$93+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Nov 29 — Dec 61
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 October 30, 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 October 30, 2026.
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/1911:59 am -
Nonstop1h 28m
Sun 11/225:05 am -
Nonstop1h 38m
Deal found 10/27![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/197:30 am -
Nonstop1h 06m
Mon 11/232:23 pm -
Nonstop1h 12m
Deal found 10/27![United Airlines logo]()
$185
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/1910:10 am -
Nonstop0h 50m
Mon 11/235:30 am -
Nonstop1h 05m
Deal found 10/29![Southwest logo]()
$185
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/196:56 pm -
Nonstop1h 04m
Mon 11/238:48 am -
Nonstop1h 27m
Deal found 10/28![American Airlines logo]()
$186
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/2411:59 am -
Nonstop1h 28m
Tue 12/15:51 am -
Nonstop1h 39m
Deal found 10/28![United Airlines logo]()
$200
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/46:29 am -
Nonstop1h 06m
Mon 12/72:38 pm -
Nonstop1h 12m
Deal found 10/27![United Airlines logo]()
$204
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/279:20 pm -
Nonstop0h 55m
Fri 12/47:18 pm -
Nonstop1h 12m
Deal found 10/29![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/279:15 pm -
Nonstop1h 00m
Fri 12/44:20 pm -
Nonstop0h 55m
Deal found 10/29![Southwest logo]()
$209
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/146:44 pm -
Nonstop1h 16m
Mon 12/212:09 pm -
Nonstop1h 21m
Deal found 10/29![American Airlines logo]()
$210
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/265:40 am -
1 stop5h 15m
Thu 12/38:00 am -
1 stop7h 30m
Deal found 10/29![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/119:15 pm -
Nonstop1h 00m
Fri 12/185:45 am -
Nonstop1h 00m
Deal found 10/27![Southwest logo]()
$223
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/257:30 am -
Nonstop1h 06m
Sat 11/289:20 am -
Nonstop1h 10m
Deal found 10/26![United Airlines logo]()
$227
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 October 30, 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 October 30, 2026.
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 1/811:29 am -
Nonstop1h 39m
Mon 1/115:15 am -
Nonstop1h 44m
Deal found 10/25![United Airlines logo]()
$180
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/1910:10 am -
Nonstop0h 50m
Mon 11/234:50 pm -
Nonstop0h 50m
Deal found 10/28![Southwest logo]()
$185
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/135:42 pm -
1 stop3h 10m
Tue 11/1712:25 pm -
1 stop4h 16m
Deal found 10/29![Delta logo]()
$265
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/2411:00 pm -
Nonstop1h 20m
Fri 11/276:39 am -
Nonstop1h 41m
Deal found 10/28![American Airlines logo]()
$271
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/2411:59 am -
Nonstop1h 28m
Tue 12/15:51 am -
Nonstop1h 39m
Deal found 10/25![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/1910:25 am -
Nonstop1h 03m
Mon 11/238:00 am -
Nonstop1h 12m
Deal found 10/27![United Airlines logo]()
$185
This deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Mon 1/1111:29 am -
Nonstop1h 39m
Wed 1/132:20 pm -
Nonstop1h 37m
Deal found 10/27![United Airlines logo]()
$200
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/196:23 am -
1 stop5h 21m
Sun 11/2212:25 pm -
1 stop4h 16m
Deal found 10/25![Delta logo]()
$265
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 1/711:29 am -
Nonstop1h 39m
Mon 1/115:15 am -
Nonstop1h 44m
Deal found 10/29![United Airlines logo]()
$200
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/116:44 pm -
Nonstop1h 16m
Fri 12/185:00 am -
Nonstop1h 26m
Deal found 10/27![American Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/215:42 pm -
1 stop3h 10m
Sun 11/2212:25 pm -
1 stop4h 16m
Deal found 10/26![Delta logo]()
$265
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/46:29 am -
Nonstop1h 06m
Mon 12/72:38 pm -
Nonstop1h 12m
Deal found 10/27![United Airlines logo]()
$204
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/254:50 pm -
Nonstop1h 30m
Sun 11/296:50 pm -
Nonstop1h 37m
Deal found 10/27![American Airlines logo]()
$285
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/279:20 pm -
Nonstop0h 55m
Fri 12/47:18 pm -
Nonstop1h 12m
Deal found 10/29![United Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/254:50 pm -
