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Private tour in Chicago Greg S
Bike Chicago With a Comedian
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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 healthy and fun way to see the Windy City
Overview of your Chicago tour
Chicago is best explored at a slow pace. So what better way to see it than to take a leisurely bike ride through some of the city's most popular neighborhoods and along its picturesque lakefront, with a guide who know hows to navigate the route and provide local knowledge. Even better, that guide is a professional comedian! We will ride SAFELY, with multiple stops for photos, history lessons and a bite to eat.This tour will not only show you where Chicagoans like to play and where we like to eat, but also where we like to LIVE!
Your Chicago tour itinerary
We begin at Bike and Roll, in the heart of the city and across from Millennium Park. Note: There are several rental facilities to choose from, and the starting location can be altered to suit the group's needs. Riders will be fitted for bikes and helmets. Safety gear must be worn on this tour. Also, riders can bring their own bikes, but every rider assumes all liability for the duration of the tour. We will explore "The Bean, Navy Pier and Buckingham fountain Continuing on the tour, we will ride down State Parkway, home to the original Playboy Mansion. Stop to see one of the wooden streets that survived the Great Chicago Fire. Continuing north and into Lincoln Park, learn the history of the park and all it has to offer. We will ride all the way up to Wrigley Field, home to the Chicago Cubs. Stop for a picture under the famous Wrigley Field sign. We head back to the lakefront and ride all the way back to the bike rental facility.
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: Private Transportation / Category: Bicycle
Walk to the bicycle facility. Rent bikes there.
What's included
What's not included
Meeting location
34 South Michigan Avenue, Chicago, Illinois, 60603, United States
We will rent bikes at 34 S. Michigan Avenue, directly across the street from Millennium Park, and a perfect starting location for this tour. https://maps.app.goo.gl/QPq9cVBwqhGE8Qsx9
- You can request a specific meeting location (for example, your hotel) during the checkout.
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4 hours
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Tour date
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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.