The Windy City, which sits on the edge of gorgeous Lake Michigan, is a world-class metropolis. This Third-Coast city (those Great Lakes are big) has 29 miles of lakefront parks and beaches plus 18 miles of lakefront biking and walking paths, and there are also countless places to view the beautiful skyline — you can take in the entire downtown in one fell swoop. There’s tons of theater, music, and culture, and some of the best food you’ll ever eat (especially the pizza).
Before You Go: Need-to-know info
Flight time: 3 hours from NYC, 5 hours from LA
Getting around: The El (elevated train), taxi
When To Go: Chicago at its best
Best weather: Spring and summer. You probably don’t want to be in here when it’s bitterly cold, though it is gorgeous when it’s decked with Christmas decorations.
Best prices: Fall and winter
Shopping: There are two main districts you’ve got to visit — State Street and Michigan Avenue. On State, down in the Loop (so named because of the elevated train tracks that ring the area), you’ll find the historic Marshall Field’s and Carson Pirie Scott flagship stores. Be sure to buy a few boxes of Frango mints at Field’s. From there, walk east to Michigan Avenue and wander north — shops line the street all the way up to Water Tower Place, one of the city’s oldest and most famous malls.
Architecture: Be sure to take a walking tour. Stop in at the Chicago Architecture Foundation and join a group headed by a knowledgeable guide. After you learn about the city’s historic buildings, plazas, public sculptures, and skyscrapers, take a trip to the top of the Sears Tower or the John Hancock Building. The views from their observatories are amazing. (Go at night for a really stunning vista!)
Culture: Be sure not to miss the world-class galleries at the Art Institute of Chicago. Or cab it down to the Field Museum of Natural History; the Shedd Aquarium, with its oceanarium looking directly out at the lake; and the Adler Planetarium. They’re all within a stone’s throw of each other, just south of the Loop off Lake Shore Drive.
Theater: There are more than 150 here, from the experimental to the ornate and traditional. Two of the most famous and well-respected are the Goodman and the Steppenwolf, a group founded by actor Gary Sinise that also counts John Malkovich and Laurie Metcalf among its members.
Comedy and the Blues: Chicago is also a capital of comedy — Bill Murray, John Belushi, or Mike Myers all got their start at The Second City. You’ll also find nightclubs to suit every taste here, but remember, this place is a blues mecca. The best place to see some is the legendary Kingston Mines.