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Day time view over Chicago

Compare the best Chicago city breaks

Admire the world's densest skyline on city breaks to Chicago, America's “Second City” and birthplace of the skyscraper. Alternatively, if soaring architecture fails to impress, tuck into a delicious deep-dish pizza and get a taste for the USA.

Why go?

TravelSupermarket compares prices on a range of Chicago city breaks. Get a cuppa, put your feet up and let us help you to find your next trip...

Chicago's skyscrapers rise abruptly from vast Lake Michigan with the Willis Tower peeping above the city skyline. The top attractions are clustered in The Loop, the historic centre circled by the Chicago River, while sandy beaches backed by a string of parks line the shore.

One thing is for certain on a city break to Chicago, you'll never be bored!

Located in the state of Illinois, next to the seemingly infinite waters of Lake Michigan, Chicago is one of America's biggest cities. It's got a great restaurant scene, sports-mad residents, more than a handful of excellent museums, family-friendly amenities, ice-skating in winter, water sports in summer and one of the most rocking live-music scenes in the US. This is a city in which people really live life to the full, and it's the perfect destination for a short break.

Flights arrive into Chicago O'Hare International Airport (ORD) - one of the busiest in the world. From here it's easy to get into the city to check in at your hotel. Many of the best tourist hotels are in the Loop, though visitors are also drawn to accommodation along the Magnificent Mile, Old Town, Lincoln Park and along the Gold Coast.

Wherever you stay, you can make use of the excellent network of public transportation, hail taxis or even hire a car in Chicago to see the main sights. Catch a game of baseball at Wrigley Field, go shopping on the Magnificent Mile, visit Grant Park, amble along the Chicago River Esplanade, drink in the views from the Skydeck of the Willis Tower... there's so much to see and do in Chicago.
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When to go?

Do you like snowy scenes or prefer to be kissed by the sun? Use our climate guide to find out when you should book Chicago short breaks...

Ever wondered why Chicago is called the Windy City? You are partly right - it's windy. The funnelling effect of the skyscrapers and the city's proximity to Lake Michigan culminates in gusts that can rattle through the streets at terrific speeds. That said, it's certainly not America's windiest city - in fact the nickname is thought to derive from an old dispute with nearby Cincinnati.

The lake breeze is a blessing during hot summer months, however, when daytime temperatures can push the mercury up to 35C. Spring and autumn are pleasant times to visit, as the weather is mild and calm. Winters are cold in Chicago. Night-time temperatures often drift below freezing, with many days lingering around 0C.

What's on?

There's no shortage of annual events in Chicago - a city that really swings to its own special beat...

St Patrick's Day Parade; March: Just like Boston and New York, Irish blood flows through many a vein in Chicago. At no time is this more wildly celebrated than on St Patrick's Day. If you're unsure as to Chicago's commitment to this city-wide Irish party - know that the river is turned green for the event! Do not miss out - book short breaks for travel in mid-March as early as possible.

Chicago Blues Festival; June: All kinds of music seep into the soul in Chicago's welcoming bars and clubs, though it's the blues that take centre stage in June. The city's jazz fest is also a hot event; it takes place in September.

Taste of Chicago; July: One of the biggest and best outdoor food festivals in the USA, lake-side Grant Park is the setting for this delectable selection of tasty bites. Music performances and family entertainment punctuates the non-stop eating experience.

What to do?

Whatever kind of holiday you're dreaming of, Chicago can turn your ideas into unforgettable reality...

Families: Ride the 150ft Ferris wheel on Navy Pier. The endless views will distract the kids from the array of carousels, swings and games lining the pier, but not for long!

Active types: Pedal the path behind Chicago's beaches. Pause to swim in the lake and see the skyline's warped reflection in the polished surface of Millennium Park's Cloud Gate sculpture.

Shopping: Splash your cash on the Magnificent Mile, a tree-lined avenue that's home to hundreds of shops. Flit between Tiffany & Co, Abercrombie & Fitch and Bloomingdale's, to name a few of the magnificent shops.