Chicago Sightseeing

Hone your Segway skills as you take an evening journey past and through some of Chicago’s most popular attractions, and then enjoy a magnificent fireworks

Feel the spine-chilling energy in the air as you and your ghoulish guide pilot your Segways through the streets of Chicago in search of supernatural

Equal parts boat and buildings, this river cruise gives you a from-the-water perspective of Chicago skyline and up-close views of its most iconic structures.

Our Bikes, Bites, & Brews Signature Edition tour combines the flavorful satisfaction of city food tours with the unadulterated fun of bicycling! Bypass

The fun begins with a meet-and-greet with your fun-loving and enthusiastic tour guide. They will take time to make sure you and your children are fitted with

Glide your way through the Windy City at night, humming past its iconic landmarks, zipping through its beautiful parks, and cruising near the shores of Lake

See Chicago’s holiday lights sparkle from the sky on a private VIP helicopter tour, complete with hot cocoa, candy canes, and magical views, for up to 4

If you're looking for an exciting and adventurous outdoor activity to do in Chicago after dark, look no further than Bobby’s Chicago Sites @ Night Tour.

Experience the VIP difference on Vertiport Chicago’s 15 Minute Chicago VIP Helicopter Tour and see all that Chicago has to offer from a breathtaking vantage

From shimmering lights to decadent bites, Chicago puts its best foot forward for the Holidays. Experience the magic and tradition that shines during this

No matter the season, the weather, or the political climate, The Windy City has two unparalleled passions: beer and improv comedy. For over a century, Chicago

Chicago Helicopter Experience provides you the most spectacular, panoramic views of the world’s best skyline from the optimal vantage point. Your journey

Get introduced to some of the world's earliest skyscrapers on a walking tour that shows off the innovations that defined the Chicago school of architecture.

This is the tour that made Bobby famous!Bobby’s Bike Hike is America’s longest running city bicycle tour company, and has been repeatedly recognized for

Appreciate Chicago’s architecture from the comfort of a coach and from the water as you cruise along the shoreline in a stunning streamliner yacht. Get a

Park your car and grab a bike to experience Chicago at your own pace. As one of the most popular bike tours, this adventure around Lincoln Park takes you down

Discover fine dining, upscale entertainment and unparalleled riverfront views aboard the brand new Odyssey Chicago River Narrated Architectural Lunch Cruise!

Chicago’s seedier side will be unveiled on this ride through the South side’s most notorious areas, including the old Bridgeport neighborhood. Learn about

The previously called the Gold Coast and Old Town Food Tour, visits seven Chicago food tasting locations within the epicurean hot-spot Near North area. Enjoy

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

Zip around on a speedy Segway to view Chicago's gorgeous skyline at sunset, flying over paved trails along Lake Michigan's waterfront. Get a new perspective

The Tequila Toriles Tour is like 4 tours at once, an experience filled with nonstop action. Take an archaeological tour, learn about handmade tortillas, watch

We start our tour under the dazzling marquee of the Chicago. First stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an

The Underground Donut Tour is Chicago's Only Donut Tour. Making 4 stops at some of the city's best donut shops, you'll sample all the best donuts Chicago has

Step into magnificent interior spaces and the underground Pedway on a creative route that weaves through buildings and secret short-cuts. Most of the tour

Embark on an interactive tour of Chicago and discover the city while using hints and completing unique challenges. See landmarks and historical locations as

Sweep through the city in serious style—atop your own steerable Segway. Offered by the guys who first came up with the Segway tour, this tour guarantees

This once-in-a-lifetime experience takes you on an epic journey through Chicago’s amazing cityscape and rich history. You’ll depart from our downtown

Eat, drink and learn on this historic Chicago pub crawl with an educational twist. You’ll explore Chicago’s entertainment history and learn about

Explore the streets of the Windy City with an experienced local guide as you pop between beautiful lakefront parks and gleaming skyscrapers in a comfortable,

Climb aboard the Odyssey for a delicious brunch cruise around Lake Michigan. Board the Odyssey, a sleek cruising vessel with air-conditioned decks and an

Delve into Chicago's colorful past during a tour that takes you to some of the Loop and South Loop's most history-filled drinking establishments. This

Get a new perspective of the Windy City on this guided streamlined adventure. Glide past iconic landmarks, along the scenic shores of Lake Michigan, and

Equal parts boat and buildings, this river cruise gives you a from-the-water perspective of Chicago skyline and up-close views of its most iconic structures.

