Plan a Trip to Pleasant Prairie

Pleasant Prairie, Wisconsin is conveniently situated midway between Chicago and Milwaukee and an easy distance of highway from the airports in either city — Chicago O’Hare (ORD) and Milwaukee’s General Mitchel (MKE).

Be sure to pack your bags appropriately for the southeastern Wisconsin climate by checking our seasonal weather trends and Fall Foliage tracker. No worries if you get here and realize you’re missing that essential item. Pleasant Prairie’s Premium Outlets and Shoppes at Prairie Ridge will have you covered.

Thompson Strawberry Farm - Family Picking Wild Flowers

Wisconsin winters are a great time to enjoy activities such as snowshoeing and sledding. Only 30 minutes from Wilmot Ski Resort, Pleasant Prairie hotels are a convenient retreat for you and your family after a day on the mountain. Lake Andrea is the perfect spot to set up ice fishing huts and return in the spring and summer for fishing from the shore or on the water. During the warmer seasons, you can enjoy the many parks and trails in the Prairie. In addition to fishing, canoeing, kayaking, and standup paddleboarding on Lake Andrea, there are many events taking place at Prairie Springs Park such as the Dragonboat Festival and Pleasant Prairie Triathlon. For competitive athletes, the accessibility, versatility, and knowledgeable staff at the RecPlex make Pleasant Prairie an ideal venue for sports events, tournaments, and championships.

Whether you’re visiting for the first time or return often for our distinctive attractions or annual events, you’ll find everything you need to plan your trip to our village right here. The easy-going and mindful, live-in-the-present philosophy of our village may have you considering relocating to Pleasant Prairie.

Check back in with us occasionally for new trip ideas and take inspiration with you by checking out our Pleasant Prairie Mini Travel Guide.