Start your day west of downtown at the Market District (Randolph, Fulton, and Lake streets), where vegetable markets, meatpackers, and fishmongers cozy up to galleries and urban residential lofts. Here, you'll also find some of the city's best restaurants and most popular nightclubs.
If it's a cold day and you want to spend some time indoors, while away the hours at the Art Institute of Chicago (111 South Michigan Avenue, 312-443-3600,
www.artic.edu), which houses 300,000 works of art. Pick your favorites - Monet? Picasso? - and stare away.
The business-lunch crowd dominates Italian Village (71 West Monroe Street, 312-332-7005), which has been serving enormous plates of pasta for almost 80 years. It's busy, but low lighting and intimate seating create a cozy dining ambience, while an impressive wine list has garnered Wine Spectator's Grand Award annually since 1984.
April through November, there's no better way to see the city's historic and architectural highlights than aboard the Chicago Architecture Foundation's River Cruises (312-922-3432, www.architecture.org), narrated by Chicago enthusiasts who know every detail about the city's skyscrapers. The organization also offers terrific, informative walking tours. Any time of year is right to visit Jackson Park's Museum of Science and Industry (5700 South Lake Shore Drive, 773-684-9844, www.msichicago.org), where you can walk through a human heart and check out another 2,000 or so amazing exhibits in 75 halls.
At sunset, stroll along the lake before dining at the Capital Grille (633 North Saint Clair Street, 312-337-9400), a classic steak house where pictures of past and present important Chicagoans adorn the walls. Dry-aged steaks are grilled with butter and fresh garlic and served with generous sides. After dinner, it's Chicago blues at Buddy Guy's Legends (754 South Wabash Avenue, 312-427-0333, www.buddyguys.com).