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Chicago Holidays

Sometimes called “America’s Second City”, Chicago is brimming with world-famous architecture, music and restaurants. Modern art and mouth-watering pizza, Chicago holidays have something for everyone.


Things to Do in Chicago

  • The incredible glass-floored Willis Tower (formally Sears Tower) and Frank Lloyd Wright’s stained glass Robie House are great places to admire the city's landscape. 
  • Be sure to visit the Art Institute of Chicago. Packed full of works by Monet, Van Gough, Gauguin and Picasso, this museum boasts an impressive collection. You may recognise it from Ferris Bueller’s Day Off?
  • Indulge in some cheesy deep-dish pizza. Burt’s Place on Ferris Ave is our favourite. Just make sure to call ahead as Burt makes the pizzas himself, so orders are limited. 
  • Of course we can’t forget Millennium Park. Here you'll find beautiful landscaping, gorgeous greenery and the iconic Cloud Gate – Anish Kapoor's bean-shaped sculpture and the park’s centrepiece. 

Best Time to Visit

May-Jun: When days are hot but comfortable, but peak season has yet to hit the city. Summer time is hot and humid with temperatures wavering between 26° – 33°. The winter months tend to bring snow and temperatures often drop below 0 from December to February. 

Summer time in Chicago is when the city truly comes alive. Locals and visitors alike soak up the sunshine at outdoor festivals, ballparks and beaches. However this is also peak season so expect to pay higher prices.

Visit Chicago in late July / early August for Lollapalooza. A world-famous festival headlined by the kings and queens of rock, pop and hip hop. South America and Europe host their own Lollapalooza festivals, however Grant Park, Chicago is the original (and the best!).


Why We Love It

JenniferI really loved Chicago, it’s a fantastic city. I would recommend a Segway tour it takes about 2-3 hours and is great craic, a really good way to see the huge city that is Chicago.

Jennifer Kearney, Sales Executive


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