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Top Things to do in Chicago For Visitors

Here is our list of top things to do in Chicago for visitors. The Windy City has a fabulously murky, dark history of notorious mobsters, gangsters and illicit dealings. Explore and be delighted! It also offers stunning modern architecture, arts and culture museums and a Planetarium. Water dominates with a massive lake and a river. Speed boat or kayak and enjoy the views of famous landmarks. This is city of fun food, pizza, hotdogs and popcorn. Experience the melting pot of cultures in the neighborhoods that add to the enchanting cuisine. Then travel into the country to learn about the local wine industry. Theatre lovers will find a host of shows to enjoy and the whole family will be thrilled on a movie tour to see where blockbusters were filmed!

Architecture Tours

Architecture Tours in Chicago

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The city offers a fascinating array of architectural styles and taking a walking tour to learn about them is a fabulous thing to do in Chicago.

This interactive tour allows you to explore the connection between art and architecture. Learn about the different designs and how history and culture influenced the design of the buildings.

Your guide will give you a thrilling insight into how Michael Jackson's Thriller inspired a skyscraper and you will get an insight into the famous soup cans of Andy Warhol. Compare the cutting-edge modern and the historical old and see how the Great Fire caused inspiration in reshaping the city.

The tour caters for small groups and is ideal for families or friends. Don't think architecture is boring, your expert guide will enthral you!

Cultural Tours

Cultural Tours in Chicago

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Exploring the rich cultural heritage of the city is something to do in Chicago. Escape the tourist areas and learn about the real Windy City. The North Side Tour exposes you to some of the most wealthy communities like Lincoln Park and the Magnificent Mile. Take a walking tour to see the smaller nuances that tourists miss. Your guide will show you hidden details and tell you stories about the iconic history.

Visit Hyde Park and see President Obama's home. Then explore the Pedway system and visit the Cultural Center, the Chicago Board of Trade and the historic City Hall. There is much to see, so plan more than one tour and get comfortable walking shoes.

Air, Helicopter & Balloon Tours

Air, Helicopter & Balloon Tours in Chicago

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Chicago is a massive metropolis filled with many famous sights to be seen. Viewing them from a luxury helicopter is one of the first things to do in Chicago.

Take a tour with a qualified professional pilot. Be awed by the astounding views of Lake Michigan and the Navy Pier. See the cityscape from the air and identity the famous Willis Tower and the glowing Trump Tower. Fly over the Lincoln Park Zoo, Wrigley Field, the United Center and the majestic Millennium Park. As you circle around, your pilot will update you via a two-way audio headset and also answer questions, making this a truly meaningful adventure. For a mind-blowing experience, see the millions of city lights on a night trip.

Cruises, Sailing & Water Tours

>Cruises, Sailing & Water Tours in Chicago

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Exploring the waterways is another exciting thing to do in Chicago. The city lies on the massive Chicago River and Michigan Lake and you can take a fabulous hour and a half cruise to discover the famous sights. Board at Navy Pier and see the iconic buildings like the Willis Tower and the IBM Building. Learn about the architecture and how it shaped the rebuilding of the city after the Great Fire. Then set off for a high speed boat ride on Lake Michigan that will thrill. Identify the major buildings and wave at the tourists as you race by with the music blasting!

For a relaxed water trip, book the Dinner Cruise which exudes class and style and offers a fine-dining experience while you admire the views.

Ghost & Vampire Tours

Ghost & Vampire Tours in Chicago

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Are you thrilled by ghosts, vampires and haunted buildings? A ghost tour is a spine tingling thing to do in Chicago. You can choose to explore the ghostly history on a Segway, by bus or on a cruise.

Glide on a Segway at night through small alleys and see areas where gruesome disasters and murders took place. Stop at haunted hotels and hear ghostly pianos tinkling in the ballrooms. Alternatively, ride on a bus and hear stories of the St Valentine's Day Massacre, visit the Old Cemetery and get spooked out at the famous Prairie Avenue.

If you want to celebrate Halloween with a difference, book the Halloween Tour where guests dress up and an unknown ghostly character navigates your boat along the murky waterways.

