Top Chicago Cultural Tours

Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of Chicago’s the most memorable buildings, many of which are featured on this tour. After the World's Columbian Exposition of 1893, Chicago was determined to become a great cultural and commercial metropolis. This tour is a testament to that era's ambitions. See buildings by Daniel Burnham, Louis Sullivan, Holabird and Roche and other noted architects and hear the stories behind the city's architectural gems.

No city embraces summer quite like Chicago. Join in the celebration with friends and family on this epic fireworks cruise. Get up-close and personal every Wednesday and Saturday night with an unobstructed 360-degree view of this exciting and thunderous spectacle.

This unique tour of Chicago will allow for tourist to see most of Chicago’s 77 neighborhoods and city parks. There is no other tour that tours multiple neighborhoods in Chicago. Some tours show 1 or 2 neighborhoods, we travel through the South Side, North Side, Southwest, Northwest and a portion of Downtown showing more then 10 neighborhoods and attractions. Our tour includes 3 meals from 3 Chicago local eateries. The breakfast meal, Monday thru Friday, is eaten at one of former President Barack Obama's frequently visited restaurants. We eat at his signed table and take pictures.

Get ready to discover the storied architecture of Chicago. You’ll take the first elevator ride of the morning up to Skydeck at Willis Tower to see the city from a birds-eye prime vantage spot. Journey back to street level for an immersive tour of the Loop guiding you from the iconic ‘L’ train circling downtown Chicago to the city’s impressive Art Deco architecture. This insider’s look will supply you with the history to truly appreciate these colossal structures. A 90-minute river cruise awaits at the end of the tour taking you from the Chicago River to Lake Michigan.

Experience one of the world’s most beautiful cities on a cruise down the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branch to the East Bank Club, and then south past Willis Tower (Sears Tower) to the old Post Office Building. Take in magnificent city skyline views as you see more than 40 notable buildings, including the John Hancock Center and the Wrigley Building, and learn about their distinctive architecture from your onboard guide, an expert in architecture.

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour will navigate through the heart of the city on all three branches of the Chicago River while your professionally-trained architectural guide tells the story of more than 130 years of innovation in design, style and technique and why it is important today. The Chicago River Architecture Tour is the most authentic and encompassing Chicago experience the city has to offer.

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in Chicago! You can get the best of both worlds with this 2 in 1, history-based guided walking tour of Chicago’s gangsters and ghost stories, right from the famous Chicago Loop Vice District! Tour departs from 71 E Wacker Drive.

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than a century of groundbreaking architecture. The journey begins with an up-close perspective of Chicago's internationally-known architecture as seen from the Chicago River. Then venture through the Chicago Lock on to the calm, cool waters of Lake Michigan for expansive views of Chicago's extraordinary 26-mile skyline. Take the selfie of a lifetime on this inspirational experience!

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Walking tour paths explore historic crime scenes with great photo opportunities. True crime stories about Chicago Gangster Al Capone, The Untouchables, The Chicago Mob, Prohibition, John Dillinger, Frank “The Enforcer” Nitti, Cap George Streeter, Leopold & Loeb, H.H. Holmes and more. Visit historic landmark buildings like: The Biograph Theater, Holy Name Cathedral, Cook County Criminal Court House, Harry Caray’s Italian Steakhouse, etc. Tour famous Chicago neighborhoods: Streeterville, River North, Gold Coast, Lincoln Park, Old Town, Loop and Magnificent Mile. Locals and tourists agree that this educational and entertaining thing to do in Chicago is a unique cultural experience.

The lakeside metropolis of Chicago is famous for its striking skyscrapers, world-class museums and colorful history. Explore the “Windy City” at your own pace, with the choice of 24 Hour and 48 Hour tickets, all which include a hop-on, hop-off sightseeing bus tour with stops strategically located near the city’s top attractions. Hop on to experience sites like the Adler Planetarium and Navy Pier or hop off along the Magnificent Mile to shop, see the great city at heart-stopping heights from Willis Tower’s Skydeck.

Admire all of Chicago's fabulous lakefront sights and attractions on this Lake Michigan boat tour. Cruise along Lake Michigan and take in amazing views of the city’s famous skyscrapers from a great vantage point. Feel free to bring a lunch and enjoy drinks from the onboard bar as you relax on this sightseeing cruise.

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.

Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish! Our two-part tour begins by exploring the heart of downtown Chicago - with its iconic architecture, both old and new, views of the Chicago River, Millenium Park, and bustling city avenues (plus, a couple tasty local treats along the way). From there, we’ll hit the Central Loop, where locals go to grab their favorite foods, day and night. Try the best of Chicago fare and get to know the history and how-tos (and how-not-tos) behind iconic street and comfort food staples - from the infamous deep dish pizza to sandwiches to a loaded hot dog! Your local guide will entertain with fascinating stories and the everyday immigrant chefs and vendors responsible for Chicago’s eclectic food scene. By the end of the tour, you’ll have a deep appreciation for both the evolution of this excellent city and the role food has played in the lives of all Chicagoans!

