Top Chicago Architecture Tours

Chicago River 90-Minute Architecture Tour

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

(10,849)

from $45

Likely to Sell Out

Join us in the daytime or evening for City lights and breathtaking views

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

(3,547)

from $28

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

Enjoy a quintessential Chicago experience—and see more of the city's highlights in less time—on an architecture-themed boat tour of the Chicago River. Pick from multiple convenient start times, and board your vessel directly from the Chicago Riverwalk. Thanks to your trained docent guide, receive a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

(16,901)

from $39

Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

Chicago River 90-Minute Architecture Boat Tour

(6,931)

from $57

Likely to Sell Out

Chicago Lake and River Architecture Tour

(1,868)

from $37

Likely to Sell Out

This tour cruises the Chicago River and Lake Michigan.

Maximize your Chicago sightseeing on a river cruise—and travel aboard a unique historical vessel, which other tours don’t offer—on this one-of-a-kind excursion. Pick from different departure times and board a classic Chicago fireboat, which served the city’s fire department from 1937 to 1981. As you sail Lake Michigan and the Chicago River, view architectural highlights including the Wrigley Building and Chicago Lighthouse, and chart the boat’s firefighting history via the on-board displays and commentary.

(2,426)

from $45

Historical and Architectural Chicago Fireboat River & Lake Cruise

Historical and Architectural Chicago Fireboat River & Lake Cruise

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

(461)

from $47

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Original Chicago Architecture Interiors Tour: Dazzling Interiors

See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.

(1,777)

from $35

Chicago Architectural River Cruise

Discover Chicago's world-renowned architecture during this sightseeing cruise. Board a comfortable riverboat for a trip down the Chicago River, viewing landmarks like the Willis Tower and the Tribune Tower while listening to in-depth commentary from your guide. Then board a speedboat for an exciting ride up the shore of Lake Michigan for views of Grant Park, the Museum Campus, and other top sights.

4.6

(854)

from $50

Chicago Architecture Tour and Speedboat Ride and Lake Michigan

Chicago Seadog River & Lake Architectural Tour

1 hour 15 minutesFree Cancellation

4.5

(289)

from $42

Chicago Architecture Tour - Skyscrapers, History and Photo Ops

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get a unique chance to combine touring by foot and by L train, and see the city’s most iconic landmarks like The Rookery Building, Chicago Cultural Center, First Arts Building, and more 19th and early 20th-century masterpieces. Be ready to see the City by the Lake from a new perspective and get to know it even closer as you stroll down its streets and travel by train. Enjoy the small-group experience and don’t miss a thing as you travel Discover the downtown and historical building together with your local knowledgeable guide Marvel at architectural landmarks of the City by the Lake and get to know the stories behind them Combine a walking tour with a train to see more landmarks and iconic sights on one tour.

2 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops

Get a fresher perspective on the Windy City—and a traffic-free one—with this Chicago River architecture cruise. As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch, listening to onboard narration about the city's architecture and history along the way. Unlike your standard walking tour, you can expect comfort, great food, and endless photo opportunities.

(1)

from $89

City Cruises Chicago: River Architectural Lunch Cruise

City Cruises Chicago: River Architectural Lunch Cruise

Take your architecture spotting off the streets and inside some of the most iconic buildings in Chicago with this unique Art Deco-themed tour. Get up close and personal with the glamorous style of the early 20th century as you delve beyond the downtown facades to explore glorious interior spaces from the 1920s and 1930s, with their ornate brass and marble details, mosaics, stained glass, and other treasures that most architecture tours miss.

4.3

(43)

from $74

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic skyscrapers and stunning lobbies, learning the fascinating stories behind their designs. This 2.5-hour tour is perfect for architecture enthusiasts and curious travelers alike, providing a unique perspective on the birthplace of modern skyscrapers. Whether you’re a local or a visitor, discover why Chicago's skyline is renowned worldwide. - Private tour lasting 2.5 hours, perfect for families and small groups - Visit landmark buildings like The Sullivan Center and The Rookery - Expert local guide shares insider knowledge about architectural history - Flexible meeting points available for your convenience

(122)

from $35

Private Chicago Loop Architecture Walking Tour

Private Chicago Loop Architecture Walking Tour

2 hours to 2 hours 30 minutesFree Cancellation

Price varies by group size

(12)

from $180

Explore the Historic Old Post Office in Chicago

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once seemed as though the stunning architectural details of Chicago's Old Post Office would be lost to time while the building sat vacant for almost two decades. But the 2.8 million square foot building, completed in 1934, recently went through a monumental renovation and now serves as a modern multi-use event and office space that meets today's need for large, light-filled workspaces. See how historic artifacts and building details have been creatively incorporated into the Old Post Office's design including the conversion of the roof to a 3.5-acre urban rooftop park. Old places can become new spaces when a developer with vision collaborates with an award-winning architectural team.

