Chicago City Private Tours
Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a unique and unforgettable experience, customizable from 2 to 8 hours. From the iconic skyline to hidden gems off the beaten path, I’ll take you on a journey that captures the heart and soul of this incredible city. I’ll also capture professional photos along the way, so you can take home memories of your adventure. With flexible pickup options, including quick tours during layovers at O'Hare, I make it easy to see the best of Chicago, no matter how much time you have. Book your tour today and let me show you the Windy City through the eyes of a local!
Duration: 2–8 hours
- Free cancellation
- Private tour
Christmas Eve Plated Dinner Cruise on Lake Michigan
Celebrate the magic of the season on the water with a Christmas Eve Premier Dinner Cruise in Washington DC. You and your guests will enjoy a holiday 3-course, plated dinner freshly prepared by our chef, full bar service, and City Cruises’ distinctive hospitality. While onboard, experience exceptional views of Washington DC’s iconic landmarks, DJ entertainment, and festive décor. Our team will happily take care of the details, leaving you to celebrate the holidays on the Potomac River with your friends and family. Happy Holidays
Includes
Three-hour Christmas Eve dinner cruise on the Potomac River
Chef-prepared, three-course, plated holiday menu
The most breathtaking views of the nation's greatest landmarks including the Washington Monument and Lincoln Memorial
DJ entertainment
Complimentary coffee, hot tea, and iced tea
Duration: 3 hours
- Free cancellation
Chicago Loop Self Guided Ghosts Gangsters and Secrets Tour
Downtown Chicago has a dark history hiding in plain sight. This self-guided audio tour takes you through the Loop on your own schedule, with narration on your phone at every stop.
Start at the Chicago Riverwalk, where the SS Eastland rolled over at its dock in 1915. Walk into Death Alley behind the site of the Iroquois Theater fire. Hear the ghost stories of the Palmer House and the Congress Plaza Hotel, the secrets of the Rookery, and the stories beneath Willis Tower, then finish on the steps of the Art Institute.
No group, no guide, and no fixed start time. Go at your own pace, stop for a drink along the way, and replay any story you like. All you need is a phone and headphones.
Duration: 1 hr 30 min – 2 hours
- Free cancellation
- Private tour
Hyde Park Walking Tour History Race and Urban Change
Discover the rich history and dynamic transformation of Hyde Park on this engaging walking tour. Delve into the neighborhood's evolution from a lakeside retreat for the elite to a vibrant, diverse community shaped by migration, policy, and social change. Explore iconic landmarks like the Museum of Science and Industry while gaining insight into the impacts of racial segregation and urban renewal. This tour is designed for history buffs and urban studies enthusiasts, offering a nuanced perspective on the intersection of race and community development.
- Walk through Hyde Park and learn about its historical significance
- Visit key sites related to civil rights and urban policy
- Understand the neighborhood's transformation and ongoing challenges
- Perfect for history lovers and those curious about social dynamics
Duration: 3 hours
- Likely to sell out
- Free cancellation
- Private tour
Lincoln Park Zoo & Nature Museum Private Tour
Cover three Lincoln Park stops on a private walking tour through Chicago: the Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and Lincoln Park Zoo. At the museum, visit the Butterfly Haven and Birds of Chicago exhibit; admission is included. Walk through Victorian-style greenhouses with orchids and tropical palms, and see zoo habitats while hearing conservation stories from your guide.
Duration: 2 hours
- Free cancellation
- Private tour
Chicago Walking Tour: Art Deco Skyscrapers Riverfront
Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish materials and geometric ornament. Discover the origins of Art Deco while admiring buildings like the Carbide and Carbon Building (now Pendry Chicago), the Chicago Motor Club Building (now the Hampton Inn) and the colorful, but often overlooked, Trustees System Service Building (now the Century Tower)—all of which are designated Chicago landmarks. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.
Duration: 1 hr 30 min
- Free cancellation
Chicago Museum of Contemporary Art: General Admission Ticket
The MCA Chicago is one of the nation’s largest multidisciplinary museums devoted to the art of our time with an international reputation for presenting ground-breaking exhibitions.
