Chicago

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.

Chicago Architecture Evening Cruise by Shoreline

Chicago City Tour with Architecture River Cruise Option

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with an expert guide in a comfortable minibus, enjoy world renowned architecture including the world's first skyscrapers, Museum Campus (for the BEST skyline view in town), Millennium Park (Home of "The Bean"), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! You also have the option to upgrade to include THE most popular Architecture River Cruise in Chicago! For good reason, our partner Shoreline Sightseeing, has been the most booked tour on TripAdvisor for the last 5 years! And yes, there is a bar on the boat. The combo option will end at Shoreline Sightseeings Navy Pier location, after you finish the boat tour you will be walking distance from many other attractions in the city! There will be no provided transportation after your boat tour

Odyssey Chicago River Architecture Dinner Cruise

• Enjoy a 2.5–hour Chicago River cruise aboard the Odyssey, complete with a gourmet plated dinner and live, curated entertainment for an unforgettable evening on the water.

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ages! You can join our friendly crew, to help raise one of the many sails on Windy, or just relax, and let others do the work! Windy has a full bar, and a gift shop, to help you enjoy the sail.

45-Min Lake Michigan Tour by Shoreline

This concise yet immersive tour provides a unique perspective of the Chicago's skyline from the waters of Lake Michigan.​

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!

Chicago at Night: River & Lake Sightseeing Cruise by First Lady

• Cruise through the Chicago River and Lake Michigan at night on a 90-minute guided journey featuring illuminated skyline views, live commentary, and guaranteed outdoor seating.

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.

Lake Michigan Dinner Cruise

• Spend 2-3 relaxing hours aboard a Lake Michigan dinner cruise, savoring a chef-crafted buffet and unlimited soft drinks as Chicago’s skyline glows in the evening light.

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!

Chicago River & Lake Sightseeing Cruise by First Lady

• Cruise through both the Chicago River and Lake Michigan on a 90-minute guided journey featuring panoramic skyline views, historic bridges, modern architecture, and passage through the Chicago Harbor Lock.

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.

Chicago Bottomless Mimosa Brunch Cruise

• Experience a 2-hour brunch cruise on Lake Michigan with bottomless mimosas and live DJ entertainment.

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!

Lake Michigan Cruise

• Experience Chicago’s iconic skyline from the water on a Lake Michigan cruise, offering a unique vantage point and engaging narration that brings the city’s history and architecture to life.

Chicago's Fireworks Show aboard Tall Ship Windy!

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a leisurely evening sail past the brilliant and beautiful Chicago nighttime skyline. Windy provides the accompanying sound track, over the ship sound system coordinated fireworks display, amazing show! Rain or Shine event. no umbrellas are allowed to be opened underway. Tall Ship Windy, located on Navy Pier, and we have a ticket booth and dock, in front of the Billy Goat Bar and Grill. Arrive early, as fireworks crowds are huge! expect travel delays.

Chicago Haunted River "Creepy Cruise" by First Lady

• Experience a 90-minute nighttime cruise along the Chicago River, where a lively guide shares chilling stories of haunted history, mobsters, eerie sightings, and hidden secrets tied to the city’s past.

Chicago Water Taxi River Fireworks Cruise

Join Chicago Water Taxi on Wednesday nights as we depart from the Magnificent Mile to view the City’s fireworks display. No city embraces summer quite like Chicago. Join the celebration with friends and family on this social fireworks cruise. The River Fireworks Cruise is aboard the Wendella LTD or Robert H, Chicago Water Taxi’s flagship vessels. The journey begins at Michigan Avenue, cruises up the Chicago River, and ends with a spectacular view of the Chicago Fireworks as seen from the Chicago River. The vessel has an open-air upper deck, and enclosed climate controlled lounge on the lower deck. There is a bar on board with beer, hard seltzer, and soft drinks.

Chicago River Architecture Cruise

• Discover Chicago’s iconic skyline from the water, with 360° panoramic views on a comfortable, two-level boat.

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.

Chicago Skyline Lake Tour

Get the perfect introduction to Chicago and its history on this 30-minute panoramic Lake Michigan tour!

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.

Chicago Sea Dog Architecture Cruise

• Enjoy a narrated architectural cruise along the Chicago River and Lake Michigan, featuring iconic skyline views and engaging commentary on Chicago’s most famous buildings.