Private tour in Chicago Greg S

Graceland Cemetery and Wrigleyville (GO CUBS!)

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Hours icon 4 hours
Walking
Private tour for 1-8 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 4 hours
Walking
Private tour for 1-8 people
Your party size

1

View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later

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.

Overview of your Chicago tour

I live in Wrigleyville, home to the Chicago Cubs and one of the most vibrant of Chicago’s 178 neighborhoods. No, this tour includes no stop at my condo (trust me, it’s probably a mess), but you will step into the stories, sights, and spirit that define this community. We’ll begin at Graceland Cemetery, resting place of retail giants like Marshall Field and architectural visionaries like Daniel Burnham. From there, we’ll stroll Clark Street toward Wrigley Field, pausing for a Chicago-style hot dog and a beer at Murphy’s Bleachers. As we circle the ballpark, I’ll share tales of rooftop traditions, curses, foul balls, and the legend of Harry Caray. By the end, you won’t just know Chicago—you’ll feel like a Cubs fan, which means we’ll be friends forever.

Your Chicago tour itinerary

- We'll start at Graceland Cemetery, the final resting place of some of Chicago's most prominent citizens. Learn about Chicago's rich retail history while standing next to the graves of Potter Palmer and Marshall Field. Discover how another Graceland resident, Daniel Burnham rebuilt Chicago after the Great Chicago Fire of 1871. Pay homage to "Mr Cub," Ernie Banks. - From there, we will walk down Clark Street toward Wrigley Field, the second-oldest major league ballpark and the last to erect lights for night games. We will stop for a "Chicago-style" hot dog at one of the city's famous hot dog establishments. We will grab a beer (or the libation of your choice) at Murphy's Bleachers, arguably the most famous Cubs bar in the area. Finally, we will walk the perimeter of Wrigley Field, pausing to learn about the famous Wrigley Rooftops, the Billy Goat curse, the Steve Bartman foul ball incident and the Harry Caray statue.

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.

What's included
Private Guide
What's not included
Food Drinks Snacks
Private Transportation
Meeting location

4001 North Clark Street, Chicago, Illinois, 60613, United States

Graceland Cemetery sits at the corner of Irving Park and Clark in Chicago's Lakeview community, It is easily accessible by car or public transportation. https://maps.app.goo.gl/ec8WV2UjbuLqB9My8

  • You can request a specific meeting location (for example, your hotel) during the checkout.
Other details
Tour categories
City Highlights
History
Art And Culture
Food And Drink
Classes And Workshops
Tour reference number
1434375
Languages
English
Activity level
Moderate
Accessibility
Kid Friendly
Wheelchair Accessible

FAQs

Who is this private tour in Chicago best suited for?

This private tour in Chicago is perfect for those who love history, sports, and a good laugh. Led by Greg S., a Chicago comedian, you'll explore the vibrant neighbourhood of Wrigleyville and learn about the city's rich history and sports culture. It's ideal for travellers who want to connect with a local for deeper insights into Chicago's unique character.

What should I bring or wear?

How long is the tour, and can the start time or duration be adjusted?

Where does the tour start and end?

How much walking is involved, and is it suitable for kids, seniors, or travellers with mobility concerns?

What languages is this tour offered in?

What's included in this private tour, and what should I budget for separately?

AI-generated. Please confirm details with your guide

-
Hours icon 4 hours
Walking
Private tour for 1-8 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 4 hours
Walking
Private tour for 1-8 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
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