Chicago Private Custom City Tour with Hotel Pick Up
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.
Duration: 3–4 hours
- Free cancellation
- Private tour
Chicago Architecture Tour: Underground Pedway and the Loop
This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago. On this tour, we will explore the famous and mysterious Chicago Pedway, a system of underground tunnels connecting 40 blocks downtown, popping in and out of buildings to see beautiful and fascinating interior spaces. You'll learn to use this system that most locals don't even fully know or use, and you'll be encouraged to continue exploring Chicago on your own after the tour!
Duration: 2 hours
- Free cancellation
Chicago's Original Gangster Tour by Bus
Our guides present an accurate account of the activities in Chicago during the 1920's and 1930's (Prohibition Era). You will hear about the exploits of Capone, Moran, Dillinger and the rest of the boys! Some sites included are: the St. Valentine's Day Massacre, the Biograph Theater, and Holy Name Cathedral. The tour is educational but also very entertaining because our Gangster Guides are actors. Our Untouchable Tour Gangster Guides take on the persona of a gangster and have fun with it.
Reservations are strongly recommended.
Duration: 1 hr 45 min
- Free cancellation
Chicago Night Crimes Tour by Bus
Join us for a fun night of exploring Chicago's crime history on this 2-2.5-hour bus tour that includes:
* World famous crime scenes like the St Valentine's Day massacre
* Stops on-and-off the bus at famous crime sites
* True Crime history
* Historic video footage
* Interactive live commentary
* Crime quiz
* Souvenir pamphlet with photos
* Luxury climate-controlled bus
* So much more!
Some of the world’s most notorious criminals, mobsters & gangsters bamboozled their way through Chicago. Escape into the city’s criminal underworld as you investigate stories about Al Capone, The Untouchables, the Chicago Mob and more. From a luxury coach, see the sites of storied crime scenes including Biograph Theatre, Holy Name Cathedral, and the St Valentine's Day Massacre, one of Chicago's most notorious murders. Snap photos of the historic criminal courthouse, and hop on-and-off the coach to walk the path that Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths.
Duration: 2 hours – 2 hr 30 min
- Free cancellation
Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults
Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s first city bike tour company, on this exciting & informative adventure which recently ranked Top 20 Food Tours in the World by TripAdvisor. The journey is a leisurely paced 13mi & includes deep dish pizza, Chicago-style hot dog, Italian Beef, & dessert. Upgrade to sample local craft beer! On the DAY version of bike tour, you’ll drink in the sights of Chicago’s beautiful northside neighborhoods, including the Lakefront and Wrigleyville, home to our Chicago Cubs baseball team. On the NIGHT bike tour, you'll ride through the major downtown attractions & see the lights of Buckingham Fountain, Millennium Park and the glorious skyline. Cruise the Lakefront Trail, one of the most popular waterfront bike paths in the country. Don’t miss out on this fun tour! You’ll leave with a profound understanding of Chicago, even if you only came for the food.
Duration: 4 hr 30 min
- Free cancellation
Skip-the-line: Art Institute of Chicago Guided Tour
Beat the crowds with an expert art historian guide on this exclusive early morning tour. Immerse yourself among the masterpieces housed within the acclaimed museum and listen as your guide brings each piece to life by sharing the story behind it. Let your guide lead you to the most important pieces of the 300,000-strong collection, taking the hard work out of finding where to go and what to see. Explore in a small group for a special, personal experience, and interact with your guide who can give insider’s insight into the museum.
Duration: 2 hr 30 min
- Free cancellation
Chicago Crime, Mobsters & Ghosts Walking Tour
Join us along the historic streets and alleys of Chicago as we walk among the spirits of mobsters and ghosts of the condemned.
This tour is for lovers of history, true crime, and haunted mysteries. Expect a sultry and gritty cocktail of Chicago's darkest stories hiding in the shadows of the Loop. From Grant Park to the Alley of Death, your expert local guide will shed light on the city’s secrets. Prepare for thrills and just the right amount of chills.
Duration: 1 hr 30 min – 2 hours
- Free cancellation
Chicago Pizza Tour
Enjoy Chicago’s only bus guided neighborhood pizza tour. Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza. Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias. In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.
Duration: 3 hr 30 min
- Free cancellation
Chicago City Tour with Architecture River Cruise Option
Uncover the Windy City on Chicago’s premier guided minibus tour! Discover 20+ top landmarks with photo stops at Cloud Gate "The Bean", Museum Campus, & the historic Palmer House.
Begin at the Palmer House, birthplace of the brownie, & see Frank Lloyd Wright’s design at the Rookery. View icons like Willis Tower & Soldier Field while learning local history.
Step off at Buckingham Fountain & Museum Campus for skyline views over Lake Michigan & Navy Pier. Pass cultural sights like Shedd Aquarium & the Field Museum.
