Things to do in Chicago Illinois United States of America

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Activities, points of interest, things to do in locations all over the world! Contact Vincent Vacations to book your travel today!

Windy City Neighborhood Boutiques Tour
Windy City Neighborhood Boutiques Tour

Explore boutiques in 2 of Chicago's hippest neighborhoods—Bucktown and Wickerpark. Your personal stylist leads you to the hard-to-find boutiques that you won’t find back home or along the Magnificent ...


Made in Chicago Designer Shopping Tour
Made in Chicago Designer Shopping Tour

Discover Chicago’s most exquisite designers, including Alice & Olivia, Kimberly Ovitz, and Wren, as you stroll through a unique and creative marketplace. Your personal shopping stylist shares succ...


Go Chicago Card
Go Chicago Card

Discover Chicago’s finest museums, restaurants, cruises, and more with your Go Chicago Card. Combining some of the city’s top attractions, with advantages such as convenient discounts and skip-the-lin...


360 Chicago Observation Deck
360 Chicago Observation Deck

Soak up the Windy City at cloud level. The 94th-floor perch atop the John Hancock Center offers floor-to-ceiling windows showcasing Chicago’s top vistas. Admire the sparkling skyline, gaze across Lake...


360 Chicago Observation Deck with Prosecco
360 Chicago Observation Deck with Prosecco

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 you panoramic vistas of downtown Chicago, L...


Art Institute of Chicago
Art Institute of Chicago

Spend the day lingering over one of the finest collections of art in the world at The Art Institute of Chicago. Born as part of The Chicago World's Fair in 1893, this beloved institution’s formidable ...


Bikes, Bites & Brews Bike Tour
Bikes, Bites & Brews Bike Tour

Burn off calories almost as fast as you consume them. Your bike ride around Chicago pauses all pedaling before the city's tastiest culinary treats. From a bubbling slice of deep-dish pizza and a musta...


City Lights at Night Bike Tour
City Lights at Night Bike Tour

A smooth, 8-mile ride along Chicago's famed urban landscapes is particularly enchanting come nightfall. With knowledgeable commentary, awe-inspiring landmarks, and incredible scenic views, this take a...


Lakefront Neighborhoods Bike Tour
Lakefront Neighborhoods Bike Tour

Pedal out of Downtown Chicago and tour the quaint and locals-favorite neighborhoods that surround the city's core. This leisurely 7-mile (11-km) loop covers ground in upscale Gold Coast, historic Old ...


Museums & Parks Sunset Bike Tour
Museums & Parks Sunset Bike Tour

Your bicycle tour begins with a journey through the local neighborhoods of Gold Coast, Lincoln Park, and Wrigleyville. Ride along the lakefront visiting parks and gardens as the refreshing lake breeze...


Favorite Food Walking Tour
Favorite Food Walking Tour

The smells of the city's most famous foods entice you right from the beginning on this delicious culinary tour. Enjoy famous Chicago-style pizza, hot dogs, craft beers, and a brownie from the folks wh...


Hop-On Hop-Off City Tour by Chicago Trolley & Double Decker
Hop-On Hop-Off City Tour by Chicago Trolley & Double Decker

From parks and piers to markets and museums—Chicago’s a cultural mixing pot of the old, the new, the cutting-edge, and the classically historic. This adjustable hop-on hop-off tour frees you up to exp...



Chicago CityPASS: 5 Must-See Museums & Attractions

Explore 5 of Chicago’s premier attractions at a discounted price, and enjoy special privileges with either VIP access or Fast Pass admission for most attractions. This pass is perfect if you want to e...


Architecture River Tour by Shoreline Sightseeing
Architecture River Tour by Shoreline Sightseeing

Equal parts boat and buildings, this river cruise features a widescreen perspective of the skyline and up-close views of its most iconic structures. Board an open-roof vessel and float with the curren...


Architecture Cruise & Fireworks Show
Architecture Cruise & Fireworks Show

Begin the night with a leisurely cruise along 3 different branches of the Chicago River while listening to the docent’s insightful commentary about renowned architects, historic buildings, and world-f...


Water Taxi Pass
Water Taxi Pass

Get away from the hustle and bustle of the city streets as you hop aboard the red, white, and blue water taxi. Forgo traffic, take in the stunning skyline and lake, and enjoy the most scenic way to ge...


