Activities & Tours: Illinois

Excellent Quality

Chicago’s Friday Night Pirates Pub Sail Aboard a Tall Ship

Take in the world-famous skyline of the Windy City from the water, and enjoy a leisurely trip on Lake Michigan aboard Chicago's Famous Pirates Pub. Your ticket includes one complimentary rum punch, domestic beer, soda or water, per person. Duration: 2 Hours Chicago’s famous Pirates Pub Sail departs every Friday night at 9pm aboard Tall Ship Windy at Navy Pier. This is a two hour charter and returns to Navy Pier at 11:00pm. Your ticket includes one complimentary rum punch, domestic beer, soda or water. Aboard the 148 foot Tall Ship Windy, you will enjoy the merriment of days of yore. You will be able to listen and sing to the traditional songs of the Pirates while enjoying the spectacular scenery that is the Chicago skyline and the wonderment of Lake Michigan. Chicago’s famous Pirates Pub Sail is an event that should not be missed.

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based on 49 reviews

See Details → Duration :2 hours
From $89

Chicago in a Day: Food and Architecture Private Walking Tour

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!

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based on 32 reviews

See Details → Duration :5 hours
From $272.5

Chicago Sunset Segway Tour

Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views as well as views of Chicago's world-famous skyline and graceful lakefront. This segway tour departs near Millennium Park as dusk arrives and passes sights like Buckingham Fountain, Chicago’s majestic lakefront, and the Museum Campus.

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based on 21 reviews

See Details → Duration :1 hours 30 minutes
From $75

Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

Enjoy a private 2-hour walking tour with Belgian-American tour guide Leentje. She will introduce you to the city she calls home since 2014. Every tour is different and custom-made. Tours are available in English, French, or Dutch. Focus can be on public or street art, architecture, food, and much more!

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based on 28 reviews

See Details → Duration :2 hours
From $220

Chicago Neighborhood Food Private Walking Tour

This Chicago food tour gives you the chance to explore the city’s foodie scene to its fullest. Explore legendary bakeries in neighborhoods around the city. You'll discover Chicago’s immigrant roots with incredible food from around the world, including Italian, Polish, and German cuisines. Let your local tour guide take you to their favorite candy shop in town, meet interesting shop owners, and hear the stories of restaurants that have been local favorites for generations. We can even include a tour stop to sample some of Chicago’s amazing craft beer from a local brewery! In between food tour stops, we’ll show you the iconic historic and architectural sights of the city as well as a wonderful variety of neighborhoods, and you’ll get your fill of the city’s

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based on 17 reviews

See Details → Duration :2 hours 1 minutes
From $245

Chicago Insta Walk with Digital and Polaroid Photoshoot

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.

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based on 24 reviews

See Details → Duration :1 hours
From $129

Chicago Insider Segway Tour

This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the totally weird stories of Chicago. We will travel back through the ages as you discover the city through the lens of the Chicago Syndicate, hear the whispers of the city’s elite (or politicians), and be entertained by stories that are rarely told. You’ll think “No, really I never would have known!” Glide around Millennium Park, through the new neighborhood of Lakeshore East, and along the Lakefront as we unveil Chicago’s forgotten past in two hours! Your imagination will come alive as you hear stories of the Chicago Mob, the truth behind the 1968 Democratic National Convention, innovations that changed history, and so much more!

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based on 51 reviews

See Details → Duration :2 hours 20 minutes
From $79.99

Walking Tour of Chicago Loop: Home of the Modern Skyscraper

We start our tour at one of the most interesting buildings in the Loop — the Fine Arts Building. Built in 1884 as a showroom and office complex, the building was converted later into its present-day use. Then we're off to the Harold Washington Chicago Public Library, the design of which was the winner of a competition to design a new library for the city. From there, we'll view three Chicago landmarks built in the late 1800s, then visit the beautiful Marquette Building, the Field Building (built on the site of the world's first modern skyscraper) and then see the amazing atrium lobby of the world-renowned Rookery Building. Next, we're off to the beautifully-restored Quincy L stop (authentic 1897 design) to take the train to our last stops. We visit the iconic Macy's to see the beautiful Tiffany mosaic then we wrap up the tour at the Cultural Center to experience the world's largest Tiffany dome. Make a day of it and book our Pedway or Historic Pubs tour for the afternoon!

