Two Hours in Town
If you've got only a bit of time, go to a museum. Although you could spend days in any of the city's major museums, two hours will give you a quick taste of Chicago's cultural riches. Take a brisk walk around the Art Institute to see Grant Wood's American Gothic, Edward Hopper's Nighthawks, and one of the finest Impressionist collections in the country. Or check out the major dinosaur collection or the gorgeous Native American regalia at the Field Museum. Take a close look at the sharks at the Shedd Aquarium. If the weather's nice, stroll along the lakefront outside the Adler Planetarium —you'll see one of the nicest skyline views in the city. Wander down State Street or the Magnificent Mile or around Millennium Park. If you're hungry, indulge in one of Chicago's three famous culinary treats—deep-dish pizza (head to Pizzeria Due to avoid the lines at Giordano's, Gino's, and Pizzeria Uno); garden-style hot dogs; or Italian beef sandwiches. After dark? Hear some music at a local club. Catch some blues at Blues Chicago to get a taste of authentic Chicago.
Remember that many of the smaller museums are closed Monday.
A Perfect Afternoon
Do the zoo. Spend some time at the free Lincoln Park Zoo and Conservatory (the tropical plants will warm you up in winter), take a ride on the exotic animal–themed carousel, and then spend a couple of hours at the nearby Chicago History Museum for a quirky look at the city's past. If you'd like to stay in the Lincoln Park neighborhood a bit longer, have dinner at one of many great local restaurants and then head to The Second City, the sketch-comedy troupe that was the precursor to Saturday Night Live.
The Second City offers free improvisation after the last performance every night but Friday.
Sightseeing in the Loop
State Street, that Great Street, is home to the old Marshall Field's, which has been reborn as Macy's; Louis Sullivan's ornate iron entrance to the Sullivan Center; and a nascent theater district; as well as great people-watching. Start at Harold Washington Library at Van Buren and State streets and walk north, venturing a block east to the beautiful Chicago Cultural Center when you hit Randolph Street. Grab lunch at the Museum of Contemporary Art's serene Wolfgang Puck café, Puck's at the MCA, and then spend a couple of hours with in-your-face art. Go for steak at Morton's or the Palm before a night of Chicago theater. Broadway touring shows are on Randolph Street at the Ford Center for the Performing Arts Oriental Theatre or the Cadillac Palace, or head elsewhere for excellent local theater—the Goodman, Steppenwolf, Lookingglass, and Chicago Shakespeare will each give you a night to remember.
Begin with a long walk (or run) along the lakefront, or rent a bike or in-line skates and watch the waves on wheels. Then catch an El train north to Wrigley Field for Cubs baseball; grab a dog at the seventh-inning stretch, and sing your heart out to "Take Me Out to the Ball Game." Afterward, soak up a little beer and atmosphere on the patio at one of the local sports bars. Finish up with an outdoor concert in Grant or Millennium Park.
Start at Navy Pier —or heck, spend all day there. The Chicago Children's Museum is a main attraction, but there's also an IMAX theater, a Ferris wheel, a swing ride, a fun house, a stained-glass museum, and, in summer, Chicago-themed miniature golf in Pier Park. If the crowds at the Pier get to be too much, walk to Millennium Park, where kids of all ages can ice-skate in winter and play in the fountain in summer, where giant digital portraits of Chicagoans spit streams of water to help cool you off. Whatever the weather, make sure to get your picture taken in the mirrored center of the Bean—the sculpture that's formally known as Cloud Gate. At night in summertime, take a stroll by Buckingham Fountain, where the dancing sprays jump to music and are illuminated by computer-controlled colored lights, or take a turn on the dance floor during Chicago's SummerDance celebration.
Fireworks explode near Navy Pier every Wednesday at 9:30 pm and Saturday at 10:15 pm Memorial Day through Labor Day.
Start at the top. Hit the heights of the John Hancock Center or Skydeck Chicago at the Willis (Sears) Tower for a grand view of the city and the lake. Then take a walking tour of downtown with a well-informed docent from the Chicago Architecture Foundation. In the afternoon, wander north to the Michigan Avenue Bridge, where you can take an informative boat tour of the Chicago River. Enjoy the architecture as you float by, resting your weary feet.
Grab your bankroll and stroll the Magnificent Mile in search of great buys and souvenirs. Walking north from around the Michigan Avenue Bridge, window-shop your way along the many upscale stores. Hang a left on Oak Street for the most elite boutiques. Accent Chicago (875 N. Michigan Ave.) is where serious souvenir hunters spend their cash. Dedicated shoppers will want to detour a little farther south to State Street in the Loop for a walk through the landmark Marshall Field's building, now Macy's. For a culture buzz, check out the Museum of Contemporary Art (closed Monday). After making a tough restaurant choice (prime rib at Smith & Wollensky's or Lawry's? or deep-dish pizza at Giordano's?), consider a nightcap at the Signature Room at the 95th-floor bar on top of the John Hancock Center—the city will be spread beneath your feet.