$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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Oct 10 — Oct 171
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Wisconsin 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 Chicago to Wisconsin
Cheapest
Best
Last-minute
One-way
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 10, 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 10, 2026.
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/149:59 am -
Nonstop1h 40m
Tue 10/207:10 am -
Nonstop1h 43m
Deal found 9/9![Delta logo]()
$117
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/283:35 pm -
Nonstop1h 25m
Mon 11/24:10 pm -
Nonstop1h 40m
Deal found 9/8![Southwest logo]()
$117
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/16:45 am -
Nonstop1h 53m
Mon 10/55:25 am -
Nonstop1h 44m
Deal found 9/9![American Airlines logo]()
$118
This Priceline deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/286:16 am -
1 stop7h 50m
Tue 11/33:01 pm -
1 stop8h 46m
Deal found 9/8![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Thu 10/17:28 pm -
1 stop13h 03m
Mon 10/57:54 pm -
1 stop9h 44m
Deal found 9/9![Frontier logo]()
$119
This Frontier deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/147:44 pm -
1 stop13h 04m
Tue 10/209:30 am -
1 stop9h 37m
Deal found 9/9![Frontier logo]()
$120
This FlightHub deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/76:30 am -
1 stop7h 08m
Sat 10/101:25 pm -
Nonstop1h 38m
Deal found 9/9![Multiple Airlines logo]()
$121
This Trip.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 11/47:15 am -
1 stop6h 51m
Thu 11/54:30 pm -
Nonstop1h 35m
Deal found 9/8![Multiple Airlines logo]()
$122
This Kissandfly.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:45 pm -
Nonstop1h 40m
Mon 10/56:00 am -
Nonstop1h 43m
Deal found 9/8![Sun Country Air logo]()
$123
This FlightHub deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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
Mon 10/262:36 pm -
1 stop9h 48m
Deal found 9/9![Multiple Airlines logo]()
$124
This Expedia deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:25 pm -
Nonstop1h 36m
Wed 10/147:40 pm -
Nonstop1h 41m
Deal found 9/7![Sun Country Air logo]()
$127
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/284:45 pm -
1 stop6h 05m
Tue 11/35:55 pm -
Nonstop1h 40m
Deal found 9/7![Southwest logo]()
$127
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 10, 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 10, 2026.
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:00 pm -
Nonstop1h 20m
Mon 10/57:00 pm -
Nonstop1h 30m
Deal found 9/8![Southwest logo]()
$188
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/248:15 pm -
Nonstop1h 10m
Mon 10/262:17 pm -
Nonstop1h 12m
Deal found 9/9![United Airlines logo]()
$193
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/15:19 pm -
Nonstop1h 02m
Mon 10/55:01 am -
Nonstop1h 13m
Deal found 9/9![American Airlines logo]()
$193
This KAYAK deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 12/25:33 pm -
Nonstop1h 42m
Fri 12/47:54 pm -
Nonstop1h 41m
Deal found 9/9![Delta logo]()
$196
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/227:45 am -
Nonstop1h 25m
Thu 10/2212:20 pm -
Nonstop1h 30m
Deal found 9/9![Southwest logo]()
$188
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:59 am -
Nonstop1h 08m
Thu 10/82:20 pm -
Nonstop1h 11m
Deal found 9/9![United Airlines logo]()
$193
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/19:55 am -
Nonstop0h 50m
Mon 10/55:55 am -
Nonstop0h 50m
Deal found 9/8![Southwest logo]()
$193
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:45 am -
Nonstop1h 03m
Thu 10/17:30 am -
Nonstop1h 30m
Deal found 9/5![American Airlines logo]()
$229
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/227:01 am -
Nonstop1h 40m
Thu 10/221:14 pm -
Nonstop1h 46m
Deal found 9/9![United Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:11 am -
1 stop9h 55m
Fri 9/255:10 pm -
2 stops18h 41m
Deal found 9/6![Multiple Airlines logo]()
$482
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:45 am -
Nonstop1h 03m
Sun 10/41:18 pm -
Nonstop1h 21m
Deal found 9/7![American Airlines logo]()
$230
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/89:55 am -
Nonstop0h 50m
Thu 10/85:00 pm -
Nonstop0h 50m
Deal found 9/9![Southwest logo]()
$221
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/3012:27 pm -
Nonstop1h 43m
Sun 11/110:10 am -
Nonstop1h 37m
Deal found 9/8![Delta logo]()
$268
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 11/19:02 am -
