Uptown

Understand

Uptown is the result of a divine message received by men with a tremendous amount of money in the early 1920s. Here, by the lake, there was to be an entertainment district of such magnificence that it would shift the entire center of Chicago to the north, and within a few years, overtake even Manhattan for supremacy in the nation. Up went canyons of Art Deco magnificence: hotels, department stores, palaces of music and the arts; all in accord with the vision. Ever see a movie where cigar-chomping gangsters escort gorgeous molls into a damn good jazz club? That's The Green Mill. Where thousands of earnest teens dance their hearts out for a famous live radio broadcast? That's the Aragon Ballroom. And the crowning achievement was the Uptown Theatre, where every man could see a movie like a king.

But there was the small matter of the stock market crash in 1929. Right as Uptown was reaching its peak, new construction slammed to a halt and Uptown never recovered. Needing tenants, many buildings were carved up for low-income housing, and maintenance was lowered to match the rent. There was still revelry, but it was seedier, and less of a destination for the fresh-faced teens of yesteryear. Unlike other parts of the city, which were reinvented by changing fortunes across the decades to come, Uptown stayed on the mat, beaten down by poverty.

At last, though, Uptown is reaping the rewards of that heritage. Years of cheap living created a diverse community that's still resident there today, highlighted by the amazing Southeast Asian pocket on Argyle between Sheridan and Broadway. (It's sometimes mistakenly known as "Little Saigon" or "North Side Chinatown," but it's too diverse for one label.) For the first time in decades, the entertainment district is growing again, with the survivors holding strong and joined by some great new options. In an area where a dilapidated pancake house from the 1950s still counts as new construction, the seedy atmosphere of Uptown can be absorbing like few others in the city, and makes for a memorable night out.

Andersonville hasn't experienced the highs or the lows of Uptown, and strikes a completely different vibe. Originally a hub for Swedish immigrants, whose influence can be seen in a few restaurants and bars, it became a hub for Chicago's lesbian community, and today has a less raucous atmosphere than the younger LGBT scene in Boystown. The stylish boutiques and inviting restaurants have made it a great place for people of all backgrounds to live, and a laid-back destination for shopping or entertainment, particularly at the Neo-Futurarium, Chicago's most inventive original theater.

Get in

By train

Uptown is well-served by public transportation from the center of the city, with all of the sights and nightlife within an easy walk of the train. The CTA Red Line runs from the Loop through Uptown (Wilson, Lawrence, Argyle) and near Andersonville (Berwyn). These are some of the CTA's oldest and worst-kept stations, so accessibility for handicapped travelers will be a major issue — plan to connect a bus instead. (The Addison Red Line station in Wrigleyville is the closest fully-accessible station.)

The walk from any of the Uptown Red Line stations to Clark Street and Andersonville is no real bother except in the winter, when you're better off waiting inside the station for a bus (see below).

By bus

• 22 Clark also runs all night on Clark Street from Edgewater (to the north) and on to Lakeview (to the south).
• 36 Broadway also runs from Edgewater (to the north), passing by the concert venues and the Southeast Asian stores, and from there to eastern Lakeview. It's only a half-block walk from the Red Line stops.
• 50 Damen runs along Damen from the Brown Line and Ashland, north of Foster, near the western edge of Andersonville.
• 78 Montrose connects with the Brown Line in North Center and the Wilson Red Line in Uptown.
• 80 Irving Park runs along Irving Park. Connections can be made with the Irving Park Brown Line stops as well as the Sheridan Red Line.
• 81 Lawrence connects with the Red Line station of the same name and operates all night. You won't need the bus to reach the concert venues, but it does run through Albany Park and to the Jefferson Park Blue Line station.
• 92 Foster connects with the Red Line at Berwyn and is the best way to reach Andersonville from the train. It also ends up west at the Jefferson Park Blue Line station.
• 151 Sheridan is a local route from downtown, running all-stops down Sheridan Road. It's an all-night route.

By car

The best way to reach Uptown by car is the fabled Lake Shore Drive, which has exits at Wilson, Lawrence, Foster, and Bryn Mawr ending at Sheridan and Hollywood in Edgewater. Drive a few blocks west from any of these and you're at Broadway, the main street in Uptown.

Clark Street is the main drag for Andersonville, with a few sights on Ashland, a short walk to the west.

Stay safe

Andersonville is safe more or less around the clock, as long as you use basic city common sense. Uptown can be a risky proposition after dark, though, especially near Wilson Avenue. You'll be fine walking between the concert venues to the CTA, but save any architecture walks for earlier in the day. A lot of transients and homeless people live in Uptown, where there are some drug/alcohol rehab centers. So while the overall crime rate is not high compared to some other parts of the city, it's advisable to be aware of your surroundings, even in daylight.

Go next

• If it's jazz history that brought you here, don't forget Bronzeville, which in its day was home to Louis Armstrong and Chicago jazz in its golden age. If you care less about the history, however, and just want to hit the current top jazz clubs, head down to the Velvet Lounge in the Near South, which should not disappoint.
• For a more expensive theater experience, the prices rise as you head south through Lakeview and Old Town.
• If the LGBT scene in Andersonville leaves you wanting more, head south on Clark and then a couple blocks east towards Boystown.
• If you had a good time on Argyle, the Red Line can take you straight to Chinatown on the South Side.