Top Chicago Night Tours

Discover the beauty of Chicago at night during a 1.5-hour cruise on the Chicago River and Lake Michigan. Watch the city sparkle as you pass landmarks such as Museum Campus, Willis Tower, Aon Center and the John Hancock Building, and the illuminated waters of Buckingham Fountain. You'll learn about the history of the city from live commentary by your knowledgeable guide as you glide along the waterfront of Chicago.

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

See a new side of the Windy City—and admire Chicago's dazzling skyscrapers and landmarks, all lit up after dark—on this sunset tour by open-top bus. While your on-board guide provides insights, check off the city's best-known attractions in just one tour, from Navy Pier and the Magnificent Mile to the Museum Campus, and the Loop's skyline.

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

Enjoy an only-in-Chicago night out—and admire views of the city's skyline (and its evening fireworks shows) that most visitors miss—on this Lake Michigan cruise. Make your own way to the departure point at Navy Pier, hop aboard your well-appointed vessel, and set sail. In between marveling at the views, you can also purchase drinks and snacks from the on-board cash bar, if you wish.

Experience Chicago’s fireworks like never before on a river cruise with 3D viewing glasses. Cruise past major sights like Buckingham Fountain, Museum Campus, and the John Hancock Building while learning about the city's history from your onboard guide. Capture stunning skyline photos and enjoy front-row views of the dazzling fireworks from the mouth of the river.

Experience Chicago’s glowing skyline and scenic lakefront on a private, fully personalized night tour. Travel in comfort with your English-speaking driver, who shares stories and insights about the city’s architecture, neighborhoods, and history as the skyline comes alive after sunset. Begin along the Magnificent Mile, where illuminated skyscrapers and elegant streets create a stunning urban scene. Continue to the Chicago River for reflections of iconic buildings, then visit Navy Pier with its sparkling Ferris wheel and waterfront views. Drive along Lake Shore Drive to admire the dramatic skyline over Lake Michigan, and finish at Adler Planetarium for one of the city’s most spectacular panoramic night views. This flexible, door-to-door private tour offers a relaxed, immersive way to enjoy Chicago’s landmarks and lakefront illuminated under the night sky.

Discover the dark side of the Windy City on this nighttime crime history bus tour of Chicago. Through your expert guide's rich storytelling, immerse yourself in tales of notorious mobsters like Al Capone, Frank Nitti, and Bugs Moran as you explore infamous crime scenes including the site of the St. Valentine’s Day Massacre.

Explore a new side of Chicago and the city's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, John Dillinger, and more famous figures hung out. There are ample chances to get out of the bus and pose for pictures in front of a historic courthouse, among other infamous sites.

Discover a dark, spooky side of Chicago that most tours miss on this adults-only ghost walking tour. Keep an eye out for sinister specters and ghastly ghouls as you explore abandoned buildings and shadowy alleyways near some of Chicago’s most popular landmarks, including the Chicago Theatre, Millennium Park, and the Art Institute of Chicago.

Skip the hassle of planning your Chicago itinerary with this convenient hop-on hop-off tour, covering the city's must-see sights. With multiple strategically located stops, explore the Windy City at your own pace, hopping off to visit top attractions like the iconic Art Institute and famous skyscrapers. Enjoy insightful audio commentary as you cruise through the city, learning about its rich history and vibrant culture. Perfect for first-time visitors or those short on time, this tour offers flexibility and ease, ensuring you don’t miss any of Chicago’s highlights. Book your ticket today and experience the best of Chicago hassle-free!

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise. Witness the stunning skyline as you glide across the water, leading up to the spectacular fireworks display at Navy Pier. This 1.5-hour cruise offers a unique perspective of the city while providing a relaxed atmosphere for friends and family to gather and enjoy the show. Boarding begins 15 minutes prior to departure, so arrive early to secure your spot and make the most of this dazzling experience. - 1.5-hour cruise featuring panoramic views of Chicago's skyline - Marvel at the iconic fireworks show off Navy Pier - Departing and returning to 111 N Lake Shore Drive

Calling all fans of the paranormal, this evening ghost bus tour of Chicago takes you into the city’s darkest recesses—and reveals a side of the city few others get to experience. Travel with ease between locations where hauntings are reported to have taken place and listen to chilling tales delivered by your guide. The City Cemetery, the site of the notorious St. Valentine’s Day massacre, and more are all included.

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.

Set sail for an unforgettable evening aboard one of our River star, Island Time, where the drinks are flowing and the views are unbeatable. Enjoy a refreshing beverage as you cruise along the Chicago River, taking in the breathtaking iconic skyscrapers. .

Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

Step into the eerie past of Chicago on this thrilling 2-hour private ghost tour led by a local through the haunted corners of the Lincoln Park area.