Chicago holidays welcome you to a city full of both excitement and refinement – from soaring skyscrapers to down-to-earth pleasures.
This is a proud US destination where you can take a sightseeing cruise through the city or feel the wind in your hair out on Lake Michigan. Stroll through picturesque parks and dine in some of America’s best restaurants.
Take the family to a baseball game and get caught up in the drama of this sports-mad city, then catch your reflection in the famous giant Cloud Gate sculpture in Millennium Park.
Children will love the Shedd Aquarium – the city’s most visited attraction – while you can even spend a day at one of its beaches.
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Packed full of endless sightseeing opportunities and jaw-dropping city views, Chicago holiday packages make the perfect getaway for family adventures, honeymoons and city breaks.
One of Chicago’s most popular areas, the Magnificent Mile is the city’s main commercial district. It boasts a fantastic mix of theatres, live music, shopping outlets and brilliant restaurants.
Visit the Navy Pier and its 150-foot Ferris wheel, followed by 360 Chicago – a tilting glass lookout 1,000 feet up the John Hancock Building.
Tours of the city run on foot, by bus, boat and even Segway. There’s also an array of museums to discover, showcasing everything from dinosaur skeletons to exhibits mimicking tornado force winds.
Did you know Chicago has its own beaches? There aren’t many US cities where you can build a sandcastle in the shadow of a skyscraper, but Chicago is one of them.
Take a family sightseeing cruise on Lake Michigan to soak up the best views of the skyline. Chicago’s First Lady cruises deliver an in-depth look at its history and architecture.
Twilight trips are perfect for romantic holidays in Chicago or get up early for a Sunday morning yoga cruise.
If you’re looking to get active during your trip you can try kayaking, bodyboarding, jet skiing, scuba diving and parasailing out on the lake.
Chicago is proud of its heritage and preserves it perfectly. It boasts classical and modern art sculptures throughout the city, alongside intriguing places to visit such as the Chicago History Museum, Alder Planetarium and the Field Museum.
Gaze up at reconstructed dinosaur fossils and take a 3D T-Rex tour – perfect if you’re looking for things to do with the kids.
Find out about the fascinating local history, from the Great Chicago Fire of 1871 to the building of the Sears Tower. Meanwhile, you’ll pass monuments old and new across the city.
Possibly one of the most thrilling views you’ll experience in the whole of America is from the vertiginous Skydeck in Willis (formerly Sears) Tower, which is open 365 days a year.
Situated on the 103rd floor, it’s a knee-wobbling 1,353-feet off the ground. From the deck, you can see out over four states in every direction.
For the truly brave, there’s the glass-floored ledge if you want to feel like you’re floating in mid-air.
Chicago has dozens of buzzing markets, selling everything from freshly grown farm produce to treasured antiques. Immerse yourself in the culture and cuisine like a true local.
Grab a coffee and head down to Randolph Street Market to find what’s on offer at stalls selling vintage jewellery, furniture and clothing.
Visit the Chicago French Market for a taste of artisan food, with everything from dim sum to Belgian fries.
For bargains and more of an international flavour, Maxwell Street Market is renowned for its excellent street food – it’s open on Sundays.
The Lincoln Park area is a great location for families, thanks to its close proximity to the city’s many top museums, public green spaces and family friendly restaurants serving up Chicago classics.
Accommodation in the area includes the Hotel Lincoln and The Willows Hotel. Hilton Chicago is child-friendly, as is the Four Seasons Hotel Chicago, which is just a short walk from the Magnificent Mile and its numerous attractions.
The River North neighbourhood is a great area to take advantage of Chicago’s thriving nightlife on a city break. Some of the accommodation on offer boast their own steakhouses for an indulgent meal after a day exploring Chicago, or even a karaoke bar in the hotel for evening entertainment.
Hampton Inn & Suites is stylish and modern, with a pool and free Wi-Fi. It’s also close to plenty of revered restaurants and nightclubs for night owls.
Those seeking an unforgettable, upmarket experience will want the height of luxury. Consider the Ritz-Carlton Chicago for spectacular views over Lake Michigan, just a couple of blocks away from 360 Chicago and the Museum of Contemporary Art.
The Langham is another high-end choice in the River North area and ideal for a luxury holiday in Chicago. Enjoy access to a full-service spa and indoor pool, just a short walk from Millennium Park and Michigan Avenue.
The currency in Chicago is the US dollar (USD). There are plenty of ATMs around the city, while Chicago’s O’Hare International Airport (ORD) has foreign exchange kiosks. Credit cards are widely accepted.
Trains, buses and taxis run regularly from the airport to downtown and around the city. Local transit is known as ‘Chicago L’, with a system called Ventra used for payments – you can pick up a card at any station on the network.
The official language in Chicago is English. Around a third of local residents speak another language, with Spanish, Polish, Arabic and Chinese widely used.
US national holidays include Memorial Day (late May), Independence Day (4 July) and Labor Day (September). On these occasions, public events are common, and opening hours may differ.
Chicago is home to numerous Michelin-starred restaurants. There’s Alinea in Lincoln Park and Acadia in West Loop, together with more humble but equally famous spots like Gene and Jude’s for some of the best hotdogs around.
Families looking to enjoy a nice evening meal out should try Crosby’s Kitchen – where kids eat free at certain times. Couples wanting a romantic meal in the windy city can try Oriole in West Loop – it’s hidden down an alley and serves up inspired fare such as sturgeon with mussel escabeche and fennel.
Those hunting traditional fare might want to venture to the German-inspired Berghoff Restaurant, which dates back to 1870. Expect generous takes on European classics such as wiener schnitzel.
If you’re sightseeing and on the hunt for Instagram-friendly snaps, visit Chicago Water Tower and the neo-Gothic Tribune Tower for some truly iconic shots.
Venture to the sprawling Millennium Park. Here you’ll find art installations such as the famous Cloud Gate (nicknamed ‘The Bean’) – a giant, polished, stainless-steel oval – and Lurie Garden, a sculpted urban sanctuary.
There’s also opera, interactive garden games, science events for children and morning nature walks. When you want a break from all these activities, head to Garfield Park, where you’ll find playgrounds, a lagoon and paths for strolling and cycling.
Sporting traditions are at the heart of this city. Visit Wrigley Field to watch the Chicago Cubs and find out what the city's baseball obsessions are all about.
The whole spectacle, from taking your seats to ordering a hot dog, is part of the all-American experience.
You’ll get caught up in the jubilant atmosphere of the 41,000-seater stadium. Join in the ‘Seventh-Inning Stretch’ – a tradition where local celebrities lead the crowd in song.
For American football fans, grab a ticket in advance for Soldier Field, where you can watch the Chicago Bears play their NFL rivals.
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