Chicago Architecture Experience by Train

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.

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.

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.

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's exclusively offered interiors-themed tours in Chicago for more than a decade, and that's INSIDE CHICAGO WALKING TOURS. Our "World Within: Dazzling Interiors of the Loop" tour is Chicago's first and best architecture interiors tour. Accept no imitations! Explore some of the most stunning interior spaces you’ll ever see – spaces you’d surely pass by without a second glance if you weren’t shown them by a seasoned, in-the-know tour guide. Ranging from stained glass mosaics from the turn of the century to soaring Art Deco spaces from the Roaring 20s, these spaces are some of the most beautiful in the city -- and open to us to explore!

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.

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!

The perfect tour for first timers to Chicago or those who want to explore Chicago's famous foods along with the city's top attractions, all on one tour. Stroll the beautiful streets of downtown Chicago & taste the Windy City’s favorite eats! Bobby’s Bike Hike, whose food tours are ranked Top 10 in America (USA Today) & Top 20 in the world (Tripadvisor), offers this ultimate food & walking tour to explore the hard-working, salt-of-the earth foods Chicago made famous; a slice of deep-dish pizza, a Chicago-style hotdog, Italian beef, popcorn & brownies. Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks; Millennium Park, State St, Chicago Theatre, Riverwalk, Michigan Ave, & the Wrigley Building, all the while explaining the tales from Chicago’s rich food-centric history. Enjoy your food tour & receive a bonus 2-hour FREE bike or kayak rental for each ticket bought, adding value to your experience. Bike along the Lakefront Trail or kayak on Lake Michigan.

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago. On this tour, we will explore the famous and mysterious Chicago Pedway, a system of underground tunnels connecting 40 blocks downtown, popping in and out of buildings to see beautiful and fascinating interior spaces. You'll learn to use this system that most locals don't even fully know or use, and you'll be encouraged to continue exploring Chicago on your own after the tour!

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! Along the way, your guide will provide historical, informational and at times humorous commentary about the area. Four photo stops are a part of each tour. The small-group atmosphere with a maximum of 10 people ensures a more personal experience.  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.

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how it has shaped the development of buildings within the Loop. The city's first elevated train started making trips in 1892. Now considered one of Chicago’s most defining features, the "L" offers incredible views of downtown. By being more than 20 feet off the ground, you'll see architectural details that are missed by most pedestrians at street level. This is our most comprehensive tour in the Loop, passing hundreds of buildings and highlighting ones of architectural significance. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

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! Start the tour at Navy Pier and 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!

Tour the streets of Chicago to see the beauty and legacy left behind by the Prohibition Era. See the amazing architecture, iconic sights (both old and new), the city's best spots and try a local sweet treat along the way as you explore on foot.

The Chicago Architecture Center (CAC) was founded in 1966 as the Chicago Architecture Foundation to save the historic Glessner House. Since then, the CAC has grown to become one of the largest cultural organizations in Chicago. Visit the CAC to view our 4,250-building scale model of Chicago, shop in our award-winning store or participate in a fun family event in our ArcelorMittal Design Studio. On the Chicago Model, view more than 4,200 buildings in one spectacular room at the cinematic and interactive Chicago City Model Experience. At the Chicago Gallery learn how Chicago became the "city of architecture," with a look at its fascinating neighborhoods, housing styles and famous architects. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Experience the best of Chicago with a Premier Plus Architectural Lunch Cruise and spend your afternoon on the Chicago River with dining, picturesque views, and a narrated architectural tour of the city. While onboard, you’ll enjoy our chef-prepared, plated menus, creative cocktails, distinctive service, and breathtaking views from our climate-controlled interior and open-air outdoor deck. Whether for a celebratory lunch for two or for a special afternoon with friends and family, our Architectural Lunch Cruises offer the most breathtaking views of Chicago with an accompanying narrated tour highlighting the history of the city from the water.

