All Chicago Tours &amp; Excursions in 2026

Route 66 Multi Day Tour from Chicago to Los Angeles

14 daysFree Cancellation

$10$10

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Englewood, led by Historian Dilla, who uncovers the unique stories and contributions of these communities, providing an authentic experience of Chicago's diverse heritage. Whether you're a history buff or simply curious about local culture, these tours offer fascinating insights into the Windy City's past and present. The tours vary in duration but typically last around 2 hours, making them perfect for a quick but enriching adventure. - Discover the history and culture of Chicago's neighborhoods - Tours available in Englewood - Led by knowledgeable Historian Dilla for an authentic experience

2 Hour Englewood, Chicago 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.

$45$43

Special Offer

Chicago Loop Self Guided Ghosts Gangsters and Secrets Tour

Chicago Loop Self Guided Ghosts Gangsters and Secrets Tour

1 hour 30 minutes to 2 hoursFree Cancellation

$20

$16

Take a time travel journey inside Chicago's best-kept secret: a 125-year-old architectural marvel. This extraordinary building was envisioned by renowned architect Solon Spencer Beman, famous for designing the town of Pullman and the iconic Pullman Palace Car Company. Get ready to be transported through time and history as you explore the legacy of this architectural genius and the fascinating stories hidden within these hallowed walls. Join us for an unforgettable adventure into the past and witness the living testament to Beman's architectural prowess.

Main doorway to the Fine Arts Building, virtually untouched as designed by Solon Spencer Beman, Circa 1885.

Inside Tour of Chicago’s Fine Arts Building

1 hour to 1 hour 30 minutes

This private historical ghost walking tour in Chicago explores stories rooted in the city’s layered past. You will walk through Lincoln Park, an area shaped by transformation from cemetery grounds to residential district. What traces of earlier history remain beneath modern streets? Architectural landmarks reflect 19th-century development and urban expansion. Historic venues such as theaters and pubs carry narratives passed through generations. These accounts reveal how memory and place intertwine within the city’s cultural fabric. The experience offers a thoughtful perspective on Chicago’s past through legend and documented history. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Private Historical Ghost Walking Tour in Chicago Lincoln Park

$869$826

Book your private departure transfer from Chicago to Chicago O`Hare Airport (ORD) Avoid the hassle of waiting in long taxi or shared shuttle queues and use our private, door-to-door airport transfer. Your driver will be waiting for you at the scheduled time, and you can travel comfortably to your destination. • We track your flight. • Our driver greets you with a name plate. • We provide door-to-door service. • There are no hidden charges. • We use clean cars and professional drivers.

Chicago to Chicago O`Hare Airport (ORD): Departure Transfer

Chicago to Chicago O`Hare Airport (ORD): Departure Transfer

30 minutesFree Cancellation

$98$93

Chicago Gangster History Walking Tour of River North

With Crazy Dash, you'll use an app to explore Chicago in this exciting scavenger hunt! Use an app to find things around the city in any order you want, take photos, and collect points. At the end, take a look at the rankings to see your score compared to others across the country. All scavenger hunts have a live remote host that will help via chat. Crazy Dash is our most easy-going scavenger hunt. Come join us in Chicago today!

Adventurous Scavenger Hunt in Chicago by Crazy Dash

Adventurous Scavenger Hunt in Chicago by Crazy Dash

$10$10

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Bridgeport /Stockyard Tour, led by Historian Dilla, who uncovers the unique stories and contributions of these communities, providing an authentic experience of Chicago's diverse heritage. Whether you're a history buff or simply curious about local culture, these tours offer fascinating insights into the Windy City's past and present. The tours vary in duration but typically last around 2 hours, making them perfect for a quick but enriching adventure. - Discover the history and culture of Chicago's neighborhoods - Tours available in Bridgeport /Stockyard Tour - Led by knowledgeable Historian Dilla for an authentic experience

2 Hour Bridgeport /Stockyard Chicago Tour

2 Hour Bridgeport /Stockyard Chicago Tour

$45$43

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!

Chicago Small Group City Tour

9 to 10 hoursFree Cancellation

Experience a seamless and stylish journey from downtown Chicago to either O'Hare (ORD) or Midway (MDW) airports with our premier SUV transfer service. Our luxury SUVs offer ample space for up to 6 passengers and 4 suitcases, ensuring a comfortable and relaxing ride for business travelers and families alike. Enjoy the privacy and professionalism of a dedicated chauffeur who guarantees punctuality and a stress-free travel experience. Book your transfer today and arrive at the airport relaxed and on time. For your convenience and peace of mind, we require a working phone number for all bookings. This allows your professional chauffeur to send you a text message with their details upon arrival, guaranteeing a stress-free travel experience. Book today and arrive at the airport relaxed and on time.

