Chicago Sightseeing cruises

Our most recommended Chicago Sightseeing cruises

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: 45-Minute Family-Friendly Architecture River Cruise

2. 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 River Architecture Cruise: Skip-the-Ticket-Office

3. Chicago River Architecture Cruise: Skip-the-Ticket-Office

Skip the lines at the ticket office and climb aboard a state-of-the-art cruise for a 60- or 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: Lake Michigan Skyline Sightseeing Cruise

4. Chicago: Lake Michigan Skyline Sightseeing Cruise

Immerse yourself in the sights and learn about Chicago’s history and architecture during a cruise on Lake Michigan. Take advantage of skip-the-line entry privileges with a barcoded ticket that lets you proceed directly to the boarding line. Whether you’re a local or a visitor to the city for the first time, taking in the spectacular views of Chicago's skyline from the lake makes for a perfect outing. You’ll see the city as never before while listening to commentary on Chicago's history and architectural gems. Simply hop on board, sit back, relax, and enjoy as you admire Chicago's most significant landmarks and striking buildings that make up the city's skyline that has appeared in so many movies and TV shows.

Chicago: 1.5-Hour Lake and River Architecture Cruise

5. Chicago: 1.5-Hour Lake and River Architecture Cruise

Experience an architecture cruise along the Chicago River and Lake Michigan, a family tradition since 1935. Admire Chicago’s historic and ever-changing skyline with a local expert guide as you cruise through the city. Choose between the open-air decks or the comfort of the climate-controlled interiors during the cruise. Start the cruise at Michigan Avenue (DuSable) bridge and go up the main branch of the Chicago River to Wolf Point before heading back past the Chicago Riverwalk towards Lake Michigan. Learn about historic skyscrapers like the Wrigley Building and the Tribune Tower, the deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building, the circular Marina City Towers, the AON Center, and modernist structures like Aqua, Trump Tower, Nuveen, and the Vista Tower. After passing through the Chicago Lock and cruising past Navy Pier, admire the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Here you can also see the twin super-skyscrapers, the famous Willis (formerly Sears) Tower, and the John Hancock Building. See the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. Enjoy several vantage points for memorable pictures throughout, and finally arrive back at Du Sable Bridge on Michigan Avenue.

Chicago: 75-Minute Architecture Cruise by Speedboat

6. Chicago: 75-Minute Architecture Cruise by Speedboat

Climb aboard a speedboat for a thrilling river and lake cruise around some of Chicago’s architectural gems. Gain insights into the city's most famous landmarks from your guide. Admire sights like Willis Tower, Tribune Tower, and Buckingham Fountain. Depart from the former Navy training center of Navy Pier on the shores of Lake Michigan on a tour along the lakefront. Sail through the locks and along the Chicago River all the way to the second tallest building in the USA, Willis Tower (formerly Sears Tower). Get up close to Chicago’s most iconic buildings and unique architecture, and enjoy amazing views and an entertaining narration as part of the exciting ride. Learn the fascinating history of structures like the neo-Gothic Tribune Tower and the Lyric Opera of Chicago. Cruise the lakefront of Lake Michigan to see monuments and attractions such as Buckingham Fountain, Grant Park, Chicago Harbor, and the Chicago Museum Campus.

Chicago: 1.5-Hour Romantic Sunset Cruise

7. Chicago: 1.5-Hour Romantic Sunset Cruise

Relax as you glide over the Chicago River and into Lake Michigan on this cruise. Enjoy the glow of the sunset on Chicago's sparkling skyline. Have the option to purchase delectable drinks and snacks at the onboard bar as you sail. Start your sunset cruise on the Chicago River at Michigan Avenue. Make your way along the main branch of the river towards Lake Michigan before entering the Chicago Locks, a modern engineering marvel, that will transfer the vessel onto the great Lake Michigan. The vessel will cruise along Lake Michigan as the sun sets behind the wonderful skyline offering several amazing views. Your local tour guide will give a very brief commentary along the Chicago River and entrance to Lake Michigan, but most of the 1.5-hour cruise is spent without narration, leaving you to watch the sun put on a beautiful display with the City skyline. Admire the many angles of the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Capture magical views of Chicago's twin super-skyscrapers, the famous Willis (formerly Sears) Tower and the John Hancock Building. You'll also get to admire the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. During your cruise, treat yourself at the full-service cash bar featuring authentic Chicago products. Try local beer and spirits and Garrett’s Popcorn. Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. 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 Seadog Speedboat Fireworks Cruise on Lake Michigan

8. Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan

Enjoy a summer or autumn evening on this Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan. This popular 60-minute narrated tour ensures you have the best views of this magnificent fireworks display. Every seat on the Seadog Speedboat Fireworks Cruise has amazing panoramic views of Chicago's historical skyline. Whether you are looking for a romantic evening, a night out with friends, or simply appreciate the art of pyrotechnics, this tour will have everyone of all ages leaving with a smile. Come and visit all of the possibilities that Chicago has to offer by enjoying a magical Fireworks Cruise on Lake Michigan. These memories are made to last a lifetime!

Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour

9. Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour

See the sights of Chicago from a unique waterside perspective on this tall ship tour. Sail around Lake Michigan onboard the tall ship Windy, a 148-foot traditional schooner. Choose from an architecture and history-focused tour or a sunset sail. On the Architecture and Skyline Sail, immerse yourself in Chicago's history and architecture. Take in the skyline, enjoy spectacular views, and discover the Windy City from the water. Learn about the people and plans that shaped Chicago’s most famous sights from the live onboard narration. On the Sunset and Skyline Sail, enjoy panoramic views of the sunset across the Chicago skyline in the company of friends or family. enjoy live educational narration about the sights you see with both options.

Chicago: City Minibus Tour with Optional Architecture Cruise

10. Chicago: City Minibus Tour with Optional Architecture Cruise

Start with a pickup from your downtown Chicago hotel. Board your climate-controlled minibus and embark on your guided sightseeing tour. Begin in the heart of downtown Chicago, at The Loop. Here you'll see incredible architecture, including the world's first skyscrapers. You'll even go inside one that features a beautiful lobby designed by Frank Lloyd Wright.  The stop also includes views of The Chicago Board of Trade and the Willis (Sears) Tower. After The Loop, head through Grant Park, which is known as the city's front yard. The centerpiece of the park is the Buckingham Fountain. Museum Campus is up next, with three museums, Soldier Field, and the most spectacular skyline views in the city. After a 10-minute photo stop, travel around Millennium Park, featuring The Bean, before heading up north along Wacker Drive, which parallels the Chicago River. Arrive in the fancy Gold Coast nightlife area and residential neighborhood - one particularly interesting sight here is the original Playboy Mansion.  Then, take a trip through part of Lincoln Park, and end the tour by zipping along Lake Shore Drive, past beaches, and old mansions, before being dropped off at your hotel. For those wanting the ultimate Chicago experience, add on the option of the world-famous architecture cruise of Chicago. After your minibus tour and a short break, climb aboard a state-of-the-art cruise vessel for a 75-minute cruise of all three branches of the Chicago River. Marvel at the architecture that has made the city so legendary. Gain insights into the buildings and engineering of a city that gave birth to the skyscraper and is the spiritual home of modern American architecture. An expert guide will lead you down the Chicago River to uncover hidden gems, as well as the city’s most renowned landmarks, such as the John Hancock building and more.

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What people are saying about Chicago

I had a very Knowledgeable and fun tour guide . The trip was interesting and funny. I learned a lot about the city and it's architecture. Highly recommended! Totally worth it.

Awesome experience! Staff was professional, funny, and knowledgeable. Highly recommend!

Superb commentary from informed, intelligent and interesting boat tour guide.

Great tour on the Chicago River. Jack was a knowledgeable guide.

The best city tour I've ever experienced! Highly recommend.