Whether you refer to it as the Windy City, Chi-town or Chicagoland, America's third largest city has a long history of contradictions. Once a haven for organized crime and crooked politicians, it later served as a gateway to westward expansion, attracting businessmen, architects and engineers. Today, you can find a swanky restaurant alongside a deep-dish pizza dive or a hot dog stand. And it's these contrasting identities, top-notch attractions and a mouth-watering foodie ... continue»
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The best times to visit Chicago are April through May or September through October, when the temperatures are warm and the city comes alive with festivities. The summer is the most popular time because the weather is temperate enough for sightseeing. However, summer travelers should be prepared for denser crowds and higher prices. The city isn't as congested in the spring or fall. If you can brave the Chicago winter, take advantage of promotions offered by both airlines and hotels.Best Times to Visit Chicago»
The city of Chicago sprawls along the southwest coast of Lake Michigan. It's divided by the Chicago River into three geographic sections: North Side, South Side and West Side (with Lake Michigan to the east). These sections surround the city's small downtown area, the Loop.
Accessible via all El lines
Located near the shores of Lake Michigan, the Loop refers to a group of high-rise buildings within a rectangular loop of elevated train tracks. As the city's central business hub, the Loop offers visitors a taste of a bona fide big-city experience. Here, you'll find the Willis Tower (formerly known as the Sears Tower), the tallest building in North America and more of the city's most famous skyscrapers. The Loop is Chicago's main business hub, and most hotels and restaurants located in this area cater to business travelers. If you are looking to enjoy the city's nightlife, consider looking for hotels away from the Loop, since this area is generally quiet after dark.
The North Side
The North Side is home to many of the popular tourist attractions, which include the Magnificent Mile, the locale of the city's best hotels and shops are found. The North Side is also home to the city's most popular, touristy and residential neighborhoods.
Near North: The Magnificent Mile & Navy Pier
Accessible via the Red Line's Grand and Chicago El stops.
Extending north from the Loop is the Magnificent Mile, a stretch of Michigan Avenue (the main downtown thoroughfare) that is home to most of Chicago's top-notch hotels and a high concentration of big-box department stores and retailers. Just east of the Magnificent Mile stretching out onto Lake Michigan is Navy Pier, home to numerous attractions such as the Crystal Gardens, the Chicago Children's Museum, a 15-story Ferris wheel, as well as several performance venues. Located west is the River North neighborhood. Once a discarded warehouse district, River North is now one of Chicago's most vibrant commercial areas, featuring some of the city's hottest restaurants, art galleries and nightlife spots.
Accessible via the Red Line's Clark/Division El stop
Farther north of the Magnificent Mile along the shore of Lake Michigan is the Gold Coast. This area is home to some of Chicago's most desirable real estate as well as a string of popular bars and late-night food joints, located on the neighborhood's southwestern edge.
Accessible via the Brown/Purple Lines' Sedgwick El stop
Immediately west of the Gold Coast is Old Town, a nice neighborhood for strolling (the city has some of the best preserved historic homes) but little else. However, if you're in the area, spend an evening at Old Town's Second City comedy club, which has been entertaining residents and visitors alike for more than 30 years.
Lincoln Park and Lakeview
Accessible via the Brown/Purple Lines' Sedgwick and the Brown/Purple/Red Lines' Fullerton El stops
The Lincoln Park neighborhood includes both the park itself and the residential streets located west. Inside the park is the Lincoln Park Zoo, one of the oldest zoos in the country. A popular attraction among tourists, the free zoo also includes a hands-on Conservation Station. The streets just west of the park feature some of Chicago's most popular restaurants, bars and the nationally acclaimed Steppenwolf Theatre Company.
North of Lincoln Park, the residential Lakeview neighborhood is popular among young families and recent college graduates. Lakeview also features a number of gay-friendly bars and restaurants along Halsted Street.
Accessible via the Red Line's Addison and Sheridan El stops
The neighborhood of Wrigleyville is located north of Lakeview and surrounds Chicago's Wrigley Field, the second oldest ballpark in the country and home of the Cubs baseball team. The streets surrounding the stadium are packed with sports bars and stores selling memorabilia.
Uptown & Andersonville
Accessible via the Red Line's Lawrence, Argyle, Berwyn and Bryn Mawr El stops
The Uptown neighborhood located just north of Wrigleyville is in the midst of a rejuvenation. Take a stroll down Argyle Street, which Uptown's residents have transformed into a bustling open-air market selling fresh fish, meat and exotic produce. Just north of Uptown is Andersonville, home to Chicago's blossoming gay and lesbian community as well as a handful of LGBT-friendly bars and clubs.
Accessible via the Red Line's Loyola and Morse El stops
Rogers Park, which occupies the northern edge of the city proper, as the most diverse part of Chicago. The area -- which encompasses Loyola University's campus -- boasts an eclectic population comprised of Asians, East Indians, Germans and Russian Jews, all of whom have left their mark on the community, especially in cuisine.
The West Side
Greektown accessible via the Blue Line's Clinton El stop (to Forest Park); Bucktown and Wicker Park accessible via the Blue Line's Damen and Western El stops (to O'Hare)
Over the past few years, this district's abandoned warehouses have been transformed into trendy condos. Located opposite the Loop on the western bank of the Chicago River, West Loop shelters Greektown, with dozens of Greek restaurants in the area between Adams and Monroe Streets. Bucktown and Wicker Park, sitting west of the West Loop, have been home to several waves of immigrants, including German, Polish and, most recently, Spanish-speaking residents. Bucktown and Wicker Park are some of the most up-and-coming areas in Chicago.
The South Side
Chinatown accessible via the Red Line's Cermak-Chinatown El stop; Pilsen accessible via the Pink Line's 18th and Damen El stops; Hyde Park accessible via the Green or Red Line's Garfield El stops
During the 1920s, Chicago's South Side was notorious for its Levee vice district, a major hub for gambling, gangsters, and home to some of the most corrupt politicians in the city's history. Today, the South Loop is one of Chicago's fastest-growing residential areas. However, many parts of the South Side can be dangerous, and it may be best to avoid this area unless you are sure of your surroundings.
Located just south of the South Loop are several residential communities, including Chicago's Chinatown, Pilsen and Hyde Park, home to the University of Chicago. Numerous upscale shops and high-end restaurants surround the college, as well as the famed Museum of Science and Industry.
According to experienced travelers, visitors to Chicago should avoid heading into the South Side unless they are sure of their whereabouts. Experts say that this part of the city -- excluding the Hyde Park district -- has never really recovered from the reputation it earned in the 1920s as a haven for violent gangsters such as Al Capone. If you do decide to tour the area, travel writers strongly recommend visiting during the day with at least one other person.
In general the other parts of Chicago are considered safe, but as with any big city, experts and recent visitors recommend caution. Keep your valuables with you at all times. Make sure to have a clear sense of your surroundings when traveling after dark, and avoid walking alone as much as possible.
The best way to get around Chicago is public transportation. The public rail system -- the El -- is cheap and easy to navigate, but there are also buses that service nearly every tourist attraction. You can use public transit to reach the city from both Chicago O'Hare Airport (ORD) and Chicago Midway Airport (MDW). Consider purchasing an Unlimited Ride Card -- valid for one, three or seven days -- for unlimited rides for one small fee. Taxis and car rentals are also available at both airports, and cabs are easy to find in the Loop and Near North areas.Getting Around Chicago»