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Holidays in Chicago

The biggest city of the Great Lakes region, 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.

-6-23 °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.

Self Drive Holidays

Illinois Self Drive

Chicago | Springfield | Alton | La Salle | Peoria | Galena | Rockford

Hotel highlights
  • The Drake - Chicago - 2 nts, Comfort Suites - Illinois - Springfield 1 nt
  • Best Western Plus Parkway - 1nt - Alton, Comfort Suite - Peoria - 1 nt
  • Best Western Designer Inn & Suites - Galena - 1 nt, Hilton Garden Inn - Rockford - 1 nt
  • Car Hire, Flight LON-ORD

What is included?



Route 66

Chicago | Springfield | St. Louis | Springfield | Tulsa | Amarillo | Santa Fe | Albuquerque | Holebrook | Flagstaff | Las Vegas | Santa Monica

Hotel highlights
  • 14 days car hire included
  • Pick-up in Chicago & drop-off in Los Angeles
  • Flights included

What is included?



Recommended Hotels in Chicago

Essex Inn


Hotel highlights
  • Flights
  • Complimentary shuttle service runs along the Magnificent Mile
  • 3 blocks from the Loop business district and Lake Michigan

What is included?



Hotel Monaco


Hotel highlights
  • Flights
  • Chicago CityPASS
  • 14-story Chicago Loop hotel with hosted wine receptions

What is included?



The Peninsula


Hotel highlights
  • Flights
  • Located along the Magnificent Mile, this Chicago hotel is 5 minutes' walk from the Museum of Contemporary Art
  • A renowned afternoon tea serving champagne and chocolate

What is included?



The Magnificent Mile is one of Chicago’s best shopping areas, known for its upmarket department stores and trendy boutiques. You’ll find a number of historic buildings dotted around here, including the landmark Wrigley Building and the Chicago Water Tower. Nearby River North is a stylish spot known for its many art galleries, antique shops and ultra-chic cocktail bars. The Loop is at the centre of the downtown area, and features some of the city’s most iconic sights. The public sculptures of Millennium Park are a must-see, and the Art Institute of Chicago is home to famous works by the likes of Manet, Renoir, Picasso and van Gogh.

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 downtown area, hotels on the Magnificent Mile range from intimate boutique-style spots to some of the most luxurious in the city..

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.

The Loop is one of the most iconic parts of Chicago, located at the heart of the downtown area. Take in the sights of Millennium Park, including the ultra-modern Frank Gehry amphitheatre and the giant steel Cloud Gate. State Street is a shopper’s paradise, and the city’s renowned theatre scene can be found here too.

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.

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. One of the best family attractions in Chicago is the Shedd Aquarium, one of the largest indoor aquariums in the world with 8000 different species of aquatic creatures. 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. 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. Chicago is also famous for its delicious all-beef hot dogs, topped with tangy mustard, relish, pickles, onions and tomatoes. One of the best hot dog places in Chicago is Portillo’s on West Ontario Street. But whatever you do, don’t order one with ketchup – it’s a serious faux pas in these parts! Head northwest of the Loop to trendy Wicker Park to discover some of the city’s coolest dining spots.

For high-class department stores and designer shops, head to the Magnificent Mile. One of the biggest shopping districts in the city, 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 the Loop in the centre of the city. Here you’ll find stores full of designer gear at affordable prices.

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
  • Dedicated online customer service
  • Over 170 years of travel experience
  • Award winning travel company
  • Thousands of destinations worldwide


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

Tuck into an authentic Chicago deep-dish pizza and discover the city’s coolest dining spots.

Take the ride of your life in a tandem paraglide at Olu Deniz, drifting slowly onto the lush lagoon.


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.


Temperatures: -6-23 (°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. 



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 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.

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