Lake Michigan Skyline Cruise
Lake Michigan Skyline Cruise

Sit back and take a break 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 the calmness of the water confirms ...


Lake Michigan Skyline & Fireworks Cruise
Lake Michigan Skyline & Fireworks Cruise

Details of the city may be clearly visible during the day, but you get an entirely new view at sunset when the city lights up. Enjoy a late-evening cruise on Lake Michigan while spectacular fireworks ...


The Field Museum
The Field Museum

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 artifacts—some up to 4.6 billion years ol...


Willis Tower Skydeck & The Ledge
Willis Tower Skydeck & The Ledge

In 60 seconds, your elevator climbs to the 103rd floor of the second-tallest building in the United States. From the breathtaking Skydeck, marvel at sights reaching 4 states, scan Chicago's iconic sky...


Arts & Architecture Segway Tour
Arts & Architecture Segway Tour

Equal parts art, architecture—and adventure, this 2-wheeled tour combines Chicago’s finest sights with a convenient and speedy Segway. With your expert guide, glide along the lakefront, see modern art...


Fireworks Segway Tour
Fireworks Segway Tour

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 display over Navy Pier. After a short orienta...


Haunted Halloween Segway Tour
Haunted Halloween Segway Tour

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 activity. Venture into the shadowy underbelly of Ch...


Holiday Lights Segway Tour
Holiday Lights Segway Tour

Kick your holiday season into high gear with a guided Segway tour through downtown. Take in the lights, activities, shop windows, and energy that exemplify Chicago during the holidays. After a short t...


Lincoln Park & Beach Segway Tour
Lincoln Park & Beach Segway Tour

Before you start your Segway journey to some of Chicago’s most impressive and popular attractions, spend 30 minutes learning how to operate and ride your personal transportation device. Once you have ...


Museum Campus & Lakefront Segway Tour
Museum Campus & Lakefront Segway Tour

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 lakefront, with informative and entertaining sto...



Blue Man Group

Blue Man Group, one of Chicago's longest-running shows, is a unique audiovisual experience—vibrant, colorful, and hilarious. Family-attentive and fabulously blue, this critically acclaimed show featur...


Introduction to Segways
Introduction to Segways

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 through the city's most charming parks. This is...


Introduction to Segways & Lakefront Tour
Introduction to Segways & Lakefront Tour

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 you’re in good hands. Comb through Chicago's gr...


Best of Chicago Tour
Best of Chicago Tour

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 on this half-day tour. From the Loop to Li...


Best of Chicago & 360 Chicago Observation Deck
Best of Chicago & 360 Chicago Observation Deck

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 Eastside Outer Drive, stop and smell the roses...


Best of Chicago & Deep-Dish Pizza
Best of Chicago & Deep-Dish Pizza

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 pizza with your name on it. Circle The Loop,...


Legendary Marquee Theatre Tour
Legendary Marquee Theatre Tour

Share the same center stage spotlight that was cast on legends like Dean Martin and Frank Sinatra. This behind-the-scenes tour through The Chicago Theatre ensures a starry-eyed evening of fascinating ...


Passion Blues Tour with Dinner
Passion Blues Tour with Dinner

Tap your toes to the lively tunes of Chicago's soulful blues. This authentic immersion into the city's deep musical history makes for a memorable evening of live guitar riffs, spellbinding rhythms, an...


Private Architecture & History Tour
Private Architecture & History Tour

Your private tour begins by exploring the historical and architectural highlights of the city. See the John Hancock Building, the Federal Reserve Bank, and many others that make up the rich tapestry o...


Criminals, Mobsters & Gangsters Bus Tour
Criminals, Mobsters & Gangsters Bus Tour

Explore Chicago's underworld on this guided bus tour of gangsters and mobsters. Investigate Al Capone, The Untouchables, the Chicago Mob, John Dillinger, H.H. Holmes, and more. Journey through the sce...


Odyssey Elegant Dinner Cruise
Odyssey Elegant Dinner Cruise

Set off for an elegant evening of dinner and dancing on stunning Lake Michigan. Your Odyssey dinner cruise offers the perfect reason to break out the cocktail attire, and combines course after mouthwa...


Odyssey Elegant Dinner Cruise with Navy Pier Fireworks Show
Odyssey Elegant Dinner Cruise with Navy Pier Fireworks Show

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 see the world-famous Chicago skyline. Relax ...