Nonstop1h 11m
Sat 11/219:23 am -
Nonstop1h 12m
Deal found 9/8![United Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:19 am -
1 stop4h 16m
Tue 10/277:10 am -
Nonstop1h 43m
Deal found 9/6![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:40 pm -
Nonstop0h 55m
Fri 10/305:50 pm -
1 stop5h 20m
Deal found 9/7![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:00 am -
1 stop6h 38m
Tue 11/33:02 pm -
Nonstop1h 38m
Deal found 9/7![Delta logo]()
$269
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/89:40 am -
Nonstop1h 12m
Thu 10/157:05 pm -
Nonstop1h 25m
Deal found 9/8![American Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:15 am -
Nonstop0h 50m
Sun 9/275:45 am -
Nonstop0h 45m
Deal found 9/5![Southwest logo]()
$229
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/319:25 pm -
Nonstop1h 34m
Mon 11/29:43 am -
Nonstop1h 46m
Deal found 9/6![United Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:10 am -
Nonstop1h 36m
Wed 10/289:02 am -
1 stop3h 57m
Deal found 9/7![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/259:40 pm -
Nonstop0h 55m
Sun 11/15:30 am -
Nonstop1h 05m
Deal found 9/7![Southwest logo]()
$229
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:45 pm -
Nonstop1h 10m
Sat 9/265:00 am -
Nonstop1h 25m
Deal found 9/5![American Airlines logo]()
$284
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:33 am -
Nonstop1h 39m
Mon 10/199:45 am -
Nonstop1h 44m
Deal found 9/5![United Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:13 pm -
Nonstop1h 47m
Sat 10/179:02 am -
1 stop3h 45m
Deal found 9/7![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/32:10 pm -
Nonstop1h 43m
Mon 10/54:50 pm -
Nonstop1h 46m
Deal found 9/5![United Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/278:15 am -
Nonstop1h 09m
Fri 1/14:54 pm -
Nonstop1h 21m
Deal found 9/5![American Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/49:40 pm -
Nonstop0h 55m
Sun 10/115:10 pm -
Nonstop0h 50m
Deal found 9/6![Southwest logo]()
$239
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/95:31 pm -
1 stop5h 26m
Sun 10/115:14 am -
1 stop3h 30m
Deal found 9/9![Delta logo]()
$288
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/138:40 am -
Nonstop1h 40m
Thu 10/156:00 am -
Nonstop1h 43m
Deal found 9/8![United Airlines logo]()
$269
Last-minute flights from Chicago to WisconsinDiscover last-minute flight deals from Chicago to Wisconsin. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Wisconsin. Data last updated September 10, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/16:45 am -
Nonstop1h 53m
Mon 10/55:25 am -
Nonstop1h 44m
Deal found 9/9![American Airlines logo]()
$118
This Frontier deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Thu 10/17:28 pm -
1 stop13h 03m
Mon 10/57:54 pm -
1 stop9h 44m
Deal found 9/9![Frontier logo]()
$119
This Kissandfly.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:45 pm -
Nonstop1h 40m
Mon 10/56:00 am -
Nonstop1h 43m
Deal found 9/8![Sun Country Air logo]()
$123
This FlightHub deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/76:30 am -
1 stop7h 08m
Sat 10/101:25 pm -
Nonstop1h 38m
Deal found 9/9![Multiple Airlines logo]()
$121
This Sun Country Air deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/96:39 pm -
Nonstop1h 50m
Sat 10/101:25 pm -
Nonstop1h 38m
Deal found 9/9![Sun Country Air logo]()
$128
This Expedia deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:25 pm -
Nonstop1h 36m
Wed 10/147:40 pm -
Nonstop1h 41m
Deal found 9/7![Sun Country Air logo]()
$127
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/149:59 am -
Nonstop1h 40m
Tue 10/207:10 am -
Nonstop1h 43m
Deal found 9/9![Delta logo]()
$117
This Frontier deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/147:44 pm -
1 stop13h 04m
Tue 10/209:30 am -
1 stop9h 37m
Deal found 9/9![Frontier logo]()
$120
This FlightHub deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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
Mon 10/262:36 pm -
1 stop9h 48m
Deal found 9/9![Multiple Airlines logo]()
$124
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/283:35 pm -
Nonstop1h 25m
Mon 11/24:10 pm -
Nonstop1h 40m
Deal found 9/8![Southwest logo]()
$117
This Priceline deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/286:16 am -
1 stop7h 50m
Mon 11/23:01 pm -
1 stop8h 46m
Deal found 9/8![Frontier logo]()
$118
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/284:45 pm -
1 stop6h 05m
Tue 11/35:55 pm -
Nonstop1h 40m
Deal found 9/7![Southwest logo]()
$127
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 10, 2026.