Explore the Historic Old Post Office in Chicago

Discover Chicago architectural treasures—and immerse yourself in the Windy City's history—on this small-group walking tour. Your focus is the iconic stained glass pieces crafted and designed by the Tiffany Glass and Decorating Company. Following your guide from the Chicago Architecture Center, visit four late-19th-century landmarks that contain glass works by Louis Comfort Tiffany and his contemporaries. This in-depth, insider tour is a must-do for history and architecture fans.

(25)

from $15

Chicago Walking Tour: Tiffany Treasures

Chicago is world-renowned for its architecture—and this small-group walking tour offers the ideal introduction to its iconic buildings, its architectural eras, and the starchitects who have left their impression on the city. Meet your guide at the Chicago Architecture Center and set off on foot: you’ll discover highlights like the Wrigley Building and Marina City, will see works by Renzo Piano and Frank Gehry, and will learn all about Chicago history.

(46)

from $35

Chicago Walking Tour: Connecting Past and Present

Chicago Walking Tour: Connecting Past and Present

1 hour 45 minutesFree Cancellation

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

(43)

from $35

The Chicago River, as seen from our stop on wacky Wacker Drive

Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

Dive into the center of the architectural boom of the roaring 1920s and take a chance to enjoy the grand facades of the Art Deco skyscrapers on this guided walking tour. Go back in history while admiring one of the epicenters of the style’s birth. Immerse yourself into the life of the Windy City between World War I and World War II, the time when the design evolved and turned into neo archaic Mesoamerican grandeur, which can’t leave anyone indifferent. Be delighted with the variety of decorations and geometrical shapes which distinguish Art-Deco from Neoclassicism. Uncover the stories behind the famous Loop district of Chicago. Delve into the atmosphere of the 1920s as you listen to more insights and facts from your enthusiastic local guide. Overview the history and pay attention to the details you wouldn’t notice without a tour. Grab the chance to get inside famous buildings and revel in the Art Deco interiors.

(734)

from $50

Chicago Art Deco Architecture Tour - History of the Jazz Age

History of the Jazz Age at Chicago Art Deco Architecture Tour

Discover one of Chicago’s most picturesque, historic neighborhoods—and learn all about the buildings that make it an architectural standout—on this small-group walking tour of Wicker Park. Meet your guide in the morning, and set off on foot: you’ll discover the 19th-century workers’ cottages that fill the neighborhood, will admire local landmarks like mansions and historic baths, and will learn all about the city’s architectural history.

3.5

from $67

Historic Homes and Cottages of Wicker Park Walking Tour

Historic Homes and Cottages of Wicker Park Walking Tour

1 hour 30 minutes

Step into the birthplace of the modern skyscraper on this immersive walking tour through Chicago’s historic Loop. Discover the stories, innovations, and hidden details behind the buildings that shaped the modern city. What makes this experience unique: • Small-group tour for a more personal experience • Story-driven guiding that brings Chicago’s architecture to life • Focus on early skyscrapers and hidden architectural details • Visit iconic landmarks in the historic Loop • One complimentary copy of my book, Chicago Beyond the Bean, is included per booking.

(48)

from $45

Chicago Early Skyscraper Walking Tour in the Loop

Chicago Early Skyscraper Walking Tour in the Loop

Chicago is renowned for its wealth of spectacular architecture—and this small-group tour gives you the special chance to discover building interiors that most visitors overlook. In the afternoon, meet your guide in Downtown Chicago, and get ready to discover the interiors of five of the city’s most striking art deco skyscrapers. As you go, soak up the skyline views, and learn more about the city’s unique architectural history.

from $39

Chicago Walking Tour: Art Deco Skyscrapers Riverfront

Chicago Walking Tour: Art Deco Skyscrapers Riverfront

Explore the Loop's famous architecture—and learn insider facts and stories that you wouldn't encounter if exploring alone—on this small-group walking tour. Led by your Chicago Architecture Center–certified guide, you'll discover some of the city's oldest skyscrapers, dating from the late 19th and early 20th centuries. Admire the Rookery building, see the Marquette building, and much more, all while soaking up the city's ineffable energy.

(102)

from $35

Chicago Walking Tour: Historic Skyscrapers

Take a time travel journey inside Chicago's best-kept secret: a 125-year-old architectural marvel. This extraordinary building was envisioned by renowned architect Solon Spencer Beman, famous for designing the town of Pullman and the iconic Pullman Palace Car Company. Get ready to be transported through time and history as you explore the legacy of this architectural genius and the fascinating stories hidden within these hallowed walls. Join us for an unforgettable adventure into the past and witness the living testament to Beman's architectural prowess.