Capture photos beneath "The Bean", see the Chicago River, & drive down Michigan Avenue past the Water Tower, Gold Coast brownstones, & Playboy Mansion.
UPGRADE YOUR TOUR: Select the Architectural River Cruise option at checkout to admire 40+ skyscrapers with live narration, the ultimate land & river experience!
75-minute cruise offered during summer (April – October)
60-minute cruise offered during winter (November – April)
Duration: 2–4 hours
- Free cancellation
Lake Michigan 30 Minute Speedboat Ride
Enjoy Chicago’s iconic skyline with an exciting speedboat Tour on Lake Michigan. Departing from Navy Pier, the Lakefront Speedboat Tour is the best way to view Chicago from the water. Seadog offers fun for the whole family (and the dog, too!) combining an exciting speedboat ride along the shoreline with informative and amusing descriptions of the world-famous Chicago skyline!
Duration: 30 min
- Free cancellation
Frank Lloyd Wright Oak Park Architecture Tour from Chicago
Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings. Travel in comfort with your English-speaking driver, who shares insights into Wright’s life, ideas, and influence on modern architecture.
Begin at the Frank Lloyd Wright Home & Studio, where he lived and developed many revolutionary designs. Continue through the Oak Park to admire beautifully preserved Prairie School homes and early residential works. Visit Unity Temple, one of Wright’s most celebrated modern religious buildings, then return toward Chicago to see The Rookery Building with its grand lobby and intricate design.
Conclude at Robie House, a masterpiece of Prairie School architecture showcasing Wright’s signature horizontal lines and integration with the landscape. This flexible experience offers architecture enthusiasts a relaxed way to explore Wright’s legacy and the evolution of modern American design.
Duration: 5 hours
- Free cancellation
- Private tour
Trickery Chicago Magic Show
Chicago’s most entertaining magic show! Fun, intimate, sometimes outrageous, and always hilarious.
Theater is located at 3453 N Halsted Street (near the SE corner of Cornelia Ave). Door opens 15 minutes before showtime and seating is general admission.
Venue is BYOB for guests 21+. Cups and bottle openers are available if needed. We do not stock ice but there is a 7-Eleven just down the street (3407 N Halsted). Performance runs approximately 1 hour.
Duration: 1–2 hours
- Likely to sell out
Save 10%
2-Hour Chicago Lakefront & Museum Campus Segway Tour
Looking for fun things to do in Chicago? Look no further! Join one of our professional guides on a scenic 6-8 mile Chicago Segway tour. Glide effortlessly through the fragrant garden paths of Grant Park to marvel at the iconic Buckingham Fountain. Enjoy the breeze as you explore the city's top attractions along the Chicago lakefront, including Museum Campus, with stops near Shedd Aquarium, Field Museum, and the historic Soldier Field, home of the Chicago Bears. This guided Segway tour offers a perfect blend of sightseeing and adventure, providing an unforgettable way to experience Chicago's most popular tourist spots that's great for locals and out of towners!
Duration: 2 hours
- Free cancellation
Chicago's Ultimate City Bike Tour of Top Downtown Attractions
Get acquainted with Chicago’s most iconic landmarks on this riotous guided Chicago bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adventure. Over the course of a 3-hour bike ride (traversed at a nice leisurely pace), you’ll get up close and personal with Chicago’s legendary Museum Campus, Grant Park, Chicago Riverwalk, Lakefront and Millennium Park. You’ll become intimately familiar with Soldier Field, The Adler Planetarium, Buckingham Fountain, The Pritzker Pavilion, and Cloud Gate (the formal name of Chicago’s dearly-beloved “Bean”). This tour is perfect for first time visitors looking to see all of the classic hotspots, and for returning guests looking to understand more about the landmarks they know and love. Hop on two wheels, and come make memories that are sure to last a lifetime! All equipment included on this Bicycle Tour of Chicago.
Duration: 3 hours
- Free cancellation
Chicago-Rosemont Indoor Skydiving with Two Flights
Feel the thrill of skydiving without jumping out of an airplane. It's true! Head to iFLY Chicago in Rosemont, a premier indoor skydiving facility powered by a state-of-the-art vertical wind tunnel. After a training session, you'll experience free-fall conditions with the help of an instructor. No experience is necessary, and afterward, you can take home a personalized flight certificate.
Duration: 1 hr 15 min
- Free cancellation
Chicago Hauntings Original Ghost Bus Tour
Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 23 years ago by the city's ghostlorist, Ursula Bielski. Ursula and her team of veteran paranormal researchers and historians have thrilled thousands of guests with firsthand experiences of this, one of the world's most legendarily notorious cities. We take you where the other walking tours simply can't--to the many shadowed corners where the fateful tales began. From the Fort Dearborn Massacre to the St. Valentine's Day Massacre. From the Great Chicago Fire to the Eastland Disaster. From ghost ships that sail Lake Michigan to the Chicago origins of "Ghostbusters" And to the lair of the Devil Baby of Hull House.
