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 Foundation
Start your day with the Chicago Architecture Foundation's "Historic Downtown: Rise of the Skyscraper" tour, which begins daily at 10am year-round. The 2-hour 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, "Modern Skyscrapers," starts daily at 1pm.)
2. The Art Institute
Across the street from the Chicago Architecture Foundation stands one of the city's most prestigious cultural institutions; if you have time for only one museum while you're here, this is the one to visit. Since you've got limited time, head right for the two must-see exhibits: first, the world-famous Impressionist collection, followed by the 20th-century American modern art gallery, which houses masterpieces such as Edward Hopper's Nighthawks.
3. Millennium Park
Just north of the Art Institute is one of the city's most popular gathering spots. Check out the massive video-screen faces on the Crown Fountain, then take a walk around (and under) Anish Kapoor's bean-shaped sculpture, Cloud Gate. The Pritzker Music Pavilion, designed by Frank Gehry, features the architect's signature ribbons of silver steel; Gehry also designed the adjoining serpentine bridge.
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 and you'll come to this bridge, which spans the Chicago River. Stop here for a great photo op — on a nice day, you'll be joined by plenty of other visitors doing the exact same thing.
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
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.