Chicago holidays

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Be blown away by the Windy City

Steely skyscrapers designed by world-famous architects, a leafy lakefront area and one of the country’s most vibrant music scenes combine to make Chicago a thrilling place to visit. The Windy City is packed with top-flight theatres and museums, not to mention a slew of tempting eateries. Eye-popping public art dots the streets and there’s prime shopping to enjoy.

Take in views of four states from 1,000 feet up at 360 Chicago and ride the ‘L’ elevated transit system. Pose for a selfie by the Bean, a mirrored sculpture in Millennium Park, grab a juicy Italian beef sandwich from Al’s Beef, then shop the retail paradise that is the Magnificent Mile. Walk along the Chicago River, cruise Lake Michigan or cycle the 18-mile Lakefront Trail, taking in Navy Pier, with its Ferris wheel, Lincoln Park Zoo and the Buckingham Fountain.

In summer, head to Montrose Beach for dunes, birding trails and live music at the Dock. Follow the cool kids to the Empty Bottle, a dive bar in the Ukrainian Village where the likes of Arcade Fire and the White Stripes cut their teeth, while comedy royalty have honed their improv skills at the legendary Second City. Book your flights to Chicago to experience all this and more.

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Make the most of your Chicago holiday

Visit in summer to make the most of Chicago’s festival scene, including Chicago Blues Festival, the world’s largest free blues festival, Taste of Chicago, the world’s largest food fest, and the 4-day music behemoth Lollapalooza.

What are the best things to do in Chicago?

1. Board the Chicago Architecture Foundation Center River Cruise and tick off more than 50 of the city’s landmark buildings on a leisurely 90-minute tour narrated by knowledgeable and amusing guides.

2. Sing Take Me Out to the Ball Game and cheer on the Cubs from the century-old stands of Wrigley Field, with its hand operated scoreboard, ivy-decked walls and iconic neon marquee. On non-match days take a tour of the ballpark, learn about the Billy Goat Curse - which prevented the team winning the World Series for 70 years - and the club’s many traditions.

3. Take a peek at the Art Institute of Chicago. Home to masterpieces by Van Gogh, Picasso, Monet, Matisse and Warhol, the gallery also has blue stained-glass windows by Mark Chagall. Delight your kids with a visit to the Thorne Miniature Rooms where they can marvel at intricately decorated dollhouse-like rooms.

4. Admire the view from the 360 Chicago Observation Deck. Take the lift to the 94th floor of this iconic skyscraper to enjoy panoramic views of the city and beyond - and if you’re feeling brave try its TILT experience where a glass box gradually tilts its way over the edge of the building looking down on the streets 1,000 feet below.

5. Stop and smell the roses at Humboldt Park. This large West Side park is perfect for lazing on the grass and strolling past its many lagoons. It’s best reached via the 606, a 3-mile-long elevated urban walking trail that follows an abandoned railway through several neighbourhoods.

Which holiday type in Chicago is right for me?

Looking for a Chicago city break? Look no further with our fantastic selection of handpicked hotels. InterContinental Chicago Magnificent Mile, in a prime location on the Mag Mile, blends Roaring Twenties architecture with cosmopolitan style and offers sweeping city views from its elegant rooms. Alternatively, try the Hyatt Centric Chicago Magnificent Mile. This urban hotel features Hyatt Grand Beds, 46-inch flat-screen HDTVs, compact fridges and sound machines, plus the sophisticated Level Two restaurant. Meanwhile, The Drake is a historic hotel in the Gold Coast district offering Serta Serenity beds, Italian marble bathrooms and deluxe bath amenities. There’s live entertainment on weekends.

For a luxury break check out The Peninsula Chicago, another Mag Mile option which offers a full-service spa, indoor pool and hot tub, plus three award-winning restaurants. While families will want to gravitate towards the Royal Sonesta Chicago River North with its living room that matches glamour with cosiness, heated pool and sky-high views of the lively River North neighbourhood.

Where are the best places to stay in Chicago?

River North offers galleries, arts fairs, boutiques, antique stores and furniture dealers. It’s also a food lover’s paradise, with an amazing assortment of dining options to satisfy every palate and budget. After dark, young and hip club-goers descend on River North for its vibrant nightlife.

Running along North Michigan Avenue, from the Chicago River to Lake Shore Drive, Magnificent Mile is the heart of the city’s shopping district. 450 stores stand alongside historic hotels and landmarks including the Water Tower – one of the few structures to survive the Great Chicago Fire of 1871.

Amid the skyscrapers of the central business district you'll find The Loop. This is the city’s famed Theatre District, which includes venues such as the Cadillac Palace Theatre, James M Nederlander Theatre, CIBC Theatre and the Chicago Theatre, with its iconic glittering marquee.

Within easy walking distance of downtown, the South Loop is a quieter residential area bordered by gorgeous lakeshore parks, the Chicago River, Chinatown, some top museums and McCormick Place. Shop for books in historic Printers Row, and sample fantastic food, from white-tablecloth artistry to snappy hot dogs. When evening comes, slip into one of the many jumping joints in this long-time hub for jazz, blues and soul.

The Gold Coast is one of Chicago’s most affluent neighbourhoods, where new mansions continue to spring up alongside the grand residences built by Chicago’s 19th Century elite. It now includes the Astor Street historic district’s beautiful brownstones. Go people watching and celebrity spotting among the trendy bars and clubs around Rush and Division.

Streeterville is a neighbourhood made up of luxurious high-rise apartment buildings, internationally renowned restaurants, popular attractions like Navy Pier and 360 Chicago, and the Magnificent Mile. Its origins involve colourful eccentric George Wellington ‘Cap’ Streeter, who laid claim to this patch of prime lakefront around his shipwrecked steamboat. Numerous gunfights with police and court battles led to his eventual eviction.