Chicago Itineraries 3 Hours or Less

2-3 Hour Itineraries


Millennium Park and Grant Park
The ‘Front Lawn’ of Chicago, Millennium Park, and its larger neighbor, Grant Park are the ideal location for a leisurely stroll. Millennium Park, completed in 2004 through the work of the City of Chicago and its philanthropist community, contains 24.5 acres of post-modern architecture. The prominently featured Jay-Pritzker Pavilion was designed by world-renowned architect Frank Gehry and is touted as the most sophisticated outdoor concert venue in North America. Also highlighting the park are the popular Cloud Gate sculpture (known as ‘The Bean’ to locals), designed by Anish Kapoor, and the Crown Fountain, designed by Jaume Plensa. During the winter months, lace up your skates for a glide on the McCormick Tribune Plaza & Ice Rink, traditionally open from mid-November to mid-March. During summer evenings, be sure to attend one of the free concerts taking place in the Jay Pritzker Pavilion. Grant Park is located on the shore of Lake Michigan and features shaded walking trails, as well as tennis courts and ball diamonds for public use.

Navy Pier
Enjoy your precious family time at the famed Navy Pier, Chicago’s lakefront playground. The 1010m (3300ft) length of the Navy Pier certainly gives mention to the grandeur of its presence. The pier features many popular attractions for the family including the 46m (150ft) tall Ferris wheel, a musical carousel, which was designed exclusively for the Navy Pier, and the ‘Wave Swinger’. Guests of the Fairmont Chicago may also enjoy testing their skills on the ropes course or their short game skills on the 18-hole miniature golf course.
Navy Pier also features the Chicago Children’s Museum, with a galaxy of creative and educational activities, programs and exhibits for children exist. Both interactive and educational, the children’s museum is one of the most popular of its kind in the United States. Also located on Navy Pier is an IMAX movie theatre, the Chicago Shakespeare Theatre, the Amazing Chicago’s Funhouse Maze, the Smith Museum of Stained Glass Windows and numerous shops, gardens, parks, restaurants and convention space.

See the city by sky and by sea
The nickname, Windy City, was given to Chicago due to its constant and relentless winds. To best experience them, a trip to the top of the Hancock Observatory is necessary. The city’s third highest building, the Hancock Observatory allows you to feel the force of the wind at 1000ft from its screened in viewing area. 
Next, head south on Michigan Avenue for a 90-minute, narrated river cruise. As you experience the city from a new perspective, your guide will point out 50 architecturally significant sites.

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