$59+ Cheap flights from Wisconsin to Chicago (CHI)
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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Oct 16 — Oct 231
Round-trip
1 adult, Economy
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Find cheap flights from Wisconsin to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Wisconsin to ChicagoExplore the most affordable flight options available from Wisconsin to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
Explore the most affordable flight options available from Wisconsin to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/85:25 am -
Nonstop1h 30m
Thu 10/157:45 am -
Nonstop1h 25m
Deal found 9/10![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/16:55 am -
Nonstop1h 35m
Mon 10/58:25 pm -
Nonstop1h 43m
Deal found 9/10![Delta logo]()
$117
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/283:01 pm -
1 stop8h 46m
Sat 10/317:25 am -
1 stop6h 41m
Deal found 9/10![Frontier logo]()
$118
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.
Wed 12/238:20 am -
Nonstop1h 48m
Mon 12/287:40 pm -
Nonstop1h 46m
Deal found 9/14![Sun Country Air logo]()
$118
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/1712:30 pm -
1 stop7h 05m
Wed 11/188:10 am -
Nonstop1h 35m
Deal found 9/10![Southwest logo]()
$127
This CheapOair deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:00 am -
1 stop17h 21m
Tue 11/37:15 am -
1 stop6h 51m
Deal found 9/11![Frontier logo]()
$127
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.
Wed 12/238:20 am -
Nonstop1h 48m
Fri 1/111:45 am -
Nonstop1h 46m
Deal found 9/14![Sun Country Air logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:30 pm -
Nonstop1h 35m
Tue 11/176:30 am -
1 stop17h 34m
Deal found 9/11![Multiple Airlines logo]()
$132
This Priceline deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Thu 10/2911:42 am -
1 stop7h 03m
Sun 11/17:30 am -
Nonstop1h 41m
Deal found 9/10![Multiple Airlines logo]()
$133
This FlightHub deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/147:40 pm -
Nonstop1h 41m
Thu 10/156:58 pm -
1 stop14h 58m
Deal found 9/10![Multiple Airlines logo]()
$134
This Trip.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:36 pm -
1 stop9h 48m
Mon 11/28:13 pm -
1 stop11h 52m
Deal found 9/11![Frontier logo]()
$135
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/287:00 am -
Nonstop1h 44m
Sat 10/3110:12 am -
Nonstop1h 41m
Deal found 9/10![Delta logo]()
$137
Best flights from Wisconsin to ChicagoDiscover carefully curated flight deals from Wisconsin to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
Discover carefully curated flight deals from Wisconsin to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
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.
Wed 10/216:15 am -
Nonstop1h 11m
Wed 10/2110:00 pm -
Nonstop0h 59m
Deal found 9/15![United Airlines logo]()
$161
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3110:35 am -
Nonstop1h 30m
Wed 11/410:05 am -
Nonstop1h 40m
Deal found 9/14![Southwest logo]()
$220
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/103:01 pm -
Nonstop1h 40m
Fri 11/135:42 pm -
Nonstop1h 32m
Deal found 9/15![Delta logo]()
$236
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.
Thu 10/88:45 am -
Nonstop1h 20m
Thu 10/1510:05 am -
Nonstop1h 07m
Deal found 9/12![American Airlines logo]()
$249
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 10/139:30 am -
1 stop9h 37m
Sat 10/176:30 am -
1 stop7h 11m
Deal found 9/15![Frontier logo]()
$321
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.
Sun 10/182:35 pm -
Nonstop1h 30m
Fri 10/2312:29 pm -
Nonstop1h 25m
Deal found 9/14![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 11/65:05 am -
Nonstop1h 38m
Sun 11/811:59 am -
Nonstop1h 28m
Deal found 9/13![United Airlines logo]()
$180
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.
Wed 10/74:50 pm -
1 stop19h 32m
Sun 10/119:33 pm -
1 stop13h 42m
Deal found 9/15![Multiple Airlines logo]()
$403
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/85:25 am -
Nonstop1h 30m
Sun 10/117:45 am -
Nonstop1h 25m
Deal found 9/10![Southwest logo]()
$231
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.
Thu 10/82:35 pm -
Nonstop1h 30m
Sun 10/1110:00 pm -
Nonstop1h 32m
Deal found 9/13![United Airlines logo]()
$200
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.
Thu 1/72:45 pm -
Nonstop1h 33m
Mon 1/1112:35 pm -
Nonstop1h 30m
Deal found 9/15![United Airlines logo]()
$200
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:00 am -
Nonstop1h 27m
Sun 10/184:59 pm -
Nonstop1h 18m
Deal found 9/11![American Airlines logo]()
$269
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:10 am -
Nonstop1h 43m
Tue 10/209:59 am -
Nonstop1h 40m
Deal found 9/13![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/157:00 pm -
Nonstop1h 30m
Fri 10/169:25 pm -
Nonstop1h 30m
Deal found 9/10![Southwest logo]()
$258
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/52:35 pm -
Nonstop1h 30m
Mon 10/1210:00 pm -
Nonstop1h 32m
Deal found 9/11![United Airlines logo]()
$205
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.
