Chicago Holidays

Miles of lakefront nestled within a stunning architectural skyline

Whether you’re a first-time visitor to the city or a seasoned Chicagoan, the famous Windy City skyline never ceases to impress with well over a thousand high-rise buildings, upward of 100 of which stand over 500 feet tall. The tallest of these huge buildings is the 108-story Willis Tower (formerly known as the Sears Tower). All in all, four of America’s tallest buildings stand proudly in the city of Chicago, making it one of the world’s most impressive skylines. Make the most of your Chicago holiday by checking out these awesome buildings on the Historic Skyscrapers Walking Tour.
Some of Chicago’s top attractions include chilling out in Millennium and Grant Parks and taking boat rides on the Chicago River. Navy Pier never fails to make you feel 12 years old again, as you sample 50 acres’ worth of family attractions, amusements and exhibition spaces, including a huge carousel, an indoor ice skating rink, a funhouse maze and the fantastic Chicago Children’s Museum. One of the best ways to see as much of what this great city has to offer as possible is investing in a Chicago CityPass.


If you’re a first-time visitor or a seasoned Chicagoan, the city skyline never ceases to impress. Our advice is to go between May and September. That’s when the city comes alive with outdoor food and music festivals. It’s also the best time to enjoy beautiful beaches on Lake Michigan, biking around the lake, chilling out in Millennium and Grant Parks and taking boat rides on the Chicago River. Navy Pier never fails to make you feel 12 years old again. But even in the wintry sub zero temperatures, Chicago has superb dining. It may be the home of pizza, but there are top-tier, boundary-pushing restaurants as well as old school steakhouses and some of the best Mexican food you’ll find anywhere in the USA. Go ahead and check out the central areas of Loop and River North; but Chicago is also a city of uniquely vibrant neighbourhoods that are definitely worth exploring. Boystown is a fun and diverse community that applauds and encourages individual expression. Try to make time for some of the fabulous museums too. The Art Institute of Chicago is a must-see, particularly the beautiful Impressionists collection. So a city that has it all – an amazing skyline, sandy beaches within cycling distance of the city centre and water that wouldn’t look out of place in the Caribbean.

Chicago has superb dining which encompasses a huge variety of flavors and styles. It may be renowned as the home of Chicago Town-style deep dish pizzas, but there are plenty of top-tier, boundary-pushing restaurants representing lots of other food types, including old school steakhouses and some of the best Mexican food you’ll find anywhere in the USA.

Of equal quality to Chicago’s food is its wide selection of craft beers which are made locally in the city’s many breweries. You can combine some sightseeing with the famous flavors of the Windy City on the renowned Chicago Pizza and Beer Tour, which takes you on a ‘hop on, hop off’ tour where you will experience the surprising variety of that fabled tomato and cheese-based dish.

While on your Chicago holiday, you should definitely try to take the time to visit some of the area’s fabulous and diverse museums as well. The Art Institute of Chicago is a must-see, particularly because of its beautiful Impressionists collection, while the Adler Planetarium and Astronomy Museum will take you on a journey through space and time, spanning across 13.7 billion years of universal history as you travel beyond our galaxy to the edges of the known universe and beyond!


The Chicago Field Museum of Natural History offers many great exhibitions based on the world’s ancient past, both natural and manmade. Highlights include Sue, the largest and most complete Tyrannosaurus rex skeleton ever found, and an amazing walkthrough of a faithfully restored ancient Egyptian tomb in all its glory. Most of the exhibitions are interactive, making the Field Museum a fun centre of learning for the young and old alike.

Chicago has a long and prosperous history with the filmmakers of America which stretches back over a hundred years. Literally hundreds of movies have been shot on location here, from modern classics such as The Untouchables and The Blues Brothers, to recent big budget blockbuster extravaganzas like Transformers 4: Age of Extinction and Batman v Superman: Dawn of Justice. You can check out the key locations from these movies, and more, on the Chicago Film Tour which runs daily.

Cementing Chicago’s love affair with the silver screen are the numerous film festivals which take place in the city on an annual basis. Highlighting the top new local and international movies, some of Chicago’s most prestigious film festivals include the Irish Film Festival, the Chicago International Film Festival and the Midwest Independent Film Festival, which runs monthly and showcases the cream of local filmmaking talent.

Away from the hustle and bustle of the Windy City, lies Lake Michigan, one of North America’s five Great Lakes. Lake Michigan is the third largest of the Great Lakes in terms surface area and the second biggest by means of overall water volume. However, what makes Lake Michigan so special among the American Great Lakes is the fact that it is the only one which is located entirely in the United States.

Where there’s a large body of water, chances are there’s also an abundance of fish, and Lake Michigan is no different in that regard. The lake attracts sports fishers in their droves, with whitefish, trout and salmon being among the most sought after catches. In fact, the Pacific salmon was introduced to Lake Michigan during the 1960s in order to help boost fishing tourism in the area. The plan was a success, with salmon numbers now plentiful and forming the basis of a well-stocked fishing industry.

As one would expect of such a large body of water, water-based sporting activities are extremely popular at Lake Michigan. Sea kayaking, lake surfing and diving are some of the most prominent activities for sporty people, while small cruise ships, ferries and even steam ferries (some of which have been in commission since the middle 1800s) bring passengers to scenic locales such as Beaver Island and Bois Blanc Island in Michigan.


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