All Chicago Tours &amp; Excursions in 2026 - page 20

Inside Tour of Chicago’s Fine Arts Building

1 hour to 1 hour 30 minutes

Enjoy a comfortable ride from your hotel or private residence—and get dropped off right outside the departure terminal—during this private one-way transfer from Chicago city center to O'Hare Airport (ORD). Get picked up right outside your door by a professional chauffeur. Travel a well-maintained car, minivan, or minibus, with room for up to 14 people. Free wait time is included in case you’re running late.

Private Transfer from Chicago City to Chicago (ORD) Airport

35 minutesFree Cancellation

Uncover the notorious history of Chicago's gangster era on this immersive bus tour that takes you through the city's most infamous landmarks. Visit the Palmer House, where Al Capone once mingled, and pass the Congress Hotel, rumored to be haunted by ghostly figures. Drive through Grant Park to learn about H.H. Holmes and the chilling Iroquois Theatre Fire. At each stop, delve into gripping tales of rivalries, secret doors, and tragic events that shaped Chicago's past. This tour is perfect for history buffs and those intrigued by the darker side of the city. - Explore key sites linked to Al Capone and Chicago's gangland history - Discover chilling tales of hauntings, Death Alley, and the tragic Iroquois Theatre Fire - Enjoy stops at iconic locations like the Holy Name Cathedral and Grant Park - Engage in a unique paranormal photo opportunity by the Chicago River

Chicago Gangsters and Ghosts Minibus Tour

2 hoursFree Cancellation

Enjoy a uniquely adventurous way to explore Chicago with this zombie apocalypse-themed smartphone scavenger hunt game. Upon booking, download the app and set off at a time that works best for you, with help from your remote interactive guide. You’ll be given a list of challenges to solve and objects to find to beat the zombies, all while exploring some of Chicago’s most popular corners.

Adventurous Scavenger Hunt in Chicago by Zombie Scavengers

1 hourFree Cancellation

Discover Chicago's vibrant history through an engaging scavenger hunt in Millennium Park. This interactive experience melds fun and learning as you uncover stories from the city’s founding in 1837 to its iconic landmarks. Explore notable sites like Cloud Gate and the Art Institute, while tackling quizzes that challenge your knowledge. The app-led format allows you to navigate at your own pace, making it perfect for families, friends, or dates. Capture memorable moments as you embark on this unique journey through the Windy City.

Chicago Scavenger Hunt Interactive Walking Activity

Your private luxury tour experience begins with a prompt pickup in downtown Chicago. Step inside the climate-controlled cabin of a world-class Rolls-Royce. Your professional chauffeur will navigate the bustling streets of the Windy City. Glance through the panoramic windows at towering skyscrapers like the Willis Tower. Coast down Michigan Avenue to admire the luxury boutiques of the Magnificent Mile. Pass by the architectural marvels of the Loop and the lakefront beauty of Grant Park. This tour itinerary maximizes your time in the city. It is ideal for couples celebrating an anniversary, travelers on a tight schedule, or anyone seeking a VIP Chicago experience. Avoid the crowds of standard tour buses. Enjoy the privacy, comfort, and prestige of DS Luxury Rolls-Royce Tour.

Downtown Chicago City Tour in a Rolls Royce[60 Minute Experience]

Let’s Roam leads the way as the top app-led adventure hunt company! Explore the city’s top landmarks and uncover hidden gems while tackling trivia questions and overcoming challenges. Whether you're collaborating with your team or sparking friendly competition, you’ll discover new facts and forge unforgettable memories. Let’s Roam Adventure Hunts are perfect for any occasion—from everyday fun to bachelorette parties, birthdays, corporate team building events, and beyond! Each participant selects an interactive role, with challenges tailored to every adventurer's spirit.

Amazing Scavenger Hunt: Time For a Go in Chicago

1 hour 30 minutesFree Cancellation

5% savings

from

US$15US$14

Explore the vibrant art scene of Chicago on the Offbeat Street Art Tour through Fulton Market. This guided walking tour takes you into a neighborhood where industrial buildings have become canvases for stunning murals and installations. Discover the stories and cultural influences that define this area, once a meatpacking district, now a hotspot of creativity and innovation. Ideal for both locals and visitors, this tour provides a unique perspective on Chicago's urban culture, with numerous photo opportunities along the way. - Guided walking tour through the artistic Fulton Market neighborhood - Discover vibrant murals and thought-provoking installations - Learn about the artists and cultural influences shaping the area - Perfect for locals and visitors seeking a fresh view of Chicago

Offbeat Street Art Tour of Fulton Market and West Loop

Offbeat Street Art Tour of Fulton Market and West Loop

2 hoursFree Cancellation

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic skyscrapers and stunning lobbies, learning the fascinating stories behind their designs. This 2.5-hour tour is perfect for architecture enthusiasts and curious travelers alike, providing a unique perspective on the birthplace of modern skyscrapers. Whether you’re a local or a visitor, discover why Chicago's skyline is renowned worldwide. - Private tour lasting 2.5 hours, perfect for families and small groups - Visit landmark buildings like The Sullivan Center and The Rookery - Expert local guide shares insider knowledge about architectural history - Flexible meeting points available for your convenience

Private Chicago Loop Architecture Walking Tour

2 hours to 2 hours 30 minutesFree Cancellation

Price varies by group size

Don’t rely on strangers or selfies to capture your vacation memories—with this private photoshoot experience, you’ll walk away from your Chicago getaway with professional photos to commemorate your experience. For solo travelers, the 30-minute Bronze Package offers 20 edited, hi-res photos; the 60-minute Silver Package is ideal for couples, and offers 35 photos; and the 100-minute Gold Package is perfect for larger groups, and offers 60 photos.