Taste your way through Chicago’s most famous recipes on this relaxing and fun walking food tour. In an exciting two and a half hours, you’ll feast on

The Underground Donut Tour is Chicago's Only Donut Tour. Making 4 stops at some of the city's best donut shops, you'll sample all the best donuts Chicago has

In a turbo-charged catamaran, glide up the Chicago River for a closer look at the city's vibrant and diverse architecture, before the power is cranked up for

What sprung from the 1893 World's Columbian Exposition now stands as Chicago's Field Museum. Its neo-Classical buildings are stocked with more than 25 million

Take in Chicago's finest sights from the back of a convenient and speedy Segway. This guided, 2-wheeled excursion covers 8 miles (13 km) of spectacular

Sit back and relax as you gaze across the water and embrace the magnitude of Lake Michigan. In many ways, you feel as though you are heading out to sea, but

Discover the neighborhood where Wright's famed Prairie Style of architecture evolved. The tour includes bus transportation to and from Oak Park with

Hear ye, hear ye! Make haste to the castle to indulge in a night of feasting, combat, and revelry. The knights and horses of Medieval Times are here to thrill

Meet your fellow crime-lovers in the heart of Near North Side and set off into the streets aboard a comfortable bus. With your knowledgeable guide leading the

Meet your fellow pizza-lovers at Pizzeria Uno in the heart of the River North neighborhood. Here, treat yourself to a slice or 2 from a gooey, deep-dish pie

Take a breezy spin around the Windy City as you discover the parks, architecture, and jazzy atmosphere of Chicago on a double-decker bus. Get a lay of the

Cruise around the Windy City in a stylish, comfortable, large windowed minibus, as you scope out the city's cloud-skimming skyscrapers, art-filled parks, and

Explore Chicago's seedy underworld on this guided bus tour of its most famous gangsters and mobsters. Investigate the former haunts of legends like Al Capone,

Feel the breeze from the open-air top of a double-decker bus or an old-fashioned trolley as you cruise the Windy City on this hop-on hop-off tour. With

At 360 CHICAGO, the guest experience begins at the ground floor with a museum-style exhibition celebrating Chicago’s history and nine of its culturally rich

This land tour will take you past all the sights of Chicago’s Historic South Side. You will head south out of the Loop down Michigan Avenue past Art

On this fun and insightful walking tour, you’ll venture into beautiful architectural spaces from the era. You will play a few thoughtfully designed games,

The diverse and exciting world of architecture is your destination on this journey through Chicago's remarkable designs. Join the Chicago Architecture

This tour will be a comprehensive tour of everything Chicago has to offer. Comprised of both the Scenic North Side Tour and the Historic South Side Tour you

Begin your luxurious evening cruise on Lake Michigan with the unique tastes of freshly prepared appetizers, and then make your way to the rooftop lounge to

Take in the view from the sky-high heights of the Willis Tower, the second-tallest building in the United States. From the 103rd floor, look out over 4 states

Unobstructed 360-degree views and sparkling white wine awaits you in the heart of Chicago. With floor-to-ceiling windows, the 360 Chicago observatory offers

Blast off at dusk in an open-air vessel cruising at 45 miles per hour across Lake Michigan. Marvel at the magnificent skyline as you race across the lake,

Experience Chicago's sights aboard a Segway on a guided excursion. Cruise through the Windy City, past iconic landmarks, gorgeous parks, and magnificent Lake

Enjoy fireworks perfectly synchronized to music over Lake Michigan on this cruise designed for fun. Climb aboard and sip cocktails on the open-air rooftop

Skip the ticket desk twice to enjoy the best panoramic views or a spectacular sunset over Chicago! Soaring 1,000 feet above Michigan Avenue is one of the

See how the lavish style of the Roaring Twenties left its mark on the Second City with a look at the Art Deco towers along Chicago's riverfront. Your expert

Cruise on a high-speed catamaran past Chicago's finest shore-side sights—adrenaline rush included. Board your turbo-charged vessel and shoot for Lake

Starting at the Palmer House Hilton this tour will take you past all the sights of Chicago’s Scenic North Side. Heading north out of the Loop past

A relaxing cruise aboard the Odyssey is the perfect way to take in views of Chicago's iconic skyline and waterfront landmarks. A perfectly prepared 3-course

From the North Side to the South Side, scenic drives to sky-high sights, this half-day excursion covers serious “Chi-town” ground. Cruise the

Explore Pisa at your own leisure on a self-guided tour of the ancient city. Spend your day seeking out cultural sights or shopping at the fashionable

