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ChicagoSightseeing 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: 1.5-Hour Lake and River Architecture Cruise

2. 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: 45-Minute Family-Friendly Architecture River Cruise

3. 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: 1.5-Hour Romantic Sunset Cruise

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

5. 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 Tour & Lake Hopper Cruise

6. Chicago: Lake Michigan Skyline Tour & Lake Hopper 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. Route: The Skyline Tour and Lake Hopper takes you out onto Lake Michigan, heading both north and south on the lake, you’ll see many of Chicago’s famous landmarks and the classic skyline vista. Enjoy the flexibility to hop-on and hop-off the Skyline Lake loop at either the Museum Campus or Navy Pier.

Chicago: Architecture Center Cruise on Chicago's First Lady

7. Chicago: Architecture Center Cruise on Chicago's First Lady

Hop onboard the only cruise narrated by Chicago Architecture Center certified volunteer docents who will share their wealth of knowledge about Chicago’s “canyon of architecture” – the Chicago River. Cruise down all 3 branches of the Chicago River, with unobstructed, open-air, 360-degree views of the city’s wide variety of architectural styles, including Art Deco, neoclassicism, mid-century modernism, and postmodernism. Discover how design shaped history and influenced life. Enjoy guaranteed seating on the open-air upper decks and purchase items at the full-service cocktail and snack bars in climate-controlled interior salons. Listen as docents share stories of over 50 buildings and 13 bascule bridges along the river, and some of the iconic figures responsible for them. If you're a non-English speaker, get access to a pre-recorded tour narration on your smartphone. Simply scan a QR code, download a mobile app, and connect it to the onboard Wi-Fi network. Narration is automatically triggered based on the location of the vessel on the tour route, so sit back and relax. You can also use your cruise ticket for discounted admission to the Chicago Architecture Center, which is just steps away from where the cruise departs. Pay just $5 compared to the normal $14 entry fee.

Chicago: 75-Minute Architecture Cruise by Speedboat

8. 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: Seadog Speedboat Fireworks Cruise on Lake Michigan

9. 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! Join us on Wednesday and Saturday evenings during the summer months for an unforgettable memory.

Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour

10. 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.

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Frequently asked questions about Chicago Sightseeing cruises

What are other things to do than Sightseeing cruises that are worth visiting in Chicago?

The other unmissable things to do in Chicago are:

Other Sightseeing Options in Chicago

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What people are saying about Chicago

One of the best things we did was take this boat tour while visiting Chicago for the first time. You will learn so much interesting facts about Chicago and it’s amazing to see the city in a different view. I highly recommend dressing for the weather. It can get windy and cold so bring a jacket and sunglasses if it’s sunny.

awesome, interesting & beautiful! make sure you know where you’re going & arrive 15 min early. our friends uber dropped them in the wrong spot so we barely made it & had to stand during the tour which honestly wasn’t bad, but the earlier you arrive you’ll get your choice of seats.

Guide was excellent. Very interesting tour. We missed our original tour and had to take the next tour which was longer and probably better because we weren’t areas that the shorter tour would not have take. Us.

Loved the tour, so beautiful, a very special point of view of the city. We were afraid it was going to be cold but it wasn’t and the bar with hot chocolate and tea that was opened on the boat helped :)

Easy access good narrative and good sense of humour