Chicago holidays
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.
Our cheapest holidays to Chicago
Be blown away by the Windy City
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.
Carefully selected Chicago holidays
Best hotels in Chicago for all types of traveller
The Hilton Chicago, near Millennium Park, has an indoor pool and hot tub, plus an Irish-themed pub. Meanwhile, Swissotel Chicago, close to both the Magnificent Mile and the Chicago River, offers two restaurants and a fitness centre with panoramic views. The Sheraton Grand Chicago, within easy walking distance of Navy Pier and the Mag Mile, has a swimming pool, a fitness centre and a steakhouse.
Stay in the Loop, literally, at the Hyatt Regency Chicago, which offers four restaurants and access to an underground shopping centre. Palmer House - A Hilton Hotel is a landmark property near the Theatre District. Dine under the historic lobby mural or visit the charming rooftop garden. The stylish Nobu Hotel blends in perfectly with its trendy West Loop setting, featuring industrial-style rooms, the signature Nobu Restaurant and a swanky rooftop lounge. Voted one of Chicago’s best hotels by Conde Nast, the Fairmont Chicago Millennium Park offers guests a soothing spa and signature cocktails. The Millennium Knickerbocker on the Mag Mile offers 1920s opulence, a Crystal Ballroom and a stylish martini bar. Omni Chicago is the only all-suite hotel on Michigan Avenue. Its 347 suites are some of the most lavish in the city. Staypineapple, An Iconic Hotel, The Loop Chicago, a boutique 4-star downtown hotel set in a historic building dating from 1895, offers a much-loved restaurant and complimentary bike hire.
Fly-drive holidays
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Chicago holiday FAQs
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
Why choose British Airways Holidays?
The British Airways experience is more than a flight.
We’re one of the UK’s largest holiday companies offering carefully chosen hotels and resorts in the most amazing places, and car hire with no hidden extras. Our access to the extensive British Airways global network and oneworld® alliance puts us in a unique position to create holiday packages with convenient flights across the globe. From start to finish consider your holiday taken care of.
Low deposits
Secure your holiday with a low deposit and spread the cost with flexible payments.
Baggage allowance
All of our holiday packages include a generous checked baggage allowance.
24-hour helpline
We have a dedicated 24-hour holiday helpline if you need to contact us while you're away.
The British Airways Club
Pay for your holiday with Avios, collect Avios and now, earn tier points too.
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Terms and Conditions
- Flight only prices are updated every 24 hours and are accurate when published. Flights at these prices are limited and may sell out quickly.
- Package holiday prices (flight + hotel or flight + car) prices are updated every 24 to 48 hours and are accurate when published and may vary upon reaching subsequent pages. Availability may be extremely limited particularly during peak periods.
- Return fares displayed are the lowest adult return prices in the cabin specified including taxes, fees and carrier charges, based on a 7-day return journey.
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- One-way fares displayed are the lowest adult prices in the cabin specified including taxes, fees and carrier charges available in this period.
- Package holiday prices (flight + hotel and flight + car) shown are in GBP per person based on 2 adults sharing one room or one car and prices include taxes, fees and carrier charges unless otherwise specified. Flight + car prices based on drivers aged 30-70 years.
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