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Midwestern City Tours

The cities of the Midwest make great destinations for return visits, but the challenge is moving beyond the “been there, done that” spots and experiences. These five city tours are great options for groups that want to dig deeper into these Midwestern destinations.

Trikke STL

St. Louis

Voted “the best cheap thrill in St. Louis” by a local newspaper, Trikke STL can give your group a budget-friendly but adventuresome way to explore the Gateway City. The tour company is centered around “trikkes” which are three-wheeled standing scooters that run by battery power. The company offers a variety of tours across the city, including two popular tours of Forest Park.

“What’s nice is that we’re a mobile business,” said Bill Smith, owner of Trikke STL. “We can go wherever the event site is.” This means that whether your group members want to just get out and ride or whether they want to explore an area not already on a scheduled tour, Trikke STL can work with you to plan an outing. The company also gives groups the option to personalize tours or activities to include extras like scavenger hunts and obstacle courses so they can enjoy riding a trikke without the more scripted aspects of a predefined tour.

For those concerned about ability levels, Smith said, “If you can stand and turn a throttle you can ride a trikke.” No special skill is needed to operate one of the battery-powered machines. Adventurers can learn how to use one in about 10 minutes, making it easier than a Segway and allowing more time to enjoy the ride.

Chicago Crime Tours


Chicago is known for deep-dish pizza and the gangsters of the Roaring ’20s, so it was a natural move for the same people who operate Slice of Chicago Pizza Tours to branch out and start Chicago Crime Tours.

Chicago Crime Tours is “a history tour in a fun way,” according to owner Mark Singer. The tours cover crime in the Windy City from 1837 through modern times and include famous stops like the Biograph Theater, which is well known for its ties to John Dillinger. The tours incorporate fun touches such as crime trivia, Chicago history and stops at famous sites like the location of the Valentine’s Day Massacre.

One popular option is the Crime and Pizza tour, where groups are able to enjoy a tour of infamous stops and stories of lawbreakers including Al Capone and George Streeter, before enjoying an authentic deep-dish pizza at Pizzeria Uno, the originator of Chicago-style pizza.

Chicago Crime Tours is also a great option for a customized tour of Chicago. The company works with groups to tailor tours to the specific type and interests of each group.

American Legacy Tours


American Legacy Tours is host to some of the most popular and highly rated tours of Cincinnati. These city tours cover a wide array of topics, including haunted history, baseball and gangsters and Cincinnati’s own Rookwood Pottery.

American Legacy Tours offers many different city tours of the Queen City, but one you won’t find anywhere else is the 1919 Baseball Tour, which allows groups to explore Cincinnati — home of the first professional baseball team — and how the city helped to shape what is called the American pastime as we know it today. The tour covers topics like the history of the Reds, the merger of the National and American leagues and, of course, the 1919 World Series between the Reds and the Chicago White Sox.

Another popular excursion for more adventurous groups is the Queen City Underground Tour. This tour takes groups through the Over-the-Rhine neighborhood, home to the area’s early German immigrants who helped shape Cincinnati’s heritage. After touring above ground, groups descend below the streets to see the famous neighborhood and its history from a different perspective.