$59+ Cheap flights from Chicago (CHI) to Wisconsin
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Oct 17 — Oct 241
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Wisconsin with Cheapflights
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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
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Cheapest flights from Chicago to WisconsinExplore the most affordable flight options available from Chicago to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
Explore the most affordable flight options available from Chicago to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
This Sun Country Air deal was found by Cheapflights users on 9/13. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2311:05 am -
Nonstop1h 46m
Mon 12/285:00 pm -
Nonstop1h 40m
Deal found 9/13![Sun Country Air logo]()
$118
This lastminute.com deal was found by Cheapflights users on 9/15. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:18 pm -
Nonstop1h 40m
Sun 11/13:35 pm -
Nonstop1h 35m
Deal found 9/15![Sun Country Air logo]()
$119
This Sun Country Air deal was found by Cheapflights users on 9/16. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2311:05 am -
Nonstop1h 46m
Fri 12/255:05 pm -
Nonstop1h 40m
Deal found 9/16![Sun Country Air logo]()
$128
This Sun Country Air deal was found by Cheapflights users on 9/16. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2511:25 am -
Nonstop1h 46m
Fri 12/255:05 pm -
Nonstop1h 40m
Deal found 9/16![Sun Country Air logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/1711:45 am -
Nonstop1h 46m
Sun 1/35:10 pm -
Nonstop1h 40m
Deal found 9/15![Sun Country Air logo]()
$134
This FlightHub deal was found by Cheapflights users on 9/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:30 am -
1 stop7h 07m
Sat 11/73:00 pm -
Nonstop1h 35m
Deal found 9/14![Multiple Airlines logo]()
$135
This FlightHub deal was found by Cheapflights users on 9/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:40 pm -
Nonstop1h 41m
Sat 11/142:33 pm -
1 stop9h 48m
Deal found 9/15![Multiple Airlines logo]()
$136
This Sun Country Air deal was found by Cheapflights users on 9/15. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:18 pm -
Nonstop1h 40m
Fri 10/3010:45 am -
Nonstop1h 38m
Deal found 9/15![Sun Country Air logo]()
$138
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:25 pm -
Nonstop1h 36m
Tue 10/202:36 pm -
1 stop9h 48m
Deal found 9/15![Multiple Airlines logo]()
$140
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:30 am -
1 stop17h 36m
Sat 10/242:36 pm -
1 stop9h 48m
Deal found 9/15![Frontier logo]()
$141
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 10/145:59 am -
Nonstop1h 08m
Wed 10/212:20 pm -
Nonstop1h 11m
Deal found 9/16![United Airlines logo]()
$161
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/105:59 am -
Nonstop1h 08m
Mon 10/126:32 pm -
Nonstop1h 13m
Deal found 9/15![United Airlines logo]()
$172
Best flights from Chicago to WisconsinDiscover carefully curated flight deals from Chicago to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
Discover carefully curated flight deals from Chicago to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
This Sun Country Air deal was found by Cheapflights users on 9/13. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2311:05 am -
Nonstop1h 46m
Wed 12/308:55 am -
Nonstop1h 48m
Deal found 9/13![Sun Country Air logo]()
$118
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/105:59 am -
Nonstop1h 08m
Mon 10/126:32 pm -
Nonstop1h 13m
Deal found 9/15![United Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 9/16. 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 10/2810:12 am -
Nonstop1h 41m
Tue 11/33:08 pm -
Nonstop1h 39m
Deal found 9/16![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/132:45 pm -
2 stops8h 05m
Tue 10/204:20 pm -
1 stop5h 40m
Deal found 9/13![Southwest logo]()
$233
This American Airlines deal was found by Cheapflights users on 9/12. 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 10/1010:04 am -
Nonstop1h 07m
Sat 10/177:19 pm -
Nonstop1h 30m
Deal found 9/12![American Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 10/1610:00 pm -
Nonstop1h 32m
Mon 10/195:00 am -
Nonstop1h 29m
Deal found 9/14![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 10/1310:00 pm -
Nonstop1h 32m
Wed 10/142:35 pm -
Nonstop1h 30m
Deal found 9/15![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 11/1311:59 am -
Nonstop1h 28m
Mon 11/162:26 pm -
Nonstop1h 39m
Deal found 9/13![United Airlines logo]()
$180
This Delta deal was found by Cheapflights users on 9/16. 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 1/912:15 pm -
Nonstop1h 30m
Mon 1/118:05 pm -
Nonstop1h 32m
Deal found 9/16![Delta logo]()
$221
This Southwest deal was found by Cheapflights users on 9/15. 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.
