USA Holidays

Expert Opinion Our Expert
Andrea Selig

"The third largest city in the USA with a buzzing small scale New York vibe. It boasts the starting point of historic Route 66, harbours a passion for sport and centres around Lake Michigan. You won’t be short of things to do here!"


Chicago is aptly named the Windy City due to its location on Lake Michigan. The city is most famous for Baseball, Blues and Al Capone. However, past visitors to the US will most likely remember Chicago from rushing through terminals for connecting flights in O’Hare Airport, which is the second busiest airport in the world. Time to step out of the airport and go to see a baseball game or some blues music!

The best way to travel around the city is on the elevated train which circles the commercial centre, giving the area the name ‘Chicago Loop’. The Magnificent Mile (or ‘Mag Mile’ to locals), stretching along Michigan Avenue from the Chicago River to Oak Street, is a shopper’s paradise. High end shops like Neiman Marcus, Saks, Norstrom and Bloomingdales are scattered throughout the area, as well as boutiques and 5* hotels and restaurants. If you have the time, take in a show at The Landmark Auditorium and Chicago Theatre, or find Macy’s at the Water Tower Place Shopping Mall.

Just north of the Chicago River, a few blocks from the ‘Mag Mile’, is River North, home to an eclectic mix of swanky galleries, trendy cafes, and themed restaurants. For something a little less expensive the tree-lined Fullerton Avenue, with its brownstone buildings, offers a variety of better value bars and restaurants. If you are looking for a local feel, head to Lincoln Park, one of the cities more gentrified areas.

The Lake Shore Drive runs adjacent to a large portion of Chicago's lakefront. Parks along the waterfront include Lincoln, Grant, Burnham and Jackson Park, and there are also 29 public beaches to be found along the shore!

For accommodation options in Chicago please call us. We can book any hotel in the city and can advise you of the best current rates and offers.

Price Guide

A 1 night Chicago add-on staying at the 4 star Hotel Allegro starts from just £95 prpn.

Please click here to request a quotation, or call us for more information and advice on 01273 224 060.