Tours & Activities in Chicago

Take a tour of Chicago's Pedway system (a network of underground tunnels that allows pedestrians to pass from one end of the Loop to the other) and enjoy seasonal holiday decorations and sights along the way. Our tour begins in the lobby of the Swissotel where we descend into the Pedway. After a tour of the Chicago Cultural Center and its famous Tiffany Dome, we return to the Pedway for a short walk to Macy's department store. There, we'll view the famous Tiffany ceiling, the "Great Tree" in the Walnut Room and the store’s decorated holiday windows. We return to the Pedway and follow it to Civic Center Plaza for a visit to the Christkindlmarket, an authentic European holiday market. We return to the Pedway for a visit to City Hall followed by a short walk to a nearby L station. A quick train ride takes us to the origin/terminus of Route 66, the Art Institute’s wreathed lion statues, and to Millennium Park to view the famous "Bean" sculpture and the city's majestic holiday tree .

This tour will show you many of these delightful cottages and the different styles they were designed and constructed in. You will also learn about their history and unique part of the growth of the city of Chicago. Plus you will hear about other fascinating Chicago history that dates back 150 years and beyond! The Oldtown Triangle is one of the oldest and most quaint areas of the city - an area that many Chicagoans love and cherish. You will feel like you have left the hustle and bustle of the city and will instantly be transported to another place, another time, specifically the late 1800's!

If you are looking to go on a wonderful tour but also want to avoid the cold weather outside, I have the experience for you: Incredible Interiors! All the tour stops are inside warm buildings with stunning architectural details. Every featured building was designed between the 1880s and 1930s, and they don’t make spaces like this anymore! You’ll discover masterpieces by Louis Comfort Tiffany, Daniel Burnham, Louis Sullivan, Frank Lloyd Wright, and so many others. These spaces are STUNNING, and I’m so looking forward to showing them off to you!

Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish! Our two-part tour begins by exploring the heart of downtown Chicago - with its iconic architecture, both old and new, views of the Chicago River, Millenium Park, and bustling city avenues (plus, a couple tasty local treats along the way). From there, we’ll hit the Central Loop, where locals go to grab their favorite foods, day and night. Try the best of Chicago fare and get to know the history and how-tos (and how-not-tos) behind iconic street and comfort food staples - from the infamous deep dish pizza to sandwiches to a loaded hot dog! Your local guide will entertain with fascinating stories and the everyday immigrant chefs and vendors responsible for Chicago’s eclectic food scene. By the end of the tour, you’ll have a deep appreciation for both the evolution of this excellent city and the role food has played in the lives of all Chicagoans!

Over the course of 90 minutes, explore some of the newest buildings around the Chicago Architecture Center, focusing on construction elements and their impact on the city’s built environment. What's New looks at some of the most recent additions to the built environment surrounding the Chicago Architecture Center. This walking tour focuses on each building's height, structure, materials, ornament and its impact on the environment, the neighborhood and the city's economy. The tour showcases several recently completed buildings, including 462 N. Park and the St. Regis, and compares them to each other in order to observe emerging patterns. These new additions are also contrasted with some of the older buildings downtown as a way to highlight developments. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish materials and geometric ornament. Discover the origins of Art Deco while admiring buildings like the Carbide and Carbon Building (now Pendry Chicago), the Chicago Motor Club Building (now the Hampton Inn) and the colorful, but often overlooked, Trustees System Service Building (now the Century Tower)—all of which are designated Chicago landmarks. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Insta Walk offers you a lot of stylish photos, shooting angles and ideas. This easy, relaxed and friendly walk will open Chicago for you from a new perspective! Throughout the tour, I'll use iPhone and Polaroid cameras to capture your perfect shot. You'll receive approximately 100 digital photos, 10 of which will be color-corrected to make them truly pop. And for a unique and timeless souvenir, I'll also give you 5 Polaroid prints that you can treasure forever.

One of Chicago’s earliest and most vibrant areas, this cultural melting pot is made up of multiple historic neighborhoods and bustling avenues. Immerse yourself in the sights and sounds of its tree-lined streets filled with galleries, local shops, award-winning restaurants, and stunning architecture all unique to this enclave of the city. Featured on the tour is the longest continually operating settlement house in the country, local art, shops, and a walk through a historic mansion-filled neighborhood.

We are Chi-Town foodies of the first order, and we're so excited to share with you all the culinary delights this historic Midwestern city has to offer. There is so much to share about Chicago: historic enclaves, stunning architecture, an extensive collection of publicly displayed civic artwork, and a culinary style steeped in history. We will discover each facet of this unique city as we eat and explore Chicago's Loop District. As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!

Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier shopping district. Hear the secrets and stories behind the striking buildings on North Michigan Avenue that have become architectural icons. Developed over the past 100 years, the street includes historically-inspired architecture in Parisian, Gothic, neoclassical and Art Deco styles sprinkled among Modern and 21st Century buildings. You’ll see skyscrapers, vertical malls, hotels, residential towers and some buildings that were designed to embody the brands sold inside. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

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- Chicago's Highest Rated Limo And Car Service - 10 Years in the limousine business - Proven track of exceptional customer service - Professional, Safe, Fully Uniformed Chauffeurs - FBI Background checks for all drivers - $350,000 Commercially Insured - GPS tracking devices on all vehicles - "Driver ON Location" automated text message - Chicago Based company Skip the stress of a taxi or shared shuttle between Chicago downtown and Midway airport with the Highest rated limousine service in Chicago on Trip Advisor and Yelp. A professional driver will pick you up at Chicago O'Hare Airport at curbside. Travel in a comfortable, newer private sedan for a safe and relaxed ride. All our drivers are licensed and insured and all our sedans carry a $350,000 insurance policy. Ensure a hassle-free arrival at Chicago Midway Airport (MDW) with this private transfer service to your downtown Chicago hotel.