Thu 11/510:05 pm -
Nonstop1h 35m
Mon 11/912:25 pm -
Nonstop1h 30m
Deal found 9/15![Southwest logo]()
$235
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 11/610:10 pm -
Nonstop1h 21m
Sun 11/82:26 pm -
Nonstop1h 39m
Deal found 9/13![United Airlines logo]()
$180
This Delta deal was found by Cheapflights users on 9/16. 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 10/209:59 am -
Nonstop1h 40m
Thu 10/227:50 pm -
Nonstop1h 37m
Deal found 9/16![Delta logo]()
$221
This American Airlines deal was found by Cheapflights users on 9/12. 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 10/35:19 pm -
Nonstop1h 02m
Sun 10/41:18 pm -
Nonstop1h 21m
Deal found 9/12![American Airlines logo]()
$250
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 12/112:29 pm -
Nonstop1h 03m
Fri 1/17:00 pm -
Nonstop1h 21m
Deal found 9/15![United Airlines logo]()
$183
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 10/1310:25 am -
Nonstop1h 05m
Fri 10/168:30 am -
Nonstop1h 11m
Deal found 9/16![United Airlines logo]()
$183
This Southwest deal was found by Cheapflights users on 9/15. 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.
Thu 10/292:45 pm -
1 stop8h 40m
Mon 11/27:55 am -
2 stops9h 50m
Deal found 9/15![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/268:33 pm -
Nonstop1h 44m
Fri 10/303:02 pm -
Nonstop1h 38m
Deal found 9/16![Delta logo]()
$250
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:10 am -
Nonstop1h 12m
Thu 10/228:04 pm -
Nonstop1h 25m
Deal found 9/14![American Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/810:00 pm -
Nonstop0h 59m
Mon 10/127:18 am -
Nonstop1h 11m
Deal found 9/16![United Airlines logo]()
$183
This Southwest deal was found by Cheapflights users on 9/15. 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 10/207:55 am -
Nonstop1h 25m
Thu 10/227:00 pm -
Nonstop1h 30m
Deal found 9/15![Southwest logo]()
$286
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 10/2310:00 pm -
Nonstop1h 12m
Sun 10/255:00 am -
Nonstop1h 14m
Deal found 9/17![American Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 9/17. 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.
Thu 10/810:12 am -
Nonstop1h 41m
Tue 10/137:00 am -
Nonstop1h 44m
Deal found 9/17![Delta logo]()
$271
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 10/166:59 am -
Nonstop1h 12m
Sun 11/17:19 am -
Nonstop1h 31m
Deal found 9/13![American Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Fri 2/129:30 pm -
Nonstop1h 22m
Tue 2/165:30 am -
Nonstop1h 35m
Deal found 9/16![United Airlines logo]()
$200
This Delta deal was found by Cheapflights users on 9/17. 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.
Thu 10/88:33 pm -
Nonstop1h 46m
Tue 10/136:00 am -
1 stop6h 59m
Deal found 9/17![Delta logo]()
$281
This Southwest deal was found by Cheapflights users on 9/15. 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.
Thu 12/103:50 pm -
1 stop6h 00m
Sun 12/137:55 am -
1 stop7h 20m
Deal found 9/15![Southwest logo]()
$320
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Fri 10/3010:10 pm -
Nonstop1h 21m
Mon 11/25:05 am -
Nonstop1h 38m
Deal found 9/16![United Airlines logo]()
$200
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 9/3011:00 pm -
Nonstop1h 13m
Sun 10/48:27 pm -
Nonstop1h 33m
Deal found 9/15![American Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 9/12. 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.
