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Cruises & boat tours

Cruises & boat tours
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Our most recommended Chicago Cruises & boat tours

Chicago River: 1.5-Hour Guided Architecture Cruise

1. Chicago River: 1.5-Hour Guided Architecture Cruise

Experience more of Chicago by boat than on any other architectural cruise. See architectural highlights and enjoy an open-air deck or climate-controlled interior as you travel the main River and its north and south branches. View all of Chicago's architectural highlights during this comprehensive sightseeing tour. Be entertained by the expert and friendly tour guides as they explain the 130 year-long history behind the skyline, while bartenders and staff keep you comfortable with refreshments.  Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. The tour starts at the Michigan Avenue (DuSable) bridge and goes up the main branch of the Chicago River past Wolf Point. It then cruises along the north and south branches of the river, before heading back past the Chicago Riverwalk towards Lake Michigan. On the way, learn about ornate, historic early skyscrapers like the Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building. Don't miss the circular Marina City Towers, the majestic Willis Tower (formerly the Sears Tower and the tallest building in Chicago) the soaring AON Center, and more modernist structures like Aqua, Trump Tower, Nuveen, and the new Vista Tower. During your cruise, have the opportunity to enjoy a full-service cash bar featuring authentic Chicago products, including local beer and spirits, and Garrett’s Popcorn. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket

2. Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket

Marvel at the views from 1,000 feet over Chicago’s legendary Michigan Avenue with this ticket to the 360 CHICAGO observation deck on the 94th floor of the John Hancock Center. Save time with skip-the-line access to this popular attraction. Head up to the 360 CHICAGO observation deck to take in breathtaking views of Chicago’s lakefront and view the city skyline from above. Take a peek at 4 neighboring states from this height. Feel the thrill of a 40-second ride in one of North America's fastest elevators to the observation deck to experience what 'Travel & Leisure Magazine' voted one of the best views in America. Enjoy an interactive exhibit on the Ground Floor that highlights Chicago’s rich history and showcases 9 of the city’s culturally unique neighborhoods. On the 94th floor, explore the history and architecture of the magnificent city stretched out before you. To enhance your experience, download the Magnicity App for a guided tour right from your smartphone. The App includes an interactive viewfinder, unique facts, stories and recommendations. Enjoy a thrilling photo opportunity at CloudWalk, a breathtaking 3D mural with the optical illusion of walking in the clouds. Relax and take in the view at the 94th floor’s Cloud Bar which serves up iconic Chicago snacks, neighborhood-inspired Cocktails, and a local brew, Moody Tongue, on tap. By purchasing this timed ticket, you get to skip the ticket desk and present your barcoded voucher to security to be scanned - you may have to wait in a short line at security, then head directly into the Ground Floor Exhibits, and then on to the Elevator Line.

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

3. Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Experience the views from the Centennial Wheel at the Historic Navy Pier in Chicago with this attraction ticket. Be suspended over Lake Michigan at the mouth of the Chicago River. Marvel at the Chicago skyline and gaze out over the sparkling waters of Lake Michigan. Choose between two options: With the Regular Barcoded ticket, skip the ticket line and enter the line to board the wheel. The Fastpass Express ticket allows you to skip both lines, and gives you VIP access. Both tickets allow you to visit within 7 days of your scheduled ticket date. Enjoy the Centennial Wheel, which was built in 2016 to celebrate the 100th anniversary of the Navy Pier opening. Featuring 42 gondolas, each holding 8 people, it operates year-round. They also feature LED lighting, padded seats, TV screens, and speakers, as well as panoramic windows on all 4 sides. A ride on the wheel gives you plenty of time to enjoy these panoramic views of Chicago as they unfold around you, and allows you to visit the top three times. Relax and take in the view, or get your camera out to snap pictures of the ever-changing Chicago landscape.

