All Destinations | Europe | Asia | North America | Africa | South America | Oceania | Hotels
| Downtown (The Loop, Near North, Near South) The center of Chicago for work and play, with shopping, skyscrapers, big theaters, and the city's most famous travel sights |
| North Side (Lakeview, Boystown, Lincoln Park, Old Town) Upscale neighborhoods with entertainment aplenty in storefront theaters and the Friendly Confines of Wrigley Field, along with a ton of bars and clubs, and one of the largest LGBT communities in the nation |
| South Side (Hyde Park, Bronzeville, Bridgeport-Chinatown, Chatham-South Shore) The historic Black Metropolis, brainy Hyde Park and the University of Chicago, Chinatown, the White Sox, soul food, and the real Chicago blues |
| West Side (Wicker Park, Logan Square, Greektown, Pilsen) Ethnic enclaves, dive bars, and hipsters abound on the fashionably rough side of town |
| Far North Side (Uptown, Lincoln Square, Rogers Park) Ultra-hip and laid-back, with miles of beaches and some of the most vibrant immigrant communities in the country |
| Far West Side (Little Village, Garfield Park, Humboldt Park, Austin) So far off the beaten tourist track you might not find your way back, but that's OK given all the great food, a couple of top blues clubs, and enormous parks. |
| Southwest Side (Back of the Yards, Marquette Park, Midway) Former home to the massive meatpacking district of the Union Stockyards, huge Polish and Mexican neighborhoods, and Midway Airport |
| Far Northwest Side (Avondale, Irving Park, Portage Park, Jefferson Park) Polish Village, historic homes and theaters, and some undiscovered gems in the neighborhoods near O'Hare International Airport |
| Far Southeast Side (Historic Pullman, East Side, South Chicago, Hegewisch) The giant, industrial underbelly of Chicago, home to one large tourist draw: the historic Pullman District |
| Far Southwest Side (Beverly, Mount Greenwood) Ireland in Chicago: authentic Irish pubs, brogues, galleries, and the odd haunted castle, all extremely far from the city center |
