Chicago Riverwalk
Tours

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Our most recommended Chicago Riverwalk 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: 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: 1.5-Hour Romantic Sunset Cruise

3. 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 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 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 the large promenades of the loop. The leisurely walking pace is suitable for people of all fitness levels.

Chicago: Food, History and Architecture Tour with Tastings

5. Chicago: Food, History and Architecture Tour with Tastings

Discover the best of Chicago on a comprehensive guided tour. Learn more about the city's history and vibrant food scene as you discover various bustling neighborhoods and historic areas. Start your tour under the dazzling marquee of the Chicago Theater, recognizable from movie-musical Chicago before heading off into the bustling city. First, stop at the Chicago Pedway, used by locals and commuters daily to move about the city in a network of underground tunnels. From here, head towards the official seat of the government for the city at City Hall. Check out its classic interior design and architecture.  Next, enjoy your first food tasting of the day, traditional Chicago-style popcorn. Weather permitting, your guide will take you for a stroll along the Chicago Riverwalk, pointing out familiar buildings such as the Marina Towers, the Britannica Building, and the Willis Tower. From here, make your way to another delicious destination where you can sample locally made chocolate from a local shop.  Then, you will either hop on the ‘L’ train or a water taxi on the Chicago River, depending on the weather and time of year. Either option offers a uniquely local Chicago experience. Feel like a local as you zip past buildings and catch even more awesome views. Next, take a stroll through the beautiful lakefront parks along Michigan Avenue. Arrive at the picturesque Millennium Park, home to the iconic Bean sculpture. By then, you’ll hopefully have built up an appetite because it’s time to begin your ultimate food experience. Travel with your guide up to the River North neighborhood, the original Chicago foodie destination. Your first food sampling is a local favorite, a Chicago-style hot dog. Next up is the world-famous Chicago deep-dish pizza, the staple of the Chicago food scene. Visit a pizza place that’s an icon to Chicago natives to try the real deal for yourself. After you’ve filled up on pizza and hot dogs, take a stroll through two more establishments, each one essential to Chicago’s food culture. Then continue your tasting journey with a classic Chicago sandwich: Italian beef. Sample this sandwich in a true Chicago institution. Your tour ends here, but don’t forget to get some recommendations from your guide of where else you visit or eat during tour time in the city.

Chicago: History, Culture and Architecture Walking Tour

6. 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, make your way to another delicious destination. Along the way, enjoy views of the world-famous Wrigley Building and the incredible Chicago Tribune building, the heart of Chicago’s thriving and historic journalism industry. Your second tasty confection is locally made chocolate from a Chicago staple. Finally, take a stroll through the beautiful lakefront parks along Michigan Avenue. Round up your tour in the picturesque Millennium Park, home to the iconic Bean sculpture. Here, your guide will conclude your tour and point you in the right direction toward more amazing sights, great lunch spots, or drink recommendations.

Chicago: Riverwalk Self-Guided Walking Tour

7. Chicago: Riverwalk Self-Guided Walking Tour

Learn about Chicago's history, culture, and architecture on a self-guided tour via an app. Enjoy animated videos allowing you to visualize what you cannot see, such as snapshots from different centuries or interior rooms. Start by downloading the app that will function as your personal guide, audio tour, and map all in one (download instructions received via email after booking). After downloading the app, head to the starting point of the tour at McCormick Bridgehouse & Chicago River Museum. As you being to walk, spot the DuSable Bridge and learn about the iconic terracotta Wrigley Building. From there, head west and pass Wabash Bridge, once voted America’s Most Beautiful Bridge. After that, see the Chicago Vietnam Veterans Memorial, a tribute to the soldiers who lost their lives during the Vietnam War. Next, stop by the 600-foot Marina Towers. Learn how these towers function as a “city within a city.” Head to the Dearborn Street Bridge and hear why an angry mob once gathered here with axes. Listen to the tale of one of the strangest and deadliest shipwrecks in American history. Learn how a devastating shipwreck happened on a river only 20-feet deep. Continue on toward the Merchandise Mart, a gorgeous example of Art Deco architecture. Learn how the Chicago River helped this city go from a small settlement to a bustling hub of culture and commerce. Next, arrive at Wolf Point, where Chicago’s very first hotel stood almost 200 years ago. Dig into the era when this place was little more than a wild frontier, then head back the way you came for the final section of the tour. Stop at the Tribune Tower containing pieces of historic buildings from across the world, including the Notre Dame Cathedral and the Berlin Wall. Next, come face to face with NBC’s Chicago headquarters, modeled after the famous skyscraper at 30 Rockefeller Center. Finally, arrive at the last bridge separating the Chicago River from Lake Michigan, where the tour concludes. Take in the soothing scenery and snap a few photos for your Instagram.

Chicago: Riverwalk Guided Walking Tour

8. 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 down the Riverwalk and hear stories at the site of Old Fort Dearborn and the disaster that was the SS Eastland. Then, pass by the Jeweler's Building and find out if Al Capone really had a super-secret speakeasy at the very top. Nearing the end of the tour, take in a Picasso gifted to the city by the artist himself, see the first church at the Chicago Temple, and end under the prisms of light filtering in the Tiffany Dome at the Chicago Cultural Center.

Chicago: Must See Chicago 90 minute Walking Tour

9. 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 this tour include soaring modernist skyscrapers (Willis Tower, John Hancock Center, and AON Building), buildings paying homage to classical styles (Wrigley Building, Tribune Building, the Chicago Theatre, and the Art Institute of Chicago), Art Deco edifices (Carbide & Carbon Building and the Chicago Board of Trade Building), and recently completed skyscrapers (Aqua & Trump Tower). Finally, admission to the Chicago Architecture Center (CAC) is also included with your walking tour ticket. CAC exhibits focus on Chicago’s diverse neighborhoods, housing types, leading architects and future projects, and include the largest scale model of the city, with more than 4,250 miniature buildings and a cinematic backdrop animating key moments in its history. The stories of the city begin at the CAC.

Chicago: Evolution of the Skyscraper Walking Tour

10. Chicago: Evolution of the Skyscraper Walking Tour

This 90-minute tour is a chronological overview of Chicago's architecture, starting with its growth on the Chicago River, its rebirth after the Great Chicago Fire and its development into a commercial and cultural hub. See how architects adapted building styles to meet the fashions of their era and used cutting-edge engineering to build taller than ever before. This tour is an enticing overview which introduces you to the most important stories of Chicago architecture. On this tour, you'll learn about the city's beginnings on the river, its rebirth after the Great Fire and its development into a commercial and cultural hub, all while viewing structures in the order they were built. These buildings—including the Page Brothers Building, Old Dearborn Bank, the Chicago Motor Club, the Carbide and Carbon Building, NBC Tower and more—tell the story of how architectural technology evolved over time. You'll see up close how each building has its own unique design, often reflecting the style that was popular or prevalent when it was constructed.

Frequently asked questions about Chicago Riverwalk Tours

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What people are saying about Chicago Riverwalk

The length of the cruise was just right…45 minutes. and the 7:45 was trip was perfect. Sun went down on the way back and the made the views even more spectacular. Our guide was very knowledgeable and gave us lots of interesting facts about the iconic buildings on the tour. I would highly recommend this cruise to see the wonderful architecture in a nutshell.

Really fun and informative! Tour guide really made it amazing :) It was a little cold from the wind and night but still super fun!

Excellent Tour guide! We had so much fun! Also, the timing was perfect. all the tour team was really nice and helpful. Thank you!

Excellent scenic views of Chicago skyscrapers on a peaceful boat ride!!

Departure is on time Rain or Shine Great Bartender Great Captain