Private tour in Chicago Sylvie S

Walking around The Loop: Discover Skyscrapers, a Cow Path, and More

5.0

(8) reviews

-
Hours icon 3 hours
Walking
Private tour for 1-10 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 3 hours
Walking
Private tour for 1-10 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

Sylvie S.

4.9

Guide rating

39

Reviews

Tours delivered

2 hrs

Avg. response time

Hello! I can't wait to share my deep love of Chicago with you. An actor, photographer, and history buff who has called Chicago home all of my adult life, I revel in sharing stories about the Windy City -- and about the people who built it, made it their home, and left an indelible mark on it. Chicago has it all: a stunning skyline, an incredible shoreline, a vibrant art scene, a bustling theater and film community, and restaurants celebrating food from all corners of the world. Chicagoans love sports, too! Chicago is home to 77 (soon to 78) communities, all with distinct personalities and traits. We can't possibly visit them all at once, but I can certainly entice you so you come back and explore some more! Join me in the "city of big shoulders" for a visit filled with history, anecdotes, and beauty. All my tours can be customized upon request. While you see more than a dozen "set" tours -- also customizable -- , I have developed more than 70 entirely personalized tours for various individuals, couples, or groups, small and large. Just let me know what you are looking for, and I'll create a tour for you!

Have a question or want to customize this tour? Message Sylvie S.

Overview of your Chicago tour

Explore downtown Chicago by foot during this three-hour walking tour of the Loop (thus named thanks to its elevated trains) and discover what makes Chicago an iconic architectural city. During the tour, we will relive the early days of Chicago's history, explore how the Great Chicago Fire reshaped the city and ushered modern architecture, and point out all the engineering feats that make Chicago unique. (Including the reversal of the Chicago River). We will relive anecdotal historical moments, and unearth stories you have never heard of until now. And for all the film and TV buffs out there, I will also point out where block busters as well as the Chicago One series have filmed. Chicago has my soul, my heart, and my life. I can't wait to share it with you.

Recent Reviews

Jean-Marc P.France
April 2026

Sylvie is an excellent guide. She explain very well and she love her city. On the top of that, she has a good sens of humour.

Jennifer K.United States
April 2026

Sylvia is very knowledgeable about the buildings in downtown Chicago. She's easy to talk to and can adapt the tour to one's main interests. She does a great job and downtown Chicago has interesting history and buildings.

Donald J D.Canada
June 2024

Sylvie est tout simplement géniale. Elle s'adapte parfaitement à nos demandes et connait la ville et son histoire sur le bout des doigts.

Jens Holger Woeldike J.Denmark
March 2024

I can highly recommend to book Sylvie as your local tour guide. Sylvie's knowledge, passion and ability to communicate clearly made the tour fantastic. We asked a lot of questions about Chicago and she knew it all. Book Sylvie for an amazing tour of Chicago.

Richard M.United States
November 2023

My family absolutely loved this tour. Sylvie knows her history and architecture. There is a lot of walking, but it's well paced and informative. Plenty of time for pictures and questions. Would highly recommend this to anyone visiting Chicago!

Pierre J.France
July 2023

Notre groupe de 10 personnes a beaucoup apprécié notre guide Sylvie. L'expérience a été extraordinaire. Nous n'avons pas vu passer les 3 heures et plus. Sylvie est très cultivée et son discours est passionnant et pédagogique. Elle alterne la grande histoire avec une foule d'anecdotes Elle possède en plus beaucoup de qualités humaines Sa maîtrise du français est parfaite. Merci beaucoup Sylvie. Nous conseillerons à nos amis votre société et nous même nous vous utiliserons ailleurs dans le monde

Your Chicago tour itinerary

We will: - Meet at Union Station (225 S Canal, under the arches) and visit the Great Hall (learn about its history, but also how it became central to films like The Untouchables) - Walk east to the Willis (Sears) tower, once the tallest building in the world - Walk east to LaSalle Street, the heart of the old Financial District. We will enter the lobby of the Chicago Board of Trade and the Money Museum - Walk north to the Rookery, with its breathtaking Frank Lloyd Wright interior court - Loop back to Jackson blvd to visit the Monadnock Building - Continue north to the Marquette Building to see the Tiffany frieze - Stop by the Picasso at Daley Plaza, and make our way to the Chicago River past the soon-to-be Google Building - Reminisce about the S S Eastland sinking disaster and learn about the "corn cobs." The tour will end on the 1. 25 mile Chicago Riverwalk, at the spot where Fort Dearborn once stood, and where DuSable established his trading post. As always, the tour is entirely customizable.

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 tour is all on foot.

What's included
Private Guide
What's not included
Other: Personal expenses.
Food Drinks Snacks
Meeting location

Chicago, IL, USA

Tour starts at Union Station, 225 S Canal, under the arcade.

  • You can request a specific meeting location (for example, your hotel) during the checkout.
Other details
Tour categories
Architecture
History
City Highlights
TV And Movie
Tour reference number
940727
Languages
French
English
Activity level
Light

Traveller reviews

5.0

FAQs

Who is this private tour in Chicago best suited for?

This private tour is perfect for architecture enthusiasts, history buffs, and film and TV fans. It's also great for those who want to explore Chicago on foot and connect with a local like Sylvie S. for deeper insights into the city's iconic landmarks.

What should I bring or wear?

Can this private tour in Chicago be customized to focus on what I want to see and skip places I've already visited?

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

Where does the tour start and end?

Is transportation included?

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

What languages is this tour offered in?

AI-generated. Please confirm details with your guide

-
Hours icon 3 hours
Walking
Private tour for 1-10 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 3 hours
Walking
Private tour for 1-10 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
More tours in Chicago by Sylvie S.
Similar tours in Chicago
Explore more of Chicago
Full Day Classic Chicago TourTour of the Art Institute of ChicagoHalf day ,Driving Tour of Oak Park & Surrounding AreaChicago Day Tour by carChicago Gangster TourThe Chicago Story - Private Half Day TourChicago by the Lake - Full Day Tour with Boat RideWalking Tour of Pilsen: A neighborhood filled with history and artBronzeville 'The Mecca" of Black CultureChicago Walking Tour with Local Food TastingLet's Polka: Half Day Chicago's Polish Heritage TourHalf Day Explore Chicago Neighborhoods TourWalking around The Loop: Discover Skyscrapers, a Cow Path, and MoreJohn Hughes Film Location TourCultural Historic South Side of Chicago TourHalf Day Driving Tour of Chicago's North ShoreUnderground Chicago Walking TourPrivate Car Chicago Highlights Half-Day TourPrivate Boat Tour Along Chicago RiverFerris Bueller Movie Tour at the Art Institute of ChicagoHighlights of Chicago - Half Day Tour in a SubaruCraft Beer Chicago Brewery TourA Walk in Jackson Park: From the 1893 Columbian Exposition to the Obama Presidential CenterArt Institute Guided TourChicago Tour: Bucktown & Wicker Park NeighborhoodChicago Tour of the Pullman National Historical Park Private Chicago Scenic Driving TourChicago P.D. TV Show Set TourWalking Tour of Old & New Chicago SkyscrapersChicago Tour: Fire and WaterChicago Architecture Walking TourWalking Art, Architecture and History TourChicago's Gilded Age: Walk around the First Millionaire Row Ferris Bueller Movie Highlights Chicago Walking TourStar Park and Chicago City TourWest Section: Downtown Chicago Walking 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 soulA Little of This and a Little of That Driving TourChicago Water Taxi and Riverwalk Tour