Nonstop1h 30m
Mon 11/3012:26 pm -
Nonstop1h 27m
Deal found 10/27![American Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/215:42 pm -
1 stop3h 18m
Sun 11/2212:54 pm -
1 stop3h 47m
Deal found 10/26![Delta logo]()
$301
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/2410:30 am -
Nonstop1h 26m
Sat 11/286:50 pm -
Nonstop1h 37m
Deal found 10/26![American Airlines logo]()
$285
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 2/28:45 am -
Nonstop1h 15m
Sat 2/610:35 am -
Nonstop1h 20m
Deal found 10/26![United Airlines logo]()
$223
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/196:23 am -
1 stop5h 19m
Sun 11/227:00 am -
1 stop3h 39m
Deal found 10/26![Delta logo]()
$329
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/257:30 am -
Nonstop1h 06m
Sat 11/289:20 am -
Nonstop1h 10m
Deal found 10/26![United Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/118:12 am -
Nonstop1h 18m
Sun 12/137:36 pm -
Nonstop1h 39m
Deal found 10/28![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 1/212:33 pm -
1 stop5h 00m
Mon 1/411:14 am -
1 stop5h 13m
Deal found 10/29![Delta logo]()
$329
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/1310:10 pm -
Nonstop1h 21m
Fri 11/202:26 pm -
Nonstop1h 39m
Deal found 10/25![United Airlines logo]()
$230
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/195:06 pm -
Nonstop1h 16m
Sun 11/226:53 pm -
Nonstop1h 37m
Deal found 10/29![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 1/151:45 pm -
1 stop6h 53m
Mon 1/186:32 am -
1 stop6h 32m
Deal found 10/30![Delta logo]()
$329
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 1/1511:05 pm -
Nonstop1h 23m
Mon 1/185:25 am -
Nonstop1h 34m
Deal found 10/30![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 1/211:47 am -
1 stop5h 46m
Mon 1/46:00 am -
1 stop6h 04m
Deal found 10/29![Delta logo]()
$329
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Sun 12/2012:30 pm -
Nonstop1h 19m
Mon 12/212:19 pm -
Nonstop1h 23m
Deal found 10/26![American Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/229:20 pm -
Nonstop0h 55m
Sun 11/296:47 am -
Nonstop1h 12m
Deal found 10/25![United Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/166:55 am -
Nonstop1h 15m
Wed 11/2510:54 am -
Nonstop1h 40m
Deal found 10/26![American Airlines logo]()
$309
Last-minute flights from Chicago to WisconsinDiscover last-minute flight deals from Chicago to Wisconsin. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Wisconsin. Data last updated October 30, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/1310:10 pm -
Nonstop1h 21m
Fri 11/202:26 pm -
Nonstop1h 39m
Deal found 10/25![United Airlines logo]()
$230
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/1911:59 am -
Nonstop1h 28m
Sun 11/225:05 am -
Nonstop1h 38m
Deal found 10/27![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/197:30 am -
Nonstop1h 06m
Mon 11/232:23 pm -
Nonstop1h 12m
Deal found 10/27![United Airlines logo]()
$185
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/1910:10 am -
Nonstop0h 50m
Mon 11/234:50 pm -
Nonstop0h 50m
Deal found 10/28![Southwest logo]()
$185
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/196:56 pm -
Nonstop1h 04m
Mon 11/238:48 am -
Nonstop1h 27m
Deal found 10/28![American Airlines logo]()
$186
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/234:00 pm -
Nonstop1h 03m
Mon 11/308:35 am -
Nonstop1h 10m
Deal found 10/25![United Airlines logo]()
$246
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/2411:59 am -
Nonstop1h 28m
Tue 12/15:51 am -
Nonstop1h 39m
Deal found 10/28![United Airlines logo]()
$200
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/257:30 am -
Nonstop1h 06m
Sat 11/289:20 am -
Nonstop1h 10m
Deal found 10/26![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/2510:00 am -
Nonstop0h 50m
Sat 11/285:40 am -
Nonstop1h 05m
Deal found 10/26![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/265:40 am -
1 stop5h 15m
Thu 12/38:00 am -
1 stop7h 30m
Deal found 10/29![Southwest logo]()
$210
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/279:20 pm -
Nonstop0h 55m
Fri 12/47:18 pm -
Nonstop1h 12m
Deal found 10/29![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/279:15 pm -
Nonstop1h 00m
Fri 12/44:20 pm -
Nonstop0h 55m
Deal found 10/29![Southwest logo]()
$209
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 October 30, 2026.
