Chicago Neighborhoods Guide

Explore like the locals with a Chicago neighborhood tour.

Chicago is a melting pot of ethnic neighborhoods, old and re-born communities, historic districts, centers of business and commerce and vast spaces that are dedicated to parks, entertainment and culture.

Connecting all the neighborhoods is Chicago’s web-like L system — the omnipresent elevated railway network that has effectively and efficiently served riders in the metropolitan area for more than 125 years. L Stop Tours utilizes the L system to explore Chicago’s unique and distinctive neighborhoods, popular sights and attractions. Below are just a few of the places you can visit on the Chicago neighborhood tours. 


A little more than two miles south of the Loop (Chicago’s central business district) is Chinatown, home to a number of restaurants, grocery stores, gift shops, banks, service business, cultural institutions, and approximately 16,000 area residents — 90 percent of which are of Chinese descent. Chinese first migrated to Chicago in 1869 via the first Transcontinental Railroad to escape violence and persecution that had broken out in California.

Today’s Chinatown neighborhood was first settled in 1912 when a Chinese merchants association constructed a building that could house 15 stores, 30 apartments and the association’s headquarters.

Accessible via Red and Green Lines


Located approximately five miles north of the Loop, Lakeview was originally a suburb that was annexed by Chicago in 1889. Settled by immigrants from Germany and Sweden, Lakeview attracted residents from across the city, thanks to the 1914 construction of Weeghman Park (now Wrigley Field) and the 1917 construction of a major department store, Wieboldt’s, which anchored a new shopping district at the intersection of Lincoln, Belmont and Ashland Avenues.

Today, Lakeview is a gentrified neighborhood that is home to two lively, distinctive mini-neighborhoods — “Wrigleyville,” an entertainment district that surrounds Wrigley Field and “Boystown,” the first officially-recognized gay village in the United States which is now well known for its restaurants, pubs, theaters, boutiques, fashion outlets, and historic architecture and landmarks.

Accessible via Red and Brown Lines

Logan Square

Over the years, Logan Square has seen a lot of changes. Originally settled in 1830 by English, Norwegian and Danish immigrants, the area attracted residents from other areas of the city and soon became home to significant Jewish and Polish immigrants, as well. The community was annexed into the City of Chicago in 1889 and was renamed Logan Square after Gen. John A. Logan, an American soldier and political leader.

Today, the neighborhood is an eclectic mix of Mexican, Cuban, Puerto Rican, Polish, and African American residents. It’s also home to a significant local arts scene and a 2.7-mile greenway called The Bloomingdale Trail, an abandoned elevated railroad line that was converted into a walking and biking trail in 2015.

Accessible On Blue Line Tour


Check out our Loop Guide for things to do!

Chicago’s central business district is so-called because of the convergence of elevated lines in the downtown area that form a loop (an unofficial boundary) around a 1.58 square mile district.

Loaded with architecturally significant buildings, museums, parks, cultural institutions, retail stores, fine dining establishments, and theaters, the Loop is the beating heart of Chicago — always teeming with people, special events, activities, and things to do. The Loop is also the starting point for all tours offered by L Stop Tours.

On Brown, Blue, Green South, Green West and Pink Line Tours

Old Town

Originally called “The Cabbage Patch” and later “North Town,” this Near North Side neighborhood received its name in the 1940s when a local art fair, the “Old Town Holiday,” became popular and local residents adopted the moniker for their community. The Old Town Triangle Association, a neighborhood residents group, gets its name from three streets that form a triangle surrounding the neighborhood — Ogden Avenue, North Avenue and Clark Street.

In addition to street after tree-lined street of beautifully restored Victorian houses and flats, Old Town is home to The Second City, Zanies Comedy Club, boutiques, emporiums, a bevy of interesting family-owned restaurants and taverns, and of course, the famous Old Town Art Fair, which occurs annually the second weekend in June.

On Brown Line Tour


Located 4.5 miles south of Chicago’s Loop, Pilsen got its name from blue-collar Bohemian immigrants who thought it reminded them of Pilsen, a city in the Czech Republic. During its first 150 years, Pilsen was Chicago’s distinctive eastern European enclave. In 1950, the first wave of Mexican immigrants began to move into the community.

