Let’s go Chicago!

This multifaceted, must-see city serves up something for everyone

Chicago, on the shores of Lake Michigan, is famed for its skyscrapers and street food – but there’s plenty more to explore. Whether you’re staying for a long weekend or a fun-filled fortnight, this friendly city has so much to offer.

For a base, try the CitizenM Chicago Downtown. It boasts chic accommodation, art-laden interiors, and a welcoming bar and lounge area to unwind in. Plus, it’s just a stone’s throw from the action.

Sights and sounds

Step out of the hotel into Chicago’s bustling downtown district, with something iconic around every corner – from the L-train to the street art, historic buildings and sculptures. The nearby Riverwalk winds alongside the Chicago River, while Millennium Park, home to the famous Cloud Gate “bean”, is a short stroll away.

For a leisurely overview, check out the Architecture River Cruise. From the open deck, you’ll travel up and down the river and learn all about the buildings that line it, their context and history.

For a less passive tour, hop on two wheels and join in Bobby’s Bike Hike’s ‘Bikes, Bites and Brews’ tour. Led by an experienced cyclist guide, you’ll ride around the city, passing points of interest – including the Hancock Tower and Wrigley Field baseball ground – and stopping for snacks and drinks along the way. Taking in the Gold Coast mansions, Old Town Historic District, Lincoln Park and Wrigleyville, the journey back to base takes in six miles of the Lakefront for a peaceful ride and a different perspective on the skyline.

For an almost bird’s eye view of the city, head to the Skydeck at the top of the Willis Tower. Formerly (and more famously) known as Sears Tower, this was once the world’s tallest building and gives extraordinary panoramic views of the city and, on a clear day, the neighbouring states, too.

Craving culture? We highly recommend the Art Institute of Chicago, which is home to some of the world’s most famous paintings – including Edward Hopper’s Nighthawks, Grant Wood’s American Gothic and an impressive collection of works by Warhol, Monet and O’Keeffe. If you’re short on time, the back page of the visitor guide gives a sympathetic ‘What to see in an hour’ overview.

Elsewhere, the American Writers Museum is a joyous exploration of American poets, authors, journalists and songwriters, and packs in a lot of fascinating information, artefacts and interactive exhibits.

For an ever-changing roster of exhibitions, Festival Hall at Navy Pier is well worth checking out. Enjoying a spectacular location at the end of the city’s iconic pier, the exhibitions here are free and varied.

There’s plenty to do once the sun goes down, too. For live music, head to The Bassment. This underground live music cocktail lounge offers plenty of ambience and atmosphere and caters to all music tastes. On the night we went, the music ranged from soul to emo, with covers of hits by local band Fall Out Boy bringing the house down.

If blues music is more your vibe, check out Buddy Guy’s Legends. This iconic blues club plays host to up-and-coming and famous acts seven nights a week. Elsewhere, Bronzeville Winery, in Chicago’s Southside, offers fine dining, exquisite wines and sophisticated live music, too.

Food, glorious food

There are two must-eats in the city – deep-dish pizza and the iconic Chicago dog.

For pizza, forget what you think you know about the deep-pan style. Authentic deep-dish pizza boasts a crumbly pastry-like base generously loaded with a thick layer of toppings. At Lou Malnati’s, the fresh tomato sauce is the star and the base extra flaky. At Giordano’s, generously loaded mozzarella stretches teasingly as each slice is cut and served.

A Chicago dog is the city’s other signature dish. More than just a regular hot dog, the Chicago dog is premium sausage loaded with onions, tomatoes, peppers, pickles, bright green relish, celery salt and mustard – but never ketchup! Chicagoans take their hot dogs seriously and adding ketchup is a major faux pas here. For the most authentic experience, head north to family-run Superdawg. This old-school drive-in was established in 1948 and its distinctive neon-clad façade has featured in plenty of films and images. We recommend the classic Superdawg with crinkle cut Superfries, followed by a delicious vanilla malt or milkshake.

For Greek-style meze, visit Avli On The Park and enjoy supersized servings in spectacular surroundings or, for something a bit spicier, check out Bar Goa River North – a lively spot that serves up delicious Portuguese-Indian food and a stunning selection of cocktails. The Sea Foam, with its Insta-worthy “cloud”, is well worth trying.

For traditional tapas, Jaleo is the place. From celeb chef Jose Andres, the food is delicious, and the setting is relaxed and friendly. Whatever you order, enjoy it with a jug of Sangria for the full experience.

If you can’t decide on just one type of cuisine or want to mix and match your meals, head to the Time Out Market. This casual food hall has every type of food under one roof and the rooftop terrace offers great views of the neighbourhood, too.

Need to know

Words: Jo Chapman