The buzzy American city that’s a fun alternative to New York

Chicago is always on the up. The biggest, buzziest city in the American Midwest, this was the home of the world’s first skyscraper (the now-demolished Home Insurance Building, completed in 1885), and the skyline has been shapeshifting since then. It has ended up a patchwork of art deco marvels, brutalist hulks and modern, glassy showstoppers, making no trip to the Windy City complete without tour of its architecture.
Beyond the mighty impressive buildings, this is a place defined by water. Chicago skirts Lake Michigan, which is trimmed with lakeside trails and sandy urban beaches, while the namesake river is plied by ever-popular boat tours. Then there are the neighbourhoods — more than 70 of them, in fact, from a still-mushrooming Chinatown to trendy hangouts such as Logan Square and Fulton Market. The result is a richly diverse city that is more approachable than New York yet more fast-paced than Boston.
• Morning: Art Institute of Chicago• Lunch: The Gage • Afternoon: 360 Chicago • Drink: Cindy’s Rooftop• Evening: The Second City club • Dinner: Avec River North
• Morning: Architecture river tour• Lunch: Chinatown • Afternoon: Walk the 606 or Lakefront Trail • Drink at: Federales Fulton• Evening: Winter’s Jazz Club • Dinner: Bronzeville Winery
• Chicago is undoubtedly one of America’s artistic heavyweights. Its entrance flanked by a pair of much-photographed bronze lions, the Art Institute of Chicago holds one of the world’s largest collections of impressionist art. The place fills up, but brave the crowds to see big-hitters such as Monet’s Water Lily Pond (adults £25; artic.edu). A morning here will land you close to some of the best-loved public art in the city too; seek out the Cloud Gate sculpture by Anish Kapoor (aka “the Bean”) and the Jaume Plensa-designed Crown Fountain, both in Millennium Park.• By now your neck may ache from gazing upwards, so shift your perspective at one of the city’s soaring observation decks. At 360 Chicago, Tilt eases strong-stomached folks out over the city in a moving glass box, until they’re looking directly down on the Magnificent Mile district (£34; 360chicago.com). The glass ledge of the Skydeck at Willis Tower is equally hair-raising (£25; theskydeck.com). • Chicago has a revered improv scene and the Second City club has nurtured some of the finest names in comedy, including Tina Fey and Amy Poehler. The snug, no-frills joint hosts consistently stellar shows, from political satire to side-splitting musical ensembles (from £8; secondcity.com).• Combine a leisurely trip on the river with a deep dive into city history on an architecture tour with Shoreline. Convivial guides will point out celebrity sights such as the beaux-arts Wrigley Building and the new St Regis hotel, a wavy, glass confection that is the world’s tallest building designed by a female architect, Jeanne Gang (from £40; shorelinesightseeing.com). • The Windy City provides ample opportunity to get active. On the Northwest Side, the 606 is its answer to the High Line in New York City — an elevated greenway born of an abandoned railway. Or there’s the Lakefront Trail, which spools out for 18 miles, revealing highlights such as the sandy Oak Street beach. The Lakefront Neighborhoods tour with Bobby’s Bike Hike whisks visitors along the water’s edge and explores districts including the historic Gold Coast area and the old town (from £36; bobbysbikehike.com).• The city’s rich jazz and blues heritage is a product of the Great Migration, in which African-Americans travelled north in great numbers through the 20th century, arriving in urban hubs such as Chicago. Modern yet intimate, Winter’s Jazz Club is a hot ticket for live sets (from £8; wintersjazzclub.com).
Straight-shooting comfort food is on offer at this restaurant, housed in a landmark 1800s building downtown, in an area known as the Loop. Sink into an inviting brown-leather booth and choose between dishes such as fish and chips or rigatoni with wild mushroom ragu (mains from £18; thegagechicago.com).
Keep things on a high with a sundowner at Cindy’s Rooftop. The popular cocktail spot tops the swish Chicago Athletic Association hotel and offers generous views over Lake Michigan and Millennium Park (cocktails from £14; cindysrooftop.com).
Mediterranean meets New American cuisine at this trendy neighbourhood spot filled with hanging plants and pendant lights. The focaccia with taleggio cheese and truffle oil is the pick of the menu — ask for a side of honey for drizzling (mains from £19; avecrestaurant.com).
Make lunch a tour of one of the few Chinese districts in the US that is still expanding. It is spread over 30 city blocks and foodie highlights include Triple Crown Restaurant for excellent dim sum (from £3; triplecrownchicago.com), Lao Sze Chuan for punchy Sichuan cuisine (mains from £11; laoszechuantogo.com) and Chiu Quon Bakery for traditional sweets, including egg tarts (from £1; cqbakery.com).
Make time to explore the happening Fulton Market district. The formerly industrial area is home to the open-air Federales Fulton, a Mexican-inspired spot known for its tequila concoctions. Try the blood-orange margarita (cocktails from £7; federalesfulton.com).
Don’t be fooled by the name — though the wine list is robust, this is a sought-after, full-service restaurant. Expect dishes such as duck breast with white cheddar grits or sea bass with salsa verde, plus DJ sets from Thursday to Sunday (mains from £19; bronzevillewinery.com).
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Affordable mid-century chicThis fashionable hotel punches above its rate, offering artfully designed, mid-century-style rooms in the River North neighbourhood — a gallery-packed art and design hub. Well-executed craft cocktails are served at the hotel’s Broken Shaker bar, which has a cool speakeasy atmosphere (room-only doubles from £127; freehandhotels.com).
Urban art fixWith locations popping up across the US, the discerning 21c brand is quickly becoming a marker of a city’s artistic clout. This offering in the downtown area of Chicago doesn’t disappoint, with sprawling gallery space, smart rooms and colourful penguin sculptures that appear to move of their own volition — now a trademark of the chain (room-only doubles from £222; 21cmuseumhotels.com).
Understated luxury The first thing you’ll notice about the Pendry is that it’s housed in a gilded champagne bottle — the striking art deco landmark was built as a defiant response to Prohibition rules in the 1920s. The hotel’s stylishly minimalist accommodation places you in the heart of the attraction-packed Loop neighbourhood. Venteux, its European-style brasserie, will see you through from breakfast to dinner too (room-only doubles from £330; pendry.com).
Fly direct to Chicago O’Hare from Heathrow with carriers including British Airways, American Airlines and United Airlines.
Unlike many American cities, Chicago is well served by public transport, with an extensive bus network and the eight “L” train lines — the Blue line links the airport with the city centre.
The city is where you’d start the classic Route 66 road trip. America As You Like it has 20 nights’ self-catering plus two nights in a hotel from £1,485pp, including flights and RV rental (americaasyoulikeit.com).
Chicago is the starting point for signature long-distance Amtrak routes, including the California Zephyr and the City of New Orleans. Jacqui Agate was a guest of Choose Chicago (choosechicago.com) and Enjoy Illinois (enjoyillinois.co.uk)
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