Extreme Speedboat Thrill Ride
Extreme Speedboat Thrill Ride

Onboard Chicago's highest horse-powered passenger boat, feel the spray of the water and the whip of the wind as you slice through Lake Michigan. Your adrenaline kicks into gear when the captain accele...


River & Lake Speedboat Architectural Tour
River & Lake Speedboat Architectural Tour

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 a wind-whipping ride along the lakefront. ...


Lakefront Speedboat Tour
Lakefront Speedboat Tour

Craving a way to make some waves? 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 Michigan’s open ...


Spirit of Chicago Dinner Cruise
Spirit of Chicago Dinner Cruise

Savor an evening of dinner, drinks, and dancing—all while cruising Chicago's stunning lakefront. Dressed in your favorite cocktail attire, your voyage aboard the luxurious Spirit of Chicago features a...


Spirit Fireworks Dinner Cruise
Spirit Fireworks Dinner Cruise

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 deck. Enjoy a savory dinner as you cruise alo...


Macy
Macy's Star Shopper Package by Shop America

Browse Macy's modern fashion while you walk through this historic department store. Formerly a Marshall Field's, the building is known for providing an extravagant and innovative shopping experience. ...


LEGOLAND® Discovery Center Chicago
LEGOLAND® Discovery Center Chicago

LEGO® bricks come to life at the LEGOLAND® Discovery Center. Let your imagination run wild as you build amazing creations, learn top tips from the Master Model Builders, ride the Technicycle, and sit...


Chicago Shop & Shuttle by Shop America
Chicago Shop & Shuttle by Shop America

Enjoy roundtrip shuttle service between downtown Chicago and 2 of the Windy City's premier shopping destinations—The Shops at North Bridge and the Fashion Outlets of Chicago. Benefit from special disc...


Fireworks Speedboat Cruise
Fireworks Speedboat Cruise

Blast off at dusk in an open-air vessel cruising at 45 miles per hour (72.5 km/h) across Lake Michigan. Marvel at the magnificent skyline as you race across the lake, gripping tightly while your speed...


EagleRider Motorcycle Rental
EagleRider Motorcycle Rental

Harley-Davidson® is the quintessential American motorcycle. Take the opportunity to climb aboard this iconic vehicle and experience your vacation destination from an entirely new perspective. Whether ...


Dining at Hard Rock Cafe with Priority Seating
Dining at Hard Rock Cafe with Priority Seating

Dine like a rock star among pop, soul, and rock 'n' roll memorabilia—costumes and instruments from your favorite musicians—at the Hard Rock Cafe. Skip the lines with priority seating and enjoy a class...


Medieval Times Dinner & Tournament
Medieval Times Dinner & Tournament

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 you with acts of showmanship and bravery ...


Chicago CityPASS: 5 Must-See Museums & Attractions
Chicago CityPASS: 5 Must-See Museums & Attractions

Explore 5 of Chicago’s premier attractions at a discounted price, and enjoy special privileges with either VIP access or Fast Pass admission for most attractions. This pass is perfect if you want to e...


Adler Planetarium
Adler Planetarium

Journey beyond the moon, through the stars, and to the edge of the galaxy—all without leaving Chicago. At the Adler Planetarium, explore the exhibits, artifacts, and interactive displays that have bee...


Private SUV: Chicago Midway International Airport (MDW)
Private SUV: Chicago Midway International Airport (MDW)

Enjoy convenient private transportation between Midway Airport and your hotel in the comfort of a SUV. For transfers to and from Midway Airport, the areas to select from include: Chicago City Center S...


Private SUV: O
Private SUV: O'Hare International Airport (ORD)

Enjoy convenient private transportation between Midway Airport and your hotel in the comfort of a SUV. For transfers to and from O'Hare to your hotel, the areas to select from include: Oakbrook Select...


Private Towncar: Chicago Midway International Airport (MDW)
Private Towncar: Chicago Midway International Airport (MDW)

Enjoy convenient private transportation between Midway Airport and your hotel in the comfort of a Towncar. For transfers to and from Chicago, the areas to select from include: City Center Select this ...


Private Towncar: O
Private Towncar: O'Hare International Airport (ORD)

Enjoy convenient private transportation between O'Hare International Airport and your hotel in the comfort of a Towncar. For transfers to and from O'Hare International and your hotel, the areas to sel...


