Chicago Holidays
Compare Holidays, Hotels, Flights and Late Deals to Chicago
Holidays in Chicago - What We Know
Chicago holidays are perfect for anyone looking to explore an exciting city destination filled with world class attractions and fascinating sightseeing spots. Located in the American state of Illinois, Chicago is famous for its skyscrapers and modern culture along with being synonymous with famous gangster names such as Bonnie and Clyde and Al Capone. There is something for everyone to enjoy during holidays in Chicago with spectacular scenery, entertainment and leisure facilities to suit travellers of all ages. Known as the ‘windy city’ this modern metropolis may not be ideal for those looking for a typical holiday full of sun, sea and sand, however there is plenty of things to see and do to take your mind off the weather! The accommodation in the city is just as varied as the attractions on offer with everything from budget to luxury Chicago hotels available to choose from. Many of the hotels boast a range of fantastic board options including self catered and half board. Those travelling as a family may wish to take advantage of the great value all inclusive Chicago holidays on offer, ideal for those looking to save money.
Sightseers will truly be in their element during a trip to Chicago with over 30 museums to explore along with galleries and monuments to discover. The Sears Tower and the famous shopping district ‘Michigan Avenue’ are just two of the must-see spots to enjoy during your holiday in Chicago. If you are looking to enjoy a unique holiday experience in one of America’s best loved cities, make sure you do not miss the great value cheap Chicago holidays on offer.
Chicago Holidays - Sightseeing And Attractions

Holidays in Chicago are perfect for those looking to take the time to explore one of America’s largest cities. With spectacular architecture, a thriving cultural scene and plenty of family friendly attractions to discover it is no surprise that many tourists find themselves returning for a second visit. One of the best things about a Chicago holiday is the many ways that you can actually view the city, for example the John Hancock observatory offers visitors the chance to experience the city from 1000ft in the air. A trip to the Navy Pier is also recommended and offers visitors the chance to experience a 3-D motion simulation of the history of this stunning city. Those looking to take in some of the legendary Chicago sights will love a trip to the original Playboy Mansion, a 70 room classic residence in the city bought by Hugh Hefner in 1959. The Buckingham Fountain is another great spot for sightseers, and is the official starting point of one of Chicago’s other legendary attractions, Route 66! The fountain represents Lake Michigan and water shows take place on the hour ever hour until 10pm, a great sight for those travelling as a family. Route 66 is known throughout the world as the ‘Main Street of America’ and has been immortalised by many famous singers, no trip to Chicago would be the same without a drive on this legendary highway! Art lovers will appreciate a trip to the Art Institute of Chicago, a majestic building guarded by two impressive bronze lions. The building is home to one of the world’s greatest art collections, a great addition to any Chicago holiday itinerary. Due to the vast amount of tourist sites around the city, it is advised to take advantage of one of the organised tours that take you around many of the most exciting spots. The city itself is easy to get around with buses and trains that run frequently around Chicago.
Chicago Holidays - Nightlife And Cuisine

Those looking for a wide selection of restaurants to enjoy during their break will not be disappointed with a Chicago holiday. There are over 6000 different eateries around the city representing a wide expanse of culinary flavours. Those looking to enjoy a typical Chicago meal will love taking a trip to one of the many pizza restaurants around the city. Chicago is home to the famous ‘deep dish’ pizza and it is hard to resist the lure of one of the city’s signature dishes. Those enjoying a holiday to Chicago can sample cuisine from all around the world with many world class restaurants offering everything from Thai to Ethiopian dishes. Chicago holidays offer a vibrant and varied nightlife with something to suit all tastes. There are several areas around the city which boasts a large number of bars collected together, perfect for those looking to really experience what the Chicago nightlife is all about. Jazz clubs are popular along with live music venues; there are also plenty of well known DJ’s that perform in the city each year. Holidays in Chicago are ideal for theatre lovers with plenty of shows and intimate plays that run throughout the year, a trip to hear the Chicago Symphony Orchestra is also recommended for visitors enjoying their holiday. Chicago has a thriving gay scene with a strip of bars located in the Lakeview district.
Weather and Climate
Chicago holidays offer a very diverse climate depending on when you choose to travel. The summers are typically very hot with temperatures regularly reaching the high thirties especially from June to September. Throughout the summer season the city is very humid therefore it is advised to ensure that your Chicago hotel has air conditioning. The spring season is fairly short with comfortable temperatures, a great time for those looking to sightsee without having to battle the extreme temperatures. The winter months are very cold with icy weather, harsh winds and frequent snowfall. Rainfall is common outside of the summer months therefore it is advised to pack waterproof clothing if you are planning a Chicago holiday during this time.

