How to Spend 72 Hours in Chicago

18 Jan 2018

Chicago is a city bursting with amazing architecture, awesome art and fantastic food! It is often unfairly overlooked in favour of New York or San Francisco, but trust us, there are a tonne of things to do here. Here are our tips for the perfect first 72 hours in the 'Windy City':

Day one in Chicago

Start your adventure in Grant Park or Chicago’s ‘front yard’, as the locals call it. The park is a lovely place for a stroll but there are so many amazing attractions here that you can easily spend your whole holiday here. First up, The Field Museum. They’ve got the most complete T-rex skeleton ever found and they’ve called her Sue. As tempting as it is to take a full day browsing the exhibits here (and you could), you should move on the sublime Art Institute of Chicago. Or if art isn’t your thing then switch that for the Shedd Aquarium, but be aware that this place gets busy so brace yourself if you are visiting on a Saturday. Finish you day in Millennium Park for that iconic photo in front of ‘The Bean’.

Day two in Chicago

Start the day with a coffee at Caffé Umbria (or if you don’t like coffee, the hot chocolate is delicious). After yesterday’s cultural exploration, today is all about retail therapy as you’ll be walking the famous Magnificent Mile. Take it at your own pace but we do recommend you make time to take in the stunning view from the look-out atop the John Hancock Building, it’s quite something. Try a slice of Chicago’s deep dish pizza while you’re here. You are never far from a Giordano’s or Lou Malnati’s in this city and both serve amazing deep dish delights.

Day three in Chicago

Our favourite way to take in Chicago’s epic architecture is on a Chicago River cruise. This way you get literally ferried between the city’s best sites and you’ll have full commentary from your guide too. After your tour, step off the beaten track a bit and head one of the best parts of town – Logan Square. Okay, it’s not an essential first-timer spot but this is one of the city’s trendiest neighbourhoods and it’s got some great places to eat and drink, not to mention a live music scene.


Book your tailor-made Chicago holiday or city break today.


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