Tour guide in Chicago Greg S.

Chicago, United States

English

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Since Sep 17, 2025

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I'm Greg S., your private tour guide in Chicago

Guide #76016

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.

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Tours by Greg S.

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Full Day Classic Chicago TourTour of the Art Institute of ChicagoHalf day ,Driving Tour of Oak Park & Surrounding AreaChicago Day Tour by carBronzeville 'The Mecca" of Black CultureChicago Gangster TourPrivate Car Chicago Highlights Half-Day TourLet's Polka: Half Day Chicago's Polish Heritage TourThe Chicago Story - Private Half Day TourChicago by the Lake - Full Day Tour with Boat RideChicago Walking Tour with Local Food TastingHalf Day Explore Chicago Neighborhoods TourWalking Tour of Pilsen: A neighborhood filled with history and artUnderground Chicago Walking TourWalking Art, Architecture and History TourJohn Hughes Film Location TourChicago Architecture Walking TourHalf Day Driving Tour of Chicago's North ShoreChicago's Gilded Age: Walk around the First Millionaire Row Private Boat Tour Along Chicago RiverFerris Bueller Movie Tour at the Art Institute of ChicagoChicago Water Taxi and Riverwalk TourHighlights of Chicago - Half Day Tour in a SubaruCraft Beer Chicago Brewery TourWalking around The Loop: Discover Skyscrapers, a Cow Path, and MoreA Walk in Jackson Park: From the 1893 Columbian Exposition to the Obama Presidential CenterArt Institute Guided TourChicago Tour: Bucktown & Wicker Park NeighborhoodPrivate Tour of the Chicago RiverwalkChicago P.D. TV Show Set Tour Private Chicago Scenic Driving TourWalking Tour of Old & New Chicago SkyscrapersA Little of This and a Little of That Driving TourChicago Downtown Tour with a LocalFerris Bueller Movie Highlights Chicago Walking TourWest Section: Downtown Chicago Walking TourChicago Tour of the Pullman National Historical ParkCultural Historic South Side of Chicago TourOk, Chef! A private journey for 2 to 3 people Inside "The Bear's" culinary soulOk Chef! A bite size trip inside "The Bear's" culinary soul