Chicago Riverwalk
Sightseeing Tours

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Our most recommended Chicago Riverwalk Sightseeing Tours

  • Chicago River: 1.5-Hour Guided Architecture Cruise

    1. Chicago River: 1.5-Hour Guided Architecture Cruise

    Experience more of Chicago than on any other architectural cruise as you travel not only the main Chicago River but also the North Branch of the river (as far as the Old Montgomery Ward Building) and the South Branch of the river (nearly as far as Chinatown). 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, and cruises along the north and south branches of the river, before heading back past the Chicago Riverwalk toward...

    The tour was great. The only problem was when my wife and I were checking in and the young man said that my ticket was invalid. The only reason we were able to go on the tour is that there was another gentleman there who knew that I had already purchased two tickets

  • Chicago: 1.5-Hour Romantic Sunset Cruise

    2. Chicago: 1.5-Hour Romantic Sunset Cruise

    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 ge...

    It was the best price for a river tour and I know sometimes if you pay less you get less but this star was outstanding. I would highly recommend

  • Chicago River: 45-Minute Family-Friendly Architecture Cruise

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

    Admire Chicago’s impressive architecture from a unique perspective aboard a 45-minute cruise sailing down the Chicago River, which features a full-service cash bar and live commentary tailored to entertain the whole family. 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- a perfect way to explore 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 o...

    We had a great time! Shorter ride was perfect for young kids. Boat was clean and staff was friendly.

  • Chicago Food Tasting: 2.5-Hour Guided Walking Tour

    4. Chicago Food Tasting: 2.5-Hour Guided Walking Tour

    Combine an enjoyable walk around Chicago's downtown to see some of the city’s top sites with stops to sample some of the city’s famous tastes. On this 2.5-hour guided walk, you'll get to taste the foods Chicago is best known for doing right. Enjoy deep-dish pizza, the original Italian pastries, Chicago-style hot dog, and a classic Italian beef sandwich. Enjoy a VIP craft beer sample for an additional fee. Along the way, you’ll see some of Chicago's most iconic spots including Millennium Park, the Chicago Riverwalk, the Art Institute, and the famous Bean. By the end of the tour, your stomach will be full of delicious food and your head will be full of fascinating knowledge about Chicago. During the colder months, the tour makes use of the unique underground Pedway system that connects much of downtown and keeps you warm and cozy. On warmer days, you’ll walk at street level to enjoy th...

    Gabe made it so fun & interesting. Felt very safe. He was great at navigating around crowds, etc. We plan on repeating this tour with friends!!

  • Chicago: History, Culture and Architecture Walking Tour

    5. Chicago: History, Culture and Architecture Walking Tour

    Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago) before heading off into the bustling city. Your first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. Then head towards the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily to move about the city in a network of underground tunnels. Afterward, head back above-ground near City Hall and head inside to see the classic interior design and architecture. Next, enjoy a sweet treat, and local tradition: Chicago-style popcorn. Weather permitting, take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Willis Tower. From there, either hop on the ‘L’ train or a water taxi o...

    I had an amazing time on this tour! In my opinion, the walking tour allowed me to see so much more of the city, up close and from my own personal viewpoint. The tour guides were very friendly, funny, and knowledgeable. We were even given "Garrett's Popcorn" and "Fannie May Chocolate" as some sweet treats. I highly recommend this tour, and I'm so glad that I did it!!

  • Chicago: Must See Chicago 90 minute Walking Tour

    6. Chicago: Must See Chicago 90 minute Walking Tour

    Starting at the Chicago Architecture Center (CAC), this tour gives you an overview of many of the must see buildings and landmarks in the City of Chicago. Led by an expert guide who has been rigorously trained by the CAC to be equal parts storyteller and educator, you will get a fantastic introduction to the city’s wide variety of architectural styles, construction methods, and materials. There is so much to see downtown, and this tour makes it easy and fun to learn about some of the buildings that make Chicago’s architecture world-class. There are lots of photo opportunities along the way, so be sure to bring your camera! The tour covers three of the main focal points of Downtown Chicago – the Chicago Loop, the heart of historic Chicago; the Chicago River, the lifeblood of the city; and Millennium Park, where the iconic “The Bean” sculpture is located. Landmark buildings covered on th...

