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Chicago Tours and Activities

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Here are your 262 search results for Tours, Attractions & Activities in Chicago, United States

Great Lakes Explorer Music Malt & Magical Mackinac

Great Lakes Explorer Music Malt & Magical Mackinac - Chicago, Illinois

Duration: 8 days
Location: Chicago, Illinois

From USD
$2865.00

The Great Lake Explorer experience focuses on the architecture, the music and the beauty of the region. This tour includes a behind the scenes look at the architectural influences of Frank Lloyd Wright, and the musical influences of Buddy Guy and Junior Wells ... More info ›

The Great Lake Explorer experience focuses on the architecture, the music and the beauty of the region. This tour includes a behind the scenes look at the architectural influences of Frank Lloyd Wright, and the musical influences of Buddy Guy and Junior Wells. We enjoy stylish wines in the Leelanau Peninsula, relax on Mackinac Island and celebrate the craft beer industry in Milwaukee. This tour is meant to immerse the traveler in the experiences of the region.

2018 Departure Dates:

May 25
August 31

DAY 1: This evening, mingle with other group members at a meet and greet reception hosted by our Tour Manager, a destination specialist.
DAY 2: Board an exclusive Chicago Architecture Foundation’s photography river cruise, designed for the photographer, or photographer at heart. This afternoon, choose between a walking tour and learn the basics of Chicago’s sinful history, all the way from the city’s first vice district, to Capone, Prohibition and the mob. Explore the basics of different beer styles and beer’s influence on criminal enterprises, especially during Prohibition. Or choose to glide along the Lakefront on your very own Segway, through the fragrant floral paths and rose gardens of Grant Park to the Museum Campus. Tonight, visit Kingston Mines. Kingston Mines is the largest and oldest continuously operating blues club in Chicago. Its two stages have been graced by the likes of Junior Wells and scores of other musical greats.
DAY 3: Travel to Holland, on the shore of Lake Michigan. The Dutch heritage is plain to see in the traditional Dutch architecture and ambiance. Stroll the quaint downtown and enjoy its galleries, shops and eateries. Continue north to the Leelanau Peninsula. Here we visit some of the peninsulas noted wineries. The evening is spent in Traverse City.
DAY 4: Board the ferry to Mackinac Island. The entire island is listed as a National Historic Landmark and is well known for its wide variety of architectural styles, including the Victorian Grand Hotel and its ban on all motor vehicles.
Day 5: You can explore Mackinac Island your way. Bicycles and horse-drawn carriages are the only modes of transportation here. You can pick up a bicycle and gear, along with trail maps guiding you on various routes throughout the island. Or relax on a guided horse-drawn carriage instead.
Day 6: Michigan ranks fifth in the nation in the number of breweries, microbreweries and brewpubs. Late afternoon we make the ferry crossing across Lake Michigan to Wisconsin. Tonight, visit Milwaukee's most unique downtown food destination, the Milwaukee Public Market.
Day 7: Visit the Milwaukee Riverwalk and Milwaukee Art Museum. Tour past the elegant mansions along Lake Michigan with numerous photo opportunities at the city’s most unique landmarks. Take in City Hall, the Milwaukee Art Museum, North Point Light-house, Miller Park, the Historic Third Ward and more. This afternoon visit the Harley Davidson Museum. Enjoy a final night dinner together at a Bavarian Bierhaus. 
Day 8: Arrive in Oak Park, once the home of Frank Lloyd Wright where he designed and built some of his earliest buildings. Tour the Wright home and see the birth-place of Ernest Hemingway before time for lunch in the village.

Less info

Chicago Private Helicopter Tour for 5

Chicago Private Helicopter Tour for 5 - Chicago, Illinois

Duration: 30 minutes
Location: Chicago, Illinois

From USD
$1525.00

The  Private Helicopter Tour for 5 is a luxury immersion experience! Take in the spectacular sights of the city and learn the fascinating history of Chicago’s famous landmarks during this 30 minute flight.  Our luxurious helicopter will soar over the city, with iconic views of Willis (Sears) Tower, Millennium Park, Magnificent Mile, Soldier Field, the Museum Campus and more! Your tour will begin and end in the beautiful dedicated tour lounge area at the Vertiport heliport, where you can relax by the full window walls and view the other helicopters taking off and landing against the backdrop of the city ... More info ›

The  Private Helicopter Tour for 5 is a luxury immersion experience! Take in the spectacular sights of the city and learn the fascinating history of Chicago’s famous landmarks during this 30 minute flight.  Our luxurious helicopter will soar over the city, with iconic views of Willis (Sears) Tower, Millennium Park, Magnificent Mile, Soldier Field, the Museum Campus and more! Your tour will begin and end in the beautiful dedicated tour lounge area at the Vertiport heliport, where you can relax by the full window walls and view the other helicopters taking off and landing against the backdrop of the city. Whether a resident or visitor, this is an unforgettable experience. Price is all inclusive. This private flight is for up to 5 passengers.  Both day and night tours available at the same price, which each giving unique perspectives of Chicago. NO additional fees.