Join a local guide on this exploration of Chicago’s amazing food scene! Navigate through the downtown streets straight to the vendors and restaurants We love most! As we pass by places like the Chicago Riverwalk and take in the city’s awe-some architecture, you’ll get to grips with the evolution of the city as immigrants brought their culinary influence to The Windy City. We’ll get to know generations-owned shops and the origins behind Chicago’s most beloved street eats, all the while appreciating fresh ingredients sourced locally from midwestern farms. Among the tastings that will add up to a full meal, you will get a taste of a local street food staple, perhaps the famous Chicago-style hot dog or Italian Beef, or another local favorite. A food tour of Chicago is not complete without a bite of the iconic deep dish pizza, and we will top it off with a sweet treat with a meaningful connection to Chicago. By the end, you'll have had the full Chicago foodie experience!

Discover Chicago by private boat with a local Chicagoan to highlight its fascinating history and architectural marvels along the way! Before we board, we’ll take a short walk in the Chicago Loop, a bustling area filled with gems like the ostentatious Marshall Field building, the stained-glass-domed Cultural Center, and the Chicago Theatre, adorned with its emblematic marquee. After arriving at the dock, you’ll board your own private boat and set sail along the Chicago River. As we glide along, your guide will point out some of the city’s most fascinating landmarks. Stare up in awe at Willis Tower, once the world’s tallest building. Spot Union Station, which you might recognize from several famous films. And gaze upon a behemoth Art Deco building so large it once had its own zip code! We’ll also pass by Wolf Point, formerly occupied by Native Americans and later by many of Chicago’s first commercial buildings. Afterwards, you might want to explore all these sites and more on foot!

On this nostalgic and educational tour, we will lead you on a "Christmas treasure hunt" through downtown Chicago in search of the most stunning and impressive Christmas trees and other holiday decorations — and we know where they are! This tour includes not only visits to well-known stops like the Christkindlmarkt and the old Marshall Field’s, but also to little-known stops that contain some of the best holiday decorations downtown. You’ll learn about the origins of some world-famous Christmas characters — some of them from Chicago, some not — as well as the history behind Christmas traditions practiced by people around the world.

- Chicago's Highest Rated Limo And Car Service - 10 Years in the limousine business - Proven track of exceptional customer service - Professional, Safe, Fully Uniformed Chauffeurs - FBI Background checks for all drivers - $350,000 Commercially Insured - GPS tracking devices on all vehicles - "Driver ON Location" automated text message - Chicago Based company Skip the stress of a taxi or shared shuttle between Chicago downtown and O'Hare airport with the Highest rated limousine service in Chicago on Trip Advisor and Yelp. A professional driver will pick you up at Chicago O'Hare Airport at curbside. Travel in a comfortable, newer private sedan for a safe and relaxed ride. All our drivers are licensed and insured and all our sedans carry a $350,000 insurance policy. Ensure a hassle-free arrival at Chicago O'Hare Airport with this private transfer service.

Skip the stress of a taxi or shared shuttle between Chicago downtown and Midway airport with the Highest rated limousine service in Chicago on Trip Advisor and Yelp. A professional driver will pick you up at Chicago O'Hare Airport at curbside. Travel in a comfortable, newer private sedan for a safe and relaxed ride. All our drivers are licensed and insured and all our sedans carry a $350,000 insurance policy. Ensure a hassle-free arrival at Chicago Midway Airport (MDW) with this private transfer service to your downtown Chicago hotel.

Created by 13-time James Beard Award-winning food journalist Steve Dolinsky, this series of tours is based on his book, "Pizza City, USA" and features four different styles of pizza. Learn about Chicago's 10 pizza styles, and discover why there's more to The Windy City than just deep-dish. Learn how pizzas are made, talk to some owners and taste the differences. Expert doughcents will share the history of Chicago pizza as well other interesting tidbits about the neighborhood you're exploring. You'll try deep-dish, artisan, Chicago's most popular - tavern-style - and finally, a Detroit-style slice. We return to Labriola no later than 2:30pm. PLEASE LET US KNOW AT TIME OF BOOKING IF YOU EAT PORK OR PREFER VEGETARIAN.

Reliable and luxury airport transfers Best and most professional Chauffeurs in the industry Up-to-date luxury vehicles High quality of service Smart rates

Reliable and luxury airport transfers Best and most professional Chauffeurs in the industry Up-to-date luxury vehicles High quality of service Smart rates

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.

Cruise the river on a less crowed, small historic yacht! When in Chicago, cruising down the Chicago River is a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50 significant buildings, wrapping up at the end of the river.

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. All charters are NON-SMOKING experiences.

For luxury Chicago limo transportation, Ryde Luxury Limousine is the trusted provider for thousands of clients. We provide the best in luxury transportation with affordable rates, professional and friendly chauffeurs, safe and comfortable vehicles, and a focus on customer service. Our limo service in the city of Chicago is the top choice if you need airport transportation, want a special night out, going sightseeing in the beautiful windy city, or need daily business transportation. Our limo services get you to your destination safely, efficiently, and comfortably.

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which provides a unique and interesting touch to the normal tour experience. Being both sturdy in the water, and fast! Reaching up to speeds of 35 Knots! We work hard to provide historical context for our great city, as well as provide an exhilarating experience through the use of high speed runs and spins!