Historical & Heritage Tours

Historical & Heritage Tours in Chicago

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Chicago has a rich heritage of architecture and is a melting pot for a wide range of cultures and a diverse population. Exploring this fascinating aspect of the city is a great thing to do in Chicago. Take a walking tour of the West Loop where you will see the location on which the city was born. Stand on the site where the first skyscraper was erected and learn about the cutting-edge modern day architecture.

Then take a fun gangster themed tour in a barrel bus and follow in the footsteps of the notorious bank robbers, west side gangs and mobsters like Al Capon and Bugs Moran. These tours are relaxed and ideal for all ages.

Literary, Art & Music Tours

Literary, Art & Music Tours in Chicago

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For those who love culture, here is a another fabulous thing to do in Chicago. Take a tour of the amazing Art Institute of Chicago, it is the second biggest art museum in the USA. Be awed by originals from iconic artists like van Gogh, Renoir and Picasso. The Museum also has a modern section which is reached by a walk over a spectacular bridge offering stunning views. Kids can take part in art lessons too. For something different, take a class and learn how to make glass jewelry. This is the city of Tiffany Glass! You will love wearing your designer piece as you stroll around. Alternatively learn how to work with felt to create a unique piece to take home.

Movie & TV Tours

Movie & TV Tours in Chicago

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When planning things to do in Chicago, don't miss the Film Tour. Movie lovers will be enthralled and it is ideal for the whole family. Chicago is the setting for many famous block busters and your bus will stop at these iconic spots. See the locations of Transformers 3, The Untouchables, Ocean's Twelve and more. The luxury coach is equipped with TV screens that play the movies clips as you pass through the area. The tour also passes through well known neighborhoods like Lincoln Park and Gold Coast. Your knowledgeable guide will keep you informed with educational information as you travel along. Relax and enjoy, this is a fun way to explore the city.

Bar, Club & Pub Tours

Bar, Club & Pub Tours in Chicago

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Learning why the sale of alcohol was banned in the USA for more than ten years is a fascinating thing to do in Chicago. Enjoy an adult's tour and find previously illicit drinking spots where mobsters ran the show and iconic jazz was born. Visit the Green Door Tavern and sample some 1920's cocktails. Learn about the Prohibition Era and characters like Al Capone who became so notorious.

Then explore the South Loop where beer is the order of the day. Visit local establishments, meet the owners and mix and mingle with locals and tourists.

As a final fun trip, ride around the city in a unique bus shaped like a beer barrel! Visit the Distillery and learn about the liquor trade while sampling vodka, brandy, gin the famous craft spirits.

Food Tours

Food Tours in Chicago

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The city is bursting with local and international cuisine and sampling some of these delicacies is a delicious thing to do in Chicago. Take a small group tour through Bucktown and Wicker Park and sample the massive sauce-dripping local hot dogs, popcorn and pastries. Stop at a Middle Eastern food restaurant and finish up with a classic donut smothered with icing.

Pizza lovers will be thrilled by the Behind-the-Scenes Pizza Tour. You will be taken into the kitchens where you can watch the chefs at work.

Sample each of the three styles, a deep-dish, coal oven and a thin-crust and become an expert.

For those who prefer a fine-dining experience, be enchanted by a gourmet lunch on the Fox River Wine Country Tour. Learn about the wines that grow in this region and sample some with your meal.

Wine Tasting & Winery Tours

Wine Tasting & Winery Tours in Chicago

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Exploring the Wine Country of the mid-west is a distinguished thing to do in Chicago. Whether you are an expert or a beginner, there is a tour to suit all. Your guide will escort you to different wineries where you will learn about the grape growing process, harvesting, fermenting and bottling. Learn how to taste and how to pair wines with food. Then visit Duneland and note how the subtle aromas and flavors differ from those grown in the mid-west. This scenic region makes for a great relaxing day out.

If Bubbly is your thing, enjoy a bottle as you admire the stunning views from the 360 Chicago at over 1000 feet in the air. These tours also include a gourmet lunch to enjoy with your exclusive wines.