Chicago: Willis Tower Skydeck and The Ledge Ticket

4. Chicago: Willis Tower Skydeck and The Ledge Ticket

Enjoy an unrivaled view over the city of Chicago on a trip up the city's Willis Tower. This famous building, once known as the Sears Tower, is not only home to a Skydeck on the 103rd floor, but it also features The Ledge, a series of 4 glass-paneled boxes that extend out from the building's facade to give visitors a view straight down. As you wind through the ground levels of the Willis Tower, you will be surrounded by museum-quality exhibits highlighting the iconic tower. Learn about Chicago's rich history and culture through these informative visuals. Watch a video presentation, "Reaching for the Sky," where you will be briefed on the history of the building and of architecture in Chicago. Then step into your elevator and you will be amazed at how quickly it ascends. As you travel, your multimedia-equipped elevator will inform you about your vertical progress. Upon reaching the 103rd floor, step out onto the Skydeck, which offers views spanning over 50 miles and across 4 states. Then summon your courage to step out onto The Ledge, a glass balcony that hangs over the edge, for vertigo-inducing views 1,353 feet (about 412 meters) straight down to the city below! Download the Skydeck Mobile App for a free viewfinder which points out many of Chicago’s notable landmarks. Learn more about sights like Navy Pier, Wrigley Field, Grant Park, Art Institute of Chicago, Shedd Aquarium, and Field Museum of Natural History.

Chicago: 45-Minute Family-Friendly Architecture River Cruise

5. Chicago: 45-Minute Family-Friendly Architecture River Cruise

Admire Chicago’s impressive architecture from a unique perspective aboard a cruise sailing down the Chicago River, which features an indoor and outdoor deck, along with live commentary tailored to entertain the whole family. Treat yourself to a full-service cash bar at your own expense. Experience the best of the Chicago River from Lakeshore Drive to the Willis Tower, navigating along the South branch of the river, before heading back past the Chicago Riverwalk towards Lake Shore Drive and Lake Michigan. Be entertained by the fun and experienced tour guides as they explain the history behind Chicago’s buildings along the river and the exceptional architects who created this ever-changing skyline. Enjoy the most relaxing way to sightsee in Chicago, exploring the city free of traffic, noise, and congestion. Make sure to visit the full-service cash bar featuring authentic Chicago products, including local beer and spirits. Explore the open-air decks that allow you to feel the cooling river breeze and see the city from many vantage points that provide perfect photo opportunities.

Chicago: Architecture River Cruise Skip-the-Ticket Line

6. Chicago: Architecture River Cruise Skip-the-Ticket Line

Skip the lines at the ticket office and climb aboard a state-of-the-art cruise for a 75-minute cruise of all 3 branches of the Chicago River, and marvel at the architecture that has made the city so legendary. Get an insight into the buildings and engineering of a city that gave birth to the skyscraper and is the spiritual home of modern American architecture. Your expert guide will lead you down the Chicago River to uncover hidden gems, as well the city’s most renowned landmarks, such as the John Hancock building, Trump Tower, Marina City, Willis Tower, and more. Relax with a glass of something cold from the cash bar, as you cruise the Windy City’s waterway, and learn its status as a modern metropolis and one of the world’s most beautiful cities. End your tour in the same place where you boarded the boat.

Chicago: Gangsters and Ghosts Guided Walking Tour

7. Chicago: Gangsters and Ghosts Guided Walking Tour

Discover a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn. Meet your guide in the heart of the Chicago South Loop, known as a notorious vice district during the 1920s and 30s. Stroll through his now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers. Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". You will also enjoy a short rest stop at a famous former gangster hangout. Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing with a visit to the Congress Hotel, one of the most haunted places in Illinois.

Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

8. Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

Experience the best of Chicago at your own pace from the unique vantage point of a Big Bus tour. Board our open-top, double-decker bus as you take a relaxing ride through the city's most iconic landmarks, from the Magnificent Mile to Millennium Park. Hop on and off at our convenient stops throughout the city to discover Chicago's vibrant neighborhoods and world-famous attractions including 360 CHICAGO, Willis Tower, the Chicago Riverwalk, Museum Campus, The Bean, and more. Spend your day shopping on Magnificent Mile, riding the Ferris Wheel at Navy Pier, or sampling authentic Chicago Deep Dish Pizza. With our flexible and convenient tour, create your own itinerary and explore the city at your own pace. Track bus arrivals in real time with our free downloadable app so you always know when the next bus is coming. Marvel at the stunning skyline as you enjoy professional digital commentary in multiple languages, with earbuds provided. Hear expert insight into Chicago's rich history and culture, as well as tips on the best places to eat, drink, and shop. With comfortable seating and panoramic views, our Hop-On Hop-Off Sightseeing Tour is the perfect way to see the city. Hop off the tour as many times as you like within the validity period of your ticket and simply hop on again when you're ready to keep exploring.

Chicago: CityPASS® with Tickets to 5 Top Attractions

9. Chicago: CityPASS® with Tickets to 5 Top Attractions

Visiting Chicago? Experience 5 must-see attractions, handpicked and packaged together at a 48% savings, with Chicago CityPASS® tickets. Spend less time planning and more time exploring. Visit the attractions at your own pace, in any order. Valid for 9 consecutive days including the first day of use. Get admission to 5 attractions. Includes: •Shedd Aquarium- All-access admission, including all habitats, Animal Spotlights and exhibits, including seasonal Stingray Touch, plus a 4-D Experience (subject to availability) •Skydeck Chicago- Expedited Entry Plus choose 3 of the following: •Shoreline Sightseeing Architecture River Tour- Architecture River Tour •Field Museum- All-Access Pass, including admission to all permanent and regularly priced ticketed exhibitions (specially ticketed exhibitions outside of All-Access Pass may be subject to additional charges) •360 CHICAGO Observation Deck- Express Entry Admission •Museum of Science and Industry- Museum entry (Science Storms, Numbers in Nature: A Mirror Maze, YOU! The Experience, The Blue Paradox, and much more), plus one timed-entry experience (Giant Dome Theater film or Motion Ride) •Art Institute of Chicago - Fast Pass Admission to permanent collection and non-ticketed special exhibitions •Adler Planetarium - All Exhibitions + Two Sky Shows

Chicago: Mob and Crime Bus Tour

10. Chicago: Mob and Crime Bus Tour

Experience Chicago’s underworld of criminals and gangsters on a luxury bus tour. Find out how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the city. Ride comfortably in an enclosed, climate-controlled bus, as you see famous Chicago crime scenes that range from the 19th century through modern times. Unlike Chicago walking tours, this Mob and Crime Tour isn’t affected by the Windy City weather. Learn from a local expert tour guide giving interactive live commentary about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, Terrible Tommy O'Connor, H. H. Holmes, the Chicago Black Sox, Leopold and Loeb, bank heists, Cap George Streeter, and more. Grab your camera for a drive-by shooting of the historic criminal courthouse, a Chicago architectural landmark where some of Chicago's most notorious cases were tried. You'll also view historic video footage, receive an informative pamphlet with photos, and can even take part in a crime quiz. Stake out crime scenes like the Biograph Theatre, Holy Name Cathedral, Clark Street Bridge, and other Chicago landmarks. See the site of the St. Valentine's Day Massacre, one of Chicago's most notorious murder scenes. Get off the bus and walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

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What people are saying about Chicago

Overall rating

4.4
(670 reviews)

Jack was our tour guide. I’m sure he has showed thousands of people this tour. However was I noticed was his enthusiasm and energy. If I didn’t know any better he sounded like it was his first week at work. It is awesome!!

We loved seeing Chicago from the river and learning about the architecture’s rich history. Our tour guide John was excellent. Very knowledgeable and entertaining!

Guide was very nice snd funny. This gave another view of the city and it was nice!

Amazing! The guide was awesome - this is a must do in Chicago!

Guide was excellent and upbeat!!! Very informative tour