SUV transfer from downtown Chicago to O'hare or Midway Airport

SUV transfer from downtown Chicago to O'hare or Midway Airport

45 minutes to 1 hour 30 minutesFree Cancellation

Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary theatre district, this tour brings the city’s spirit to life—one step and wave at a time. Highlights: • Discover downtown Chicago on foot with a 5-Star Private Guide leading the way • Cruise Lake Michigan with included tickets and audio commentary onboard • See breathtaking skyline views and snap iconic photos from the water • Learn the city’s best-kept secrets through fascinating stories and history • Get tailored recommendations on top spots to eat, visit, and explore next Did you know there’s a sculpture in Chicago that reflects the whole skyline? With Rosotravel’s private tour, you'll walk through the city’s most iconic spots, then see it all again from the water on a relaxing lake cruise. It's a fun, personal way to experience the best of Chicago in just a few hours.Reserve your spot ow!

Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets

3 hoursFree Cancellation

$263$250

Leave the city's hustle behind and embrace the tranquility of Mackinac Island, a destination where cars are absent, and the charm of horse-drawn carriages prevails. This tour includes a beautiful drive through the Midwest and a scenic ferry ride across the Straits of Mackinac, leading you to explore stunning limestone formations like Arch Rock, the historic Fort Mackinac, and the picturesque Victorian architecture downtown. Treat your taste buds to the island's world-famous fudge amidst the serene surroundings, making this a perfect escape for history enthusiasts and nature lovers alike. - Scenic drive from Chicago to Mackinac Island - Discover the unique charm of a car-free island - Explore Arch Rock and Fort Mackinac's rich history - Sample local fudge while enjoying Victorian architecture

2 Day Private Tour Chicago to Mackinac Island Exploration

2 Day Private Tour Chicago to Mackinac Island Exploration

2 daysFree Cancellation

Bucktown has a knack for keeping secrets - and most of them are deeply unsettling. On this self-guided walking tour, you'll hear the true stories behind the neighborhood's murders, hauntings, and disappearances, encountering a real-life fugitive, the ghost of a pub owner who still tends bar, and a winged creature with red eyes spotted across Chicago. Starting at the former Lincoln Tavern, where a 1980 robbery ended in multiple murders, you'll pass the spot where a 12-year-old boy was killed by a train in 1902. You will see where residents still report signs of his presence, and walk by the only Opus Dei-operated church in the country. The tour ends at Club Lucky, where three bullet holes still visible in the bar mark the spot where a Polish immigrant named Walter met his unfortunate end in January 1967. Sweet dreams.

Dark Tales of Bucktown: A Self-Guided Chicago Tour

40 minutes to 1 hour 20 minutesFree Cancellation

$12$11

2 hours Private Evening Walking Tour with the Ghosts of Chicago

See Chicago’s most iconic sights, hear the stories behind the city, and enjoy a comfortable sightseeing experience without the stress of navigating traffic or parking.With us, you’ll explore the highlights of the Windy City with a friendly, knowledgeable guide and comfortable transportation. From the spectacular Chicago skyline to world-famous landmarks, we make it easy to experience the best of Chicago in one memorable journey. Why Book with us? Comfortable transportation Friendly sightseeing guide Great photo opportunities ️Iconic Chicago landmarks Relaxed and enjoyable experience ‍‍‍Great for families, couples, groups, and visitors of all ages Whether this is your first visit to Chicago or you're returning to discover more, we helps you experience the city’s highlights comfortably and conveniently. Sit back, relax, and let us show you Chicago!

Chicago Private SightSeeing Tour

7 hoursFree Cancellation

$89$85

Skip the crowds this is a private tour for your group only! Embark on a captivating journey through the Loop’s architectural wonders with our Loop Architecture Tour in Chicago. Explore the iconic Chicago Board of Trade Building and the historic Rookery Building, steeped in timeless elegance. Marvel at the striking Calder sculpture in Federal Plaza, a highlight of the city’s public art scene. Admire the innovative design of the Marquette Building, a masterpiece of the Chicago School of Architecture. Step into the luxurious Palmer House, a landmark boasting historical significance. Discover the rich legacy of the Marshall Field and Company Building, a symbol of Chicago’s commercial prowess. Finally, delve into the cultural richness of the Chicago Cultural Center, showcasing the city’s artistic diversity. Join us on this unforgettable journey through Chicago’s architectural gems in the heart of the Loop.