(72)

from $35

Main doorway to the Fine Arts Building, virtually untouched as designed by Solon Spencer Beman, Circa 1885.

Inside Tour of Chicago’s Fine Arts Building

1 hour to 1 hour 30 minutes

Chicago River 90-Minute Architecture Tour

(26)

from $45

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What are people saying about Chicago

Kristian_S, Aug 2026

Worth every penny!

Plan to get in line at least 30 minutes before your tour to get the best choice of seats. The information was very informative and interesting. We would do this every time we come to town! It is a relaxing way to see and learn about the city. We highly recommend this tour!

Chicago Architectural River Cruise

Lynette_K, Aug 2026

This was the perfect...

This was the perfect activity for us to enjoy the stunning city views on a late summer day on the water and to learn more about Chicago and its fascinating architectural history. Our guide was engaging, the drink bar was a nice perk as we had been and continued to tour and play in the city. Highly recommend

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Lisa_K, Aug 2026

Discovering Chicago’s hidden treasures

We really enjoyed this architectural tour which revealed so many hidden gems in the interiors of some of Chicago’s most historic buildings. Spencer was a knowledgeable and entertaining guide who clearly has a passion for Chicago and its history. Would recommend this tour to any one.

Chicago Architecture Center River Cruise aboard First Lady

Suzanne_M, Aug 2026

Great, except if you have trouble walking long distances

Excellent! Our volunteer narrator's comments were interesting and folksy, with fun anecdotes about particular buildings. My only negative content is that getting there is very difficult for those with mobility issues, having to walk so far along the ramp. Perhaps directions coukd be provided on the web page fto privide to taxi drivers to drop off passengers in the parking garage area nearest the ticket booth (Dock 2?)

Chicago in a Day Walking Tour: Food, History & Architecture

mazndene, Aug 2026

Great tour guide and experience.

Great tour, David our guide was very knowledgeable. He took us to places we never would have looked at but WOW. Food was a real bonus it will fill you up. The popcorn stop was an eye opener who would have thought cheese and caramel would be so tasty 😂. Would definitely recommend this tour Chicago is an amazing city and thanks to David it was such an enjoyable experience.

Historical and Architectural Chicago Fireboat River & Lake Cruise

DavidFran_B, Aug 2026

An Unforgettable Chicago Experience

We had an amazing two hour historical and architectural boat tour in Chicago! Our tour guide, Cliff, was fantastic. He was incredibly knowledgeable and shared so many fascinating facts about Chicago’s history and the beautiful architecture along the river. Cliff was also so personable and genuinely interested in getting to know us. He came over to ask where we were from and even recommended some great places for us to visit during our time in Chicago. This tour was absolutely worth every penny! Seeing the incredible buildings while learning the history and stories behind them made the experience so much more enjoyable. I highly recommend this tour to anyone visiting Chicago. Be sure to request Cliff because you won’t be disappointed!

Chicago Seadog River & Lake Architectural Tour

ROMANA_K, Jun 2026

Speed boat ride in Chicago

This was fantastic experience from the start to finish! We did the 7:15 pm ride and it was the best time to do it in June. It was hot during the day but for the 7:15 pm ride the weather was much cooler which felt great! We boarder and finished at the Navy Pier. The pier is great to walk, have drink and food and enjoy some live music! It is fun amusement place! First we went on the river to downtown which was awesome! So informative and spectacular to see all the buildings!!! Wow! To see the buildings from the river and considering that it was slowly getting to sunset hour, I would do it again in a heartbeat! The reflection of the sun going down on the buildings at different angles was incredible! After the river Seadog team took us on the speed boat on the lake when Sun completed its sunset! We went fast on the boat, water splashing, music playing and everyone was laughing and having so much fun! IT WAS the BEST THING we did in Chicago! Book your tickets for the 7:15pm only with Seadog Speed Boat! The time of the ride and the company matters very much for the experience. And the boat is smaller than the other ones from other companies so we were smaller group of people given great fun and informative experience from the Crew! Thank you SEADOG! We love it!😍

Chicago City Tour with Architecture River Cruise Option

Marty_R, Mar 2026

Wonderful tour with Alan!

Alan was a great tour guide - lots of fun information and entertained all of our questions. It was my 17 year old daughter’s first trip to Chicago, so I wanted her to get to see as much of the main parts of the city as possible, and we definitely hit all the ones I had on my list! The bus itself was clean and well cared for, and I like that it was smaller than the other buses because it made it much more personal. Alan also had great recommendations for places to go, where to eat, and was able to give ideas for spots that were of interest to us specifically. Highly recommended!