Chicago Holidays

Chicago Holidays

Whether it’s your first Chicago holiday or you have visited several times, 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 holiday to Chicago by checking out these awesome buildings on the Historic Skyscrapers Walking Tour.

Chicago Attractions

Some of the top Chicago 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.

When to Visit Chicago

Our advice is to visit Chicago 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.

Things to do in Chicago

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. Chicago is also a city of uniquely vibrant neighbourhoods that are definitely worth exploring. Go ahead and check out the central areas of Loop and River North. Boystown is a fun and diverse community that applauds and encourages individual expression. There are so many places to explore and things to do in Chicago, 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.

Chicago Holiday Deals

A Chicago holiday is an ideal city break, Chicago 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. Be sure to check out our exciting range of holiday deals to Chicago now.

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.

Staff Tips

  • Adrienne Keogh
    Chicago's annual summer dance festival is held for 11 weeks each year. Get a free one-hour dance lesson and follow that by indulging in two hours of live music and dancing.
    Adrienne KeoghSales and Operations Manager
  • Fiona Kelly

    Chicago- Head to the underwater viewing area to catch a glimpse of swimming sea lions or take a guided tour of the hundreds of species on view at the Lincoln Park Zoo. Admission to the zoo is free seven days a week.

    Fiona KellyPersonal Travel Planner
  • Claire Somers

    Chicago - You can't go wrong with the Wiener Circle or Byron's, both by Wrigley Field, for a genuine Chicago dog & fries experience. For deep dish pizza, Uno/Due are owned by the same place so you'll get an equally wonderful meal at either. Be prepared to wait though, the lines can be 2 hours long in summer. Giordano's is an acceptable alternative.

    Claire SomersPersonal Travel Planner
  • Denise Walsh

    Chicago - See a free water display every hour at the Buckingham Fountain from mid-April to mid-October. The best time to go is between dusk and 10 p.m. when the fountain's 134 spouting jets are accompanied by a music and light display.

    Denise WalshPersonal Travel Planner
  • Adrienne Keogh

    Chicago - Definitely check out Wrigley Field, home of the Chicago Cubs baseball team. Catch a game and enjoy the experience of attending an American baseball game or enjoy a stadium tour. With over 100 years of history there's lots to see and learn!

    Adrienne KeoghSales and Operations Manager

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