Fri 10/25:03 am -
Nonstop1h 22m
Sun 10/48:51 pm -
Nonstop1h 03m
Deal found 9/12![American Airlines logo]()
$278
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/296:45 pm -
Nonstop1h 30m
Wed 2/1012:45 pm -
Nonstop1h 30m
Deal found 9/11![Southwest logo]()
$259
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:10 am -
Nonstop1h 43m
Sun 10/186:20 am -
Nonstop1h 34m
Deal found 9/15![Delta logo]()
$286
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.
Sun 10/185:00 am -
Nonstop1h 29m
Sat 10/2410:00 pm -
Nonstop1h 32m
Deal found 9/14![United Airlines logo]()
$205
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:15 am -
Nonstop1h 30m
Mon 11/23:10 pm -
Nonstop1h 30m
Deal found 9/11![Southwest logo]()
$259
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:00 am -
1 stop6h 59m
Fri 10/166:20 am -
Nonstop1h 34m
Deal found 9/11![Delta logo]()
$289
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.
Sun 10/45:00 am -
Nonstop1h 25m
Fri 10/166:59 am -
Nonstop1h 12m
Deal found 9/12![American Airlines logo]()
$289
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.
Thu 10/155:00 am -
Nonstop1h 29m
Thu 10/2212:29 pm -
Nonstop1h 25m
Deal found 9/15![United Airlines logo]()
$205
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:54 pm -
Nonstop1h 39m
Wed 11/188:29 am -
1 stop5h 07m
Deal found 9/11![Delta logo]()
$289
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.
Thu 12/242:19 pm -
Nonstop1h 23m
Fri 1/89:33 am -
Nonstop1h 27m
Deal found 9/15![American Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:30 am -
1 stop27h 56m
Sun 10/49:36 pm -
1 stop26h 18m
Deal found 9/11![Multiple Airlines logo]()
$413
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 10/207:15 am -
Nonstop1h 30m
Thu 10/222:05 pm -
Nonstop1h 25m
Deal found 9/15![Southwest logo]()
$286
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 12/227:40 am -
Nonstop1h 58m
Mon 1/189:30 pm -
Nonstop1h 43m
Deal found 9/15![United Airlines logo]()
$221
This KAYAK deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/66:10 am -
1 stop6h 23m
Fri 1/812:30 pm -
Nonstop1h 39m
Deal found 9/11![Delta logo]()
$305
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.
Thu 12/106:00 am -
Nonstop1h 42m
Sat 12/122:10 pm -
Nonstop1h 47m
Deal found 9/15![United Airlines logo]()
$221
Last-minute flights from Wisconsin to ChicagoDiscover last-minute flight deals from Wisconsin to Chicago. Data last updated September 16, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Chicago. Data last updated September 16, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:00 am -
Nonstop1h 47m
Sat 10/38:21 am -
Nonstop1h 53m
Deal found 9/11![American Airlines logo]()
$144
This Sun Country Air deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:25 pm -
Nonstop1h 38m
Tue 10/135:25 pm -
Nonstop1h 36m
Deal found 9/11![Sun Country Air logo]()
$128
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/129:00 am -
Nonstop1h 38m
Thu 10/227:45 pm -
Nonstop1h 40m
Deal found 9/14![Sun Country Air logo]()
$138
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.
Tue 10/137:19 pm -
Nonstop1h 30m
Tue 10/208:39 pm -
Nonstop1h 08m
Deal found 9/15![American Airlines logo]()
$161
This Trip.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:36 pm -
1 stop9h 48m
Mon 11/28:13 pm -
1 stop11h 52m
Deal found 9/11![Frontier logo]()
$135
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.
Tue 10/272:33 pm -
1 stop9h 48m
Sat 10/316:30 am -
1 stop17h 34m
Deal found 9/15![Frontier logo]()
$141
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 10/282:32 pm -
1 stop9h 49m
Thu 10/297:18 pm -
Nonstop1h 40m
Deal found 9/15![Multiple Airlines logo]()
$140
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:00 am -
1 stop17h 21m
Wed 11/46:30 am -
1 stop7h 07m
Deal found 9/14![Frontier logo]()
$154
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/294:40 pm -
Nonstop1h 38m
Sun 11/17:30 am -
Nonstop1h 41m
Deal found 9/15![Sun Country Air logo]()
$148
This CheapOair deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:00 am -
1 stop17h 21m
Tue 11/37:15 am -
1 stop6h 51m
Deal found 9/11![Frontier logo]()
$127
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:00 am -
Nonstop1h 44m
Tue 11/35:31 pm -
Nonstop1h 44m
Deal found 9/11![Delta logo]()
$137
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:50 pm -
Nonstop1h 37m
Tue 11/312:30 pm -
Nonstop1h 39m
Deal found 9/11![Delta logo]()
$137
One-way flights from Wisconsin to ChicagoSearch for one-way flight options from Wisconsin to Chicago. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
Search for one-way flight options from Wisconsin to Chicago. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:40 am -
Nonstop1h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Southwest logo]()
$59
This Sun Country Air deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:00 pm -
Nonstop1h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Sun Country Air logo]()
$59
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.