The Private Helicopter Tour for 5 provides thrilling views of Chicago in true VIP style with a private tour aboard a luxurious sightseeing helicopter.  Create an itinerary that includes landmarks such as:  Willis (Sears) Tower, Millennium Park, Magnificent Mile, Wrigley Field, Soldier Field the Museum Campus and more!

Your experience begins the moment you arrive at heliport, Vertiport Chicago, located in the Illinois Medical District at 1339 South Wood Street, easily accessible and free onsite parking.  Relax in the beautiful dedicated tour lounge surrounded by glass windows, with views of the vast tarmac and activity of the helicopters as they take off and land against the iconic backdrop of the city. 

When your scheduled tour time arrives, you and your group will be escorted to the tarmac VIP style, walking the red carpet to where your luxury aircraft awaits.  Pause for a photo behind the red velvet ropes next to your luxury helicopter to commemorate this day for you and your group!

Your VIP experience continues as your highly experienced pilot soars towards the downtown skyline where you will take in the spectacular sights of the city.   As you travel amongst Chicago’s most famous sights, your tour will include engaging narratives about Chicago’s historically and architecturally significant buildings.  

The Private Helicopter Tour For 5 is perfect for families, small groups of friends or for entertaining and impressing clients.  Both day and night tours are available at the same price.  Whether an out of town visitor or lifelong resident, a Chicago Premiere Private Helicopter Tour For 5 is an VIP experience you will not forget!

Highlights of helicopter tour:                                       

  • Pilot narrated tour
  • Custom-designed itinerary to see your favorite Chicago sights
  • Willis (Sears) Tower
  • Millennium Park
  • The Magnificent Mile
  • Wrigley Field
  • Museum Campus
  • Soldier Field
  • And more!
  • Engaging narratives about Chicago’s historically and architecturally significant buildings

Less info

Chicago Premiere Private Helicopter Tour for 4

Chicago Premiere Private Helicopter Tour for 4 - Chicago, Illinois

Duration: 30 minutes
Location: Chicago, Illinois

From USD
$1019.00

Chicago’s Premiere Private Helicopter Tour For 4 will take you and your group to new heights above the city.  In this 30 Minute Tour, you will experience the best views in town from Chicago’s only Enstrom 480B Helicopter, with windows above, below and all around! Take in the spectacular sites of the city and learn the fascinating history of Chicago’s famous landmarks as you soar along the skyline.  This 30 Minute Premiere Tour will include iconic views of Willis (Sears) Tower, Millennium Park, Magnificent Mile and more! Your tour will begin and end in the beautiful dedicated tour lounge area at the Vertiport Chicago heliport, where you can relax by the full window walls and view the other helicopters taking off and landing against the backdrop of the city. Whether a resident or visitor, this is an unforgettable experience ... More info ›

Chicago’s Premiere Private Helicopter Tour For 4 will take you and your group to new heights above the city.  In this 30 Minute Tour, you will experience the best views in town from Chicago’s only Enstrom 480B Helicopter, with windows above, below and all around! Take in the spectacular sites of the city and learn the fascinating history of Chicago’s famous landmarks as you soar along the skyline.  This 30 Minute Premiere Tour will include iconic views of Willis (Sears) Tower, Millennium Park, Magnificent Mile and more! Your tour will begin and end in the beautiful dedicated tour lounge area at the Vertiport Chicago heliport, where you can relax by the full window walls and view the other helicopters taking off and landing against the backdrop of the city. Whether a resident or visitor, this is an unforgettable experience. Price is all inclusive. This private flight is for up to 4 passengers; with day or night tours available at the same price. NO additional fees.

Chicago’s Premiere Private Helicopter Tour For 4 offers the best view of the city from Chicago’s only Enstrom 480B Helicopter!  The Enstrom was designed for the ultimate tour experience, with windows above, below and all around, providing unobstructed views as you soar over the city on this 30 minute helicopter ride. 