Search for one-way flight options from Chicago to Wisconsin. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/245:59 pm -
Nonstop1h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$93
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/1010:10 am -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Southwest logo]()
$93
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/105:29 pm -
Nonstop1h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$112
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/279:15 pm -
Nonstop1h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$112
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/610:25 am -
Nonstop1h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$132
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Sun 12/610:10 am -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$132
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/281:55 pm -
Nonstop1h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$135
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/2810:10 am -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$135
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/2610:30 am -
Nonstop1h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$136
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/219:40 am -
Nonstop1h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![American Airlines logo]()
$141
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/258:16 am -
Nonstop1h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![American Airlines logo]()
$143
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/213:47 pm -
1 stop5h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Delta logo]()
$151
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $180 (United Airlines) |
One-way from | $93 (American Airlines) |
Good round-trip deal | $368 or less |
Good one-way deal | $259 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 October 30, 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
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Tue 11/24
5:59 pm-7:03 pm
Nonstop1h 04m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$93
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Tue 12/1
9:10 pm-10:15 pm
Nonstop1h 05m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$93
Quickest round-trip
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Thu 12/10
10:10 am-11:00 am
Nonstop0h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$93
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Fri 11/27
9:15 pm-10:15 pm
Nonstop1h 00m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$112
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Sun 12/6
10:10 am-11:00 am
Nonstop0h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$132
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Sat 3/6
4:20 pm-5:13 pm
Nonstop0h 53m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Sat 11/28
1:55 pm-2:58 pm
Nonstop1h 03m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
ChicagoWausau
ORD Chicago O'Hare Intl - CWA Wausau Central Wisconsin
ORDCWA
Chicago O'Hare Intl
Sat 11/21
9:40 am-11:04 am
Nonstop1h 24m
Wausau Central Wisconsin
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$141
ChicagoGreen Bay
ORD Chicago O'Hare Intl - GRB Green Bay Austin-Straubel
ORDGRB
Chicago O'Hare Intl
Fri 11/27
6:42 pm-7:58 pm
Nonstop1h 16m
Green Bay Austin-Straubel
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$143
ChicagoWausau
ORD Chicago O'Hare Intl - CWA Wausau Central Wisconsin
ORDCWA
Chicago O'Hare Intl
Fri 11/27
3:47 pm-9:00 pm
1 stop5h 13m
Wausau Central Wisconsin
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$151
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-MKE
MDW-MKE
ORD-LSE
ORD-CWA
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-MKE
MDW-MKE
ORD-LSE
ORD-CWA
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 $254). Flying from Chicago to Wisconsin in October is currently the most expensive (average of $533). 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 October 30, 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 26% on airfare.
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 October 24, 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 October 30, 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.
Food
6.7
Boarding
7.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Boarding
7.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Boarding
7.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Overall
7.3
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
See prices for flight routes from nearby airports that may be better suited for you.
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 October 30, 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 October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$361 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$181 | Average$444 | FlexibilityNo cancel fee | On-time69% |