Search for one-way flight options from Chicago to Wisconsin. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Sun Country Air deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:25 pm -
Nonstop1h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Sun Country Air logo]()
$59
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/411:40 am -
Nonstop1h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$59
This Frontier deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 11/176:30 am -
1 stop7h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$60
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:16 am -
1 stop7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$60
This eDestinos deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2711:00 am -
Nonstop1h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Sun Country Air logo]()
$62
This Super.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/17:28 pm -
1 stop13h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$64
This Super.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/238:42 pm -
1 stop15h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$64
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:30 am -
1 stop17h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$66
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:00 pm -
1 stop6h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Southwest logo]()
$69
This Mytrip deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:38 pm -
Nonstop1h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Sun Country Air logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Fri 10/96:39 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Sun Country Air logo]()
$72
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$74
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 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (American Airlines) |
One-way from | $59 (Sun Country Air) |
Popular in | May |
Cheapest in | February |
Average price | $288 |
Good round-trip deal | $268 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 10, 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
Mon 10/12
7:01 am-8:41 am
Nonstop1h 40m
Minneapolis St Paul
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$59
ChicagoMinneapolis
MDW Chicago Midway - MSP Minneapolis St Paul
MDWMSP
Chicago Midway
Sat 10/3
9:59 am-11:40 am
Nonstop1h 41m
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
Wed 10/21
10:33 am-12:12 pm
Nonstop1h 39m
Minneapolis St Paul
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$59
ChicagoMinneapolis
MDW Chicago Midway - MSP Minneapolis St Paul
MDWMSP
Chicago Midway
Sat 10/31
6:05 am-11:35 am
1 stop5h 30m
Minneapolis St Paul
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$69
ChicagoMinneapolis
MDW Chicago Midway - MSP Minneapolis St Paul
MDWMSP
Chicago Midway
Wed 12/2
5:20 pm-10:55 pm
1 stop5h 35m
Minneapolis St Paul
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$69
ChicagoMinneapolis
MDW Chicago Midway - MSP Minneapolis St Paul
MDWMSP
Chicago Midway
Wed 10/14
4:30 pm-10:25 pm
1 stop5h 55m
Minneapolis St Paul
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$69
ChicagoMinneapolis
MDW Chicago Midway - MSP Minneapolis St Paul
MDWMSP
Chicago Midway
Sat 10/3
4:00 pm-10:10 pm
1 stop6h 10m
Minneapolis St Paul
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$69
ChicagoMinneapolis
ORD Chicago O'Hare Intl - MSP Minneapolis St Paul
ORDMSP
Chicago O'Hare Intl
Fri 10/16
6:20 am-7:54 am
Nonstop1h 34m
Minneapolis St Paul
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$86
ChicagoMinneapolis
ORD Chicago O'Hare Intl - MSP Minneapolis St Paul
ORDMSP
Chicago O'Hare Intl
Fri 10/2
8:17 pm-9:55 pm
Nonstop1h 38m
Minneapolis St Paul
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$86
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Sat 10/24
8:57 am-10:07 am
Nonstop1h 10m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$97
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.
MDW-MSP
ORD-MKE
ORD-MSP
MDW-MKE
ORD-ATW
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
MDW-MSP
ORD-MKE
ORD-MSP
MDW-MKE
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 10, 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 38% 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 10, 2026.
The most flights from CHI to USWI are scheduled on a Tuesday (50 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (16 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 5, 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 10, 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
Boarding
7.7
Comfort
7.3
Food
6.6
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Entertainment
7.1
Overall
7.4
Boarding
7.7
Comfort
7.3
Food
6.6
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Entertainment
7.1
Overall
7.4
Boarding
7.7
Comfort
7.3
Food
6.6
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.
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
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
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 September 10, 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 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$332 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$396 | FlexibilityNo cancel fee | On-time69% |