101 USA Holidays

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Mike Gerrard Donna Dailey
Award-winning travel writers Mike Gerrard and Donna Dailey.

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Chicago city breaks

Mike & Donna's verdict:

We’ve spent a lot of time in Chicago and still haven’t done everything we want to do. Its skyscrapers are stunning from the outside, and going to their top decks is not for the nervous. We’ve had the best pizza ever, admired the art and science museums, found the friendliest people and had fun every day. We love Chicago. Everyone loves Chicago.

Recommended tour operator: American Sky

Chicago's famous clockChicago music scene

American Sky says

Phew! Quite simply, a short break in Chicago will leave you wanting more.

From the jaw-dropping lakefront skyline and cultural scene to the shopping, restaurants and galleries – and the jazz and blues clubs – the Windy City will blow you away.

We would kick off a weekend in Chicago with a ride to the top of Willis Tower (formerly Sears Tower) for a bird’s eye from the Skydeck. Then, explore it by bus, by boat, on a bicycle, by Segway and on foot as you discover the distinct neighbourhoods.

Some of our favourite spots are the Ukrainian Village, trendy Boystown, Lincoln Park (home to a zoo and even a lakeside beach), the Millennium Park and Navy Pier with its giant Ferris wheel, Chicago Children’s Museum, live music and a lot more.

If you like the craic, celebrate St Patrick’s Day in Chicago – there’s a rich Irish cultural seam running through the city and the celebrations are immense.

Chicago is a magnet for foodies with an impressive restaurant scene. The fine-dining scene is stuffed with award-winning chefs and you can enjoy diverse international cuisines in Little Italy, Greektown and Chinatown, Pilsen (for Mexican food), Andersonville (for Swedish delis) and Hyde Park for soul food.

The chic boutiques and designer labels can be found on The Magnificent Mile (a section of Michigan Avenue) plus department stores such as Barney’s, Saks Fifth Avenue, Bloomingdale’s and Macys. The Chicago Premier Outlets in Aurora are worth a visit for some bargain-hunting and there’s discount shopping too at Gurnee Mills. Check out these discount vouchers.

In Chicago, we have selected a range of hotels to suit all budgets. They include The Langham Chicago, a luxury hotel in the heart of the city;  on The Magnificent Mile, the lakeside Fairmont Chicago and the Inns of Chicago, half a block from the Magnificent Mile.

Check out our full range of city breaks in Chicago.

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