Fri 12/48:50 pm -
Nonstop1h 30m
Sun 12/66:35 pm -
Nonstop1h 35m
Deal found 9/12![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 10/910:00 pm -
Nonstop1h 32m
Sun 10/112:35 pm -
Nonstop1h 30m
Deal found 9/15![United Airlines logo]()
$200
Last-minute flights from Chicago to WisconsinDiscover last-minute flight deals from Chicago to Wisconsin. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Wisconsin. Data last updated September 17, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/105:59 am -
Nonstop1h 08m
Mon 10/126:32 pm -
Nonstop1h 13m
Deal found 9/15![United Airlines logo]()
$172
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/109:34 pm -
Nonstop1h 08m
Mon 10/125:00 am -
Nonstop1h 13m
Deal found 9/15![American Airlines logo]()
$173
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:25 pm -
Nonstop1h 36m
Tue 10/202:36 pm -
1 stop9h 48m
Deal found 9/15![Multiple Airlines logo]()
$140
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 10/1310:00 pm -
Nonstop1h 32m
Wed 10/142:35 pm -
Nonstop1h 30m
Deal found 9/16![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 10/145:59 am -
Nonstop1h 08m
Wed 10/212:20 pm -
Nonstop1h 11m
Deal found 9/16![United Airlines logo]()
$161
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:30 am -
1 stop17h 36m
Sat 10/242:36 pm -
1 stop9h 48m
Deal found 9/15![Frontier logo]()
$141
This FlightHub deal was found by Cheapflights users on 9/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:45 pm -
Nonstop1h 40m
Sat 10/242:36 pm -
1 stop9h 48m
Deal found 9/15![Multiple Airlines logo]()
$146
This lastminute.com deal was found by Cheapflights users on 9/15. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:18 pm -
Nonstop1h 40m
Sun 11/13:35 pm -
Nonstop1h 35m
Deal found 9/15![Sun Country Air logo]()
$119
This Sun Country Air deal was found by Cheapflights users on 9/15. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:18 pm -
Nonstop1h 40m
Fri 10/3010:45 am -
Nonstop1h 38m
Deal found 9/15![Sun Country Air logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/297:18 pm -
Nonstop1h 40m
Sat 10/312:33 pm -
1 stop9h 48m
Deal found 9/15![Multiple Airlines logo]()
$145
This Orbitz deal was found by Cheapflights users on 9/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:30 am -
1 stop17h 34m
Sat 11/73:00 pm -
Nonstop1h 35m
Deal found 9/16![Multiple Airlines logo]()
$142
This Expedia deal was found by Cheapflights users on 9/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:30 am -
1 stop17h 34m
Sun 11/89:00 am -
Nonstop1h 41m
Deal found 9/16![Multiple Airlines logo]()
$150
One-way flights from Chicago to WisconsinSearch for one-way flight options from Chicago to Wisconsin. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
Search for one-way flight options from Chicago to Wisconsin. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Sun Country Air deal was found by Cheapflights users on 9/14. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:40 pm -
Nonstop1h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Sun Country Air logo]()
$59
This Jetabroad deal was found by Cheapflights users on 9/12. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1711:45 am -
Nonstop1h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Sun Country Air logo]()
$61
This Sun Country Air deal was found by Cheapflights users on 9/13. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:26 pm -
Nonstop1h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Sun Country Air logo]()
$69
This Super.com deal was found by Cheapflights users on 9/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:30 am -
1 stop7h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$70
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:30 am -
1 stop7h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$71
This eDestinos deal was found by Cheapflights users on 9/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2711:00 am -
Nonstop1h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Sun Country Air logo]()
$72
This Priceline deal was found by Cheapflights users on 9/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:39 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Sun Country Air logo]()
$74
This Expedia deal was found by Cheapflights users on 9/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:30 am -
1 stop17h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$76
This Super.com deal was found by Cheapflights users on 9/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:30 am -
1 stop17h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$77
This Expedia deal was found by Cheapflights users on 9/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:30 am -
1 stop17h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$78
This United Airlines deal was found by Cheapflights users on 9/15. 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 11/144:40 pm -
Nonstop1h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![United Airlines logo]()
$81
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/1310:00 pm -
Nonstop1h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![United Airlines logo]()
$88
Find flight deals from Chicago to Wisconsin
Keep the following information in mind while searching for Chicago to Wisconsin flight deals. Data was last updated September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $119 (lastminute.com) |
One-way from | $59 (Sun Country Air) |
Popular in | May |
Cheapest in | February |
Average price | $289 |
Good round-trip deal | $308 or less |
Good one-way deal | $88 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Wisconsin 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 7,457,451 searches. Data last updated September 17, 2026.