Shared Shuttle: Chicago Midway International Airport (MDW)
Shared Shuttle: Chicago Midway International Airport (MDW)

Enjoy convenient and cost-effective shared transportation between Midway International Airport and your hotel aboard a shuttle. For transfers to and from Midway International Airport, the areas to se...



Shared Shuttle: O'Hare International Airport (ORD)

Enjoy convenient and cost-effective shared transportation between O'Hare International Airport and your hotel aboard a shuttle. For transfers to and from O'Hare International Airport, the areas to se...


Million Dollar Quartet
Million Dollar Quartet

Relive the rock 'n' roll excitement of the most celebrated musical artists of the 20th century with the smash-hit musical Million Dollar Quartet. Join in celebrating the only time that Johnny Cash, Je...


GO Private Express - Private Towncar: O
GO Private Express - Private Towncar: O'Hare International Airport (ORD)

Enjoy convenient private transportation between O'Hare International Airport and your hotel in the comfort of a towncar. City Center Select this option for hotels in Chicago's city center.


GO Private Express - Private SUV: O
GO Private Express - Private SUV: O'Hare International Airport (ORD)

Enjoy convenient private transportation between O'Hare International Airport and your hotel in the comfort of an SUV. City Center Select this option for hotels in Chicago's city center.


Holiday Hike - A Seasonal Walking & Food Sampling Tour
Holiday Hike - A Seasonal Walking & Food Sampling Tour

When the weather outside is frightful, there's nothing like some holiday spirit and seasonal treats to warm you up from the inside out. Follow a guide through Chicago's winter wonderland, sampling loc...


GO Private Express - Private Town Car: Midway International Airport (MDW)
GO Private Express - Private Town Car: Midway International Airport (MDW)

Enjoy convenient private transportation between Midway International Airport and your hotel in the comfort of a town car. City Center Select this option for hotels in Chicago's city center.


GO Private Express - Private SUV: Midway International Airport (MDW)
GO Private Express - Private SUV: Midway International Airport (MDW)

Enjoy convenient private transportation between O'Hare International Airport and your hotel in the comfort of an SUV. City Center Select this option for hotels in Chicago's city center.


Blacklane - Private Towncar: Chicago Midway Airport (MDW)
Blacklane - Private Towncar: Chicago Midway Airport (MDW)

Enjoy a take a breaked journey in a high-quality towncar between the airport and your hotel. There’s no waiting in a taxi line, and guaranteed fixed rates include flight tracking, 1 hour of wait time,...


Blacklane - Private SUV: Chicago Midway Airport (MDW)
Blacklane - Private SUV: Chicago Midway Airport (MDW)

Enjoy a take a breaked journey in a high-quality SUV between the airport and your hotel. There’s no waiting in a taxi line, and guaranteed fixed rates include flight tracking, 1 hour of wait time, and...


Blacklane - Private Towncar: Chicago O
Blacklane - Private Towncar: Chicago O'Hare International Airport (ORD)

Enjoy a take a breaked journey in a high-quality towncar between the airport and your hotel. There’s no waiting in a taxi line, and guaranteed fixed rates include flight tracking, 1 hour of wait time,...


Blacklane - Private SUV: Chicago O
Blacklane - Private SUV: Chicago O'Hare International Airport (ORD)

Enjoy a take a breaked journey in a high-quality SUV between the airport and your hotel. There’s no waiting in a taxi line, and guaranteed fixed rates include flight tracking, 1 hour of wait time, and...


Shared Shuttle: O
Shared Shuttle: O'Hare International Airport (ORD)

Enjoy convenient and cost-effective shared transportation between O'Hare International Airport and your hotel aboard a shuttle. For transfers to and from O'Hare International Airport, the areas to se...


Shop, Dine & Shuttle from Downtown or O
Shop, Dine & Shuttle from Downtown or O'Hare International Aiport

Enjoy roundtrip shuttle service between downtown Chicago or O'Hare International Airport and Chicago's premier shopping outlet destinations—the Fashion Outlets of Chicago. Benefit from special discoun...


Shop, Explore, Play or Spa at The North Bridge Shops
Shop, Explore, Play or Spa at The North Bridge Shops

The Shops at North Bridge span 6 blocks of Michigan Avenue, just steps from downtown Chicago's charming lakefront. Benefit from special discounts and rewards as you shop for deals at brand-name and hi...


