Welcome to Chicago - a world-class city offering enough attractions, entertainment and character to charm even the most discerning urbanite. Take a Chicago tour with a friendly local guide and discover the best the Windy City has to offer.

Take a riverboat cruise for a fresh perspective on Chicago's striking architecture. Your guide will point out the world's first skyscraper, whose steel frame revolutionized the building of office towers. Stroll around captivating pieces of public art, including Frank Gehry's Pavilion, on display in Millennium Park and make sure to visit the Art Institute's legendary galleries. If you're in need of retail therapy, head straight to Chicago's Magnificent Mile, and don't forget to indulge in a deep-dish pizza; your guide will make sure to take you to the best spot in town.

Whether you want to hang out at Wrigley Field or the Theatre District, your guide can customize a Chicago tour to suit your unique travel interests.

Chicago

Chicago is a great walking city but sometimes time and other issues call for a driving tour.

We can cover a lot in a couple of hours primarily along the Lake Michigan East side Lake Shore Drive. Sit back and enjoy an overview of Chicago. We will begin in the loop (business district) near the birthplace of the City where the River meets Lake Michigan. We will then trace the history of the city to the south side Hyde Park site of the 1893 World's Columbian Exposition. Proceeding north along the Lake Front will take us to the Museum campus with its breathtaking view of the city and continue north to the 1200 acre Lincoln Park.

Our trip will span much of the 18 mile long Lake Shore Drive along beautiful Lake Michigan. Several stops, including the Museum Campus, will allow opportunities for brief walks and discussions of Chicago's history, beauty, art, architecture and culture.

The maximum number for this tour is 4 - but 3 is most comfortable. I offer a different van tour for up to 6. Contact me for a quote.

An overview of the city in a private vehicle

Chicago Driving Tour

Chicago offers an interesting and complex history. Let's check out some of the highlights dating back to the mid 19th century through modern times. We'll start with some of my favorite places along Michigan Ave. Our tour will ultimately take us to the southside of Chicago: home to the 1893 Columbian Exposition

Cocktails in a secret Athletic Club-turned-hipster-bar are a definite must. There we'll get an awesome view of the lakefront that'll make your friends jealous. We'll also check out buildings along the Chicago River and learn about their historical significance. Have you ever ridden on a manually operated 19th century elevator? That'll also be on the agenda.

This tour will combine transportation via car, uber/public transport, and walking. All of my tours are fully customizable.

A fantastic view of Millennium Park from a private balcony.

A fun way to see architecture along the river 

A former Athletic Association turned hipster bar.

The awe inspiring Tiffany Dome at the Chicago Cultural Center.

Explore and experience the best of Chicago by foot and private transportation on this highlights tour.

Full Day Classic Chicago Tour

The Art Institute of Chicago is a treasure trove of amazing works of art from all over the world.
Having attended the school there as a child &amp; receiving my my master's degree from there,
I know the place like the back of my hand !
I will take you on a journey through its famous collections and give a historical context of the art in relationship to the history of the museum.
The art collections are one of the finest in the world.
I look forward to showing you the museum , as a person with great love of this Chicago treasure !

Experience all that the second largest museum in the United States has to offer!

Tour of the Art Institute of Chicago

Come explore with me, a passionate native (and former Chicago Architecture Center docent), and see the amazing public art, architecture and hear the fascinating history of Chicago. This tour is a great introduction & overview perfect for the beginning of your stay to give you the lay of the land. Did you know we are home to the first skyscraper built in1885? As technology advanced buildings grew vertically using steel frame construction known as the first Chicago School.

We'll see many styles of architecture ranging from classic Beaux-Arts, Chicago School to Art Deco and International Style. We'll also see beautiful world-class art including Tiffany stained glass, Alexander Calder, Marc Chagall & Picasso.

Let the urban adventure begin!

Explore the city's architecture, art & history on this express Chicago walking tour!

Downtown Chicago 'Loop' Highlights Tour

Chicago Tour of the Pullman National Historical Park

Take a train ride* with me to the town of Pullman, home of the company town created by George Pullman in 1880 and now recognized as a National Park.

Did you know that initially, George Pullman did not want to build the town near Chicago?