Originally conceived as a "Kunsthalle" or non-collecting art hall hosted temporary exhibitions of new and experimental artists, the museum has no permanent exhibits on view. Instead, you'll find work by living artists across media in exhibits that change every few months.
The MCA also boasts an award-winning Store and Marisol, the restaurant and bar, featuring innovative flavors in an immersive art environment. Please call the Box Office for questions or exchanges.
Duration: 1–3 hours
- Free cancellation
Chicago All Day Water Taxi
Shoreline water taxis are the fast and fun way to get to Chicago’s top attractions. Our water taxis aren’t tours, but they are a great way to get around town. Offering multiple docks conveniently located near major attractions including Navy Pier, the Willis (Sears) Tower, Michigan Avenue, Museum Campus, and Union Station.
Duration: 15 min – 20 min
- Free cancellation
Chicago Small Group City Tour
Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods with personalized attention and insider knowledge. Enjoy a hassle-free day with transportation, tickets, and lunch included. Explore Millennium Park, Navy Pier, and more, with plenty of photo opportunities and fascinating stories. Book now for an unforgettable Chicago adventure!
Duration: 9–10 hours
- Free cancellation
Chicago Architecture Walking Tour: Incredible Art Deco Interiors
Though the Art Deco style throws us back in time, it’s actually a futuristic style — it’s meant to make people in the 1920s think of the future. The gleaming materials, the perfect precision of the details… it’s the epitome of glitz, glam, and elegance. On this tour, you’ll walk in the footsteps of those high on the potential of the future, before the infamous Crash of ‘29. We’ll explore several stunning interior spaces within the Loop and near the Chicago River, going inside not only the great Art Deco buildings of the Loop, but also a few buildings you’ll recognize from popular boat tours. But the great thing is that you’ll go where most boat tour guests won’t ever go: inside these gorgeous Art Deco buildings, where you’ll be amazed by the beauty that people don’t know is right there behind closed doors.
Duration: 2 hours
- Free cancellation
Chicago Tour South Side
The Blue-Collar side of Chicago many call it! This tour will show The Ford Factory, home of the steel mills, the blue-collar neighborhoods and many places on the South Side, home to the 44th President of The United States, Barack Obama. We tour Bronzeville! A historical African American neighborhood and early business district as well as Hyde Park, home of the World renowned University of Chicago (the spot where the atomic bomb was born and yes we show the spot!) We explore South Lake Drive and life along the lake. Chicago has a border with Indiana, we show how that special dynamic works. We visit Beverly Hills, Chinatown, and the large and highly populated Puerto Rican Neighborhood “Little Village”. We also pass through Pilsen, a proud Mexican community. Cook County jail, we pass by it too! We go thru Little Italy Greektown. It’s blue-collar! We visit a lime quarry in the Bridgeport neighborhood. After this tour you will know tons about The Southside of Chicago.
Duration: 4 hours
- Free cancellation
Save 10%
Chicago Art Heist: Millennium Park Puzzle Adventure
You just stole Edward Hopper's Nighthawks from the Art Institute of Chicago. Now you need to disappear into the city before anyone notices. This self-guided escape game turns Millennium Park into a thrilling art heist where every landmark hides your next move.
Solve 14 puzzles at Chicago's most iconic public art. Decode clues at Cloud Gate, crack a cipher at Crown Fountain, lose your tail on the BP Bridge, and face a moral reckoning at Buckingham Fountain.
Download the Questo app, activate with your booking code, and start at the Art Institute on Michigan Ave. No guide needed, just your phone, clues and a map in the app.
Discover why Calder's Flying Dragon was his final sculpture, how Frank Gehry convinced the mayor with squiggles on paper, and the story of a boy sculptor pulled from an Illinois coal mine.
About 95 minutes, 14 stops, 3.4 km through Millennium Park and Grant Park. Available all day. Perfect for art lovers, couples, and first-time visitors to Chicago.