Today, Pilsen is 80 percent Latino, however, many of the commercial buildings and homes located throughout the neighborhood still reflect the architecture and style of the community’s early residents. It’s a fascinating neighborhood — filled with outdoor murals, beautiful churches, cultural institutions, great restaurants, and much more.

On Pink Line Tour

Prairie Avenue District/South Loop

A stone’s throw north of McCormick Place, Chicago’s sprawling convention center, is Prairie Avenue, home to some of the most historically significant residences in the city. After the Great Chicago Fire of 1871, many of the area’s most affluent families built grand Victorian mansions on Prairie, cementing the street’s legacy as the original “Gold Coast” of Chicago. Among the elite businessmen who lived here were Marshall Field (Marshall Field & Co.), George Pullman (Pullman Car Co.), Philip Armour (Armour & Co.), and John Glessner (International Harvester).

Many of the mansions have been preserved and the entire district is listed on the National Register of Historic Places. Also located in the district is the oldest house in Chicago, the Clarke House, which was built in 1836 and is now a museum. Just west of Prairie Avenue are other areas of interest — Motor Row, where early-20th century Chicagoans purchased new cars, the former site of the Levee, Chicago’s notorious turn-of-the-century vice district and Chess Records, home of the Willie Dixon Blues Heaven Foundation.

On Green Line South Tour

River North/Streeterville

River North and Streeterville are both located on the north bank of the Chicago River — River North occupies the western portion of the river bank and Streeterville occupies the eastern portion. While it’s obvious how River North got its name, Streeterville is named after a scalawag steamboat captain, George Wellington Streeter, who beached his 35-ton boat on a nearby sandbar in 1886, claimed the land for his own and that it was not subject to the laws of Illinois or Chicago. He was evicted by Chicago police in 1893.

During Streeter’s “reign,” the neighborhood resembled a shantytown. Today, ironically, both River North and Streeterville are among the most prosperous and well-to-do areas of the city. River North contains popular restaurants and bars, landmark architecture, art galleries, museums, and culture. Streeterville is home to the Magnificent Mile (Chicago’s premier shopping district), Navy Pier, several of the city’s tallest skyscrapers, and the downtown campus of Northwestern University, which includes several affiliated hospitals and the university’s law school.

On the Brown Line Tour

Southport Corridor

Located just west of Wrigley Field in Lakeview is a lively, vibrant area called the Southport Corridor, which offers an intriguing mix of the “old” and the “new.” On the “old” side of the ledger are Southport Lanes, one of the last bowling alleys in the U.S. to still employ human pinsetters and the Music Box Theatre, a beautifully restored movie palace that opened for business on August 22, 1929.

On the “new” side is some of the best shopping this side of the Magnificent Mile. The Southport Corridor boasts a wide range of major retailers as well as upscale independent boutiques with offerings to fit every budget. The neighborhood also features many popular restaurants and taverns and is home to several off-Loop theatre companies, such as Mercury Theater Chicago and Athenaeum Theatre.

Accessible via the Brown Line

West Loop/Fulton Market

What used to be nothing but factories and warehouses has recently been transformed into one of Chicago’s fastest growing neighborhoods with trendy restaurants, bars, nightclubs, and a host of new residential construction — high rises, lofts, renovated walk-ups — all within a few blocks of downtown Chicago.

In this neighborhood, you’ll find everything from sushi bars to sports pubs, art galleries, a French Market, antique shops, design showrooms, and Chicago’s Greektown neighborhood, which is located at Halsted Street and Jackson Blvd.

On the Green line West tour

Wicker Park/Bucktown

Located on Chicago’s near Northwest Side, Wicker Park and Bucktown are neighborhoods that have experienced a lot of change over the years. Both areas were settled by Germans and Scandinavians in 1870; were home to several rich beer barons at the turn of the century (their restored mansions survive); welcomed waves of Polish immigrants between 1900-1930; experienced decline in the 1960s and 70s; and experienced a rebirth in the 1980s and ‘90s when artists, yuppies, and others were attracted by cheap rents and the area’s close proximity to downtown.

Today, Wicker Park and Bucktown are models of what gentrification can do for a community. Here you will find quaint shops and boutiques, award-winning restaurants, lively bars and taverns, art galleries, restored vintage hotels, and a 1930s-era bank building that has been converted into a friendly, neighborhood drug store — with most of the bank’s features still intact.

On the Blue Line Tour