In keeping with their proximity to the towers of power, many of the restaurants in the Loop feature expense-account-style prices, but it's still possible to dine here for less than the cost of your hotel room. The South Loop -- a neighborhood just west of the lake and south of Congress Parkway -- has seen a mini-boom in restaurants in the past few years, accompanying a rash of condo conversions and new construction in the area. Note: Keep in mind that several of the best downtown spots are closed on Sunday.
The West Loop
The stretch of Randolph Street just west of the Chicago River -- once known as the Market District -- used to be filled with produce trucks and warehouses that shut down tight after nightfall. In the 1990s, in an echo of New York's Meatpacking District, a few bold restaurant pioneers moved in, bringing their super-hip clientele with them. It wasn't long before industrial buildings began their transformation into condos, and now it seems like there's a construction zone on every corner. Despite the upheaval, the West Loop still feels like a neighborhood in transition. It's home to some of the city's coolest restaurants and clubs, but not much else.
Transportation to the West Loop is easy. You can get there by bus (no. 8 or 9) or El (the Green Line has a stop at Clinton, which is within a few blocks of most restaurants listed), but it takes about 5 minutes and costs less than $10 to take a cab from Michigan Avenue. The walk from the Loop is pleasant and secure in the daytime and early evening, but it's best to catch a cab if you're returning to your hotel late.
The Magnificent Mile & the Gold Coast
Many tourists who visit Chicago never stray far from the Magnificent Mile and the adjoining Gold Coast area. From the array of restaurants, shops, and pretty streets, it's not hard to see why. The Gold Coast is home to some of the city's wealthiest, most tradition-bound families, people who have been frequenting the same restaurants for years. But newer places, such as Table Fifty-Two, have carved out their own culinary niches here as well.
River North, the area north of the Loop and west of Michigan Avenue, is home to the city's most concentrated cluster of art galleries and a something-for-everyone array of restaurants -- from fast food and themed restaurants to chains and some of our trendiest dining destinations. Whether you seek a quick dog or burger, contemporary American fine dining, or world-class Mexican fare, River North has it all -- within easy walking distance of many downtown hotels.
Lincoln Park & Old Town
Singles and upwardly mobile young families inhabit Lincoln Park, the neighborhood roughly defined by North Avenue on the south, Diversey Parkway on the north, the park on the east, and Clybourn Avenue on the west. In the southeast corner of this area is Old Town, a neighborhood of historic town houses that stretches out from the intersection of North Avenue and Wells Street. You'll find a few fine-dining spots, but most restaurants here are more casual, with average prices lower than you'll find in River North or along the Magnificent Mile.
Wrigleyville & the North Side
The area surrounding Wrigley Field has a long history as a working-class neighborhood, and although housing prices are now beyond the reach of most blue-collar workers, the neighborhood still attracts hordes of recent college grads who prefer chicken wings to truffles. Overall, restaurants here are more affordable and low-key than downtown, though most aren't worth a special trip if you're staying elsewhere. Throughout the North Side -- a catch phrase encompassing the neighborhoods north of Lincoln Park -- you'll find mostly casual, neighborhood restaurants and a good range of ethnic eats.
The booming Wicker Park/Bucktown area followed closely on the heels of Lincoln Park and Wrigleyville in the race to gentrification. First came the artists and musicians, followed by armies of yuppies and young families -- all attracted by cheap rents and real estate. The result is a well-established, happening scene, which includes some of the city's hippest restaurants and clubs. Get yourself to the nexus of activity at the intersection of North, Damen, and Milwaukee avenues, and you won't have to walk more than a couple of blocks in any direction to find a hot spot. Cab fares from downtown are reasonable, or you can take the El's Blue Line to Damen.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.