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City breaks to Chicago

Emerging in a high jagged silhouette from the shores of Lake Michigan, Chicago's skyline is a wonderful sight to behold.

The biggest city in the State of Illinois, Chicago needs little introduction as one of America's most famous midwest landmarks. Known affectionately as the Windy City, Chi-town and even, Second City, Chicago is hugely popular with visitors and no wonder as it is a destination with a vast number of attractions. 


The city was a hotbed of gansgsters in the 1920's with Al Capone as it's most infamous resident and, during the Prohibition era, Chicago boasted 1,000's of dangerous gangs. Today, the city is far too busy with its sporting heroes from the Chicago Bears, Cubs, White Sox et al to worry about the flaky past. Some of New England's most talented architects are responsible for an amazing array of buildings including the Wrigley Building, John Hancock centre, Willis Tower (formerly Sears Tower) and Trump Tower and, if you travel to the suburb of Oak Park, you can visit the home of the renowned architect, Frank Lloyd Wright.


A must see on any vistor's itinerary is a trip to Navy Pier. A pure pleasure place, Navy Pier skirts the lake shore and offers great diversion for all the family. Don't forget to visit Lincoln Park Zoo either to see the animals in a great naturalised environment.


If you enjoy art, Chicago will not disappoint. The Art Institute of Chicago is a superb gallery (2nd only to the Metropolitan Museum of Art in New York City) where a world class international and national collection or art is displayed. Music lovers will be in heaven with the tradition of blues, jazz and hip hop and, easily accessible, hugely atmospheric club are dotted all over the city.


Chicago also has a great foodie culture and is proud home to the origins of the deep-pan pizza. Famous also for it's own type of hot-dog, food has embraced many different ethnic backgrounds and has many regional specialities.


A trip to Chicago is a pleasure to be savoured and, once tasted, you will come back for more!

Holidays in Chicago

Chicago Millennium Knickerbocker Hotel - Chicago
Millennium Knickerbocker Hotel
31 August
3 nights
Room Only
Flights + accom.
Chicago Warwick Allerton Hotel  - Chicago
Warwick Allerton Hotel
27 September
3 nights
Room Only
Flights + accom.
Chicago The Ambassador Chicago - Chicago
The Ambassador Chicago
26 October
3 nights
Room Only
Flights + accom.
Chicago Fairmont Chicago - Chicago
Fairmont Chicago
08 November
3 nights
Room Only
Flights + accom.
Chicago Le Meridian Essex Chicago - Chicago
Le Meridian Essex Chicago
19 December
3 nights
Room Only
Flights + accom.
Chicago Arlo Chicago - Chicago
Arlo Chicago
31 January
3 nights
Room Only
Flights + accom.
Chicago  Hyatt Place Chicago Medical/University District - Chicago
Hyatt Place Chicago Medical/University District
28 February
3 nights
Bed & Breakfast
Flights + accom.
Chicago Hyatt Regency Chicago - Chicago
Hyatt Regency Chicago
01 March
3 nights
Room Only
Flights + accom.

Did You Know...?

Did you know?

You can see four states from the Skydeck of the Willis Tower.

Did you know?

Chicago is the third-largest city in the U.S.

Did you know?

Chicago is home to 26 miles of lakefront with 25 beaches.

Top Reasons to Visit Chicago

  • Stunning City Spots

  • Parks & Museums

  • Unique Things to Do

Stunning City Spots

Navy Pier

This over 1,000-metre-long pier on the shoreline of Lake Michigan is a beautiful place to explore. Packed with parks, gardens, shops, restaurants, family attractions, and special exhibits, it's one of Chicago's top places to go. 


Magnificent Mile

Chicago's main commercial district, the Magnificent Mile is lined with high-end shops, top-notch eateries, and luxury hotels. The mile includes the strip of North Michigan Avenue running between Chicago River and Oak Street.

Cloud Gate

Cloud Gate is the true name of Chicago’s famous “Bean” sculpture. Located in Millennium Park, Cloud Gate is one of the most famous sights in Chicago and a must-see in the city. There’s nothing quite like this enormous sculpture, which is probably what makes it among the city’s most photographed spots. 


Buckingham Fountain

Located in the centre of Grant Park, Buckingham Fountain is a major landmark in Chicago and one of the largest fountains in the world. It was dedicated in 1927 and inspired by the Latona Fountain outside the Palace of Versailles.

Parks & Museums

Millennium Park

A beautiful public park in downtown Chicago, the site was built to celebrate the third millennium and remains one of Chicago’s most visited tourist attractions. Located near the shoreline of Lake Michigan, the park is also the site for the city’s annual Christmas tree lighting. 


Grant Park

Located in the Loop area community of the city, Grant Park encompasses a variety of other attractions, like the Museum Campus. It borders Lake Michigan and includes performance venues, public art, sporting facilities, and gardens. Popularly called “Chicago’s Front Yard,” Grant Park hosts a number of popular events every year. 

The Art Institute of Chicago

A world-renowned art museum, the Art Institute of Chicago is one of the largest and oldest art museums in the United States. It hosts a permanent collection of around 300,000 works of art, and welcomes 1.5million visitors each year!


The Museum of Science and Industry, Chicago

A fun, interactive science museum located in Jackson Park, the Museum of Science and Industry is a great spot to check out some fascinating exhibits. With attractions like a full size model of a coal mine or a German submarine U-505 captured during World War II, this museum has plenty to entertain people of all ages.

Unique Things to Do

Skydeck, Willis Tower

Formerly known as the Sears Tower, the Willis Tower is the tallest building in Chicago and one of the tallest buildings in the country. The Skydeck is located on the 103rd floor of the Willis Tower, offering views of four different states from clear glass observation boxes.


Shedd Aquarium

Located on Lake Michigan within the Museum Campus, Shedd Aquarium is an enormous indoor aquarium featuring 32,000 incredible sea animals. It often ranks as the most visited aquarium in the United States and the most popular cultural attraction in Chicago.

Chicago Riverwalk

Within downtown chicago, the Riverwalk is an open, scenic pedestrian walkway along the Chicago River. The walkway extends from Lake Shore Drive to Lake Street in the centre of the city. A leisurely stroll on the Riverwalk is a great way to see Chicago!


Lakefront Trail

Similarly, the Chicago Lakefront Trail extends along the western shore of Lake Michigan. The 18.5-mile strip is perfect for walking, cycling, jogging, or skateboarding, and is an excellent vantage point to enjoy views of the expansive lake.

Chicago Airport Transfers & Weather

Airport: Chicago O'Hare International Airport (ORD)


The Blue Line runs 24/7 and connects the Airport to downtown Chicago. The journey takes about 45 minutes and costs $5 per ticket.


A taxi from the Airport to downtown Chicago would take about 35 minutes and cost approximately $50. 

* Prices and times for transport from the airport are subject to change

Average temperature

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