Chicago River 90 Minute Architecture Tour
Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour will navigate through the heart of the city on all three branches of the Chicago River while your professionally-trained architectural guide tells the story of more than 130 years of innovation in design, style and technique and why it is important today. The Chicago River Architecture Tour is the most authentic and encompassing Chicago experience the city has to offer.
Duration: 1 hr 30 min
- Likely to sell out
- Free cancellation
Chicago Architecture River Cruise
Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building.
Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including:
John Hancock Center: An iconic skyscraper that defines the Chicago skyline.
Wrigley Building: Known for its distinctive white facade and clock tower.
As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities.
Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes.
Duration: 1 hour – 1 hr 15 min
- Free cancellation
Chicago River 45-Minute Architecture Tour from Magnificent Mile
Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.
Duration: 45 min
- Likely to sell out
- Free cancellation
Chicago Architecture Center River Cruise aboard First Lady
The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago.
As a certified nonprofit, all ticket purchases directly support education efforts and community engagement projects. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.
Duration: 1 hr 30 min
Flyover in Chicago
The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover Chicago from a whole new perspective, as Flyover transports you over, around and through remarkable locations. You'll explore in motion with scenes captured by an award-winning creative team using custom-made drones and helicopter-mounted cameras, while scents, sounds and music deepen the immersion. It’ll take your breath away (we promise you’ll get it back).
Duration: 30 min
- Free cancellation
Chicago River 90-Minute Architecture Boat Tour
Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome.
Each architecture river tour is narrated by a professional guide which leads passengers down the Chicago River to discover the city’s most renowned landmarks. In addition to historical insight on well known structures such as the Civic Opera House, Trump Tower & the Merchandise Mart, passengers will also get a chance to learn about current and upcoming developments. This Chicago River Cruise is the only cruise that navigates the three primary branches of the river including the main branch to Navy Pier, the north branch to Goose Island, and the south branch to Chinatown. It is also the cruise closest to Skydeck, has the least expensive parking, and is great for those coming from the suburbs due to its location off Interstate 290.
Duration: 1 hr 30 min
- Likely to sell out
- Free cancellation
Chicago Sightseeing River and Lake Cruise
Our popular 90-minute daytime river and lake sightseeing tour delights family members of all ages with incredible views of Chicago's world-renowned buildings and stunning skyline. Lively, knowledgeable tour guides bring Chicago’s rich history to life with fun stories and interesting facts. Relax and unwind on a scenic tour of the city from the unique perspective of the Chicago River and Lake Michigan. Welcome aboard!
Duration: 1 hr 30 min
- Free cancellation
Chicago By Night River and Lake Cruise
Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night! Enjoy breathtaking views of the dramatic skyscrapers and Buckingham Fountain's spectacular light display. Hear lively commentary as you feel the night breeze and see Chicago’s skyline transformed into a glittering jewel. A one-of-a-kind experience to scratch off your Chicago bucket list. Family-friendly cruises are our specialty!
Duration: 1 hr 30 min
- Free cancellation
360 CHICAGO Observation Deck Admission
The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers. Located in the heart of downtown on Michigan Avenue, the observatory is steps away from other top Chicago attractions. It will be the high point (literally) of your Chicago trip!
Upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. The Sip menu includes a rotating selection of beer, wine and cocktails. Once onsite, you can purchase tickets to TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. You may also choose to upgrade your Sip and View ticket from the Sip Menu to the Elevated Menu for an additional $8.
*TILT not included in purchase
Duration: 1–4 hours
- Free cancellation
Chicago Lake and River Architecture Tour
An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than a century of groundbreaking architecture. The journey begins with an up-close perspective of Chicago's internationally-known architecture as seen from the Chicago River. Then venture through the Chicago Lock on to the calm, cool waters of Lake Michigan for expansive views of Chicago's extraordinary 26-mile skyline. Take the selfie of a lifetime on this inspirational experience!
Duration: 1 hr 30 min
- Likely to sell out
- Free cancellation
Chicago Skyline Snap Tour Helicopter Flight Over Chicago
Witness Chicago’s stunning skyline from above on this exhilarating helicopter tour. Departing from the Vertiport, the flight offers breathtaking views of the city’s iconic architecture, including Soldier Field and the Shedd Aquarium, as well as the picturesque Lake Michigan shoreline. This unforgettable experience showcases 8 key points of interest along a scenic 10-mile route, perfect for photography enthusiasts and those seeking a unique perspective of the Windy City.
