Published 17th Jul. 2023
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Thinking about a trip to the Windy City? We’re sure it’ll blow you away. You can easily enjoy 24 hours in Chicago as long as you know where to go and what to see. It’s one of the largest and most vibrant cities in the United States and is home to a variety of attractions and experiences, from the famous deep-dish pizza pies to world-renowned museums, parks and public art. With so much to explore on your holiday to America, it can feel overwhelming (especially when you only have a day to do it all in). So, you’ll probably be in need of a well-planned itinerary. That’s where we step in. Take a look at how we’d spend 24 hours in Chicago.
There’s no snoozing when you only have 24 hours in Chicago. Rise and shine as early as possible to make the most of what little time you have to explore this bustling city. Fuel up on pancakes, waffles and omelettes in one of the West Loop’s myriad cafes, or opt for more unique dishes in Bridgeport where plates of corned beef hash, sticky buns and Greek-style eggs will be waiting. With a takeaway coffee in hand head to Millennium Park to see one of Chicago's most iconic landmarks: the Bean. This giant, reflective sculpture is officially known as Cloud Gate and is without a doubt a must-see for anyone visiting this city. Reflecting both the sky and the skyline, it’s worth hanging out for a while, taking pictures and soaking up the superb views of the surrounding landscape. For any budding aesthetes, the next stop should be to the Art Institute of Chicago. The second largest art museum in the country, it houses an impressive 300,000 works of art, including pieces by artists like Monet, Van Gogh and Picasso. If you’re tight for time, go straight to the impressionist collection so you can get up close and personal with Monet's Water Lilies.
Time flies when you’re admiring art. It’s lunchtime already (half way through your 24 hours in Chicago) and thankfully, you’re in a city that loves eating. From classic deep-dish pizzas to contemporary fusion pop ups, there's no shortage of flavoursome options for lunch. So, if your stomach has started rumbling, it might be time for a trip to Giordano’s for their iconic Chicago classic deep dish, piled high with cheese and meats. Or maybe you’ll swing by Gene & Jude’s Red Hot Stand for one of their legendary hot dogs that come topped with a fistful of fries, mustard, onions, pickles and peppers. For the carnivores among you, the classic Chicagoan Italian beef sandwich is a must. Made up of thinly sliced, slow-cooked roast beef, it comes served in a long French roll soaked in flavourful beef jus. The sandwich is typically served with giardiniera – a spicy pickled vegetable mix – and sweet peppers, which makes it a particularly comforting bite on a cold and windy day.
After those taste buds have been truly tickled, it’s time to head to Navy Pier. This popular destination offers stunning views of Lake Michigan and the city skyline, so make sure you’ve got space on your camera roll to snap a few shots. There are lots of attractions here too such as the Children's Museum, the Chicago Shakespeare Theater and the Centennial Ferris wheel. Alternatively, you could take a stroll along Chicago Riverwalk, a pedestrian pathway that runs alongside the Chicago River. Walk the walk alongside Chi Town locals or hit the water on boat tours and kayaking adventures. If the weather isn’t on your side, spend a couple of hours in the River North Gallery District, which features numerous art galleries and street art installations. Got some souvenirs to buy? Head to the Magnificent Mile: a stretch of Michigan Avenue known for its high-end shopping and stunning architecture, including the Tribune Tower and Wrigley Building. There are plenty of department stores and luxury boutiques to visit, even if it’s just for a bit of window shopping.
Although your 24 hours in Chicago are coming to an end, there’s still plenty to do (and eat). After a day exploring the city, you’re bound to be at least peckish. Grab a slice of pizza (which is always a good idea in Chicago) or join locals for a spot of alfresco dining. Navy Pier is the place to go. Whether it be fast food, fine dining or just a cocktail by the water, you can do it all at the pier. After dinner, you might want to experience Chicago’s thriving nightlife scene. The River North and West Loop neighbourhoods are popular destinations for bars and clubs. However, if you’d prefer a more laid-back evening, there are plenty of speakeasy bars and rooftop lounges that’ll suit the vibe. And if you are feeling up for a more cultural experience, head to Chicago’s theatre district to catch a late-night comedy show.
From New York to California and all the states in between, our team knows the USA's hotspots incredibly well. What we really excel at, though, is the under-the-radar regions, thanks to our in-depth experience and the hand-picked guides we work with on the ground. Whether you’re travelling as a family or à deux, road trips are the ultimate way to explore the USA, and we're brimming with suggestions to improve journeys, from scenic route options to photogenic stop-off points (all based on our own experiences, of course). And if that's not enough, you'll have our in-country Concierge team on hand at all times for extra help and advice.
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