The day begins with a walking tour of the Loop, which is the best way to get your bearings (and understand why Chicago's architecture is world-famous). Then you can squeeze in a quick visit to one of the city's preeminent museums before strolling along Michigan Avenue, Chicago's most famous thoroughfare, which takes you to the ritzy Gold Coast neighborhood. If possible, follow this itinerary on a weekday, when downtown offices are open and the sidewalks buzz with energy. This route works fine on weekends as well, but you won't experience quite the same big-city rush.

Start: Green, Orange, Brown, or Purple lines to Adams, or Red Line to Jackson.

1. Chicago Architecture Center

Start your day with the Chicago Architecture Center's "A Walk Through Time" tour, which begins at 11:30am on certain days of the week (2pm on others; check website for details). The 90-minute walking tour takes you to the oldest high-rises in the Loop, and the docents explain why these early office buildings were revolutionary. Sure, you'll get a basic architecture education, but this is also a great way to get a sense of the Loop's layout and dramatic canyonlike vistas. Another popular tour is "Modern Skyscrapers."

2. The Art Institute 

Even if you are hard-pressed for time, make sure to at least stop in to view the Impressionist collection on the second floor, a highlight of Chicago’s grande dame of museums. With 33 paintings by Claude Monet, dancers by Degas, and Seurat’s legendary A Sunday Afternoon on the Island of La Grande Jatte, this museum is a must for art lovers.

3. Millennium Park

With its up-close-and-personal skyline views, this sprawling greenspace is universally loved for its gorgeous landscaping, classically inspired architecture, and public entertainment spaces.

If the weather is fine, Millennium Park is an ideal spot for a picnic lunch, which you can buy at the Park Grill & Cafe (11 N. Michigan Ave.; tel. 312/521-7275). The Crown Fountain, and its two towers of glass blocks with a shallow reflecting pool between them, is the place for kids to splash around in warm weather (late at night, you’ll find revelers doing the same). Faces of Chicagoans are projected through the glass—and their mouths spew water when you least expect it. A tourist rite of passage is having a photo taken in the reflection of “The Bean,” (officially Cloud Gate), which is Chicagoans’ unofficial favorite sculpture, made of highly polished steel that reflects the nearby skyline, landscape, and lights. For the most mind-bending funhouse view, stand underneath the sculpture. The park’s centerpiece is the Jay Pritzker Pavilion, an outdoor music venue designed by Frank Gehry and host to the nation’s only free, outdoor, municipally supported classical music series, the Grant Park Music Festival; massive stainless steel ribbons top the stage. Another Gehry-designed standout, BP Pedestrian Bridge, curves and winds its way over Columbus Drive to Maggie Daley Park. This may well be the park to end all parks, with an elaborate playground, mini golf, tennis courts, a climbing wall, and, in the winter, a skating ribbon. Finally, stroll The Lurie Garden, where 250 varieties of native perennial plants re-create a Midwestern prairie.

4. Park Grill

In the winter, this restaurant overlooks Millennium Park's ice-skating rink; come summer, the rink transforms into an outdoor cafe, perfect for sipping a drink and admiring the skyline. Stay for a full meal or grab a sandwich to go.

5. Michigan Avenue Bridge
Walk north along Michigan Avenue to the Chicago River, where you can gaze up at the Gothic splendor of the Tribune Tower and the white brilliance of the Wrigley Building from Chicago’s most famous bridge, dating back to 1920. Views from every direction are stunning, but for one of the city’s best photo ops, look west down the river. 

6. The Magnificent Mile

The 14-block stretch of Michigan Avenue from the river to Oak Street, known as the "Magnificent Mile," is shopping central, a dense concentration of high-rise malls, designer boutiques, and practically every mass-market clothing brand. Even if you're not a shopper, it's worth a stroll; busy at almost all hours, it's great for people-watching. Some Chicagoans dismiss the Mag Mile as too touristy, but I think walking here makes you feel like you're part of a vibrant metropolis.

7. 360 Chicago
875 N. Michigan (formerly the John Hancock Center) may only be Chicago's third-tallest building, but the view from the top is spectacular: In the right weather conditions, you can see all the way to three other states (Wisconsin, Indiana, and Michigan). The "talking telescopes" help you get your bearings by pointing out landmarks in each direction.

8. Oak Street Beach
Where Michigan Avenue merges into Lake Shore Drive at Oak Street, head down the underpass to get to Oak Street Beach, a curved stretch of sand that's a summertime hotspot and a great background for photos. Bikers, skaters, and joggers fill the paths, while kids play in the sand. Think of it as Chicago's own miniresort getaway — just don't plan on swimming in the frigid water.

9. 3rd Coast
If you're tired of generic chain coffeehouses (of which Chicago has plenty), stop by this somewhat shabby lower-level cafe that welcomes both well-heeled locals and the occasional starving artist. In addition to the usual lattes and muffins, there's a full lunch and dinner menu, and wine and beer are available.

10. The Gold Coast
To get an idea of how Chicago's wealthiest live, take a stroll through this neighborhood of historic town homes (including the original Playboy Mansion, at 1340 N. State Pkwy.). The tranquil, tree-lined streets are only a few blocks away from Michigan Avenue, but they feel like a different city. Finish up the night with dinner at one of the many restaurants in River North, or catch a show and discover Chicago's vibrant theater scene.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.