- 10-mile scenic helicopter flight over Chicago's skyline
- Fly past famous landmarks like Soilder Field and Chinatown
- Minimum of 2 passengers required, maximum of 3 per flight
- Free parking available at the Vertiport Chicago
Duration: 7 min – 10 min
- Free cancellation
Chicago River Ghost & Dark History Night Cruise
See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the Chicago River while hearing chilling tales of disasters, infamous criminals, and eerie legends tied to the city’s past.
This relaxed river cruise blends atmospheric storytelling with some of the best nighttime views of Chicago’s renowned skyline and landmarks. Grab a drink from the onboard bar, settle in, and let the city’s shadowy history unfold as you cruise through the heart of downtown.
By the end of the journey, you’ll have experienced Chicago’s skyline in a whole new way—while uncovering the chilling events, legends, and mysteries that shaped the city.
Please arrive 30 minutes in advance!
Duration: 1 hr 30 min
- Free cancellation
Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus
Discover Chicago at your own pace with Big Bus. Travel aboard an open-top, double-decker bus and enjoy panoramic views of the city's most famous landmarks, including the Magnificent Mile, Millennium Park, Willis Tower, The Bean, Navy Pier and more.
Hop on and off at conveniently located stops to explore Chicago's top attractions, vibrant neighbourhoods, world-class dining and shopping. Use our free app to track bus arrivals in real time and plan your day with ease.
Enjoy multilingual digital commentary throughout your journey, packed with fascinating stories, local insights and recommendations.
48-hour and 72-hour tickets also include 4 Self-Guided Audio Walking Tours, covering topics such as Architecture, the Chicago Riverwalk and Public Art.
The 72-hour Explore option also includes the Chicago South Side & Presidential Center Shuttle, connecting Downtown Chicago with the Obama Presidential Center & Jackson Park and the Griffin Museum of Science & Industry.
Duration: 2 hours
- Free cancellation
Chicago Crime and Mob Bus Tour
Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities. Hear true crime stories about Chicago Gangster Al Capone, The Untouchables, The Chicago Mob, Prohibition, John Dillinger, Frank “The Enforcer” Nitti, Cap George Streeter, Leopold & Loeb, H.H. Holmes and more.
Visit historic landmark buildings like: The Biograph Theater, Holy Name Cathedral, Cook County Criminal Court House, Harry Caray’s Italian Steakhouse, etc.
Tour famous Chicago neighborhoods: Streeterville, River North, Gold Coast, Lincoln Park, Old Town, Loop and Magnificent Mile. Locals and tourists agree that this educational and entertaining thing to do in Chicago is a unique cultural experience.
Duration: 1 hr 30 min – 2 hours
- Free cancellation
Lake Michigan Sunset Cruise in Chicago
The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago River, through the Chicago Lock and out onto Lake Michigan. Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise.
Duration: 1 hr 30 min
- Likely to sell out
- Free cancellation
Skydeck - Willis Tower Admission
Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- the Skydeck offers spectacular sweeping views and is full of interactive exhibits. To complete your exciting Chicago experience, head to the Ledge, a glass balcony showcasing unbeatable views of Chicago’s top attractions like Wrigley Field and the Navy Pier.
We added a brand new Chicago Experience that you start with by the box office prior taking the elevator trip to the 103rd floor. It is a 45,000 sq ft. museum of today. The New Experience is part Chicago History, part Architecural tour, part Selfie Museum and part Children's Museum. This is fun and interactive for all ages. Ride our "L" Train, see our infinity pizza bed, take pictures ontop of Willis Tower and so much more! This is the best way to see Chicago in one setting.
With mobile tickets, simply scan your phone for direct entry into the SkyDeck
Duration: 30 min – 1 hr 30 min
- Free cancellation
Lake Michigan Skyline Cruise in Chicago
Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions.
Cruise along Lake Michigan and enjoy stunning views of Chicago's renowned skyscrapers from a unique vantage point. This tour offers an amazing opportunity to admire the city's breathtaking skyline and architectural wonders.
Sunday – Friday Cruises departing prior to 8:00pm feature recorded narration of the city’s skyline, cruises departing after 8:00pm enjoy some music and the sounds of Lake Michigan aboard our Groove Cruise.
November - April 9 tours are 30 minutes.
Highlights:
Spectacular views of Chicago's famous skyscrapers
Onboard bar serving refreshing drinks
Relaxing and enjoyable sightseeing cruise
Experience Chicago like never before on this serene and scenic Lake Michigan boat tour. Remember to bring your camera to capture those social media worthy photos!