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based on 33 reviews

See Details → Duration :3 hours 30 minutes
From $60

Chicago Walking Tour: Modern Architecture

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.

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based on 29 reviews

See Details → Duration :1 hours 30 minutes
From $30

Chicago Full Day Bike Rental

Explore Chicago at your own pace on an independent bike tour. With your full-day bike rental, pedal along Lake Michigan and visit top Chicago attractions such as Lincoln Park, Navy Pier, Millennium Park, Wrigley Field and the Shedd Aquarium. This is a fun and active way to experience the city with the whole family, and you can enjoy the flexibility to create your own itinerary with the help of your provided map.

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based on 44 reviews

See Details → Duration :1 days
From $29.99

Chicago Prairie Ave District Walking Tour: Street of the Elite

This extraordinary tour of the Prairie Ave District is one not to be missed. Get a sense for how Chicago's wealthiest residents lived around the turn of the century and what remains today. This unique Chicago tour begins with an exploration of one of the city's newly-revitalized spaces: The stunning Chicago Athletic Association Hotel. A short ride on the Green Line takes us to the Prairie Ave District, home to many historic sites such as Motor Row, the former Chess Records and the oldest house in the city. As we wander along Prairie Ave, we're treated to historic mansions and a beautiful park. The highlights of the tour, however, are TWO private, docent-led mini tours at the national landmark Second Presbyterian Church (with its many Tiffany windows) and the Glessner House. We'll also take a mid-tour break at a local employee-owned/woman-owned cafe. Then we board the train back to the Loop for our final stop (and a sweet treat) at the elegant Palmer House Hotel.

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based on 15 reviews

See Details → Duration :4 hours
From $75

Chicago Shoreline Adventure Boat Tour

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!

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based on 36 reviews

See Details → Duration :1 hours 30 minutes
From $90

Chicago Walking Tour: Art Deco Skyscrapers Riverfront

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.

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based on 31 reviews

See Details → Duration :1 hours 30 minutes
From $30

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

Though the Art Deco style throws us back in time, it’s actually a futuristic style — it’s meant to make people in the 1920s think of the future. The gleaming materials, the perfect precision of the details… it’s the epitome of glitz, glam, and elegance. On this tour, you’ll walk in the footsteps of those high on the potential of the future, before the infamous Crash of ‘29. We’ll explore several stunning interior spaces within the Loop and near the Chicago River, going inside not only the great Art Deco buildings of the Loop, but also a few buildings you’ll recognize from popular boat tours. But the great thing is that you’ll go where most boat tour guests won’t ever go: inside these gorgeous Art Deco buildings, where you’ll be amazed by the beauty that people don’t know is right there behind closed doors.

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based on 15 reviews

See Details → Duration :2 hours
From $35

Workers Cottages of Oldtown Triangle Walking Tour

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!

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based on 38 reviews

See Details → Duration :1 hours 45 minutes
From $45

Activities & Tours: Illinois

Chicago’s Friday Night Pirates Pub Sail Aboard a Tall Ship

Chicago in a Day: Food and Architecture Private Walking Tour

Chicago Sunset Segway Tour

Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

Chicago Neighborhood Food Private Walking Tour

Chicago Insta Walk with Digital and Polaroid Photoshoot

Chicago Insider Segway Tour

Walking Tour of Chicago Loop: Home of the Modern Skyscraper

Chicago Walking Tour: Modern Architecture

Chicago Full Day Bike Rental

Chicago Prairie Ave District Walking Tour: Street of the Elite

Chicago Shoreline Adventure Boat Tour

Chicago Walking Tour: Art Deco Skyscrapers Riverfront

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

Workers Cottages of Oldtown Triangle Walking Tour

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