Chicago’s Most Talked-About Walking Tours

Photo by Lance Anderson on Unsplash

From restaurants to landmarks and everything in-between Chicago’s got so much to see. Try out a walking tour to dive deeper into the rich history and culture this city has to offer.

Gangsters and Ghosts

Get two tours in one with this spooky tour! Walk around the historic Chicago Loop Vice District as you learn about some of the most infamous gangsters in history and how they met their demise. Become immersed in the 1920’s as you discover the haunting truth about the speakeasy saloons and underground secrets that made this city what it is today. 

Millennium Park Exploration Game and Self-Guided Tour

Take a turn as the tour guide for this unique self-guided tour around one of Chicago’s most famous parks! Download a mobile app that prompts you to solve puzzles and uncover clues to learn more about iconic landmarks and locations around Millennium Park. Described as a “perfect mix between a tour, outdoor escape room, and treasure hunt,” you’re sure to get your money’s worth with this one.

Deep Dish Pizza Tour

Say Cheese! My taste buds are tingling just thinking about this tasty tour. This self-guided adventure takes you and your friends and family on a delicious outing to three of Chicago’s world renowned deep dish pizza restaurants! Stroll the magnificent mile and satisfy your cravings with one of the most iconic meals this city has to offer. 

History, Culture, and Architecture Tour

Chicago’s architecture is known as some of the best in the world and you’ll know why after taking this tour. Starting at the Chicago Theatre, you’ll travel across the city to see some of the most famous landmarks in the United States. On this tour you’ll get breathtaking views of the skyline, photo-ops at Millennium Park’s “The Bean,” tasty Chicago treats, and memories to last a lifetime!

Chicago Underground Donut Tour

This tour through the heart of downtown is known as one of the best food tours in the city. Make stops at some of the best donut shops in Chicago and try treats from each one while taking in the sights of Michigan Avenue. As their website suggests, “bring your walking shoes and your appetite, because you’ll need both.”

The Chicago Theatre Marquee Tour

If you’re looking to really dive deep into some of the richest history this city has to offer, take this tour of the legendary Chicago Theatre. Learn about the origins of the theatre as well as some of the most iconic performers to have graced the stage, all while taking in the beautiful architecture and decor. You’ll get a once in a lifetime opportunity to hop up on the stage and see what the performers see when putting on a show at this renowned Chicago location!

Art Institute Before Hours

With over 1.5 million visitors each year, The Art Institute of Chicago is one of the most popular sites in the city. This tour gives you the chance to skip the lines and beat the crowds with a guided tour of the museum before it opens to the public! Get up close and personal with the art as an expert leads you through works from Picasso to Dali, and everything in-between.    

There’s no other place in the world where you can get history, culture, food, architecture, and more quite like this, so put on your walking shoes and get ready to immerse yourself in the Second City. Try out some of these tours and let us know which ones are your favorites!

Written by: Lindsey LeBeda

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