Duration: 30 min – 45 min
- Free cancellation
Chicago Favorites Ultimate Food and Walking Tour
The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the beautiful streets of downtown & taste the Windy City’s favorite eats on this iconic Chicago Food Tour! Bobby’s Bike Hike & Food Tours, whose food tours rank Top 20 worldwide on Tripadvisor, offers this ultimate walking & food experience featuring the hard-working, salt-of-the-earth classics Chicago made famous: a slice of deep dish pizza, a Chicago-style hot dog, Italian beef, popcorn & dessert. Expert guides lead you through downtown’s most iconic landmarks on our Day tours—Millennium Park, Chicago Theatre, Riverwalk, Michigan Ave—Night tours go a different route, please check itinerary for details-we share Chicago’s rich, food-loving history. It’s one of the tastiest Things to Do in Chicago! Enjoy your tour & get a BONUS 2-hour FREE bike or kayak rental gift per ticket. Cruise the Lakefront Bike Trail or paddle Lake Michigan for extra fun!
Duration: 3 hours
- Free cancellation
Chicago Seadog River & Lake Architectural Tour
Soak in unobstructed views of Chicago’s world-famous architecture from the water with an exciting ride on our Seadog River and Lake Architectural Tour! Sail through the Chicago Harbor Locks to the River’s iconic skyscrapers. Enjoy amusing and informative narration for a fascinating tour through the city’s architectural history as you pass the Civic Opera House, the Merchandise Mart, and the Willis Tower. Buckle up for a thrilling finale on Lake Michigan to top off this family and dog-friendly experience and cruise along the skyline at top Seadog speed!
Duration: 1 hr 15 min
- Free cancellation
Chicago Gangsters and Ghosts Walking Tour
We are the original, top-rated Gangsters and Ghosts tour! Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn.
Walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through this now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers.
Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business".
Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing outside the Congress Hotel, one of the most haunted places in Illinois.
Duration: 2 hours
- Free cancellation
Museum of Ice Cream Chicago Admission Ticket
Step into a world of color, creativity, and sweetness at the Museum of Ice Cream in Chicago! This immersive, Instagram-worthy experience brings together art, interactive exhibits, and, of course, ice cream. Wander through vibrant rooms filled with unique, larger-than-life installations, from sprinkle-filled pools to playful, ice cream-inspired art. Indulge in a variety of delicious ice cream treats throughout the tour, including exclusive flavors that change seasonally. With engaging activities designed to spark joy and creativity, the Museum of Ice Cream is a fun, family-friendly adventure for all ages. Whether you’re a dessert lover, an art enthusiast, or simply looking for a fun outing, this experience promises a memorable, sweet escape. Don't forget your camera – every corner is a photo op! Reserve your spot today for a sugar-filled journey like no other.
Duration: 1 hr 30 min
Chicago Architectural River Cruise
Take in the views on this award-winning 90-minute Architectural Tour, a jaw-dropping excursion through a city that defies all expectations!
Please Note: We have three different vessels in our fleet. The boat you will be on is determined by the date and time you're choosing to sail. If you're interested in being on a specific boat please reach out to us directly at [email protected] and we can assist you.
Duration: 1 hr 30 min
- Free cancellation
City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River
Sail along the magnificent skyline on our Premier Plus Chicago Brunch Cruise. A chef-curated menu of plated brunch specials will delight your palate while unparalleled panoramas of the city’s iconic architecture are marveled at from our glass-enclosed vessel. Enjoy the awe-inspiring views of landmarks such as the Willis Tower, Navy Pier, and the Old Chicago Post Office in the comfortable interior or from the open-air spaces. This upscale experience on the Chicago River is complete with bottomless mimosas and a fully stocked cash bar, light architectural narration, masterful DJ entertainment, and exceptional service. Elevate your weekend with an unforgettable afternoon brunch cruise against a backdrop of Chicago’s most spectacular scenery.
Duration: 2 hours
- Likely to sell out
- Free cancellation
Chicago's Chinatown Food and Walking Tour
Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked Top 10 in America by USA Today & Top 20 in the world by Tripadvisor, for a day of interesting stories and scrumptious eats on this delicious Food Tour in Chinatown. This 3-hour Walking and Chintown Food Tour, you’ll see the bustling Chinatown Square, then get to sampling some of the richest cuisine around; including Cantonese dim sum, Portuguese-Chinese bakery treats, Szechuan style, and even Xi'an cuisine, all while learning about the history of how these foods & culture arrived in Chicago. This is a totally unique culinary tour experience, and not to be missed! Upon arrival to the tour, you can add a VIP Drink option for alcoholic and ethnic drink pairings! Chinatown can be challenging to navigate on your own, so let our expert local guides show you the way & discover 5 of our all-time favorite dishes.
Duration: 3 hours
- Free cancellation