Chicago has it all – amazing architecture, great food, and iconic sights both old and new. This walking tour takes you to some of the city’s best spots alongside a local guide where you’ll get the inside scoop on what makes Chicago so special. Not only that, we’ll throw in a couple of sweet, local treats to keep you going as we explore on foot.

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour semi-private (8 Guest Maximum) guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way. Highlights Generally Include: (if artwork is not on loan or being restored etc.) Paris Street, Rainy Day by Gustave Caillebotte Sunday on La Grande Jatte - Georges Seurat Sky Above Clouds - Georgia O'Keefe Nighthawks - Edward Hopper A Picture of Dorian Gray - Ivan Albright America Windows - Marc Chagall The Old Guitarist - Pablo Picasso Inventions of Monsters - Salvador Dali Four Mona Lisas - Andy Warhol

Enjoy Chicago’s iconic skyline with an exciting architecture cruise on the Chicago River. Departing from Navy Pier, this 75-minute narrated cruise is the best way to get up-close views of Chicago’s unique architecture and famous landmarks. Seadog offers fun for the whole family (and the dog, too!) with live narration along the city’s shore. Enjoy the speed of Seadog afterward during a short speedboat ride on the lake!

Short and highly selective information in the audio commentary for top 15 tourist attractions in around Chicago Highlights of this Self-Guided Audio Tour • It allows you to go as per your own convenience of time, pace and location. • Simply use our personally created itinerary which starts from main train station of the city then gradually moves one by one (if required). • Not necessary to download any location tracking apps. It can be listened online in any devices (smartphones, tablets, laptops, etc.) • Available in multiple languages, you can choose the one you’re most comfortable with (should be selected at the time of booking) • It is one of the best options with lowest price for travelers who prefer flexibility on their tour. • If you have any questions about any attractions, No worries, we will answer in your language instantly.

This small-group Best of Chicago tour highlights the best ways to experience the Windy City's most prominent sites and attractions including the breathtaking Chicago architecture illuminated at night. You'll visit the former tallest building in the world, visit Adler viewpoint and enjoy a relaxing boat tour on a Skyline cruise. You'll also experience a narrated drive through the Windy City passing by multiple points of interest including the remarkable Aqua Tower and stop at Buckingham Fountain to witness an outstanding night light show.

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago.  Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more.  The tour will be interactive and entertaining, covering history, architecture and culture.  We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.

Join a local guide on this exploration of Chicago’s amazing food scene! Navigate through the downtown streets straight to the vendors and restaurants We love most! As we pass by places like the Chicago Riverwalk and take in the city’s awe-some architecture, you’ll get to grips with the evolution of the city as immigrants brought their culinary influence to The Windy City. We’ll get to know generations-owned shops and the origins behind Chicago’s most beloved street eats, all the while appreciating fresh ingredients sourced locally from midwestern farms. Among the tastings that will add up to a full meal, you will get a taste of a local street food staple, perhaps the famous Chicago-style hot dog or Italian Beef, or another local favorite. A food tour of Chicago is not complete without a bite of the iconic deep dish pizza, and we will top it off with a sweet treat with a meaningful connection to Chicago. By the end, you'll have had the full Chicago foodie experience!

Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier shopping district. Hear the secrets and stories behind the striking buildings on North Michigan Avenue that have become architectural icons. Developed over the past 100 years, the street includes historically-inspired architecture in Parisian, Gothic, neoclassical and Art Deco styles sprinkled among Modern and 21st Century buildings. You’ll see skyscrapers, vertical malls, hotels, residential towers and some buildings that were designed to embody the brands sold inside.

Chicago is home to some of the world’s earliest skyscrapers. Get an up-close look at these 19th Century marvels, learn about innovations used to build them and discover how they transformed Chicago into a center of skyscraper design and engineering. Highlights on this walking tour include Burnham and Root’s Rookery (1888), a transitional building with a Moorish and Romanesque exterior and a stunning interior atrium re-designed by Frank Lloyd Wright; Adler and Sullivan’s Auditorium Building (1889), a masterpiece of acoustical and structural engineering; and Holabird and Roche’s Marquette Building (1895), an outstanding example of the metal frame expression with traditional details and decorations.

Learn about the life and work of Louis Comfort Tiffany as we visit some of Chicago’s most magnificent art-glass and mosaic installations, each designed and crafted by the Tiffany Glass and Decorating Company. In the late 19th Century, the Arts and Crafts movement revived an interest in decorative glass. New, well-regarded homes and public buildings from the era were considered incomplete without decorative glass or mosaics. Louis Comfort Tiffany, the preeminent practitioner of this art, gained great exposure for a chapel he designed for the 1893 World's Columbian Exposition in Chicago. Today, the city is home to one of the largest collections of Tiffany art glass in the United States. This tour introduces some remarkable examples of Tiffany's work.