Your Premiere experience begins the moment you arrive at Chicago’s only downtown heliport, Vertiport Chicago, located in the Illinois Medical District at 1339 South Wood Street, easily accessible and with free onsite parking.  Relax in the beautiful dedicated tour lounge surrounded by glass windows, with views of the vast tarmac and activity of the helicopters as they take off and land against the iconic backdrop of the city. 

When your scheduled tour time arrives, you and your group will be escorted to the tarmac VIP style, walking the red carpet to where your luxury aircraft awaits.  Pause for a photo behind the red velvet ropes next to your luxury helicopter to commemorate this day for you and your group!

Your VIP experience continues as your highly experienced pilot soars towards the downtown skyline where you will take in the spectacular sights of the city.  Learn the fascinating history of Chicago’s famous landmarks and historical sights as your pilot narrates your 30 minute flight.  Be sure to take advantage of the Enstrom’s strategically placed windows to catch views above and below as you fly through the city.  This breathtaking tour aboard the Enstrom offers amazing views of the Chicago that are not available on any other helicopter.    

This unique vantage point from high above the city also provides you with unmatched perspective of Chicago’s most famous sights, including:  Willis (Sears) Tower, the Magnificent Mile, Millennium Park, Wrigley Field, the Museum Campus, Soldier Field and more!

This private flight tour accommodates up to 4 passengers in the price.  It is a perfect way to share a unique VIP Chicago experience with your family, friends or colleagues.  Celebrate a birthday, go on a double date or treat clients to a one-of-a-kind outing!  The possibilities are endless.

Book your Chicago Premiere Private Helicopter Tour For 4 today! Day or night tour options are available at the same price.

Highlights of helicopter tour:                                       

  • Pilot narrated tour
  • Willis (Sears) Tower
  • Millennium Park
  • The Magnificent Mile
  • Wrigley Field
  • Museum Campus
  • Soldier Field
  • And more!

Less info

Chicago Fireworks Helicopter Tour

Chicago Fireworks Helicopter Tour - Chicago, Illinois

Duration: 30 minutes
Location: Chicago, Illinois

From USD
$1019.00

Get the best view of Chicago’s Navy Pier Fireworks  on the Chicago Fireworks Helicopter Tour!  Imagine viewing the brilliant colors illuminating the sky from Chicago’s only Enstrom 480B helicopter with unobstructed views from windows above, below and all around.  All summer long, Chicago is treated to the brilliant burst of color in the sky during the  Navy Pier summer fireworks show every Wednesday and Saturday night.  Experience Chicago’s famous skyline and landmarks back lit by the bursts of color and lit up by the nighttime city lights!  Space is limited – only one flight will be offered for each Wednesday and Saturday Fireworks show.  Reserve your flight today!  This private helicopter tour accommodates up to 4 passengers.

Chicago’s Fireworks Helicopter Tour offers the best view of the city’s visually exploding fireworks from Chicago’s only Enstrom 480B Helicopter!  The Enstrom was designed for the ultimate tour experience, with windows above, below and all around, providing unobstructed views as you soar over the city to catch glimpses of the fireworks from all angles in the sky.

All summer long (from Memorial Day to Labor Day), Chicago is treated to the brilliant burst of color in the sky during the Navy Pier fireworks show every Wednesday and Saturday night. Take a special Fireworks Tour and see the city and its landmarks lit up against the sky as you travel above the skyline and its towering skyscrapers!  Reserve early to get the best seat in the city, as only one Chicago Fireworks Helicopter Tour will go out each Wednesday and Saturday night ... More info ›

Get the best view of Chicago’s Navy Pier Fireworks  on the Chicago Fireworks Helicopter Tour!  Imagine viewing the brilliant colors illuminating the sky from Chicago’s only Enstrom 480B helicopter with unobstructed views from windows above, below and all around.  All summer long, Chicago is treated to the brilliant burst of color in the sky during the  Navy Pier summer fireworks show every Wednesday and Saturday night.  Experience Chicago’s famous skyline and landmarks back lit by the bursts of color and lit up by the nighttime city lights!  Space is limited – only one flight will be offered for each Wednesday and Saturday Fireworks show.  Reserve your flight today!  This private helicopter tour accommodates up to 4 passengers.