A Slice of Chicago Pizza Tour
A Slice of Chicago Pizza Tour

Food is a big deal in Chicago, from hot dogs to 3-star restaurants, but if there's one food Chicagoans rave about most, it's undoubtedly Chicago-style pizza. This gooey, cheesy, deep-dish pie with its...


Chocolate Lover
Chocolate Lover's Walking Tour

Satisfy your sweet tooth on this mouthwatering walking tour of the Magnificent Mile, stopping at several artisan chocolate boutiques for samples of their finest produce. Walk with an expert guide who ...


Cupcake Walking Tour
Cupcake Walking Tour

There's simply no sweeter treat than the cupcake. Since the pint-sized-dessert trend swept Chicagoland, shops peddling these personal pastries have popped out of the oven by the baker's dozen. Sample ...


Italian Food Tour
Italian Food Tour

Taste your way through Chicago's vibrant Magnificent Mile and Gold Coast on this Italian food-focused walking tour. Try mouthwatering Italian beef, homemade meatballs and marinara as well as savory ri...


Explorer Pass: Choose up to 4 Museums, Attractions & Tours
Explorer Pass: Choose up to 4 Museums, Attractions & Tours

Choose from more than 25 of Chicago's most amazing attractions, museums, and tours with this Explorer Pass and experience the city at your own pace. With your choice of up to 4 activities, enjoy acces...


On Your Feet! The Story of Emilio & Gloria Estefan
On Your Feet! The Story of Emilio & Gloria Estefan

Explore the lives of popular music’s most celebrated Cuban couple, Emilio and Gloria Estefan. Using expert choreography, fascinating storytelling, and award-winning tunes, this new musical lets you ex...


Evolution of the Skyscraper Walking Tour by the Chicago Architecture Foundaiton
Evolution of the Skyscraper Walking Tour by the Chicago Architecture Foundaiton

Start with simple stones and end with high-strength steel as you embark on an architectural adventure to track the development of Chicago’s iconic skyscrapers. From stately columns to ostentatious faç...


Historic Treasures of Culture & Commerce Architecture Walking Tour
Historic Treasures of Culture & Commerce Architecture Walking Tour

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


Exploring Old & New Architecture Walking Tour by the Chicago Architecture Foundation
Exploring Old & New Architecture Walking Tour by the Chicago Architecture Foundation

Uncover the dynamic architectural scenes unfolding amid the bustling streets and intersections of downtown Chicago. See elegant stonework displayed next to modern high-rises and find out how the city’...


Millennium Park: Beyond the Bean Walking Tour by the Chicago Architecture Foundation
Millennium Park: Beyond the Bean Walking Tour by the Chicago Architecture Foundation

Stroll the grounds of Millennium Park to explore marvelous sculptures, sprawling gardens, and wide-open fields beneath geometric trellises. Originally designed to commemorate the new millennium, and h...


Modern Skyscrapers Walking Tour by the Chicago Architecture Foundation
Modern Skyscrapers Walking Tour by the Chicago Architecture Foundation

Examine the rise of Chicago’s skyline as you wander between stunning modernist structures and elegant minimalist skyscrapers on this fascinating architectural tour. With a volunteer from the Chicago A...


Art Deco Skyscrapers: Riverfront Trolley & Walking Tour by the Chicago Architecture Foundation
Art Deco Skyscrapers: Riverfront Trolley & Walking Tour by the Chicago Architecture Foundation

Crane your neck and gaze at the looming Art Deco edifices that dot the streets of downtown Chicago. This classic architectural style is emblematic of the Windy City, and your tour takes you to 3 of it...


Downtown & Skyline Vistas Trolley Tour by the Chicago Architecture Foundation
Downtown & Skyline Vistas Trolley Tour by the Chicago Architecture Foundation

Climb aboard a charming trolley and dive into the dynamic parks, scenic drives, and vital waterways of the Windy City. Hear about the intriguing development of this Midwestern metropolis and enjoy var...


Self-Guided Audio Tour by the Chicago Architecture Foundation
Self-Guided Audio Tour by the Chicago Architecture Foundation

Examine the rise of Chicago's skyline as you wander between stunning modernist structures and minimalist skyscrapers on a fascinating tour. With a personal listening device and your choice of the Hist...


Smartphone-Guided City Scavenger Hunt
Smartphone-Guided City Scavenger Hunt

Embark on an interactive tour of Chicago and explore the city while using hints and completing unique challenges. See landmarks and historical locations as you solve clues on your smartphone that lead...


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