There's no need to spend a lot of money as a tourist in Chicago. Some of the city's best sights are right there in public--Gothic architecture, a boardwalk packed with people, parks upon parks and a lakefront so big it looks like an ocean. And that's just the free stuff; for $10 to $30 you can gain admission to some of Chicago's best entertainment and cultural venues.
Chicago's museums charge admission, but sometimes they host free or reduced-price days. If you want to visit several, such as the Field Museum, the John G. Shedd Aquarium, the Museum of Science and Industry and the Adler Planetarium, buy a CityPass. The CityPass saves you money on admission to these sights as well as the Willis (formerly Sears) Tower and John Hancock Building. As of July 2009, individual admission to each location averaged $20 to $30, but a CityPass valid for five admissions and cost $69.
The library is named after a congressman who became Chicago's first black mayor and died in office in 1987. The library pays tribute to his spirit and accomplishments in a permanent exhibit. The library also holds extensive collections of music, including Chicago blues, has a large garden room and holds traveling exhibits. Admission is free.
Grant Park is perfect for an afternoon walk within sight of Lake Michigan. In the summertime, you might be treated to some free music. Grant Park also is the site for many music festivals and cultural events, such as The Taste of Chicago, that charge admission, so plan accordingly.
Chicago has a proud tradition of theater, from off-Broadway shows to small productions. An inexpensive local favorite is the Neo-Futurarium, whose signature production is a nighttime, for-adults show in which the ensemble performs 30 short plays in 60 minutes in an order selected by the audience. These plays are sometimes funny, sometimes abrasive, sometimes somber and sometimes just weird, but they are all performed with heart and honesty. Admission is part of the fun: it's a small flat fee plus the roll of a die. The Neo-Futurarium is at 5153 N. Ashland Ave.
This downtown park opened in July 2004 and was developed as a marvel of modern architecture and design. Millennium Park hosts many cultural events, and even when nothing's going on, there are fountains, sculptures, gardens and the Jay Pritzker Pavilion, an outdoor music venue. Audio tours are available for download on the Millennium Park website.
Chicago had a building boom in the 1930s, when Gothic architecture was the style of the day. This left the city with a collection of handsome business buildings and churches. The Tribune Tower at 435 N. Michigan Ave. is one such building. The building's large ground-level windows allow passersby to stop and watch a live broadcast on WGN radio.
But there's more to Chicago landmarks than Gothic buildings; the city has identified the most popular, designed self-guided tours and posted the maps on the city website.
Located on the north end of the lakefront and marked by a giant Ferris wheel, Navy Pier is a boardwalk and collection of shops, bars and restaurants. Admission is free, and the people-watching is spectacular. Food selections include dog-and-burger stand fare, which is a bit less expensive than the sit-down restaurant options.
No matter what its proper name is (it was renamed Willis Tower in July 2009) people in Chicago will always call this behemoth building the Sears Tower. It is downtown at 233 S. Wacker Dr., and it stands 1,450 feet, making it the tallest building in North America. Tourists can ride an elevator to the top and look out the windows for a stunning view of the greater Chicago area.
Buddy Guy's Legends opened in 1989, and though it's still a bit new and frankly a bit clean for a blues club, it is a destination for blues lovers. The club is at 754 S. Wabash Ave. Admission for headlining shows falls in the $10 to $20 range, but the club often has free acoustic opening acts during the early evening.
A local favorite is the Elbo Room, 2871 N. Lincoln Ave. This small basement nightclub hosts local and touring acts from every genre, seven nights a week. Admission usually is $10 to $15.
Chicago is at its best during the summer, and part of the reason is that the city is home to two baseball rivals: the Chicago Cubs of the North Side and the Chicago White Sox of the South Side. The Cubs play at Wrigley Field, 1060 W. Addison St., and many home games are played during the day (a tradition; Wrigley Field did not get stadium lights until 1988). The White Sox play at U.S. Cellular Field, 333 W. 35th St.
Ticket prices generally hinge on how well the teams are doing. Weeknight admission is generally cheaper, and in some cases under $10, but be prepared to sit high up.