Mon 10/129:00 am -
Nonstop1h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Sun Country Air logo]()
$60
This Trip.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:25 pm -
Nonstop1h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Sun Country Air logo]()
$61
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:30 pm -
Nonstop1h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Sun Country Air logo]()
$63
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/89:00 am -
Nonstop1h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![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 10/277:00 am -
1 stop17h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$74
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:00 am -
1 stop17h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$76
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:33 pm -
1 stop9h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$77
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:00 am -
1 stop13h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$78
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:45 am -
Nonstop1h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Sun Country Air logo]()
$79
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.
Tue 10/65:00 am -
Nonstop1h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![American Airlines logo]()
$81
Find flight deals from Wisconsin to Chicago
Keep the following information in mind while searching for Wisconsin to Chicago flight deals. Data was last updated September 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (United Airlines) |
One-way from | $59 (Southwest) |
Good round-trip deal | $336 or less |
Good one-way deal | $200 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Wisconsin to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 16, 2026.
Use the filters below to find and compare flights from Wisconsin to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MinneapolisChicago
MSP Minneapolis St Paul - ORD Chicago O'Hare Intl
MSPORD
Minneapolis St Paul
Sat 11/7
3:00 pm-4:35 pm
Nonstop1h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$59
Quickest round-trip
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Mon 12/14
9:15 am-10:27 am
Nonstop1h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$92
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Mon 10/12
6:32 pm-7:45 pm
Nonstop1h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$92
Eau ClaireChicago
EAU Eau Claire - ORD Chicago O'Hare Intl
EAUORD
Eau Claire
Sun 10/4
2:35 pm-4:05 pm
Nonstop1h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$93
Eau ClaireChicago
EAU Eau Claire - ORD Chicago O'Hare Intl
EAUORD
Eau Claire
Sun 11/1
5:05 am-6:43 am
Nonstop1h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$93
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Mon 11/23
6:47 am-7:59 am
Nonstop1h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$97
Eau ClaireChicago
EAU Eau Claire - ORD Chicago O'Hare Intl
EAUORD
Eau Claire
Wed 10/28
5:05 am-6:43 am
Nonstop1h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$103
MinneapolisChicago
MSP Minneapolis St Paul - MDW Chicago Midway
MSPMDW
Minneapolis St Paul
Tue 10/27
10:10 am-11:47 am
Nonstop1h 37m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$104
MinneapolisChicago
MSP Minneapolis St Paul - MDW Chicago Midway
MSPMDW
Minneapolis St Paul
Sat 12/12
10:10 am-11:59 am
Nonstop1h 49m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$104
MinneapolisChicago
MSP Minneapolis St Paul - ORD Chicago O'Hare Intl
MSPORD
Minneapolis St Paul
Tue 12/8
12:45 pm-6:26 pm
1 stop5h 41m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$114
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Wisconsin to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Wisconsin with our price prediction graph.
MSP-MDW
MSP-ORD
MKE-ORD
EAU-ORD
MSP-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Wisconsin to Chicago
USWI-CHI
MSP-MDW
MSP-ORD
MKE-ORD
EAU-ORD
What is the cheapest month to book a flight from Wisconsin to Chicago?
Currently, November is the cheapest month in which you can book a flight from Wisconsin to Chicago (average of $239). Flying from Wisconsin to Chicago in August is currently the most expensive (average of $379). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from WI to CHI?
Find hourly flight availability from Wisconsin to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2026.
One of the essential ways to save on airfare from Wisconsin to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 34% on airfare.
Weekly flight availability from Wisconsin to Chicago
Explore weekly flight availability from Wisconsin to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 16, 2026.
The most flights from USWI to CHI are scheduled on a Monday (61 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (48 on average).
What is the cheapest day to fly from Wisconsin to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Chicago. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Wisconsin to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Wisconsin to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Alternative routes for Wisconsin to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 16, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Wisconsin to Chicago by cabin class
Find flights from Wisconsin to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Wisconsin and Chicago flights
Browse other Wisconsin and Chicago flight options. Last updated on September 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Wisconsin to Chicago flights
Consider these flights traveling from Wisconsin to Chicago.
Top 2 airlines flying from Wisconsin to Chicago
Discover the top 2 airlines that operate flights from Wisconsin to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$171 | Average$261 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$179 | Average$304 | FlexibilityNo cancel fee | On-time71% |