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Chicago has world-class museums, legendary blues bars, and incredible dining, but arguably the best bit, especially for a big American city, is that you can reach most of it on foot. Whereas so many American cities sprawl for miles, Chicago feels compact and manageable, with most of the main sights within easy reach along the shores of Lake Michigan and the Chicago River.
Millennium Park & the Lakefront: See your reflection in The Bean, stroll along the Riverwalk or relax on a city beach on Lake Michigan
Skyscrapers & Views: See the skyline from the water or from 1,300 feet up on a glass ledge
World-Class Museums: Impressionist masterpieces, the world’s most complete T. rex and a WW2 U-boat
Sport: Baseball, basketball, hockey, and American football at iconic venues
Beyond Downtown: Lincoln Park, bohemian Wicker Park and the colourful murals of Pilsen
Live Music: Blues and jazz nights, plus the world’s biggest free blues festival
Food & Drink: Deep-dish pizza, the Chicago dog, Italian beef and craft beer
Millennium Park is the place most people head to first. At its centre is Cloud Gate, better known as ‘The Bean’, a huge, shiny sculpture by Anish Kapoor. It’s essentially like a giant funfair mirror. If you walk underneath it, you’ll see your warped reflection with the skyscrapers curving overhead. Nearby, Crown Fountain features two tall glass towers, each displaying the faces of Chicago locals. Water spouts from their mouths into a shallow pool below, and it’s a really fun place for children (and adults!) to splash about and cool off in the summer. For more water spectacles, the grand Buckingham Fountain in Grant Park sends a jet of water 150 feet into the air every hour, with a lights-and-music show on summer evenings.
Next to Millennium Park, you can take the pleasant Riverwalk for over a mile along the Chicago River, lined with bars and cafés tucked beneath the bridges. Beyond it lies Lake Michigan, which is so vast it feels almost like the seaside. Between late May and early September, you can even enjoy a proper beach day right on the water’s edge, at the lively North Avenue Beach (pictured above) or the quieter Ohio Street Beach. And out on the lake itself, Navy Pier juts into the water with its big wheel, an old-fashioned carousel and fireworks on summer evenings.
Chicago is the birthplace of the skyscraper, and a great way to take in the city skyline is from the water. Take a guided river cruise and glide past the skyscrapers that made the city famous, with a guide bringing each one to life along the way. Head out on a late afternoon trip if you can, when the light on the buildings is at its most golden.
For the best views in the city, you have two main options, and the views are superb from both. Willis Tower, the tallest building in the city, has a Skydeck on the 103rd floor, where you can step out onto ‘The Ledge’ – a set of glass boxes that leave you standing more than 1,300 feet above the street. Not for the faint-hearted! The other option is 360 Chicago, set in the former John Hancock building on the Magnificent Mile, Chicago’s famous shopping street, lined with department stores and landmark buildings such as the Wrigley Building and the old Water Tower. Here you’ll find ‘TILT’, a moving platform that slowly leans you out over the streets below.
If you only have time for one museum, make it the Art Institute of Chicago (pictured below). It’s the second-largest art museum in the US, with some of the best collections of Impressionist art outside Paris. It features works by Monet, Degas and Renoir, plus two of America’s most famous canvases: Grant Wood’s American Gothic and Edward Hopper’s Nighthawks.
For more of a family-friendly trip, head to the Field Museum on the lakefront Museum Campus to see ‘Sue’, the most complete T. rex skeleton ever found. On the same campus, the Shedd Aquarium is another fantastic option for marine life lovers, home to sharks, beluga whales and dolphins. Meanwhile, in Hyde Park, the Museum of Science and Industry lets you climb aboard a captured German U-boat and watch a tornado form indoors.
The locals are mad about sports, and watching a live game is one of the best ways to spend an evening in Chicago. In the summer, the sport of choice is baseball. There are two local teams: the Cubs, who play at Wrigley Field, and the White Sox on the South Side. Tickets are generally easy to pick up as both teams play dozens of home games over the summer. During the colder months, you can catch the Bulls playing basketball or the Blackhawks playing ice hockey in the United Center. Or if you fancy a spot of American football, you can watch the Bears at Soldier Field, the oldest stadium in the NFL.
While all the main sights in the city are walkable, it’s also worth venturing out a little further. Lincoln Park (pictured below) is a leafy, green part of the city with large old houses, a free zoo and Second City, the comedy club where Bill Murray, Tina Fey and many other Saturday Night Live stars got their break.
Wicker Park has more of a bohemian vibe with record shops, vintage clothing and brunch spots. Pilsen, the heart of the city’s Mexican community, is covered in colourful murals and home to the excellent National Museum of Mexican Art. You can also walk part of the 606, a park built along a disused railway line that runs for nearly three miles above the streets, with views over the rooftops as you go.
Chicago is known for its music. It’s the city that gave the world the ‘Chicago Blues’ after WW2, and that musical pedigree is still strong today. You can easily find live music somewhere most nights of the week, but for the real thing, head to Buddy Guy’s Legends. Alternatively, head to the Green Mill, a jazz club that’s been going since 1907 and was once Al Capone’s favourite haunt. It’s barely changed since Prohibition, and you can still even sit in his favourite booth, which is ideally placed so he could keep an eye on both doors!
If your trip coincides with a festival, you’re in for a treat. The Chicago Blues Festival, in early summer, is the largest free blues festival in the world, while Lollapalooza takes over Grant Park in late July, a four-day event with more than 170 acts across eight stages.
Chicago is famous for its deep-dish pizza, invented here in 1943. It’s more of a pie than a pizza, though, and definitely one for a knife and fork rather than eating with your hands. There are other must-try specialities too, including the Chicago-style hot dog with mustard, relish, onion, tomato, and a pickle (but never ketchup!), plus the Italian beef sandwich. For something more sophisticated, the city has a fabulous fine-dining reputation, with around 20 Michelin-starred restaurants.
Chicago has a thriving brewing scene, with plenty of craft beers to try at one of the city’s many brewpubs and taprooms. And if you’re brave, knock back a shot of Malört, a local bitter spirit, but be careful, it’s very much an acquired taste!
Chicago makes a brilliant starting point for a bigger American adventure. Kick off a classic Route 66 road trip from here, winding all the way to the California coast or weave it into a city-hopping tour on our Best of USA Cities itinerary. Whatever you have in mind, we can build the perfect trip for you. Simply get in touch with our team.
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