Top 10 Small Group in Chicago

Destination: Chicago.
This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which provides a unique and interesting touch to the normal tour experience. Being both sturdy in the water, and fast! Reaching up to speeds of 35 Knots! We work hard to provide historical context for our great city, as well as provide an exhilarating experience through the use of high speed runs and spins!
Known For: Chicago Historical Tours, Chicago Excellent Quality, Chicago Extreme Sports, Chicago Adventure Tours, Chicago Water Tours, Chicago Small Group, Chicago Zombie, Chicago Jet Boat Rentals, Chicago Zombie Slice, Chicago Speed Boat Rentals.
Duration: Around 1 hour and a half.

Destination: Chicago.
Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a recent transplant to Chicago or have lived among the Windy City’s ‘others’ for years, you’re about to get a haunted history that may leave you with more memories than you dare to retain.   Tours begin at the haunted Harry Caray’s Italian Steakhouse in downtown Chicago. A costumed guide will lead tour goers on a walking journey exploring the creepy past of one of Chicago’s most famous bootleggers, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home.
Known For: Chicago Ghost Tours, Chicago Small Group, Chicago Historical Tours, Chicago Excellent Quality, Chicago Food & Drink, Chicago Walking Tours.
Duration: Around 1 hour and a half.

Destination: Chicago.
We’ll begin our photo walk in Millennium Park with portraits at Cloud Gate (The Bean) — one of Chicago’s most iconic landmarks. During our time together, we’ll visit a rooftop spot for skyline views, cross the scenic DuSable Bridge, and stop by the elegant Wrigley Building — all perfect for beautiful photos. Along the way, I’ll guide you with natural poses and creative ideas, helping you feel relaxed and confident. By the end of this walk, you’ll not only have a beautiful photo gallery — you’ll have also visited many of the MUST-SEE places in downtown Chicago.
Known For: Chicago Small Group, Chicago Excellent Quality, Chicago Walking Tours.
Duration: Around 1 hour.

Destination: Chicago.
Take a tour of Chicago's Pedway system (a network of underground tunnels that allows pedestrians to pass from one end of the Loop to the other) and enjoy seasonal holiday decorations and sights along the way. Our tour begins in the lobby of the Swissotel where we descend into the Pedway. After a tour of the Chicago Cultural Center and its famous Tiffany Dome, we return to the Pedway for a short walk to Macy's department store. There, we'll view the famous Tiffany ceiling, the "Great Tree" in the Walnut Room and the store’s decorated holiday windows. We return to the Pedway and follow it to Civic Center Plaza for a visit to the Christkindlmarket, an authentic European holiday market. We return to the Pedway for a visit to City Hall followed by a short walk to a nearby L station. A quick train ride takes us to the origin/terminus of Route 66, the Art Institute’s lion statues, and Millennium Park to view the famous Cloud Gate sculpture, aka, The Bean and the city's holiday tree .
Known For: Chicago Christmas, Chicago Walking Tours, Chicago Small Group, Chicago Likely To Sell Out, Chicago Half-day Tours, Chicago Historical Tours, Chicago Likely to Sell Out, Chicago Seasonal, Chicago Cultural Tours, Chicago Excellent Quality.
Duration: Around 3 hours.

Destination: Chicago.
This is the only tour in Chicago that explores the movie "Ferris Bueller's Day Off" from the perspective of art. It's also the only walking tour that immerses you in the actual artwork featured in the 1986 American teen film. Over the course of the tour, you'll visit 3 floors of the museum, see 16 pieces of art, and leave with an appreciation of the works, their relationship to characters, and their placement in the camera's frame. ⚠️ NOTE: Admission to the Art Institute of Chicago is NOT included in the public walking tour. The tour starts under the stairs in the *Modern Wing* of the Art Institute, Griffin Court. Guests must digitally sign a general waiver of liability. Guardians must sign waivers for children under the age of 18.
Known For: Chicago Likely to Sell Out, Chicago Small Group, Chicago Likely To Sell Out, Chicago Art Tours, Chicago Cultural Tours, Chicago Seasonal, Chicago Walking Tours, Chicago Movie Tours.
Duration: Around 1 hour and a half.

