5 Recommended Tours in Chicago

If you book only one tourist activity while in Chicago, make sure it’s the Architecture River Cruise. The outing combines the relaxation of a boat ride with the fulfillment of learning about the buildings that border the river. Chicagoans will love the new perspective of floating by structures such as the Apple Michigan Avenue flagship store. Tourists, on the other hand, will be in awe of skyscrapers such as the Willis Tower, all while taking note of which river restaurant to stop by for a bite to eat after the tour.

History buffs will love peering into architectural spaces from the era of the 1893 World’s Fair on this tour, which challenges guests on a visual scavenger hunt. Participants are split into two teams to compete, deciphering clues and looking for the answers inside 125-year-old buildings. The tour is sprinkled with bar stops; therefore, you can get your German-style lager fix inside a century-old pub along the way. Whether you’re familiar with the 1893 World’s Fair and read The Devil in the White City or not, this tour will ripen your understanding of the late 19th century and Chicago history in general.

A short walk from the lakefront, the John Hancock Building has something for everyone. There’s a mall, a fine-dining restaurant, a hotel and best of all, a 94th-floor observation deck. Ride the elevator up to the 17,000-square-foot (1,579-square-meter) platform, which boasts 360-degree views of Chicago’s dazzling skyline and turquoise lakefront. Skip the long line at the ticket counter, and head straight to the bar for a drink instead. The bar comes with a thrilling view that will take your breath away – or at the very least provide a solid Instagram backdrop.

Pizza is more than a carb in Chicago – it’s a legacy. Legend has it that deep-dish pizza was invented at Pizzeria Uno in Chicago back in 1943. New York City might think they have Chi-town beat on the pizza front, but you can settle that debate once and for all by tasting your way through four prominent pizzerias on this tour. Even if you think you’ve tried it all, this tour will surprise you. Go classic with the famous burnt cheese caramelized crust at Pequod’s, and then dig into Chicago-style pizza at Al Capone’s former speakeasy, Exchequer. And since it’s a walking tour, the calories don’t count.

Chicago’s Wicker Park neighborhood is known for having unique shops and celebrated restaurants. However, before the boutiques and mood-lit bars, the residential streets acted as stomping grounds for out-there artists, radicals and mobsters. This tour tells the stories of the neighborhood’s bizarre past, complete with unsolved murders and lingering fables. The storied history of community activism and secret scandals will amaze you. Walk by iconic churches and taverns, and peer into the remains of Victorian-era warehouse buildings. Also, there will be a chance to visit shops that have repurposed old storefronts. This tour might just leave you with more questions than answers.