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Chicago holidays offer the chance to explore a city that echoes with the sonance of jazz and blues; a city that boasts the perfect combination of culture and adventure. Dip your toes in the water of Lake Michigan at one of 26 free beaches, while Chicago’s impressive skyline towers behind you. 

There’s a reason why Frank Sinatra couldn’t help but sing about this city. It buzzes with fascinating stories and its people with passion and the kind of generosity that the Midwest is famed for. With so much art, sports, shopping, music and waterfront activities, there’s something here to delight everyone. Chicago is particularly famous for its architecture and it’s plain to see why. The city is full of exquisite buildings, just as captivating to the untrained eye as they are to the most informed enthusiast. Take a tour of Chicago and appreciate its breathtaking skyline from ground level, visiting the likes of Millenium Park and Museum Campus along the way. For an even more breathtaking view, head to the Magnificent Mile and scale the iconic John Hancock Building up to the 360 Chicago Observation Deck and gaze out over the sprawling city and see the expanse of Lake Michigan. 

Chicago: A City of Music 

In a city so famed for its jazz and blues, the streets aren’t short of restaurants, breweries and bars that welcome you in with the sweet sound of a saxophone. Spend a relaxed night at Green Mill Cocktail Lounge, a friendly but sophisticated bar where musicians, so in love with the music, often play on until the early hours of the morning. 

As the city sits at the start of Route 66, a Chicago holiday makes for a great starting points for multi centre holidays. Stop off in other iconic destinations, including St Louis, Las Vegas and the Grand Canyon National Park.

Destination Highlights

  • Take a walk around Millennium Park, 25 acres of green space with incredible public art
  • See a show or hit the shops at Navy Pier
  • Visit Museum Campus, a park that’s home to the Adler Planetarium, the Shedd Aquarium and the Field Museum of Natural History
  • Marvel at Chicago’s infamous architecture

Great sample itineraries

Browse our selection of sample itineraries for your Chicago holiday or give our Destination Specialists a call and we’ll put together a holiday that's uniquely tailored to you.

a bridge over a body of water with a city in the background

Washington Dc Multi Centre Holidays

  • 7 Days
  • Guide Price £1,899 PP
Washington DC and Chicago combine to give the perfect mix of city sights, history and culture. Arrive in awe-inspiring Washington...
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Adventure holidays
Route 66

Route 66 Road Trip Holiday

  • 16 Days
  • Guide Price £2,399 PP
Our Historic Route 66 Self Drive is a journey you’ll never forget, beginning in Chicago and ending at the Santa...
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City holidays
Eaglerider road trip along Route 66

Route 66 Guided Motorcycle Tour

  • 15 Days
  • Guide Price £5,299 PP
The EagleRider Route 66 Guided Motorcycle Tour is a journey to the American interior on the world’s most famous road...
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Iconic journeys

Explore Chicago

Time Zone

GMT -6 hours

Flight Time

Approx 8 hours; direct flights from the UK are available


USD - US Dollar

Visa Information

Endure you have a valid ESTA prior to travel



Health Info

No vaccinations required

You won't be lost for things to do in Chicago, with attractions and tours found across the city. The only question you'll need to ask yourself is what shall we do first.

Tfeature Chicago

360 Chicago

Offering the best view of across the city from 1000 feet above the magnificent mile, we love the TILT for it's jaw dropping experience of being tilted over the Chicago Skyline. This is an attraction you don't want to miss.

Mill Park Chicago

Millennium Park

A year round attraction, if your travelling in winter head to the park for some ice skating. If you're travelling during the summer months, find dozens of free events to attended from films in the park to outdoor concerts. With so much to be explored make sure you head to the park.

a group of people walking in a city

Magnificent Mile

Hit the shops on the Magnificent Mile for an adventure in itself, Michigan Avenue not only has some great shopping but also has great restaurants, entertainment and plenty of history. Along the Magnificent Mile you will find three malls and many high end shops. If you are looking for bargain we recommended heading to Nordstorm Rack.

Navy Pier Chicago

Navy Pier

Navy Pier is the place to go for rides, entertainment, shopping, dining and nightlife. Children will love a ride on the Ferris Wheel and musical carousel before visiting the Children museum. For the adults from the Pier you'll be able to join a tour boat or a dining cruise ship.

Chicago Tours

Discover Chicago from the river

Take a guided river boat cruise, this is the best way not only to see the amazing architecture of Chicago but to learn about the history of the city. For something a little more thrilling join a guided kayak tour and paddle your way through the heart of downtown on the famous Chicago River.

Route 66

The start of Route 66

Chicago is the place most people start the iconic Route 66 road trip. Almost 2,500 miles of stateside scenery, this journey should be on everyone's bucket list. There are many ways to take this journey from escorted tour in a coach to on the back of a Harley Davidson, to driving it yourself.

Isla, Destination Executive

"If your Chicago holiday lines up with St. Patrick’s Day, make sure to be down by the river when it is turned green – it’s quite a sight."

Destination Executive
a woman wearing glasses and smiling at the camera

"Take a dinner cruise on Lake Michigan. It’s the perfect way to take in Chicago's famous skyline and you get to enjoy a delicious meal too." 

Commercial Executive

Events & Festivals

From street festivals to open-air concerts, Chicago puts on one hell of a show. The summer season sees a whole host of events and festivals that are well worth a visit. 

Taste Of Chicago

Taste of Chicago is an outdoor festival that’s been held in Grant Park every summer since 1980, usually in July. Visit the festival and you’ll get to sample some truly incredible food, bringing together all the tastes of the city, as well as amazing live music from local acts and some big-name artists. 

Local Cuisine

Chicago’s culinary landscape is incredibly vibrant and diverse so, whether you’re enjoying street food or a Michelin 3-star dinner, Chicago’s food is certainly something to write home about. 

Chicago’s Deep Dish Pizza

This is one you simply cannot miss on a trip to Chicago. It’s part pizza, part pie, and fully delicious. Though there are many imitations around the world, nowhere can make this iconic dish quite like Chicago. 

Italian Beef Sandwiches

Chicago’s Italian immigrants first created this famous sandwich during the Great Depression and it’s been a Chicagan delicacy ever since. The classic Italian Beef Sandwich consists of thinly sliced and well seasoned roasted beef dipped in gravy, served on an Italian roll and topped with sweet peppers or spicy Giardiniera.

Pizza Puff

This slightly unusual take on pizza consists of a deep fried dough pocket, filled with everything and anything you’d expect to find on top of a pizza: cheese, tomato sauce, vegetables and meats. You’ll find pizza puffs at many fast food eateries and street food trucks in Chicago.

Chicago Hot Dog

While many places all over the world serve hot dogs, like many of its cuisines, Chicago’s hot dog is made in a particular way. The sausage is an all-beef frankfurter and is served in a poppy seed bun and topped with yellow mustard, onion, dill pickle, pickle relish, tomato, pickled peppers and celery salt.

Types of Chicago holidays

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