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Holidays in Chicago

The biggest city of the Great Lakes region, and the third largest in the United States.  Chicago sits on more than 26 miles of uninterrupted lakefront, offering 15 miles of sandy beaches and hundreds of beautiful parks, all nestled within a skyline of architectural wonders. You’ll find world-renowned museums, theatre, nightlife and music of every style, and some of the best foodie hot spots in the States.

Chicago is known as a city of diverse neighborhoods, all with unique culinary, music, and shopping experiences to offer. The streets are wide, the buildings are tall, and it’s all easy to access via the city’s “L” public transit system, or 360 km of protected bike lanes. Chicago is known among many seasoned U.S. travelers as one of the friendliest, most aesthetically pleasing, and cleanest big cities in the States.  Spend a city break here, and you’ll wonder why you ever did a city break anywhere else.

-6-32 °C

Chicago experiences a continental climate with four distinct seasons.

8-9 hours

Fly to: The main airport in Chicago is O’Hare Airport (ORD), around 29km southeast of downtown Chicago.

Recommended Hotels in Chicago

Known as The Windy City, Chicago is a melting pot of authentic jazz clubs, unique museums and futuristic skylines. From stargazing at the Adler Planetarium, to enjoying views across the city on a cruise or helicopter ride, there’s something for everyone. Just don’t leave without ordering one of their world-famous deep dish pizzas.

The Loop is one of the most iconic parts of Chicago, located at the heart of the downtown area and named for the “L” train which does a loop around the city centre. Take in the sights of Millennium Park, including the ultra-modern Frank Gehry amphitheatre and the giant steel Cloud Gate. Catch a Broadway in Chicago show in the theatre district, or visit one of the finest and most expansive impressionist art collections in the world at the Art Institute of Chicago. State Street is a shopper’s paradise.

With a wealth of shops, restaurants and bars, Chicago’s Magnificent Mile is home to some of the city’s tallest buildings, such as the John Hancock Center and Trump International Hotel & Tower. Close to the Loop area, hotels on the Magnificent Mile range from intimate boutique-style spots to some of the most luxurious in the city.  Come for the Magnificent Mile Lights Parade in late November for a magical holiday season experience with the kids.

Bordering the Magnificent Mile, the area known as River North is the place to go for trendy bars and fine art galleries. The area’s abandoned factories and warehouses were taken over by artists and small businesses in the 70s and 80s, transforming it into one of the most cutting-edge spots in Chicago.

Directly to the east of the Loop, this neighborhood was historically home to very large warehouses.  It has since been converted in to a booming culinary scene.  If you’re a foodie you should explore West Loop first and check out the diverse offerings and award winning restaurants on Randolph Street and Fulton Market. While there, you can catch a musical performance at City Winery.  Bordering West Loop you’ll also find ethnic neighborhoods like Greek Town and Little Italy.

Chicago sits directly on Lake Michigan, a massive, brilliant aquamarine colored body of water, so large you cannot see across it.  The entirety of Chicago’s lakefront is preserved for the public to enjoy. The Lakefront trail itself does not boast any accommodations, however it spans the entire lakefront in Chicago for 30 Km and is the perfect way to explore this gem of park space as it leads you past the Museum campus, Navy Pier, 26 natural sand beaches, multiple parks, and beach side bars and cafés along the way.

Catch a glimpse of Chicago’s breathtaking skyline with a tour through the city on a boat along the Chicago River. Shopaholics will want to explore the many stores, malls and arcades dotted along the busy pavement of North Michigan Avenue – otherwise known as the ‘Magnificent Mile’. For splendid views, head to the top of one of Chicago’s iconic skyscrapers such as the John Hancock Center or the Willis Tower, one of the tallest buildings in the USA. Discover the city’s cutting-edge music scene at legendary hotspot, Metro, just north of Wrigley Field ballpark. Artists including Bob Dylan, James Brown and New Order have all graced Metro’s iconic stage.

One of Chicago’s many nicknames, “The Second City”, refers to Chicago rising from the ashes and undergoing a complete rebuild and re-design after 1871’s great Chicago Fire destroyed most of the city centre. Since the fire, Chicago had a second life, and became a booming metropolis, home to the world’s first skyscrapers.  Its skyline is adorned with everything from elegant and classic Art Deco, to the most cutting edge contemporary sky scraper designs, with every era in between. This can all be experienced via guided segway, bicycle, hop-on hop-off bus, river cruise, kayak, and even helicopter tours.