Duration: 1 hr 35 min
- Free cancellation
- Private tour
Nitti’s Supper Club: Chicago Mobster Speakeasy Dinner Show
Step inside landmark building of Harry Caray's Italian Steakhouse in River North, once owned by infamous Chicago mobster Frank Nitti, and travel back in time for dinner and a show based on the real-life murder of Eddie O'Hare.
This irreverent comedy features an ensemble cast of characters, many of whom walked the very halls of 33 W. Kinzie back when Nitti called it home. The immersive experience invites you to step into the role of partygoer at Frank Nitti's birthday, and delve into the unsolved murder of Edward J. "Easy Eddie" O'Hare -- Al Capone's lawyer and father of war hero Butch O'Hare for whom the airport is named. The crime was never solved, but suspects included Frank Nitti, his wife Annette, Al Capone and several others. Can you crack the case?
The interactive show is filled with historical anecdotes, laughs, audience interaction and toe-tapping musical productions.
Duration: 3 hours
- Free cancellation
Classic Chicago Food Lovers Tour in River North
Get a taste of Chicago on this small-group walking food tour and explore the specialties of River North neighborhood. Dive deeper into the culinary history of the place while trying out the best dishes to illustrate different cuisines.
Follow your guide’s advice not to get lost in a great diversity of options and enjoy the most peculiar delicacies including deep dish pizza, Italian beef, and hot-dogs. Feel your stomach with delight and your head with new information as you walk and learn something new with every step you make.
- Eat your way through the River North neighborhood to get a real taste of the City by the Lake.
- Combine walking tour with history insights and culinary tips from your guide.
- Enjoy a small group for better personalized experience.
- Benefit from your guides expertise and learn more about restaurants and cafés of Chicago.
Duration: 2 hours
- Free cancellation
Field Museum Basic Admission Ticket Plus VR Experience
A visit to the Field Museum unlocks a world of discovery with access to captivating exhibitions like the Griffin Halls of Evolving Planet and the iconic SUE the T. Rex. Explore the Grainger Hall of Gems and delve into Native Truths: Our Voices, Our Stories. Enhance your experience with a choice of one virtual reality adventure upon arrival, either 'Drop in the Ocean' or 'VR Transporter'. This ticket promises an enriching day filled with knowledge and wonder.
Duration: 4–5 hours
- Free cancellation
- Skip the line
Chicago's Fireworks Show aboard Tall Ship Windy!
Enjoy the most Unforgettable Fireworks Cruise in Chicago!
A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a leisurely evening sail past the brilliant and beautiful Chicago nighttime skyline.
Windy provides the accompanying sound track, over the ship sound system coordinated fireworks display, amazing show!
Rain or Shine event.
no umbrellas are allowed to be opened underway.
Tall Ship Windy, located on Navy Pier, and we have a ticket booth and dock, in front of the Billy Goat Bar and Grill. Arrive early, as fireworks crowds are huge! expect travel delays.
Duration: 1 hr 30 min
Chicago River Spectacular Fireworks Show and Tiki Bar Cruise
Fireworks Cruise Aboard Island Time – See the Sparks Fly the Island Party Way!
Experience Chicago’s dazzling fireworks like never before—from the deck of our floating Tiki Bar, Island Time! Cruise along the scenic Chicago River, soaking in the iconic downtown Chicago architecture as the city begins to glow.
Enjoy a drink, relax to island vibes, and take in the stunning views before the grand finale: a spectacular fireworks show lighting up the night sky. It’s the perfect mix of laid-back fun and unforgettable scenery.
Curious about the historic and modern buildings lining the river? Our friendly crew is happy to answer questions and share fun facts as you cruise.
Fireworks, cocktails, and Chicago charm—see it all the Island Party way!
Duration: 1 hr 30 min
Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights
Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davidson Museum, free time at the Milwaukee Public Market, and an optional Miller Brewery tour and tasting. Enjoy scenic views along the lakefront and an outside visit to the Milwaukee Art Museum before returning to Chicago. Ideal for travelers looking for a relaxed, well-rounded introduction to Milwaukee.