Use the filters below to find and compare flights from Chicago to Wisconsin that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMinneapolis
ORD Chicago O'Hare Intl - MSP Minneapolis St Paul
ORDMSP
Chicago O'Hare Intl
Thu 10/29
7:18 pm-8:58 pm
Nonstop1h 40m
Minneapolis St Paul
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$59
ChicagoMinneapolis
ORD Chicago O'Hare Intl - MSP Minneapolis St Paul
ORDMSP
Chicago O'Hare Intl
Tue 12/22
11:25 am-1:11 pm
Nonstop1h 46m
Minneapolis St Paul
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$59
ChicagoMinneapolis
ORD Chicago O'Hare Intl - MSP Minneapolis St Paul
ORDMSP
Chicago O'Hare Intl
Fri 12/11
11:48 am-1:29 pm
Nonstop1h 41m
Minneapolis St Paul
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$79
ChicagoMinneapolis
ORD Chicago O'Hare Intl - MSP Minneapolis St Paul
ORDMSP
Chicago O'Hare Intl
Fri 10/9
6:39 pm-8:29 pm
Nonstop1h 50m
Minneapolis St Paul
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$79
ChicagoEau Claire
ORD Chicago O'Hare Intl - EAU Eau Claire
ORDEAU
Chicago O'Hare Intl
Tue 10/13
10:00 pm-11:32 pm
Nonstop1h 32m
Eau Claire
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$88
ChicagoEau Claire
ORD Chicago O'Hare Intl - EAU Eau Claire
ORDEAU
Chicago O'Hare Intl
Mon 10/26
10:10 pm-11:31 pm
Nonstop1h 21m
Eau Claire
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$88
ChicagoEau Claire
ORD Chicago O'Hare Intl - EAU Eau Claire
ORDEAU
Chicago O'Hare Intl
Fri 10/30
10:10 pm-11:31 pm
Nonstop1h 21m
Eau Claire
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$88
ChicagoEau Claire
ORD Chicago O'Hare Intl - EAU Eau Claire
ORDEAU
Chicago O'Hare Intl
Sat 10/24
10:00 pm-11:32 pm
Nonstop1h 32m
Eau Claire
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$88
Quickest round-trip
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Mon 12/14
6:29 am-7:35 am
Nonstop1h 06m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$92
ChicagoEau Claire
ORD Chicago O'Hare Intl - EAU Eau Claire
ORDEAU
Chicago O'Hare Intl
Thu 10/29
11:59 am-1:27 pm
Nonstop1h 28m
Eau Claire
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$94
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Chicago with our price prediction graph.
ORD-MSP
ORD-MKE
ORD-EAU
MDW-MSP
ORD-GRB
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 Chicago to Wisconsin
CHI-USWI
ORD-MSP
ORD-MKE
ORD-EAU
MDW-MSP
What is the cheapest month to book a flight from Chicago to Wisconsin?
Currently, January is the cheapest month in which you can book a flight from Chicago to Wisconsin (average of $194). Flying from Chicago to Wisconsin in April is currently the most expensive (average of $524). 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 CHI to WI?
Find hourly flight availability from Chicago to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2026.
One of the essential ways to save on airfare from Chicago to Wisconsin is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 29% on airfare.
Weekly flight availability from Chicago to Wisconsin
Explore weekly flight availability from Chicago to Wisconsin. 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 September 17, 2026.
The most flights from CHI to USWI are scheduled on a Monday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 on average).
What is the cheapest day to fly from Chicago to Wisconsin?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Wisconsin. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Chicago to Wisconsin flight should consider departing on Thursday at noon when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Wisconsin
Get insights into the airlines that provide service to Wisconsin. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Wisconsin. Reviews last updated September 17, 2026.
See what other customers who have flown with United Airlines and American Airlines from Chicago to Wisconsin have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.1
Overall
7.4
Comfort
7.3
Boarding
7.7
Food
6.7
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Entertainment
7.1
Overall
7.4
Comfort
7.3
Boarding
7.7
Food
6.7
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Entertainment
7.1
Overall
7.4
Comfort
7.3
Boarding
7.7
Food
6.7
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Wisconsin
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Complete your trip
Complete your trip to Wisconsin by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Wisconsin by cabin class
Find flights from Chicago to Wisconsin, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Wisconsin flights
Browse other Chicago and Wisconsin flight options. Last updated on September 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Wisconsin flights
Consider these flights traveling from Chicago to Wisconsin.
Top 2 airlines flying from Chicago to Wisconsin
Discover the top 2 airlines that operate flights from Chicago to Wisconsin. 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 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$344 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$391 | FlexibilityNo cancel fee | On-time69% |