Chicago Holidays
Things to see and do
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The Mother Road Festival, Route 66 - Illinois
Each September, the International Route 66 Mother Road Festival brings the streets of Springfield alive with the rumble of engines from hot cars, cool trucks, vintage motorcycles, street rods, customs and everything in between.
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Chicago Greeters - A great introduction to the Windy City
Experience Chicago's unique charm, captivating sights and world-class attractions with a local!
View Chicago Greeters - A great introduction to the Windy City
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See Chicago With A Cop
Yes – you read that correctly! Since 1999, Off-duty (active and retired) Chicago Police officers have been giving visitors the inside track on Chicago.
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Navy Pier
Navy Pier is a 3,300-foot long pier along Chicago's Lake Michigan shoreline.
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Chicago's Skyscrapers
In 1885, the first steel-framed high-rise building rose in Chicago ushering in the skyscraper era. Today, Chicago's skyline is among the worlds tallest.
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Chicago Festivals
From May to September, the lakefront, Grant Park and various neighborhoods come alive with festivals nearly every weekend.
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Magnificent Mile
The Magnificent Mile is the portion of Michigan Avenue that serves as the main thoroughfare between Chicago's Loop business district and its Gold Coast - the wealthiest neighborhood in Chicago.
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"The Ledge" at the Willis Tower, Route 66 - Illinois
The Skydeck’s new ‘Ledge’ attraction is now open atop the Willis Tower! (formerly Sears Tower). Only for the brave!
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Shop America Tours
A Shop America shopping or cultural package is the perfect addition to your next city break or holiday.
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Al Capone and The Burnham Hotel
Sure, you’re heard of Al Capone. In the late 1920s and 1930s he ran organised crime rings in Chicago, moving about the city as quickly and mysteriously as a crate of bootlegged gin.
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