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Fun Things to Do in Chicago, Illinois, Milwaukee, Wisconsin Dells, Madison

Things to do / Travel Guide

Horse-Drawn Carriage Rides in Chicago and Southern Wisconsin

Regardless of the temperature outside, snuggling up in a carriage ride is a great way to see the region of Chicago and southern Wisconsin. Horse-drawn carriages are a throwback to yesteryear, and it's still an amazing way to get to know an area. Tours can last between 20 minutes and one hour, depending on your desires.

Chicago offers walk-up carriage rides in the downtown Loop area. Stands can be found along Michigan Avenue and State Street. The carriage rides in Chicago highlight the Loop area like the skyscrapers and riverfront, Michigan Avenue, the lakefront, Grant Park, and the amazing architecture and design of Millennium Park.


While in the southern Wisconsin cities of Milwaukee and Madison, carriage-ride reservations are required. Tours in southern Wisconsin are a bit more flexible than those in Chicago, with a wider range of destinations all over the cities.

Fun Things to Do in Chicago, Illinois

Another fun thing to do in Chicago (and it also includes horses) is a visit to the unique Noble Horse Theatre. Shows like The Nutcracker and other classics are performed on stage by…horses! There are also horse rides and other activities that will appeal to the entire family here.

Another fun option is the Amazing Chicago Funhouse Maze. Here guests will encounter a 4000 square foot sensory maze, including mirrors, spinning tunnels, and more. And since it's located on Chicago's Navy Pier, you can make an afternoon of visiting other sights and attractions along the water.

Fun Things to Do in Milwaukee

Milwaukee is located on the water, so if the weather is nice, it's there where you'll find a ton of fun things to do. We recommend taking a sailing lesson from the Milwaukee Sailing Center, rent a paddleboat for a few hours, or stay on land and tour the lakefront on a Segway. The Milwaukee River Walk is filled with attractions, shops, and restaurants and the RiverSculpture exhibit, which you won't want to miss.

Fun Things to Do in Wisconsin

Snowshoe trails are a popular pastime in Southern Wisconsin. It's a great way to experience the great outdoors, take in scenery, get a good workout, and have some good old fashioned fun! There are a number of snowshoeing trails, including the Indian Marker Tree Trail in Blue Mounds and a number of trails in Kettle Moraine State Forest that are ranked from easy to difficult to accommodate snowshoe-ers of all ages and levels.

Fun Attractions in Chicago, Illinois, Milwaukee, Wisconsin Dells, Madison

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