Chicago, Illinois has a variety of exciting attractions. For this reason, when planning your vacation, it behooves you to set up a detailed Chicago itinerary. Our suggested itineraries Chicago are dependent upon how many days you plan to stay.

Suggested itineraries for Chicago

1-3 Days

Since downtown Chicago is relatively compact, if you only have one day, you probably want to stay in this area. The Sears Tower should definitely be part of this one day Chicago itineraries. At 1,450 and 110 stories high, the Sears Tower is the tallest building in North America and the third tallest building in the world. The Hancock Observatory provides a wonderful view of the city, as well as a variety of interesting exhibits. The 1869 Water Tower, which survived the 1871 fire, is a Chicago landmark that should be included in the one day itinerary.

You also have a few choices for evening entertainment. If you like musicals and comedies, check out the Apollo Theatre, located in the Lincoln Park Theatre District. Are you a fan of Gilbert and Sullivan? Take in a performance by the world-renowned Chicago Lyric Opera Company. located in the Civic Opera House.

4-7 Days

Once you get your bearings on the first day of your suggested itineraries Chicago, it's time to venture out and explore the rest of the city. A visit to the city's great museums is an essential part of our Chicago suggested itineraries. The Field Museum of Natural History has some exciting exhibits that include a recreation of ancient Egyptian life, as well as the largest Tyrannosaurus Rex fossil ever discovered.

The Navy Pier is another popular attraction that is part of our extended Chicago suggested itineraries. This is a particularly fun place to visit if you are taking a Chicago family vacation. Kids can enjoy a variety of rides and attractions, which include the popular Build a Bear workshop. They get to make their own stuff animal, give it a name and a birth certificate, and take it home! At night, be sure to visit Joe's Be-Bop Café and Jazz Emporium. It is considered to be one of the best jazz clubs in town. If you like cruising, from Navy Pier, Shoreline Sightseeing offers half-hour cruises on Lake Michigan and architectural cruises along the Chicago River.

If you are a baseball fan a visit to Wrigley Field is another part of our two-day suggested Chicago itinerary. Wrigley Field is the second oldest major league stadium. It is home to the Chicago Cubs.

If your tastes run more towards art than baseball, be sure to check out the Chicago Picasso Statue at the Richard J. Daly Center on Washington Street. This unpainted, three-dimensional, cubist sculpture stands 50 feet tall. It weighs 162 tons, and is made of Corrosive Tensile steel, which is the same material used to build the Daley Center. The Chicago Picasso was originally rust colored. However, the sculpture now has a darkish gray patina that matches the patina of the Daley Center building behind it.

7 + Days

If you are lucky enough to have three days planned for your Chicago itineraries, you can venture outside of downtown and spend some time on the north side of the city. Those of you on Chicago family vacations will enjoy the Lincoln Park Zoo, which is one of the few zoos in the country that actually has free admission! If you are an Oprah fan, you can try to get a seat in the audience, but don't expect miracles. Reservations fill up months in advance. You can also enjoy shopping along Armitage Avenue, where you will find a number of chic and interesting boutiques. At night, be sure to visit the famous Second City Improv Comedy.

If you're having trouble choosing between the attractions we have listed for our suggested Chicago itineraries, be sure to read the detailed descriptions of the Sears Tower, the Field Museum and other places of interest in Chicago.