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Private tour in Chicago Greg S
Learn and Laugh about the Windy City
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4 hours
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4 hours
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Greg S.
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Hi! I'm Greg, a Chicago Tribune humor columnist and full-time stand-up comedian, a career I've enjoyed for more than 30 years. Maybe you've seen me on my own Drybar comedy special, or opening concerts for the likes of Celine Dion and Keith Urban. HuffPost called me "Your boss's favorite comedian!" When I'm not making people laugh at corporate events, at comedy clubs and aboard cruise ships, I give tours of the city I love. Why? Because Chicago is an incredibly diverse, friendly and ENTERTAINING city. Let's explore it together on foot or on bikes. We'll share some laughs, eat the food you've heard so much about and get some exercise along the way. (I promise you'll burn off that deep dish pizza or hot dog that I know you're going to want to try) All of my tours are customizable; you tell me what you want to see, and I'll make it happen. We can explore the Mag Mile, take selfies in front of the Bean, and stroll the Riverwalk. Or venture north through the neighborhoods and let me show you where I live...right by Wrigley Field! We can have a drink (or several) at some famous Cubs bars, learn the history of the city's favorite baseball team and more. I look forward to meeting you.
Have a question or want to customize this tour? Message Greg S.
A tour of Chicago's Most Popular Sights with a Chicago Comedian
Overview of your Chicago tour
Ever wonder why some of America's funniest entertainers honed their craft in Chicago? We're talking John Belushi, Tina Fey, Steve Carell, David Schwimmer and many more. Because not only is Chicago a city rich in culture and history, it's also a very ENTERTAINING city. Come along with me, a full-time Chicago comedian, as I take you on a tour of the city's most iconic streets and landmarks, with a few movie locations thrown in. We'll begin at the Chicago Water Tower and learn about the Great Chicago Fire of 1871 and the rebuilding efforts that followed. The tour heads down Michigan Avenue, veers over to State Street and ventures into Millennium Park before ending at the Palmer House Hilton. There will be plenty of stories, history and laughter.
Your Chicago tour itinerary
We begin at the famed Chicago Water Tower, a structure that survived the Great Chicago Fire of 1871. We'll stop outside the new Harry Potter store (Muggles welcome) and the world's largest Starbucks. Continuing south, view Tribune Tower and the Wrigley Building. Head UNDER the Wrigley Building for a hot dog stop at the famous Billy Goat Tavern where Saturday Night Live icons John Belushi and Dan Aykroyd conceived their famous "Cheeboogah" sketch. Next, visit State Street, pausing to view the Chicago River. Learn why we dye the river green on St. Patrick's Day. We'll stop to view Chicago's "corncob condominiums," Take in the view and grab some photos before we head down State Street towards the Chicago Theater. Learn about Chicago's thriving entertainment scene. Next is Millennium Park, home to Pritzker Pavilion and Chicago's #1 tourist attraction...the Bean! We end our tour at a wedding present, the Palmer House Hilton. Yes, Potter Palmer built the Palmer House as a gift to his bride, Bertha.
Want to customize this tour?
Tell your guide which places matter to you, skip what doesn't, and tailor the experience for your group's needs. Not finding what you want? Message your guide to build something unique.
Transport details
Type: Walking
This is a walking tour with one food stop.
What's included
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Meeting location
806 Michigan Avenue, Chicago, Illinois, 60611, United States
The Chicago Water Tower is directly across from Water Tower Place, one of the city's premiere shopping areas. https://share.google/4Zxn2K6RsYmDmayDc
- You can request a specific meeting location (for example, your hotel) during the checkout.
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4 hours
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4 hours
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Book with a deposit
If your tour is valued over $200 USD and booked at least 45 days before the tour date, you can book with a deposit!
How it works
- Your credit card will be authorized only for the deposit amount.
- Funds will not be withdrawn until your tour booking is fully processed.
- 30 days before your tour date, the remaining balance is automatically charged.