Duration: 3 hours
- Free cancellation
Chicago Architecture River Tour & Hop-on Hop-off Sightseeing Tour
Save 20% when you bundle these two iconic Chicago experiences!
Discover Chicago by road and river with a 48-hour Hop-on Hop-off Ticket and Shoreline Architecture Cruise combo! This ticket includes a 48-hour pass for our hop-on, hop-off Chicago sightseeing bus tour, and a pass for admission to Shoreline Sightseeing's must-do Architecture River Cruise! You'll see the city's world-famous architecture from iconic streets like Magnificent Mile, Lake Shore Drive, State Street, Clark Street and Grand Ave, and from all three branches of the Chicago River.
Create your own itinerary and explore at your own pace with unlimited bus exit and entry. Over 40 Chicago landmarks await you on the Shoreline Architecture Cruise, from hidden architectural treasures to the city’s most famous landmarks. Expert live guides explain how Chicago’s buildings, architecture and engineering made the city famous.
Duration: 2 hours
- Free cancellation
Art Institute of Chicago Private Expert Guided Tour
Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse the hallowed halls, you’ll discover an extraordinary collection spanning centuries and cultures, from classical masterpieces to cutting-edge contemporary works. Our expert guides will illuminate the stories behind each brushstroke, sculpture, and masterpiece, providing a rich narrative that breathes life into the art.
Duration: 2 hours
- Free cancellation
- Private tour
Chicago Candle Making Class On Magnificent Mile
Looking to experience something new? Great crafty event for date night, girl's night out, corporate events, or just plain ole solo.
Learn step by step techniques to make your own 100% soy wax candles. Experience cultivating your own personal customized fragrances for each candle. All the supplies are provided for you to create your own 8 oz custom candle - 100% soy wax, fragrances, vessels, etc.
Classes are 60-75 minutes.
Duration: 1 hr 15 min
- Free cancellation
Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"
Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air!
Fun for all ages!
You can join our friendly crew, to help raise one of the many sails on Windy, or just relax, and let others do the work!
Windy has a full bar, and a gift shop, to help you enjoy the sail.
Duration: 1 hr 15 min
City Cruises Chicago: Premier Lake Michigan Brunch Cruise
Enjoy a picturesque day dining on Lake Michigan with our Premier Chicago Brunch Cruise. You’ll indulge in a chef-prepared buffet meal featuring savory and sweet classics, bottomless mimosas, top-notch service, and breathtaking views of the city skyline, all while our live DJ sets the mood. Capture photos in front of Chicago’s famous landmarks, such as Adler Planetarium and Willis Tower, and soak in the sweeping panoramic views from the comfort of our comfortable indoor spaces and open-air decks. Join us for a spectacular brunch cruise that will not be forgotten.
Includes
2-hour brunch cruise on Lake Michigan
Chef-prepared buffet-style dining
Bottomless mimosas (must be 21 or older with valid ID)
Spectacular views of the Chicago skyline including the Willis Tower and Adler Planetarium
DJ curated music
Guaranteed table for your party size
Complimentary coffee, hot tea, and iced tea
Duration: 2 hours
- Free cancellation
River North Food Walking Tour
On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor foods from Chicago's best deep dish pizza restaurant, Rick Bayless' amazing Mexican fare and more.
In addition to all the delicious food, your guide will discuss the history, culture and food scene of the neighborhood. We have vegetarian options at all the food stops and can accommodate other dietary restrictions with advance notice.
Join us on a culinary adventure of Chicago's River North neighborhood. We've done all the delicious research to showcase the best eats in Chicago. Wear your comfy shoes, bring your appetite and we'll take care of the rest...
Duration: 3 hours
- Free cancellation
Fortune Reading with Cheese in Chicago
I am the only person in the US, and possibly the world, that offers this experience. It is both a demonstration and an interactive opportunity where you'll have tons of fun learning about the history of cheese magic and getting to try it yourself. And then you get to eat your fortune!
Duration: 1 hour
- Free cancellation
- Private tour
Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour
Discover Chicago’s dark side on a chilling 2-hour walking tour. Strolling just under 2 miles at an easy pace, we reveal stories of gangsters, tragedies, and restless spirits hidden behind the city’s glamorous façade. Hear of hidden mob headquarters, psychopaths in plain sight, and disasters like the Iroquois Fire and Eastland Disaster.
Join us in exploring historic interiors where gangsters once gathered and ghosts are said to linger. Along the way, explore the roots of ghost lore—are they real sightings or tricks of architecture? Decide for yourself if Chicago’s most haunted tales are fact or fiction. Perfect for fall nights and curious minds, this tour blends true crime, gangster history, and ghost stories into an unforgettable experience.
Duration: 2 hours
- Free cancellation