Chicago—the Windy City, the City of Big Shoulders, Paris on the Prairie—is known for deep-dish pizza, a cursed baseball team, stunning skyscrapers, and Barack Obama. The only thing that could possibly be more impressive than the city's colorful history is gigantic Lake Michigan, often referred to by visitors simply as "the ocean." Lake Michigan is a great place to sail, boat, or fish, and Chicago's lakefront is dotted with places to dock your boat. Here's a guide to two of our favorite Chi-town neighborhoods, both of them beguiling, action-packed, and—best of all—a cinch to access by water. Step ashore!
Things to See and Do
Lincoln Park An upscale enclave with a youthful, sophisticated vibe. The many boutiques and cafes are full of young professionals, families, college students, and recent grads, and the eponymous 1,208-acre park stretches along the lake.
Tucked in the upper reaches of the park, next to tennis courts, a bird sanctuary, and a well-kept, nine-hole public golf course. Amenities include 730 slips, fuel facilities, a store for supplies, free pump-out services, and an unofficial dog beach. (3600 Recreation Dr., 312-742-7673,www.chicagoharbors.info
Less than a mile south of Belmont, with 714 slips, free pump-out services, a fueling facility, and easy access to the park's Peggy Notebaert Nature Museum and acclaimed zoo. (2601 N. Cannon Dr., 312-742-7762, www.chicagoharbors.info
Where to Eat
Ann Sather Café Part of a beloved mini-chain founded by a Swedish granny more than 60 years ago. The made-from-scratch items include broiled salmon with mustard-dill sauce and open-face meatball sandwiches. The entire menu is available for take-out. (3411 N. Broadway, 773-305-0024)
The Bagel Restaurant & Deli The immense menu is crammed with the same traditional Jewish dishes—chopped liver, knishes, noodle kugel—that the deli has been known for since 1950. There's also an excellent selection of sandwiches, burgers, and smoked-fish platters. (3107 N. Broadway, 773-477-0300)
Frances' Deli The oldest deli in Lincoln Park, and one of the city's best breakfast spots: housemade blintzes, Nova lox, dozens of omelettes. They also serve lunch and dinner, and whip up to-die-for milkshakes and malts. (2552 N. Clark St., 773-248-4580)
Goose Island Brewpub One of the largest craft breweries in the Midwest; their 312 Urban Wheat Ale is a regional favorite. Swing by to sample their more than 10 draft beers and the top-notch pub grub (tilapia po' boys, grilled Italian sausage), or call in advance to set up a tour. (1800 N. Clybourn, 312-915-0071)
Lou Malnati's Pizzeria The name signifies more than a restaurant—Lou Malnati's is a Chicago institution. They've been serving Chicago-style deep-dish pizza since 1971, and there are now 30 outlets scattered throughout the city. (958 W. Wrightwood, 773-832-4030)
What to Do
Kingston Mines Established in 1968, and among the city's most venerable blues venues; there's live music on two stages seven nights a week. (2548 N. Halsted, 773-477-4646)
Lincoln Park Zoo Open 365 days a year and free of charge, the zoo houses more than 1,200 animals and is enormously popular with tourists and locals alike. There are two children's areas, and rentable paddleboats are available for cruising around the lagoon and enjoying the knock-out skyline views. (Main entrance at W. Fullerton Pkwy. & N. Cannon Dr., 312-742-2000)
The Vic Opened in 1912 as a luxurious vaudeville house, these days the Vic hosts cult and second-run movies in a program billed as Brew & View; the three bars mean that you can nurse a beer while taking in the show. A few times a month the theater also holds concerts and comedy nights. (3145 N. Sheffield, 773 472-0449)
Wrigley Field Also known as the Friendly Confines, Wrigley Field is a must-see for any sports fan. Tickets to Cubs games are hard to come by, but the surrounding area is loaded with lively bars where you can grab a drink and catch the game on wide-screen TV. (1060 W. Addison St., chicago.cubs.mlb.com
Downtown More than just the city's financial heart, the downtown district contains world-class architecture, great shops, chic restaurants, and a bevy of first-rate cultural institutions.
Burnham Harbor The 1,1,20 slips are nestled in a protected crook of the lake, and surrounded by excellent museums; Soldier Field, home to the Chicago Bears, is just to the west. Among the amenities are fuel pumps, a store, free pump-out services, and laundry facilities. (1559 S. Lake Shore Dr., 312-747-7009)
DuSable Harbor Slightly north of Burnham, DuSable has 420 slips, free pump-out services, a fuel facility, and a basic store, and is a few blocks from some of the city's best shopping on tony Magnificent Mile. (111 N. Lake Shore Drive, 312-742-3577)
Where to Eat
Billy Goat Tavern The Greek diner that served as inspiration for John Belushi's infamous "cheezborger, cheezborger, cheezborger" skits on "Saturday Night Live." The original owner is also said to have been the won who cast the Billy Goat curse on the Chicago Cubs. (430 N. Michigan Ave. at Lower Level, 312-222-1525)
Oysy Pronounced "oh-ee-she," the name of this restaurant means "delicious" in Japanese, and the food at the sleek izakaya-style space is just that. The menu runs from sushi and sashimi to tempuras and stir-fries. (888 S. Michigan Ave., 312-922-1127)
Yolk The city's most buzzed-about breakfast place; the pecan waffles and avocado-stuffed crepes make it easy to understand why. It's almost guaranteed that there will be a line for a table, but it's always worth the wait. (1120 S. Michigan Ave., 312-789-9655)
What to Do
Art Institute of Chicago One of the premier fine art museums in the United States, with a permanent collection made up of significant Impressionist, American, and old master works. Additional exhibits through the summer include a selection of nature-inspired Cy Twombly pieces and "Photography on Display: Modern Treasures, "a presentation of master photographs in the museum's just-completed new galleries. (111 S. Michigan Ave., 312-443-3600, www.artic.edu)
Museum Campus The sprawling compound is the site of the Field Museum (1400 S. Lake Shore Dr., 312-922-9410, www.fieldmuseum.org), proud keepers of Sue, the world's largest and most complete T. rex skeleton; the Shedd Aquarium (1200 S. Lake Shore Dr., 312-939-2438, www.sheddaquarium.org), which has an impressive, newly renovated Oceanarium exhibit; and the dazzling Adler Planetarium (1300 S. Lake Shore Dr., 312-922-7827, www.adlerplanetarium.org).
Navy Pier An amusement complex with a food court and scads of restaurants, as well as such attractions as the Chicago Children's Museum, an Imax theater, a giant Ferris Wheel, a beer garden, the Smith Museum of Stained Glass Windows, and the Chicago Shakespeare Theater. Fireworks displays light up the sky on Wednesday and Saturday nights. (600 E. Grand Ave., 312-595-7437, www.navypier.com)
Theater District Long a hot bed of up-and-coming talent, the city's Theater District is home not just to Broadway-caliber shows such as "Jersey Boys" and "Mary Poppins" (www.broadwayinchicago.com), but also to renowned, cutting-edge companies like Steppenwolf (1650 N. Halsted St., 312-335-1650, www.steppenwolf.org) and the Lookingglass Theatre (821 N. Michigan Ave., 312-337-0665, www.lookingglasstheatre.org).