Duration: 8–10 hours
- Free cancellation
Chicago's West Side Foodie Ride Bike Tour
Take a detour off the beaten path, and explore the flavors of Chicago’s delicious West Side with Bobbys's Bike Hike & Food Tours, America's longest running city bike tour company, who recently ranked as Top 20 Food Tours in the World by TripAdvisor and Top 10 Food Tours in America by USA Today! This 4-hour guided food and bike tour is the perfect way to learn more about Chicago's immigrant neighboroods and taste authentic Chicago culinary dishes along the way. You’ll explore the cultural cuisines of historic Fulton Market district, Ukrainian Village, Wicker Park, and Lincoln Park. The Chicago Bike and Food tour finishes with a chocolate tasting in Old Town. You’ll learn the history of these beautiful neighborhoods and the tradition behind each of the dishes we sample. Ride through Chicago's gorgeous and unique neighborhoods, plus our legendary Lakefront Trail! There is no better way to explore Chicago than by bike! All equipment is included on this food and bicycle tour of Chicago.
Duration: 4 hours
- Free cancellation
Chicago Attractions Pass: Save up to 50% - Includes 360 CHICAGO
Enjoy admission to more than 30 of Chicago's most popular attractions with Go City's All-Inclusive Pass. Go City lets you create your own itinerary and save far more than if you were to purchase individual attraction tickets. Take a hop-on hop-off bus tour of the Windy City, admire the stunning views from Skydeck Chicago, and much more. You can visit as many attractions as you like over the course of 1, 2, 3 or 5 days.
Access your Pass in the Go City App and simply simply show it at the gate or ticket office to gain admission. The App acts as your digital guidebook including attraction information and details on which attractions require reservations in advance.
Duration: 1–5 days
Chicago Private Rental Yacht Charter
S. Silvera Charters offers a unique luxury yacht rental for those looking to create unforgettable memories on the water. Perfect for special events or leisurely cruising, this charter allows you to set your own schedule and enjoy a personalized experience. With a minimum rental of three hours, you can relax on board while exploring beautiful coastal views. Captain's fees are separate, ensuring a tailored experience for your group.
- Exclusive yacht rental for luxury experiences
- Flexible scheduling with afternoon and evening options
- Minimum three-hour rental for ample exploration
- Personalized service with optional captain at an additional fee
Duration: 3–8 hours
- Free cancellation
Chicago City Tours See It All No Time Wasted
Skip the corny jokes and never-ending speeches — our shared tours are built for travelers who want the real Chicago, not a stand-up routine.
✔️ Over 20 iconic stops
✔️ Zero wasted time
✔️ Only the best views, landmarks, and photo spots
We don’t stall, we don’t drag things out — and when we say “See All of Chicago,” we mean it. From skyline views and lakeside gems to architectural icons and hidden local favorites, our guided route is packed with unforgettable stops — and none of the filler.
Let’s explore the city — the right way.
Duration: 4–8 hours
- Free cancellation
Private Chicago Guided Tour with Hotel Pickup
One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour guide take you around the most important sites and locations of Chicago.
Being a private tour, stop whenver you want to take pictures and also explore by foot specific locations.
Pick up is included from your hotel or place of choice inside the city and downtown Chicago. Please include this information as well as a contact number when booking.
This private tour will give you a great experience to get to know Chicago. This is a 4 hour private tour with driver and separate tour guide.
During this tour, you will explore great locations in Chicago like the Richard J. Daley Center. There will also be a photo stop at the Lakefront Trail and South Michigan Avenue.
Don't miss the Grant Park, Cloud Gate and of course the Downtown / The Loop.
This private tour will finish off at your hotel in Chicago.
Duration: 4 hours
- Free cancellation
- Private tour
Chicago Sunset Segway Tour
Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views as well as views of Chicago's world-famous skyline and graceful lakefront. This segway tour departs near Millennium Park as dusk arrives and passes sights like Buckingham Fountain, Chicago’s majestic lakefront, and the Museum Campus.
Duration: 1 hr 30 min
- Likely to sell out
- Free cancellation