Uncover the Windy City’s exceptional architecture as you stroll between historic department stores, luxurious hotels, and towering office buildings. With a

Get ready to satisfy your craving for a true taste of Chicago. This comprehensive coach tour around the city’s finest sights concludes with a Chicago-style

The South Shore of Chicago is bursting with cultural institutions, history, and beauty. Board a comfortable coach to take in the many sights along the

Let the Windy City carry you away as you explore Chicago top to bottom, scoping out the city's must-see parks, can't-miss lake views, and iconic architecture

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city's 'Second Lakefront', the Riverwalk contains

Chicago's incredible lakefront is the setting for this outing to see some spectacular sights in the evening. A smooth Segway ride carries you past famous

Experience the vitality and excitement of Chicago’s North Side, home to many flagship retail stores, one of the busiest financial centers in the world, and

Chicago boasts a picturesque Lakefront Trail for cycling, running and walking and this tour aims to show you what we feel is the best part of it. Starting at

Welcome to Chicago’s Millennium Park & Riverwalk audio guide. Millennium Park is home to the famous “Bean”! Millennium Park is one of Chicago’s

Take a morning flight to New York and explore all the exciting art, culture, and history the city has to offer. Your experience includes a convenient hop-on,

On our walking tour of the Noble Square and Wicker Park neighborhoods, we will explore the past and present of the people, architecture, and foods of these

Kick off your holiday season with a trolley tour of the festive Christmas lights. Chicago’s Lincoln Park and the shops along the Magnificent Mile are

Glide along the sidewalks and lakefront while taking in the luminous, iconic Chicago skyline and listening to your guide point out the city highlights. Your

This 1/2 hour ride takes you on a trip over the Northwest suburbs covering Woodfield Mall, beautiful Barrington Hills, the Fox River, and the Grand Victoria

Day 1: Complimentary airport pickup between 9:00AM to 9:00PM at O'Hare Airport. No complemetary pick up service at Midway airport. There is a paid 24 hour

Day 1: In the morning, we are heading to the capital of automobiles-Detroit. We will stop at the headquarters of the General Motors Company, and then visit

Day 1: Complimentary Airport pickup from 9:00AM to 9:00PM at O'Hare Airport. A 24 hour charged pick up service is also avaliable. Thouse who arrive before

The Magnificent Mile. Considered by many to be one of the great retail boulevards in the world. On this tour, you'll find out why. Stand on the same spot as

Visit: American Writers Museum, Chicago, IllinoisVisitors will explore the great writers’ hometowns and learn about all of the AWM Affiliate homes in

Spend an enchanting evening biking to Chicago's main attractions as they're illuminated by the twinkling lights of the city. See The Bean sculpture at

Take a detour off the beaten path and explore the flavors of Chicago’s vibrant Near West SIde neighborhoods! This four-hour guided food and bicycle tour is

Get ready to brave your way through the Windy City with excellent narrators as they unleash their annual Halloween tour. This guided bike tour explores some

Chicago Safaris provides the city’s guests and locals a city touring experience, escorting them in a luxury excursion vehicle through a private tour of the

Experience the best of bustling Chicago in just a day on this easy adventure from New York City. Touch down in the Windy City in just a few hours and head off

This is a very thorough and relaxing city highlights tour! We pick up at three downtown hotels before beginning our adventure at 875 N. Michigan, the former

Fly doors-off for the ultimate photo experience on this 12-15 minute flight and capture the perfect images for your social media posts. This two passenger all

Follow in the footsteps of some of the most famous bootleggers in Chicago history on this haunted gangster pub tour. Stories on this tour explore some of the

Experience spooky stories and unexplained events as you visit some of the most historic and haunted spots in the city—and steady your nerves with a few

Make memmories that last a lifetime and experience the city of Chicago like never before! Your adventure begins at the schaumburg regional airport, located

This land tour will take you past all the sights of Chicago’s Scenic North Side. Heading north out of the Loop past Millennium Park and up the Magnificent

ItineraryThis is a typical itinerary for this productStop At: Chicago Cultural Center, Chicago, IllinoisBe amazed by the stunning mosaics and the art glass of

Welcome to Millennium Park - home to the famous “Bean”. Learn how architects, artists, and engineers collaborated with Chicago’s movers and shakers to

See Chicago in a different light on our panoramic Chicago Night Tour. Tours begin at Stop 1: Chicago Riverwalk and will take you on a journey down the

Take in the spectacular sights of the Chicago and see the fascinating history of city’s famous landmarks during this private 30 min tour. This breathtaking