Shows, Concerts & Sports

 in Chicago

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Show and sports lovers will be spoilt for choice and enjoying these spectacular events is another thing to do in Chicago.

Start with an evening at the famous Blue Man Group, the longest running show in the city. It offers fabulous visual experiences and is ideal for the whole family. Football is a must for sport's lovers and Copa America is attracting visitors from around the globe. Be part of this exciting celebration that features teams from Chile, Brazil, Columbia and more.

The iconic Flanagan and Finn offers laughs a minute for those who love comedy and if medieval is your style, be treated to a unique dinner experience in an 11th century castle, where jousting knights in suits of armor will thrill you as you enjoy a lavish banquet.

Sightseeing Passes

Sightseeing in Chicago

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To get a feel for the city, sightseeing tours are the thing to do in Chicago. A Chicago CityPass or Explorer Pass gives you access to the main attractions at discounted rates. See the fabulous shows at the Shedd Aquarium and visit the Field Museum. Be awed by the 360 degree views from the Skydeck and then explore the Museum of Science and Industry. Star gazers will love the Alder Planetarium and kids and the young at heart cannot miss Legoland. Take a walking tour to learn about Tiffany Glass and art lovers can spend time enjoying the displays at the Art Institute. Your local hotel or travel agent will be more than happy to advise on how to obtain these special tickets and passes.

Sightseeing Tours

Sightseeing Tours in Chicago

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Sightseeing in the Windy City offers a host of things to do in Chicago. The tours are fabulous fun and can be done by luxury bus, walking, driving on a Segway or in a helicopter! Choose one of each and enjoy.

The hop-on-and-off bus lets you explore at your own pace. Jump off at the venues that interest you and then jump back on when you are done.

Take a half day tour and visit Washington Park, Adler Planetarium and the Wrigley Building. The Segway Tour cruises along Lakeshore Drive and passes Navy Pier and Buckingham Fountain. For a bird's eye view, try a helicopter ride at night when the glittering city lights will astound you.

All tours offer friendly and knowledge guides who will inform you on all the famous sights you are seeing.

Segway Tours

Segway Tours in Chicago

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Driving around the city on a Segway is a super cool thing to do in Chicago. These fun two-wheel motorized vehicles offer an unforgettable experience. The trip begins with a short training session. You then put on your helmets and goggles and follow your guide. Cruise along Lakeshore Drive and stop at Navy Pier. See the Lincoln Statue and the Buckingham Fountain. Learn about Grant Park and see the marine life at Shedd Aquarium. This is also an educational tour as your guide will update you as you drive along.

Then enjoy the city at night! The Night Tour offers a totally different view as your cruise along the brightly lit streets. Tours are personal and limited to only 8 people, making this a unique experience.

Walking & Biking Tours

Walking & Biking Tours in Chicago

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If a Segway seems too innovative for you, walking or biking to see the sights is a great thing to do in Chicago. Your group can explore everything from classic art to eating the famous hot dogs.

Ride through the iconic neighborhoods and meet the locals. Sample craft beer, cupcakes and learn about the pizza culture. Then discover the beautiful modern architecture as you walk or bike past the contemporary buildings. See the Harold Washington Library and the Inland Steel Building, covered in Stainless Steel. Your guide will keep you informed as you go along. Take a River Walk tour and learn about the history and culture of the Windy City before settling down to a scrumptious brunch.

Water Sports

Water Sports in Chicago

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Lake Michigan and the Chicago River dominate the city and exploring these waterways is something to do in Chicago. Enjoy an exhilarating speed boat ride on the lake. Depart from Navy Pier and race off to the Museum Campus. See the famous landmarks along the way.

If you prefer something slower, paddle down the river in a two-man kayak with a trusty guide. Be inspired as you pass under the looming bridge system and see the towering Willis Tower. Paddle along the Promenade and wave to the tourists on the land!

An evening kayak tour for the brave, takes you past the haunted spots of gangsters, horrible massacres and executions. Learn about the mobsters and murky characters who contributed to the dark side of this fascinating city.


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