Private Architectural Walking Tour in Chicago Loop Landmarks

Private Architectural Walking Tour in Chicago Loop Landmarks

$869$826

This family friendly tour uncovers the powerful legacy behind Fort Dearborn, the devestation of the Great Chicago Fire, and the re-birth tied to the World's Columbian Exposition, while witnessing Chicago's world-famous skyline. Explore a variety of breathtaking iconic landmarks, legends, and resilence that shaped the city, while learning the meaning behind the symbols of the Chicago flag. Learn how each star, stripe and historic site tells the story of innovation, preserverence, and civic pride.

Journey of the Chicago Flag Bus Tour

Discover a cherished Chinese tradition through a fun and creative Kite Coloring Workshop in Chicago's Chinatown. Learn about the fascinating history of kites, which were first invented in ancient China, and hear the cultural stories behind this centuries-old art form. Then, let your creativity shine as you design and color your own blank silk kite under the guidance of experienced instructors. Once your masterpiece is complete, you'll take it home as a unique keepsake of your cultural experience. This hands-on activity is suitable for all ages and offers an engaging way to connect with Chinese heritage through art and storytelling. - Learn the history and cultural significance of traditional Chinese kites. - Design and color your own silk kite to create a one-of-a-kind souvenir. - Enjoy a hands-on cultural activity suitable for participants of all ages. - Take your finished kite home as a memorable keepsake

Kite Coloring Workshop in Chicago

45 minutesFree Cancellation

$15$14

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local stories, historical insights, and highlights the architecture and communities that shape the city’s unique character. Begin in the Gold Coast Historic District with its elegant mansions and tree-lined streets, then explore Lincoln Park with its scenic paths, gardens, and historic zoo. Visit Wrigley Field to experience Chicago’s sports culture, followed by Hyde Park and the University of Chicago, known for its stunning architecture and intellectual heritage. Conclude in Chinatown, a lively cultural district with colorful streets, markets, and traditional restaurants. With a flexible, door-to-door itinerary, this private tour offers a relaxed, immersive way to experience Chicago’s history, culture, and diverse neighborhoods.

Chicago Private Neighborhoods Tour to Lincoln and Hyde Park

Chicago Private Neighborhoods Tour to Lincoln and Hyde Park

4 hoursFree Cancellation

Enjoy an effortless start to your Chicago trip with this private transfer service from O’Hare International Airport. After landing, grab your luggage and meet your driver, who will be waiting for you directly at the terminal. Then, climb aboard your luxurious, air-conditioned vehicle: you can sit back and relax—and take in the Chicago scenery—as your driver whisks you directly to your destination.

Meet and Greet Private SUV Transfer from ORD to Downtown Chicago

Meet and Greet Private SUV Transfer from ORD to Downtown Chicago

30 minutes to 1 hour 30 minutesFree Cancellation

Discover Chicago’s infamous gangster past on a private, fully personalized tour through the city’s historic Prohibition-era streets. Travel in comfort with your English-speaking driver, who shares captivating stories about Al Capone, rival gangs, speakeasies, and legendary crime events of the 1920s and 1930s. Begin at Biograph Theater, where John Dillinger was shot, then visit the St. Valentine’s Day Massacre site, a pivotal moment in Al Capone’s rise. Explore Holy Name Cathedral, the Cook County Criminal Court Building, and Harry Caray’s Italian Steakhouse, all linked to Chicago’s mob history. Conclude in the Chicago Loop, uncovering hidden speakeasies and secret nightlife spots from the Prohibition era. With a flexible, door-to-door itinerary, this private tour offers an immersive, thrilling look into the city’s dramatic gangster history.

Chicago Gangsters and Prohibition Private History Tour

Your journey begins with a southeast departure from the Vertiport, offering early views of the city’s iconic skyline. Flying east, you’ll head toward the lakefront and cruise south along the shoreline, passing Soldier Field, the Museum Campus, and continuing down to the historic Museum of Science and Industry in Hyde Park. From there, the route turns north, following Lake Michigan’s edge past Navy Pier, the John Hancock Center, and up to Montrose Harbor; a favorite city escape with marinas and beaches. You’ll then loop south once more, enjoying a sweeping view of Chicago’s lakefront before heading west to return to the Vertiport. It’s a dynamic tour showcasing both downtown and the scenic south shore in one unforgettable flight.

Chicago Helicopter Tour: City to Shoreline

Chicago Helicopter Tour: City to Shoreline

20 to 25 minutesFree Cancellation

Discover the very best of New York City in one unforgettable experience! From the majestic Statue of Liberty and the historic Brooklyn Bridge to famous neighborhoods, hidden gems, and picture-perfect skyline views — this tour captures it all. Enjoy guided stops at iconic landmarks, learn fascinating stories from your local guide, and experience the true energy of the city that never sleeps. Perfect for first-time visitors or anyone wanting to see it all, this experience blends history, culture, and unbeatable photo ops at every turn. Come ready to explore, snap amazing pictures, and make lasting memories on the ultimate NYC adventure!