At the Field Museum of Natural History you’ll travel back to the time of the dinosaurs and explore an Egyptian tomb with a collection of ancient mummies. The Shedd Aquarium, one of the largest indoor aquariums in the world has 1,500 different species of aquatic creatures. The Museum of Science and Industry, one of the largest science museums in the world, has an abundance of interactive exhibits that will engross children in fun/learning for hours.  If you’re looking for things for kids to do in Chicago, don’t miss the Lincoln Park Zoo. One of the oldest zoos in the US, here you’ll see rare black rhinos, fluffy gibbons and cute red pandas, and it’s completely free.  Millennium Park, Maggie Daley Park next door, or Navy Pier are all free attractions guaranteed to entertain the kids for days.  Pick up a Chicago Citypass for great savings on VIP access to some of the city’s best attractions.

For a real taste of Chicago, try the city’s famous deep-dish pizza. A thick and hearty base is topped with sweet tomato sauce and creamy mozzarella, and whatever other toppings that might take your fancy. Head northwest of the Loop to trendy Wicker Park or West Loop to discover some of the city’s coolest dining spots.  Chicago has become known as one of the most diverse and critically acclaimed dining scene’s in the world. It doesn’t stop at food, there are over 70 craft breweries in Chicago, which has recently climbed the list as having more breweries than any other US city. 

For high-class department stores and designer shops, head to the Magnificent Mile. One of the biggest shopping districts in the city, and home to 460 stores.  It’s located on North Michigan Avenue close to some of the city’s most spectacular skyscrapers, so you can fit in a spot of sightseeing after an afternoon of shopping. On the north side of the city is Lincoln Park, a charming, tree-lined district of independent stores and sophisticated boutiques. If you love a bargain, one of the best places to visit in Chicago is State Street.  It is home to Macy’s Chicago, the second largest department store in the world, and you’ll find stores full of designer gear at affordable prices along the entire street.

Chicago has a robust and diverse music scene, and is particularly famous for its Jazz and Blues.  Buddy Guy’s Legends, The House of Blues, Kingston Mines, Winter’s Jazz Club, or the Green Mill are just a few of the many great venue’s showcasing this scene. If you’re in town in early June, check out Blues Fest or check out Jazz Fest in September.  Both festivals are located in Millennium Park and free to attend. Chicago is also the birthplace of electronic House Music, and home to the Chicago Symphony Orchestra, ranked one of the best Orchestra’s in the world.  In short, regardless of your taste in music, you can find it in Chicago.

Chicago is best for...

See some of the most famous paintings in the world at the Art Institute of Chicago.

Tuck into an authentic Chicago deep-dish pizza or discover Chicago’s diverse dining scene, often hailed as the best the States have to offer.

Walk State Street, home to Macy’s, the second largest department store in the world.  Explore The Magnificent Mile, home to 460 retailers and 275 restaurants.

Fast facts

Language: The language spoken in Chicago is English.

Currency: The currency used in Chicago is the American Dollar ($).

Local time: Chicago is 6 hours behind GMT/UK time.

Fly to: The main airport in Chicago is O’Hare Airport (ORD), around 29km southeast of downtown Chicago.

Flight time from UK: 8-9 hours

Tourist Information: Further Chicago tourist information can be found here.

Visa & Health: Before you travel click here for recommendations and advice on visas and health for your holiday to USA.

Weather and climate

Temperatures: -6-32 (°C) 

Chicago turns into a snowy winter wonderland during the colder months, with average temperatures falling below zero. Though it’s cold, this is a perfect time of year to visit the museums or enjoy some retail therapy. The city warms up in spring, with temperatures hovering in the mid-teens at the peak of the season. For the warmest weather, come in summer, or book your holiday for the beginning of autumn when the weather's still pleasant. 

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Getting around

By L Train: Chicago’s elevated ‘L’ trains serve 144 stations. They’re efficient, reliable and great if you’re on a budget.

By bus: For the best value, buy an Unlimited Ride Pass and you’ll have free use of Chicago’s buses for one, three or seven days.

By water taxi: A fun way to explore the city’s hotspots, particularly during the warm summer months.

By taxi: Cabs are convenient and plentiful throughout the city. Remember to tip your driver 15-20% of the total fare.


Foodie fun In July, indulge your senses at the Taste of Chicago, the world’s largest food festival. Three million visitors descend on Grant Park to taste the city’s diverse cuisine, from traditional deep-dish Chicago pizza to spicy African stews.

Summer sounds June features Chicago’s Blues Fest, the world’s largest blues festival. August is the time to rock out at Lollapalooza, one of the city’s biggest music festivals. Previous performers include Muse, Coldplay, Depeche Mode and Lady Gaga.

Winter festivities Get into the Christmas spirit with a trip to the Magnificent Mile Lights Festival at the end of November. Trees along North Michigan Avenue are illuminated with 1 million lights, and there’s also a colourful parade and a fireworks display to keep the little-ones amused.

Neighborhood festivals No matter when you visit during summer, this city of neighborhoods has something happening.  There are over 60 food and music festivals from May – September each year.

Why choose Thomas Cook

With hotels available to suit every person and every budget look no further than Thomas Cook for your getaway this year!

  • Thousands of hotels to choose from
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