 stop5h 01m
$192
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Sat 7/4
9:00 am-1:04 pm
1 stop4h 04m
Chicago O'Hare Intl
Tue 7/7
6:30 am-8:04 am
Nonstop1h 34m
$216
Quickest round-trip
MilwaukeeChicago
MKE - ORD
MKEORD
Milwaukee-Mitchell
Thu 6/11
10:00 am-11:12 am
Nonstop1h 12m
Chicago O'Hare Intl
Sun 6/14
8:00 pm-9:05 pm
Nonstop1h 05m
$219
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 6/6
6:10 am-12:42 pm
1 stop6h 32m
Chicago Midway
Sat 6/6
7:13 pm-8:55 pm
Nonstop1h 42m
$222
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
GRB-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, 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 January is currently the most expensive (average of $179). 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 May 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 42% on airfare.
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 May 9, 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.
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 May 17, 2026.
The most flights from USWI to CHI are scheduled on a Saturday (66 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 on average).
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
Hammond
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
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
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 May 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 May 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 May 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$168 | Average$275 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$251 | FlexibilityNo cancel fee | On-time69% |