2 to 7 hoursFree Cancellation

Chicago VIP Private Tour

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Must-Dos in Chicago

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What are people saying about Chicago

Chicago Sightseeing River and Lake Cruise

Nahrain_C, Oct 2026

Beautiful Chicago Experience

The boat guided was wonderful. The narration of Chicago's architectural history was interesting and informative. Everyone on board was friendly and accommodating. My only drawback was that it was not handicap accessible (not that I saw, anyway). Taking 2 flights of stairs down and then up again afterward is not easy for seniors or people with leg injuries/medical issues.

Chicago Architecture River Cruise

Tamsin_N, Oct 2026

Highly recommend

Great experience. There are wonderful views from the boat and our guide (Victor) was very informative and entertaining with his storytelling and historical facts. The architecture tour really brought the history of Chicago to life through the changing structures and styles of the buildings.

Lake Michigan Sunset Cruise in Chicago

michelle_m, Oct 2026

Solo Vacation Week -KCMO Visitor

I have always wanted to have a fun adventure. My bucket list of my things to do includes riding the Subway Train, Boat Ride on Lake Michigan as the Sun sets and be Solo. It's been a challenging year for me. I lost a family member, a personal friend and a professional colleague of mine. This is my way of honoring my friends and family and celebrating them.

Chicago River 90-Minute Architecture Tour

Val_S, Oct 2026

Perfect Day on the River

We did a 12:15p tour on Sunday in September. I booked tickets online the day before via the Viator app. We arrived a bit early because we didn’t really know where we were going. We got in line and waited there until the boat started boarding. There were a lot of other people there early too. I did not see a restroom at the waiting area but there is one on the boat. Once boarded, the tour guide, David, made announcements and we started off. I think we were moving by 12:20p. The tour was about an hour and a half - down one way, turn around and go back down by the Navy pier and back to the starting point. David told us about all of the buildings we passed and history of the city. He was awesome - he is very knowledgeable and easy to understand and listen to. It was fun to get a different visual perspective of all of the buildings along the river. Deboarding was as easy as boarding. We had perfect weather and we really enjoyed this.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Brenda_N, Oct 2026

Take the tour.

It was a fun experience. Give yourself extra time to find the appropriate meeting spot… There are a lot of similar tours in that area. There are limited shaded spots on the boat. The torque gives great views of the city, informative commentary about the surrounding buildings and a nice vantage point of the Riverwalk.

Chicago By Night River and Lake Cruise

Ravi_V, Oct 2026

It was a really good...

It was a really good experience. It got a bit cold when we got to Lake Michigan, but that was expected. It was great to listen to the history of the awesome architecture in Chicago. Anna, our guide was fantastic. She was extremely articulate and kept the tour interesting and funny at the same time. Cheers!

Chicago Favorites Ultimate Food and Walking Tour

Eunice_T, Sept 2026

Great Tour with a fantastic tour guide

Our tour guide, Casandra, was great. She shared some great information about the history of Chicago and provided answers to other questions that we inquired about. The food stops were great. I enjoyed the pizza, hotdog, popcorn, beef sandwich, and brownie. We were definitely full by the time our tour ended. Thanks for a great experience.

Flyover in Chicago

Angela_S, Sept 2026

Flying rollercoaster of fun around downtown Chicago

If you’re good with heights and motion, it is an AMAZING experience and way to see downtown Chicago. I recommend doing Flyover after you’ve been around downtown. day or two so you recognize some of the buildings as you fly. The one thing that would make it better is if they had a little better customer service and communicated about the number of stairs or even verbally offered an elevator option instead of just ushering everyone to the stairs. There are already a lot of stairs in Chicago so taking what seemed like 2-3 flights of stairs (as in going down to the L) was a surprise. The ride made up for this. It was so cool to fly all around the riverfront and downtown area. At one point, I put my hands in the air because it felt like we were on a rollercoaster drop. So much fun!

Chicago River 90-Minute Architecture Boat Tour

Angela_S, Sept 2026

Wonderful Architectural River Tour

I would absolutely recommend this tour to anyone who enjoys fun. Our tour guide, Tila, was informative, fun and hilarious. I learned so much about Chicago’s architecture and history, and how much the people of Chicago love this beautiful city. Take a drink, make sure your phone is charged and enjoy!

Chicago Crime and Mob Bus Tour

Su_O, Sept 2026

Best Crime Tour in Town

Our first time in Chicago and my daughter really wanted to see the crime tour. We had an amazing time driving thru Chicago and listing to the stories. We stopped in 3 locations and was able to get out of the bus and explore. See the actual "crime scene" We did it on Sunday morning, so traffic and places were not as crowded. TOTALLY WORTH IT