  • Chicago River: Guided Tour of Historic Chicago by Kayak

    7. Chicago River: Guided Tour of Historic Chicago by Kayak

    Join this guided kayak excursion on Chicago River’s Main Branch to paddle through a modern urban setting while imagining the city’s early historical locations. Kayak alone or in a tandem (2-person) kayak. Begin your experience with a 20-minute pre-tour session on land, where professional guides go over safety issues and the rules of the river. There will also be a brief paddling demonstration for those who are new or beginner kayakers. Afterward, your adventure on the water begins. Travel for about 2.5 miles along the Chicago River, stopping frequently to rest and chat. During your periodic stops, hear stories and details about Chicago’s rich history from the lead tour guide. Pass some of Chicago's most iconic sights along the way, including the Wrigley Building, Merchandise Mart, Aqua, Tribune Tower, and much more. Since the city grew up on the Chicago River, this tour is a great w...

  • Chicago: Food, Architecture and History Tour

    8. Chicago: Food, Architecture and History Tour

    Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago) before heading off into the bustling city. Your first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. Then head towards the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily. Afterward, head back above-ground near City Hall and head inside to see the classic interior design and architecture. Next, enjoy a sweet treat, and local tradition: Chicago-style popcorn. Weather permitting, take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Willis Tower. From there, either hop on the ‘L’ train or a water taxi on the Chicago River (depending on the weather and time of y...

    This was my first time to Chicago this tour was absolutely amazing. Kelly was knowledgeable about everything Chicago..she was able to answer all questions & gave great recommendations. Would highly recommend..

  • Chicago: Downtown Family Food Tour by Bike with Sightseeing

    9. Chicago: Downtown Family Food Tour by Bike with Sightseeing

    Hop on a bike and enjoy this easy ride around Downtown Chicago to explore the cities best sights and food. Cruise through Millenium Park, Museum Campus and along the lakefront with regular stops to sample delicious treats as you go. Your guide will take you to some of the best spots to try deep-dish pizza, a true Chicago hot dog, Italian beef, and a dessert for good measure. Try them all (or their veggie alternatives) and learn about the foods that made Chicago famous. In between snacking, visit some of Chicago’s most popular downtown districts as you cruise through Grant Park (Buckingham Fountain), the Chicago Riverwalk, and more. Along the way, your guide will point out highlights like Navy Pier, the Magnificent Mile and the Chicago River. The stops are well-timed so, even though you’ll be working up an appetite, all ages and fitness levels can get involved and enjoy this ride. If y...

  • Chicago: Riverwalk Guided Walking Tour

    10. Chicago: Riverwalk Guided Walking Tour

    Tag along on this essential Chicago experience: a guided walking tour of the Chicago Riverwalk. Spend your day exploring art, architecture, and all the locals’ favorite spaces. Visit the Meatpacking District, Chelsea Market, DuSable Bridge, and more. Birthed around the banks of the (now) Riverwalk, Chicago is a city teeming with tales. With the help of your local guide, discover the stories behind the sites you visit and see. Visit all four districts of the Riverwalk, each offering its own flavor of Chicago. Pass iconic sites including the Wrigley Building, Tribune Tower, DuSable Bridge, and the Marina Towers. As an added perk, become a Chicago insider with behind-the-scenes access at the McCormick Bridgehouse & Chicago River Museum. Stop at Heald Square and see the city’s many monuments and memorials. Along the tour, spot the touching Vietnam Veterans Memorial. Continue strolling d...

    Very knowledgeable. Hard to hear w all the noise at times. Went well beyond river walk. It was good but long.

Other Sightseeing Options in Chicago Riverwalk

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What people are saying about Chicago Riverwalk

Jack, our guide, made the tour! He was extremely knowledgeable and entertaining! It’s probably one of the best guided tours I’ve taken and I’ve traveled around the world. He’s a keeper!

It was the best price for a river tour and I know sometimes if you pay less you get less but this star was outstanding. I would highly recommend

It was a very good experience. I enjoyed the boat ride, the weather and the information about all the buildings and Chicago.

We had a great time! Shorter ride was perfect for young kids. Boat was clean and staff was friendly.

Absolutely loved seeing the architecture of Chicago!