Destination: Chicago.
Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour will start by meeting our knowledgeable Guide/Driver who will pick you up at your hotel or other location provided and then proceed with the exploration of the beautiful windy city.
Known For: Chicago Bus Tours, Chicago City Tours, Chicago Car Tours, Chicago Architecture Tours, Chicago Small Group, Chicago New Product, Chicago Excellent Quality.
Duration: Around 2 hours.

Destination: Chicago.
Get an exclusive behind-the-scenes look at the hit NBC drama Chicago P.D. TV Show Set Tour. Visit the actual filming locations where the show comes to life. Tour Highlights: - Explore the iconic Firehouse 51 exterior. - Visit the Molly's Bar a fictional bar on the show, but a real pub in Chicago. - Visit District 21 Station (UIC Police HQ) exterior. - Visit the famous Bean (Cloud Gate) at Millennium Park. - Visit the Chicago Cultural Center renowned for its stunning architecture. This tour is subject to filming schedules, and it can be customized to your needs. Tour participants are respectfully advised that this is an active firehouse; please be mindful of operations and follow guidelines, noting that the tour is independently operated and separate from the fire department. Additionally, For visits to Firehouse 51, the Bean, and the Chicago Cultural Center, please note that the tour guide will not accompany visitors, but detailed instructions will be provided.
Known For: Chicago Small Group, Chicago Excellent Quality, Chicago New Product, Chicago Movie Tours, Chicago Car Tours, Chicago Bus Tours, Chicago TV Tours.
Duration: Around 2 hours.

Destination: Chicago.
Eat, drink and discover Chicago's Loop and River North neighborhoods on our Chicago historic pub tour via the Brown Line!  Join us on this "over age 21" adventure for a combination of great Chicago stories and adult beverages as we tour historic sites and legendary pubs in the city’s Near North Side. We'll kick off our Chicago tour at the beautiful Marquette Building then head to the Adams Street Brewery, part of The Berghoff, Chicago's oldest, continuously-operating restaurant for a drink and a snack. Next stop, we board the Brown Line for a brief train ride to River North. In River North, we'll visit Brehon Pub with a fascinating story involving bribery and the Chicago media. The Green Door Tavern is next on our list. It's the oldest pub in Chicago and sits above a well-hidden, authentic Prohibition-era speakeasy.  We'll then board the train again and make our way back to the Loop where we'll have "last call" at historic, antique-filled Monk's Pub.
Known For: Chicago Walking Tours, Chicago Small Group, Chicago Likely To Sell Out, Chicago Half-day Tours, Chicago Historical Tours, Chicago Likely to Sell Out, Chicago Cultural Tours.
Duration: Around 3 hours and a half.

Destination: Chicago.
Capture your Chicago moments with a creative twist! Using both iPhone and Polaroid cameras, you’ll get a mix of vibrant digital images and timeless instant prints that showcase the city’s charm in every frame. Enjoy a relaxed and fun photoshoot experience—no posing pressure here! I’ll guide you through natural, flattering poses to help you look and feel your best. You’ll receive approximately 50 digital photos, 5 beautifully edited images, and 5 one-of-a-kind Polaroid prints to keep as stylish mementos of your Chicago adventure.
Known For: Chicago Photo Shoots, Chicago Small Group, Chicago Photography Tours, Chicago New Product.
Duration: Around 40 minutes.

Destination: Chicago.
Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigley Field exterior (Ferris Bueller's Day Off), the Chicago Board of Trade exterior (The Dark Knight), Union Station's staircase (The Untouchables), and Millennium Park's Cloud Gate (Source Code). Enjoy a seamless and comfortable experience exploring these famous sites.
Known For: Chicago Car Tours, Chicago Small Group, Chicago Bus Tours, Chicago Full-day Tours, Chicago TV Tours, Chicago Half-day Tours, Chicago Movie Tours, Chicago New Product.
Duration: Around 3 hours.