5 Recommended Tours in Chicago

Discover Chicago’s unique history via fascinating tours
Discover Chicago’s unique history via fascinating tours | © Jon Lovette / Alamy Stock Photo
Jacquelyn Lumley

From turn-of-the-century architecture to glistening lake vistas, Chicago is a playground of landmarks with stories. Take some time to get to know the fifth most populated city in the US by booking one of these five recommended tours.

1. Learn about famous landmarks on Chicago Architecture River Cruise

Architectural Landmark

An architecture cruise ship and barge on the Chicago River
© Jerry Lai / Alamy Stock Photo

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.

2. Indulge in a tipple on the 1893 World’s Fair Tour with Bars

Historical Landmark, Market, Park

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.

3. See the best city views at 360 CHICAGO at the John Hancock Building

Architectural Landmark

Observation deck, John Hancock Building, Chicago.
© Gerard Lawton / Alamy Stock Photo

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.

4. Grab a slice of pie on the Chicago Pizza Tour

Pizzeria, American

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.

5. Travel back in time on the Bizarre Wicker Park Tour

Historical Landmark

Milwaukee and Damen Avenues in the trendy Wicker Park in Chicago
© Richard Ellis / Alamy Stock Photo

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.

Culture Trips launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes places and communities so special.

Our immersive trips, led by Local Insiders, are once-in-a-lifetime experiences and an invitation to travel the world with like-minded explorers. Our Travel Experts are on hand to help you make perfect memories. All our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

All our travel guides are curated by the Culture Trip team working in tandem with local experts. From unique experiences to essential tips on how to make the most of your future travels, we’ve got you covered.

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