Published 27th Nov. 2023
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‘Chicago is my kinda town’, so sang the legendary Frank Sinatra. Spend a few days here and you might find it’s your kinda town too. There’s lots to love about this spirited, skyscraper-strewn city on the shores of Lake Michigan. Planning your next USA trip? From lakeside lounging to moseying around the marvellous museums and parks, here are eight of our favourite things to do in Chicago. According to Sinatra, it’s ‘one town that won’t let you down’. We tend to agree.
1
Must-see Millennium Park is best known for Cloud Gate, the shining silver sculpture by Anish Kapoor that has been lovingly nicknamed ‘the Bean’. Unveiled in 2006, this polished, legume-like landmark has become an icon of Chicago. Stop to admire the skyline reflected in its glossy façade (snapping a selfie here is one of the most popular things to do in Chicago), before exploring the rest of the park. There’s something to enjoy in every season, from splashing in the Crown Fountain spray on a hot summer’s day to practicing your pirouette on Chicago’s largest outdoor ice rink in winter. Summertime also sees a programme of free concerts performed at the Pritzker Pavilion; a bandstand bedecked with a headdress of steel ribbons that is just as impressive as that beguiling Bean.
2
Also known as The 606, the Bloomingdale Trail is Chicago’s answer to New York’s High Line. Once a trainline, this elevated greenway runs for three miles above the city streets, providing a pedestrian-friendly place to stretch your legs. Beloved by walkers, runners and cyclists, there’s plenty of space to share (it’s wider than the High Line), plus rotating art exhibitions and free family events in summer.
3
Set on the shores of Lake Michigan, Chicago has 26 miles of scenic lakefront to explore, including some great urban beaches. North Avenue Beach is one of the most popular; a bustling stretch of sand complete with beachfront bars and endless options for entertainment. Hire a kayak to enjoy a leisurely paddle on the lake, join a yoga class on the shoreline or unfurl your towel for a languid afternoon of doing very little. If the weather calls for sweatshirts instead of swimwear, borrow a bike and cycle the 18-mile Lakefront Trail – the perfect place for pedalling, people-watching and glimpsing some grand views of the Chicago skyline. The beach is also adjacent to Lincoln Park, the city’s largest and home to the Lincoln Park Zoo, where families can spot their favourite animals free of charge.
4
Immerse yourself in the lives and work of some of the country’s finest novelists, poets and essayists at the American Writers Museum. Interactive exhibits chart the history of American literature, as well as the habits of successful writers and how stories come to life. For example, the Story of the Day exhibit sees visitors to the museum contribute a single line to a collective narrative that extends and evolves throughout the day. Just one way to express your creativity at this museum dedicated to America’s greatest wranglers of the written word.
5
If you’re travelling with children, Maggie Daley Park is playground perfection. The three-acre Play Garden is a colourful landscape of interconnected spaces designed with under 12s in mind. In fact, it’s so fantastically child-centric that we wouldn’t be surprised if the designer was in fact under 12. Highlights include ‘The Harbor’, a nautical-themed area with three full-sized play boats, as well as ‘The Slide Crater’, where there are slides of all shapes and sizes to be slipped and glided down. There’s also a climbing wall for older children and roller blades and scooters to hire, plus ice skating between November and March. An afternoon spent here is one of our favourite family-friendly things to do in Chicago. It’s an ideal place for little ones to let off some steam or wake up those jet-lagged legs.
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As one of the largest cities in the USA, Chicago has a pleasing number of places to escape the hectic hustle and bustle. Chicago Botanic Garden is one such spot. This 385-acre space houses more than 2.8 million plants growing across 28 different gardens, so there’s plenty for nature-lovers to savour. From tropical trees to bright blooms, it’s a lush oasis of botanical beauty. It’s also one of the most-visited botanic gardens in the country, welcoming more than one million visitors each year. We recommend becoming one of them next time you’re in town. And if the botanic garden leaves you wanting more of nature’s soothing ways, you could also visit the Garfield Park Conservatory. The glass domes contain a flourishing display of flora that thrives in the tropically humid conditions. It’s a sprawling space that at times seems wild and untamed; a place to pause for a deep breath of fresh, fume-free air courtesy of the plants. If you’ve ever tried (or failed) to fill your home with the verdant greenery of healthy houseplants, you’ll love it here.
7
Chicago’s Navy Pier has all the hallmarks of a good seaside (or, in this case, lakeside) pier. Ferris wheel? Check. Carnival rides? Check. Boat cruises and cool breezes? Check and check. Visiting Navy Pier is one of the most popular things to do in Chicago, whether you’re hopping aboard a cruise or simply admiring the views. Summer also brings fabulous firework displays on Wednesdays and Saturdays, illuminating the sky above the lake in a riot of sparks and spirals. The Chicago Children’s Museum can be found on the pier too, with plenty of hands-on exhibits that little ones will love.
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With a small permanent collection and an eclectic, ever-changing selection of temporary exhibits, the Museum of Contemporary Art is different with every visit. Situated just off the Magnificent Mile (Chicago’s main shopping strip), this boxy building holds a treasure trove of works by both established names and up-and-coming artists. This excellent museum is most definitely not just for a rainy day.
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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