Private Photo Session with a Local Photographer in Chicago

Private Photo Session with a Local Photographer in Chicago

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s most influential neighborhoods. Guests will enjoy curated tastings from locally owned Black restaurants while learning about the people, businesses, and historical moments that helped shape Chicago’s Black cultural landscape. Along the route, we visit significant landmarks, including the site where Barack and Michelle Obama’s love story began, historic community gathering spaces, public art, and locations connected to the neighborhood’s rich legacy of entrepreneurship, music, education, and civil rights. Unlike traditional food tours that focus primarily on dining, this experience connects each tasting to the larger story of the community, providing travelers with insider knowledge and meaningful cultural context.

Explore Chicago Black Culinary Heritage

2 hours 45 minutesFree Cancellation

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenient pickup and enjoy a scenic drive as your expert guide shares insights about the region. Once at Lake Geneva, you’ll have free time to explore its picturesque lakeside paths, historic estates, and even take an optional cruise. Afterward, immerse yourself in the serene pathways of Anderson Japanese Gardens, where elegant bridges, koi ponds, and peaceful landscapes await. This personalized tour offers a relaxing and enriching experience, perfect for couples, families, and small groups seeking a nature‑filled escape.

Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

9 to 10 hoursFree Cancellation

Dive into Chicago’s Magnificent Mile on an interactive scavenger hunt, perfect for families, friends, or team building! Guided by clues on your phone, you’ll solve puzzles, unlock local legends, and discover iconic sites like the Old Water Tower, Tribune Tower, and bustling Riverwalk—plus hidden gems along the way. Go at your own pace, compete for fun, and see the best of Chicago’s lively downtown in a whole new way. Teams of up to six welcome; no local knowledge required—just curiosity and comfy shoes.

Magnificent Mile Scavenger Hunt: Chicago Walking Tour and Game

2 hoursFree Cancellation

Price varies by group size

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Lake Michigan Skyline Cruise in Chicago

Tess_K, Sept 2026

Captain Bob is the Best!

Info is great but pre-recorded. The route took us out along the breakwater and also ran closer to shore. Captain Bob was open to some questions, once we were docked. Ask him about the lock between the Chicago River and Lake Michigan…critical infrastructure that seems largely unnoticed…

Chicago River 90-Minute Architecture Tour

Judy_H, Sept 2026

So interesting.

The tour guide was very knowledgeable and funny. Devin ( i think that was his name ) I do believe he was co-captain. We just called him captain. While trying to get to where the boat was. We noticed a gentleman with a jacket that said Wendella We told him we were headed there now. He gave us directions. Then of course we 3 very mature ladies were confused again. So he rescued us again. He took us to the boat.Very kind and helpful man. We loved the tour. We just had a hard time ( sometimes ) figuring out which building she was talking about. I would recommend this boat tour to all. The bartender was also pretty cool. I got a fun foo foo drink. It was very good. ❤️

Lake Michigan Sunset Cruise in Chicago

Susanna_M, Sept 2026

Fun way to see the city from the lake

Not an architecture tour so don’t take this if that is what you’re looking for. A great way to see the sites at night. A very enjoyable evening and Bobby are guide was knowledgeable and available to everyone for any question they may have had! Highly recommend this tour!

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

Chicago Sightseeing River and Lake Cruise

Kim_D, Sept 2026

Worth Every Dollar Spent

This was a well worth the time and money spent on a water boat. Juniper who was the speaker on the boat let us know all kinds of good information and told us about some good history about the buildings and even some information about Lake Michigan . She talked about the Navy Pier to . My husband and I really enjoyed the ride looking at the beautiful lake and Downtown Chicago. We would totally recommend this 1 1/2 ride to all who would like a great ride with no shake up and hear some good knowledge from the staff on the boat. (Thanks Juniper)

Chicago Architecture River Cruise

beatrice_o, Sept 2026

Highly recommend

We really enjoyed the architectural tour. It was my favorite thing from our Chicago trip. Charley made it informational but also had a good time getting to know all the buildings and history of Chicagos skyline. Will def be back! I do recommend booking during sunset hour! We did the 90 min tour at 6:30pm

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Noah_G, Sept 2026

Just buy the ticket

Todd was excellent! Pay attention and ask questions because the tour guides are very knowledgeable. The scenery up and down the Chicago river is unmatched. The unique architecture and stories behind them are incredible. The boat is not fast, so take your time looking up and down each building. Sunset is the best time to go! Everything was lit up pink for Dolly Parton as well.

Chicago By Night River and Lake Cruise

Deidre_S, Aug 2026

A great experience

First Lady boat ride was a great experience. You will start on the Chicago river and merge into the Michigan lake. The view was amazing I mean amazing especially at night! The con was it can get a little bit chilly at night so bring a jacket. They sell blankets if you were to get cold and they also have a bar so you can sip and enjoy the ride. I would definitely recommend it.