This is a story of the American dream, a social experiment in company-owned towns, and the birth of the trade union and the civil rights movements in the USA.

On this tour, we will walk around the streets of Pullman together and learn why the town was created, its struggle to survive, its importance to the history of the trade union movement, and its impact on the civil rights movement.

We'll grab some lunch at a local eatery and discuss the lifestyle of George Pullman.

On the train ride back to Chicago we'll talk about what happened to the Pullman company and the subsequent struggles for the town.

*(Tour also available by car for an additional fee)

Join me!

Join me on a half day tour the historic town of Pullman and learn about the town and company created by George Pullman!

Private Car Chicago Highlights Half-Day Tour

Chicago is a spectacular city with so much to see and experience. You'll want a local guide to show off the best parts of the city while bringing you to those picturesque places to enjoy the views.

This tour takes you to the iconic Wrigley field and Wrigleyville neighborhood so you can take in some of the city's hometown spirit. A city in a garden, I know the perfect places to take a stroll with a view while I enlighten you about Chicago's rich history and vibrant culture.

We'll cruise through Chicago's premier shopping district and I'll show off the spectacular architecture in this famous neighborhood. While driving through downtown, I'll provide an overview of the hot tourist areas and give you ideas to maximize your time and visit the best attractions that you'll enjoy. Plus one more photo opportunity with a spectacular skyline view!

I'm happy to end the tour at an attraction or drop you back off at your hotel, or wherever you are staying.

Experience Chicago's beautiful sites and fantastic attractions with a city native who knows how to have a great time!

Walking around Downtown Chicago Architecture 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. My photographic "eye" will show you specific details and ornamentation you might not see otherwise. Be prepared to take a lot of pictures looking up, up close, and panoramically, all the while discussing the rich history of this city, starting with the natives on which land Chicago was built, the fur traders who came afterwards, and how the Great Chicago Fire reshaped the city and ushered modern architecture. 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.

An Introduction to Chicago's Downtown Architecture and Art

The Chicago Story - Private Half Day Tour

The first half of our tour consists of a two-hour stroll through downtown Chicago, past sites that evoke stories about fires, immigrants, riots, political shenanigans, plus titans of industry and finance. I will share the story of how Chicago went from a city of only 300 people to over a million -in less than 70 years-.

The other half encompasses a visit to the Chicago History Museum.

I grew up near Chicago, and it was the centre of my universe. I watched Chicago TV and sports, read Chicago newspapers, and envied its size and wealth. Annual trips into the city were highlights of my early life.

Chicago's ethnic tapestry, political dramas, and influence in American history were part of the reason I went on to earn academic degrees in history and religion. That scholarly background in turn has helped me continue to experience Chicago as a "lab" for my lifelong learning.

I am eager for you to experience a slice of Chicago with someone who is in love with the people, the place, and the story. I'm your guide!

St. Patrick's Church, survived the Great Fire

The Grand Hall inside Chicago's Union Station

Untitled Picasso sculpture in Daley Plaza

One of 37 moveable bridges spanning the Chicago River, most of any city in the world

Unveil the city's history from rivers & railroads to reformers & rebels.

A Little of This and a Little of That Driving Tour

Embark on a cultural adventure through Chicago as this tour guides you through the vibrant neighborhoods of Greek-town, Little Italy, and The Historical Mexican Community of Pilsen. Immerse yourself in the distinct flavors, traditions, and artistic expressions of these diverse communities, experiencing the rich tapestry of cultural heritage that makes Chicago a melting pot of unique and authentic experiences.

One clear example of this is Chicago's century-old Chinatown that transports you straight to eastern Asia. As soon as you set foot in this historic neighborhood, you're in for the best kind of sensory overload. Chinatown is filled with elaborately adorned streets filled with traditional specialty shops, ornate architecture, storefronts packed with colorful wares and souvenirs, and family owned restaurants.

Join me to discover more!

Church group enjoying a tour through Greektown.

This is a portrait representing true love. This art piece is one of many public art works located throughout the Historic Pilsen community.

The Mexican art museum, one of the stops on the tour.

The (Men in Action Group) enjoying a tour inside "The kAM Isaiah Israel Synagogue".

This is where you can experience the greatest "Italian Ice" ever. Little Italy Chicago.

