Michigan Avenue

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Michigan Avenue: Our most recommended tours and activities

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 peak at four neighboring states from this height Feel the thrill of a 40-second ride in North America's fastest elevators to the observation deck to experience what 'Travel & Leisure Magazine' voted one of the best views in America. 360 Chicago provides easy access to Chicago’s premier shopping and dining districts.   360 CHICAGO also offers an interactive exhibit on the Ground Floor highlighting Chicago’s rich history and showcasing nine of the city’s culturally unique neighborhoods. Then, on the 94th floor, audio tours in 5 languages allow you to further explore the history and architecture of the magnificent city stretched out before you. If you wish, upgrade onsite to experience the Tilt. By pre-purchasing your timed ticket today, 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 Elevator Line.

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: Hop-on Hop-off Open Top Bus Tour

4. Chicago: Hop-on Hop-off Open Top Bus Tour

From your vantage point on the double-decker sightseeing bus, you'll enjoy panoramic views of Chicago’s finest skyscrapers, including the 875 N Michigan, the Willis Tower, and the Wrigley Building. Take in the city's impressive landmarks as your tour guide provides entertaining commentary and insight into Chicago's history. Enjoy exploring this dynamic city with the freedom to hop on and hop off as many times as you wish to visit attractions such as the Shedd Aquarium and the Field Museum. You’ll travel down the famous Magnificent Mile, considered one of the great avenues of the world, and continue across the Michigan Avenue Bridge over the Chicago River. The bridge connects the north and south sides of the city. This hop-on, hop-off bus tour of Chicago makes it easy for you to explore the city's sights at your own pace. There are 12 stops, where you can hop off to visit attractions and explore places of interest. The stops are conveniently located to make navigating your way around the city easy, and with a choice of 24- or 48-hour tickets, you can take your time discovering Chicago. Be sure to take advantage of admission to the Chicago Architecture Center, included if an appropriate option is selected, to dive deeper into the city that invented the skyscraper. So don't wait, just hop on an exciting journey through Chicago.

Chicago: 1.5-Hour Open-Top Double-Decker Night Tour

5. Chicago: 1.5-Hour Open-Top Double-Decker Night Tour

From the top deck of a double-decker bus, experience Chicago at night. Enjoy a 75-minute, live-guided panoramic tour and take in unique views of the Chicago Skyline, comprised of world-famous skyscrapers and revolutionary architecture. Take a photo overlooking downtown from the Museum Campus in front of the Adler Planetarium. Be amazed by the beautiful water and light display of The Buckingham Fountain as you discover the bustling nightlife of Chicago. Marvel at the magical light show of the one-of-a-kind Art on the Mart, displayed on the facade of the Merchandise Mart. See the city reflect off of The Bean (Cloud Gate) at the famous Millennium Park. Experience the city that built the skyscraper and see architectural marvels like 875 N Michigan Ave (formally the John Hancock Building), the Wrigley Building, the Chicago Tribune Building, and the Willis Tower. End the tour at the Chicago Riverwalk, with the knowledge that you can continue exploring the city with confidence. From the pioneering skyscrapers, to the Great Chicago Fire, this night tour will take you on a journey you won't soon forget. Be sure to soak up the exciting atmosphere that makes the Windy City such a fascinating and dynamic place.

Chicago: Beautiful Lakefront and Museum Campus Segway Tour

6. Chicago: Beautiful Lakefront and Museum Campus Segway Tour

Segways are amazingly fun and there is no better way to tour a world-class city like Chicago than on your own personal set of wheels--a Segway! Our eight-mile Lakefront Chicago Segway tour lets you learn about and view and many Chicago's attractions in a highly unique way. As you glide effortlessly and enjoy the lakefront, you can learn the history of our city from your friendly and professional tour guide. Immerse yourself in the area's countless attractions, gorgeous parks and gardens, and stunning photo opportunities. See sights like Grant Park, the BP Bridge, the Bean, and the Buckingham Fountain, as well as generous views of Lake Michigan and the majestic skyline. Segways are safe to use, easy to learn, and fun to ride. We offer a thorough training session from our certified guides before we begin the tour.

Chicago: Treasures of the Golden Age Walking Tour

7. Chicago: Treasures of the Golden Age Walking Tour

This Historic Treasures of Chicago tour covers the most significant historic architectural landmarks in Chicago’s Loop. Your expert guide, trained by the Chicago Architecture Center, will focus on great cultural buildings from the late 19th and early 20th centuries, which harkened back to earlier time periods and were designed in revival styles such as Beaux Arts, neo-Georgian and neo-Gothic. Marvel at exteriors and interiors of dazzling beauty and startling originality, and get a glimpse inside some of the city's most beloved buildings.    The highlights of this walking tour will include the Chicago Cultural Center, home to the world's largest Tiffany dome; the iconic Marshall Field's department store, now Macy's on State; and the Palmer House, a beautifully restored hotel from the 1920s. 

Chicago: Food, History and Architecture Tour with Tastings

8. 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

9. 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: Underground Pedway & Downtown Secrets Walking Tour

10. Chicago: Underground Pedway & Downtown Secrets Walking Tour

Come experience Chicago's famous "Pedway" – the mysterious underground tunnels downtown that keeps us all warm & dry in bad weather. Wandering the Pedway, through hidden corridors of stained glass and even underground swimming pools, you'll access interiors that seem to come up out of nowhere. In the first part of our 2-hour walk, on weekdays, you'll see beautiful and historic government building interiors, learning not only about the design and history of the buildings, but also about the movies filmed there. On weekends, as government buildings are closed, we instead explore a couple stunning interiors with stained glass mosaics that will leave you awe-struck. You'll walk under full blocks of buildings, up and down staircases, accessing these buildings through the Pedway's secret passages. In the second part of our walk, you'll discover some of the other "secrets of the Loop" hidden in plain sight. What is the meaning behind "The Bean"? What is the significance of Chicago and Route 66? How can someone walk right by a garden and not even SEE it -- or walk by a building and not see it, for that matter? You'll find so many secrets, packed into a leisurely 2-hour walk with your expert Chicago guide. Ending with a fabulous “secret” interior near the Art Institute, you’ll be in the perfect central spot for continuing your exploration of downtown Chicago on your own after the tour!

Other Sightseeing Options in Michigan Avenue

Want to discover all there is to do in Michigan Avenue? Click here for a full list.

What people are saying about Michigan Avenue

Overall rating

4.6 / 5

based on 2,089 reviews

Wendella Boats never disappoints with its architecture tours. Anytime we have family, friends, or colleagues in town, I always reserve a tour with Wendella.

Frankie was an excellent guide and gave us a great tour. Lots of little gems around the city hidden in plain sight. Highly recommended!

Excelente experiencia. La información brindada de mucha utilidad. 100% recomendado

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

Departure is on time Rain or Shine Great Bartender Great Captain