Chicago’s Fireworks Helicopter Tour offers the best view of the city’s visually exploding fireworks from Chicago’s only Enstrom 480B Helicopter!  The Enstrom was designed for the ultimate tour experience, with windows above, below and all around, providing unobstructed views as you soar over the city to catch glimpses of the fireworks from all angles in the sky.

All summer long (from Memorial Day to Labor Day), Chicago is treated to the brilliant burst of color in the sky during the Navy Pier fireworks show every Wednesday and Saturday night. Take a special Fireworks Tour and see the city and its landmarks lit up against the sky as you travel above the skyline and its towering skyscrapers!  Reserve early to get the best seat in the city, as only one Chicago Fireworks Helicopter Tour will go out each Wednesday and Saturday night. Please note that the fireworks schedule is at the discretion of Navy Pier, and its sponsors, and any changes are out of the control of helicopter tour operator.    

Your Chicago Fireworks Helicopter Tour VIP experience begins the moment you arrive at Chicago’s only downtown heliport, Vertiport Chicago, located in the Illinois Medical District at 1339 South Wood Street, easily accessible and with free onsite parking.   

When your scheduled tour time arrives, you and your group will be escorted to the tarmac VIP style, walking the red carpet to where your luxury aircraft awaits.  Pause for a photo behind the red velvet ropes next to your luxury helicopter to commemorate this day for you and your group!

Your VIP experience continues as your highly experienced pilot soars towards the downtown skyline where you will take in the spectacular sights of the city and magical lights of the night sky.  Catch the views from all of the Enstrom’s windows as the brilliant lights of the city sparkle against the starry night sky.  Imagine the twinkle of the lights as you get an unparralled view of Chicago’s famous landmarks including:  Willis (Sears) Tower, Millennium Park, Magnificent Mile, Soldier Field, the Museum Campus and more!

Learn the fascinating history of Chicago’s famous landmarks and historical sights as your pilot narrates your flight.  This breathtaking tour aboard the Enstrom offers amazing views of the Chicago and the spectacular Navy Pier Fireworks that are not available on any other helicopter.    

The Chicago Fireworks Helicopter Tour is a private flight for up to 4 passengers and a perfect, special evening for a family, a group of friends or to entertain out of town guests.  Reserve early to secure your spot on this limited tour!

Highlights:                                             

  • Best seat in Chicago for the Fireworks
  • Pilot narrated tour
  • Willis (Sears) Tower
  • Millennium Park
  • The Magnificent Mile
  • Wrigley Field
  • Museum Campus
  • Soldier Field
  • And more!

Less info

Booking.com

Chicago Girls Getaway Luxury Shopping Experience

Chicago Girls Getaway Luxury Shopping Experience - Chicago, Illinois

Duration: Flexible
Location: Chicago, Illinois

From USD
$995.00

Designer boutiques, home decor, or gourmet food, chocolate and wine! Your guide will curate a day just for you and your crew! Visit upscale Lincoln Park or trendy Bucktown and Wicker Park. Discover why Chicago's design and food scene is hot! You'll travel in complete comfort in a luxury mini-coach stopping where you desire ... More info ›

Designer boutiques, home decor, or gourmet food, chocolate and wine! Your guide will curate a day just for you and your crew! Visit upscale Lincoln Park or trendy Bucktown and Wicker Park. Discover why Chicago's design and food scene is hot! You'll travel in complete comfort in a luxury mini-coach stopping where you desire. Choose from a 5 or 7 hour day to immerse yourself in the best of the city! With a 7 hour day, your guide can make advance lunch reservations for the group to dine on their own. One small cooler of champagne is permitted per group. Other alcohol consumption on the coach is prohibited.   
Great for:

  • Birthdays
  • Celebrations
  • Icebreakers
  • Convention Activities
  • Team Building

Your expert local guide and professional chauffeur will arrive in a luxury mini-coach with comfortable seating for up to 12 guests plus the guide and driver. Upon booking, you'll have the chance to tell us about your "dream day out." Please let us know if you're looking for a day centered on fashion, home decor, the culinary scene or a fun mix of it all! 

Pick up and drop off from any downtown hotel, landmark or train station. If the 7-hour tour is chosen, pick ups can be arranged in nearby suburbs.  

On arrival, your guide will give an overview of the plans for your 5 or 7-hour tour. Let the guide know your preferences!
Embark on your custom tour – don’t hesitate to tell the guide when you’d like more time somewhere. There's plenty of room on board for shopping bags! 

