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Visit Chicago


The 'windy city' of Chicago got its nickname from its unique politics, not the weather, so you can expect a laid back city built for all seasons, with world-class museums, miles of lakefront vistas, award-winning restaurants and luxury hotels. The 'Magnificent Mile' of Michigan Avenue has plenty to keep you entertained with lots of shops, as will the 250 local designers to be found in neighbourhood boutiques.

As the home of the legendary blues, expect free downtown and neighbourhood festivals with some of the world's best musicians. Chicago is the city where the skyscraper was born and you can take a tour to discover the architecture of Chicago's buildings and historical hotels or take advantage of plenty of free tourist attractions.

Top itineraries in Chicago

Historic Route 66 – Great American Road Trip

19-day tailor-made self-drive from £4,135 pp incl. flights

Celebrating its 90th year, Route 66 is America’s most celebrated highway; one that’s inspired countless films, books and songs, from Jack Kerouac’s On the Road to Woody Guthrie’s 'The Ballad of Tom Joad' and Bobby Troup’s classic '(Get Your Kicks On) Route 66'.

Chicago City Breaks

Tailor-made city break

Under nine hours from London and with superb sightseeing, shopping, entertainment and dining, Chicago, the so-called "windy city" on the shores of spectacular Lake Michigan, is fast becoming one of the USA's favourite short-break destinations.

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Top places to stay in Chicago

Chicago Millennium - The Knickerbocker, Illinois

Contemporary hotel

The Millennium Knickerbocker Hotel offers sleek and stylish accommodation in a great location, at the start of the Magnificent Mile with its endless shopping, dining and entertainment. Attractions such as the Museum of Contemporary Art, Art Institute of Chicago and 360 Chicago (formerly the John Han

The Thompson, Chicago

Contemporary hotel

This boutique hotel is set in one of Chicago’s hippest neighbourhoods, having won several Condé Nast awards.

The Peninsula, Chicago

Designer hotel

One of the city’s best-regarded hotels, the Peninsula has consistently been awarded the Forbes Five Star and AAA Five Diamond awards year on year.

The Burnham, Chicago

Designer hotel

Built in 1895, this landmark hotel was termed one of the city’s first skyscrapers. Today, you’ll find the historic exterior complemented by contemporary, designer interiors.

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Meet our Chicago experts

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Why book with Wexas Travel?

At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

Contact one of our consultants on 020 7590 0636 to discuss how we can tailor your holiday.

Learn why Wexas is the leader in creating luxury holidays. What is tailor-made travel?

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Let our travel specialists curate the perfect holiday:

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Every step of the way

Every step of the way

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