Embark on the adventure of a lifetime! Step aboard the iconic California-Chicago Train Expedition as we whisk you away on a journey that combines the thrill of train travel with the magic of California's breathtaking scenery. From the vibrant streets of Oakland to the sun-kissed Lakes of Salt Lake City, discover the majestic United States, like never before. Immerse yourself in the glitz and glamour of Las Vegas, experience the majesty of the Sierra Nevadas, and savor the world-class views of the Rocky Mountains. With luxurious accommodations, gourmet dining, and expertly guided excursions, this is the tour that dreams are made of. You can start from either CA, CO, or IL. Don't worry about other people, this tour is completely tailored to you with the Pintours App! With our app, you can pause the tour, and check out the locations as long as you want! You can skip a stop you don't like, and you have all the best information about each stop at your fingertips.

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying architectural styles and see how older structures connect to new skyline additions. On this tour, we'll make seven stops in downtown Chicago where we can compare the histories and styles of buildings located within sight of each other. The tour features 19th-Century Commercial, Beaux-Arts, Mid-Century Modern and Postmodern buildings, as well as the latest in architecture from Frank Gehry, Renzo Piano and Adrian Smith. At each stop, we’ll look at the connections between the past and present and discover what inspires design today. The tour culminates with a visit to Millennium Park, where world-class art and architecture combine, creating a unique urban fabric. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Elevate your evening with a delicious dinner and jaw-dropping panoramic views of the Navy Pier fireworks display illuminating the Chicago city skyline! On our Fireworks Signature Dinner Cruise on Lake Michigan, a dazzling show of light and color will be the backdrop to a chef-prepared buffet meal, specialty cocktails, live DJ entertainment, and dancing. From the breezy open-air decks and comfortable indoor spaces, you’ll soak in spectacular views of Chicago’s most famous landmarks, such as the Willis Tower and the Alder Planetarium. A spectacular fireworks dinner cruise on the water awaits!

Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM) and a city ready and willing to accept them. Find out what set these buildings apart from their predecessors and how they helped set the stage for the future. If you’re interested in iconic buildings, public art, urban planning or government this is your tour. Find out the stories behind inland steel, Marina city, the IBM building and other "Mad Men" worthy skyscrapers. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Immerse yourself in Chicago’s distinct skyline with bold skyscrapers and incredible views of Lake Michigan .Enjoy the efficiency of having your own local expert and personal guide to share unique and fascinating stories about the surrounding area including exclusive local insights, historic highlights and personalized recommendations. You and your private small group will enjoy complimentary downtown Chicago hotel pick up. To begin your tour your Tripshepherd guide will take you to the Adler Planetarium Pier, a must-stop while in the Windy City. Aboard the Shoreline Architecture Cruise you will enjoy a narrated boat tour where you will see the breathtaking views of over 40 Chicago iconic landmarks, from hidden architectural features to the Windy City's most famous monuments. To finish your exclusive, private tour, you will get to visit two iconic Chicago landmarks - the Buckingham Fountain and the Chicago Bean (Cloud Gate). Enjoy complimentary downtown Chicago drop off.

Get the best of Chicago with a local guide on this walking tour featuring the city’s best neighborhoods, top attractions, and the Chicago ‘L’! We’ll start by exploring the Chicago Loop, home to an array of mind-blowing architecture. See the Willis Tower, Union Station just across the river, and admire the Beaux-Arts beauty of the Art Institute of Chicago. No downtown Chicago experience is complete without a stop at Millennium Park’s Cloud Gate, AKA The Bean. We’ll then head north to stroll along the Chicago Riverwalk before exploring the River North neighborhood, home of the iconic Wrigley Building. Over in the Magnificent Mile district, grab post-tour tickets for the Museum of Contemporary Art or brave the 94 floors up to 360 CHICAGO observation deck. End your tour here or nearby in the attraction- and entertainment-filled Navy Pier. During your tour, your guide will treat you to a local snack as well as a $5 train pass so we can really maximize our time sightseeing in Chicago!