Compare All Inclusive Resorts & Hotels in Chicago

The largest city in the Midwest, Chicago, Illinois, is rich in cultural and historical curiosities from offbeat to outre. Home to the Field Museum of Natural History, Shedd Aquarium, Soldier Field, Comiskey Park and Wrigley Field, ‘The Windy City’ is peppered with architectural, musical, gastronomic and historical gems, as well as being known for its famous deep-dish pizza and Chicago-style hot dogs.

Key facts

The Chicago Transit Authority runs buses, the Elevated Train (or ‘The El’) and the subway system, which services the downtown Loop area via the transportation hub known as Union Station. The Near North Side, the Loop and Michigan Avenue, aka The Magnificent Mile, are popular destinations with ample hotels ranging from mid-level to ultra-high-end. Chicago also houses many of the world's tallest buildings--including former Number 1, the Willis Tower—and is served by two major airports: O'Hare International (CHI) and Midway International (MDW).

Hints and tips

From the Rush Street jazz clubs and hole-in-the-wall restaurants to the shopping of the Magnificent Mile and the carnival-midway feel of Navy Pier, Chicago offers plenty to keep visitors busy. History buffs with an interest in mobsters will appreciate the Prohibition-era historical monuments. Average temperatures range from lows of around 15 degrees Fahrenheit in the winter to highs of around 85 degrees in July and August.