Chicago Vacations

Tourists flock to Chicago during spring and summer, when Chicagoans emerge from hibernation into outdoor cafes, legendary sports stadiums and the city's gorgeous parks for music, food and cultural festivals including the Taste of Chicago and Lollapalooza.

If a Chicago vacation happens during the winter, pack a down coat and take advantage of off-peak rates at downtown Chicago hotels. The city's public transportation is among the best in the nation, making it easy to travel to museums, bars, restaurants, landmarks and even far-flung locations in the suburbs.

For great people watching and impressive skyline views, hit Oak Street Beach, where singles flock to play volleyball and sunbathe. Families stick to Montrose and Loyola beaches a little further north, which are a lot less crowded and pose better chances for finding a parking spot.

If you're planning to visit this famous restaurant, book your reservation at least two months in advance. If you do score a table, don't be discouraged if you can't spot the restaurant immediately. It's in a grey brick storefront with no sign.

For a leisurely lesson on Chicago's architecture, catch a boat cruise from Navy Pier or at the bottom of the Wrigley Building.

Looking for an offbeat place for cocktails in one of Chicago's hippest neighborhoods? Consider the Bedford in Wicker Park, located in a former bank building. Imbibe old-school cocktails in the actual vault, which is dotted by safe deposit boxes.

Shake up your Sunday brunch with the bottomless mimosas and drag shows at Kit Kat Lounge, Boys Town's favorite martini bar and lounge.

Chicago's most fashionable boulevard is at the center of the downtown action. Lined by colorful tulips in the springtime and white lights during the holidays, the Mag Mile is as flashy as its posh department stores and notable landmarks, from the Wrigley Building to the historic Drake Hotel.

Capture your postcard moments along the way, starting with a snapshot of the stone fragments from landmarks around the world affixed to the Tribune Tower.

Chicago never sounded so sweet than at this iconic blues den in the South Loop. The stage jams seven nights a week – with heavy hitters such as Eric Clapton and John Mayer among the past featured acts.

For a side of Cajun spice to go with your blues, order from a menu of Southern classics, including okra, gumbo and jambalaya.

Chicago is blessed with an 18.5-mile path along the shores of Lake Michigan, a stretch bustling with bikers, runners, soccer fields, beaches and parks. Connecting neighborhoods as far south as the South Shore to as far north as Edgewater, the path is an easy way to combine sightseeing with recreation.

Expect to feel like a kid again throughout the lakeside treat, which boasts a Ferris wheel, the Chicago Children's Museum, Chicago Shakespeare Theater, bikes for rent, boat rides, miniature golf and headlining acts such as Cirque Shanghai Extreme.

Come summertime, pull up a chair at an al fresco restaurant -- Harry Caray's is a favorite -- to watch the twice-weekly fireworks.

If the careers of John Belushi, Gilda Radner, Tina Fey, Mike Meyers and Steve Carrell have proven anything, it's that a stop at Second City could help rocket a career. The talent incubator in the heart of Old Town hosts both sketch-based and improv performances in an intimate setting.

Take the elevator up 96 flights to soak in the views from the Signature Lounge, the best seat in Chicago. While there is no admission fee, expect pricy cocktails -- but paired with floor-to-ceiling panoramas of the Windy City, they're worth it.

If time permits, opt for the Sunday brunch or a special occasion dinner at the Signature Room, equally dazzling with oversized windows and an impressive wine list.

No curse can deny Chicago's unwavering love for the Cubs -- and it's as much about the scene as it is about the fantasy of winning a World Series. And it doesn't get any more Chicagoan than seeing fans swig beers during a rowsing rendition of "Take Me Out to the Ball Game," or cheering from the rooftop decks in Wrigleyville. Expect as much flavor surrounding the stadium, as diehards continue the party along Clark, Addison and Waveland.

Its name may have changed, but in the hearts of Chicagoans, Willis Tower will always be Sears Tower. The building soars 110 stories above the Windy City, and is home to the world's tallest green roof on the 90th floor. The Skydeck invites visitors to look down at the metropolis via clear ledges, but only if you dare.

Home to Cloud Gate, Crown Fountain, the Jay Pritzker Pavilion and more attractions, the park leaves visitors impressed by striking landmarks, lake access and buzz from the neighboring Magnificent Mile.

The best part: Many summer activities are free, including outdoor yoga and Pilates, Chicago SummerDance, and the Family Fun Festival at Chase Promenade North.

Housing more than 300,000 works of art, this Michigan Avenue gem spans centuries' worth of masterpieces, from the "A Sunday on La Grande Jatte" by Seurat and "American Gothic" by Grant Wood. A 2009 expansion enhanced the appeal thanks to the super sleek Modern Wing designed by Pritzker Prize–winning architect Renzo Piano.

The Ryan's Education Center invites the tykes to engage in their environment with interactive exhibits. Organic restaurant Terzo Plano fuels the romance with glorious views of the Pritzker Pavilion.

A Chicago vacation offers more variety than some people might realize, and it’s not uncommon to hear tourists say how pleasantly surprised they are after a first visit to “the second city”—but not all locals embrace that nickname. Folks here prefer the well-deserved moniker Windy City, as they strongly believe their home is second to none. Once famous for a restless cow burning it to the ground and Al Capone’s Prohibition-era gangster violence, today Chicago is more likely to be associated with Oprah Winfrey, Michael Jordan and President Barack Obama. And family travelers, sports enthusiasts, foodies and lovers of the arts flock to its world-class museums, attractions, award-winning restaurants and special events, making it one of the top ten most popular U.S. destinations for both domestic and foreign tourists. Visitors also rave about the city’s architectural beauty, cleanliness and Midwestern friendliness. A vibrant green city—and not just when the eponymous river that winds through it gets dyed for St. Patrick’s Day—Chicago boasts pristine parks, beaches and bike paths stretching along the shores of Lake Michigan, which is often dotted with sailboats. Shoppers can stroll the Magnificent Mile and Oak Street for luxury retailers, while those looking to discover young designers and tastemakers should head to any of the city’s several diverse neighborhoods—preferably via the famous elevated “el” train.

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