Cultural adventure around the world in Chicago

Ferris Bueller Movie Tour at the Art Institute of Chicago - Orientational Walking Tour

In Ferris Bueller's Day Off, three suburban teenagers skip school, drive into Chicago, and explore well-known sites like Sears Tower, Wrigley Field, and the Art Institute of Chicago.

The scene that takes place inside the Art Institute of Chicago lasts only 2 minutes. But it is one of Ferris Bueller's most memorable. That's why I've created an entire tour around it. (Yes, really. )

Are you ready to experience firsthand the artwork and hear behind-the-scenes stories that inspired one of the most famous scenes in Chicago-based cinema?

A Rodin sculpture and Seurat painting are front and center in the movie

Do you remember where this reclining figure sits in the teen comedy?

Characters in the movie memorably mimic Rodin's 'Portrait of Balzac'

The characters Ferris and Sloane sneak a kiss in front of this stained-glass art

A Jackson Pollack work makes its way into 'Ferris Bueller's Day Off' as well

Don't leave the Art Institute without mimicking the character Cameron

The lions welcome you to the Art Institute of Chicago

Our group before Marc Chagall's 'America Windows'

Our final stop on the Ferris Bueller walking tour, Marc Chagall's 'America Windows'

Secure your spot on the most unique 'Ferris Bueller's Day Off' tour in Chicago

Being retired, I check my email and texts only about every two days.  Believe me, phone is best: 312-550-3807.   Yes, texting is possible, but other than the most utterly simple question, such as you wanting to postpone the start by five minutes,  I am likely to text you back saying,  "It'll be way easier if we just get on the phone.  Plus, we can customize your tour by chatting!"  Believe me, customizing the tour will make for a MUCH more rewarding experience for you, your time, and your investment.

In addition to what is listed in the itinerary below, you'll get the massive 1 square block, ultra grand City Hall (1895) , the iconic, sleek, art deco 40 story Board of Trade Building from 1930, several other 1920s-1930s very tall art deco buildings with beautiful lobbies, the two story high world famous Picasso sculpture, and the one of a kind, blue, reflective, round State of Illinois building with an amazing atrium,
Old and ultra new, cultural and business, all in one tour.

The throbbing heart of Chicago: giant, ultra-modern buildings, and plenty of cultural monuments as well

Downtown Chicago: Eastern Portion Walking Tour

Did you know that Chicago has been described as the Paris of the Midwest?

Your private tour will begin at the Museum Campus. Where three world-class museums are on over 20 acres of dramatic lakefront.

The Planetarium is your gateway to the stars, the Shedd Aquarium housing the mysteries of the seas, and the Field Museum home to Dinosaurs, a mummy's grave, ancient American Indian & Eskimo Culture, and much more collected from all over the world.

We will discover the Art Institute, the second largest in the U. S. Where you will be dazzled by a collection of art assembled to show the beauty and history of painting consisting of the most important Impressionist artists, we will venture right outside to the Magnificent Millenium Park. This a 21st Century landmark composed of beautiful gardens, amazing architecture & sculpture. We will also tour The Cultural Center, with the largest Tiffany SkyDome in the world.

I attended the Art Institute and as a student lived this tour every day - so join me!

An exhibition of sculpture of a Japanese artist at the Art Institute created in WWII internment camp.

Celebrating Andy Warhol at the World Famous Art Institute of Chicago

A recent private tour on the river exploring Architecture & history

A tour enjoying Great Art! The famous Grant Wood that lives at the Art Institute

The iconic Picasso for you to see at the Art Institute

Amazing Tiffany Dome at the Cultural Center; largest in the World!

Oak park tours

Explore with 65 tours and 11 guides.

Nancy K.

$ 350 (USD)

Johanna W.

$ 550 (USD)

Bob K.

$ 200 (USD)

Mimi F.

$ 245 (USD)

Colm R.

$ 325 (USD)

Colleen

$ 500 (USD)

Sylvie S.

$ 400 (USD)

J. Michael S.

$ 450 (USD)

Alicia D.

$ 250 (USD)

Kelli M.

$ 375 (USD)

Joe G.

$ 199 (USD)

Bob K.

$ 390 (USD)

Meet your local guides in Oak park

Customize your tour