To save on the cost of your flight from Wisconsin to Chicago, book at least 20 days before your planned departure. Booking around this time can save you about 10% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $137 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $157.
Due to multiple factors, expect to potentially pay more when booking in December. For low rates, April can be a great choice for travel to Chicago. Flights to Chicago from Wisconsin in April are about $135 on average during April, but can be found for as low as $33.