FASHION: Let your guide know your style. Are you interested in the city's top designers, trendy boutiques, designer resale, vintage - or a little of everything? Glide through the city's most fashionable neighborhoods without worrying about parking or directions! 

HOME DECOR: Pop into some of the city's most delightful shops for home accessories where you're sure to find something unique! Immerse yourself in showrooms featuring modern, antique, or vintage furniture. Discover some of the most exciting trends in Kitchen and Bath design.  Home decor shopping options more limited on Sundays.

CULINARY: Chicago is Foodie Heaven! Your guide can help you discover the best bites in the city with stops at local provisioners who helped put us on the map!  From incredible chocolates to fanciful cupcakes and mind-bending donuts, this is a day about indulgence!

MIX IT UPEnjoy a little of everything above as your guide helps you plan a day where your interests are the key! 

LUNCHOn a 7-hour tour, relax over lunch at one of the city's renowned restaurants. Your guide will make reservations for the group. Just let us know if you're looking for casual, upscale or neighborhood dining. Lunch is at client's expense.



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Private Guided Tour of Chicago - Deluxe Coach for 12 - International Languages

Private Guided Tour of Chicago - Deluxe Coach for 12 - International Languages - Chicago, Illinois

Duration: 4 hours
Location: Chicago, Illinois

From USD
$975.00

Explore Chicago on a custom tour, in the language of your choice, with a private guide in a deluxe vehicle that seats up to 12 guests. Arabic, French, German, Italian, Mandarin, Portuguese, Russian and Spanish speaking guides are available ... More info ›

Explore Chicago on a custom tour, in the language of your choice, with a private guide in a deluxe vehicle that seats up to 12 guests. Arabic, French, German, Italian, Mandarin, Portuguese, Russian and Spanish speaking guides are available.

You will see attractions such as the Loop, Museum Campus, Millennium Park, Lake Shore Drive, Wrigley Field or you can explore the neighborhoods with visits to Chinatown, Pilsen, Little Italy, University of Chicago/Hyde Park, Fulton Market’s restaurant and gallery scene. See world-renowned buildings by Frank Lloyd Wright, Mies van der Rohe, and Louis Sullivan and the world’s most beautiful skyline at your own pace in complete comfort. Your local guide and professional chauffeur will customize the experience for you.

Your expert local guide and professional chauffeur arrive at your hotel in a luxury mini-coach with comfortable seating for up to 12 guests plus the guide and driver. Make sure to bring your camera while you head out on this tour.

Your guide will give an overview of the options for your 4-hour tour. Let the guide know your preferences and embark on your custom tour but don’t hesitate to tell the guide when you’d like to get out and walk or when you need more time for photos.

Your tour can end at your hotel or the downtown location of your choosing. Itineraries could include:

Loop: Daley Center, Marina City, Willis (Sears) Tower, Merchandise Mart, Harold Washington Library, Board of Trade, the Rookery, Art Institute, Chicago Cultural Center and Louis Sullivan’s masterpiece Auditorium Building. The “L” transit system, Chicago’s Public Art by Calder, Picasso, Miro, Chagall. Historic sites from the Great Chicago Fire, the Civil War and Abraham Lincoln, Gilded Age Mansions on Prairie Avenue, Prohibition and the Al Capone era, Route 66, the Daley “Machine”, Grant Park and Obama’s Chicago.

Lakefront: Lake Shore Drive, Lincoln Park, Navy Pier, Museum Campus, Buckingham Fountain, Northerly Island, McCormick Place Convention Center. Stunning views of the skyline with plenty of time for photos.

Millennium Park: Chicago’s new centerpiece park, home of “the Bean” (Cloudgate), the Crown Fountain, Frank Gehry designed Pritzker Music Pavilion and Lurie Gardens. Stroll thru the park as your guide explains the how this incredible “green roof” park came to be.

Neighborhoods: Get off the beaten path and explore the city’s many ethnic enclaves. Shop Chinatown for exotic wares, see the Mexican murals of Pilsen, visit a deli in Little Italy or the stunning cathedrals of the Ukrainian Village.

Sports: Create your own “Photo Op” in front of the legendary Wrigley Field, home of the Chicago Cubs or the United Center for Blackhawks or Bulls Fans.

Nightlife: Chicago is city of “Foodies” and craft brewers. Fulton Market is home to some of the city’s Michelin rated restaurants alongside wholesalers in fish, meat, produce and trendy art galleries. If music is your passion, your guide can point out some of the best clubs for jazz and blues, playing nightl.

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