Uptown is a scruffy, jazz-inflected neighborhood on the north side of Chicago. Within its boundaries, off to the side of the action, are the residential areas of Sheridan Park and Buena Park, and an exciting Southeast Asian community based around Argyle Street.

This article also includes Andersonville, a short walk to the west, which is an upscale, lesbian-friendly neighborhood.


"Eternal Silence" by Lorado Taft, Graceland Cemetery

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 GLBT 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

Train in vain

On a transit system full of oddities and abnormalities, the Wilson Red Line station has to be near the top of the list. The marble steps and ornate façade are hopelessly cracked and water-damaged, and the only places that are remotely well-lit are the food mart and the fried chicken restaurant. With some effort, you can mentally reverse the decayed grandeur and imagine the station as it was in 1923, when it replaced an inferior structure built by some dink named Frank Lloyd Wright. Originally, this was the northern terminus for the CTA, and an extra platform was built for passengers changing to the North Shore Line for transit further north. When the CTA took over the full system, the extra platform was stripped of its canopy and abandoned, and has remained that way ever since, with not even a billboard by the ad-happy CTA to adorn it. Believe no rumors of a magical express boarding over there...

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.


Uptown is rich with Art Deco buildings large and small, albeit in varying stages of preservation or neglect. The Wilson Red Line station is worth a look for the arch over the original entrance at the corner of Wilson & Broadway, into which a Popeye's Chicken has been incongruously crammed. Tourists who are crows will find this arch especially enjoyable, judging from the number of crows that spend time here. In much better shape is the Bridgeview Bank Uptown at Lawrence and Broadway, the tallest building in the area, with a well-kept green and white façade. Back on the other end of the scale is the magnificent sandstone Uptown Broadway Building at 4707 N Broadway, crumbling and covered in netting for a possible (expensive) renovation.

Another worthy stroll for architecture enthusiasts is the Hutchinson Street District, from 600-900 W Hutchinson, closer to the lake. It's the post-Mies apartment blocks that dominate the Uptown skyline from the lake, but Hutchinson has some lovely street-level Prairie School houses by George Maher.


Uptown has one of the best collections of concert venues in Chicago, most of which are renovated holdovers from the area's Roaring Twenties heyday.

One that isn't renovated is the huge Uptown Theatre on Broadway. It was built by the Balaban and Katz movie kings in 1925 to be as lavish as possible, and when it opened, it was described as "an acre of seats in a magic city," second only to Radio City Music Hall in size. With the declining fortunes of the neighborhood, it was shuttered in the early 1980s, and has remained in limbo ever since; too expensive to demolish, but too expensive to fix. It could yet be restored, although it would be a difficult task, especially with the still-shaky state of the Uptown economy. Until something happens, the majestic façade and marquee will peer out over Broadway, eerie in the darkness.

The Green Mill, Uptown





You'll find several cute, stylish clothes boutiques for women in Andersonville. With the number of cafes and bakeries sharing the streets, it's a great place to shop, stop, and shop again.


Shopping in Uptown

With the glory days of Goldblatt's long past, Uptown isn't much of a destination for shopping — save, of course, for the Asian imports on and around Argyle.




Argyle is the wonderland. The Red Line drops you right in the midst of it — three blocks, from Sheridan to Broadway, of cheap and delicious Asian food. If you believe in eating where the locals eat, Argyle is most certainly the place to go; this is authentic cooking, with no tourist traps to be found. Vietnamese restaurants and bakeries are the most plentiful, with various disciplines of Chinese food a respectable second, and Thai dishes included on the menus of several non-Thai restaurants.


Cheap fast food can be found around the Wilson Red Line station, but there are several better options for eating well on a budget.



Hopleaf in Andersonville (see Drink) deserves consideration for anyone looking for a terrific meal (with beer included).




If you're looking for a drink in Uptown, don't forget to raise a glass at the Green Mill (above).


Don't book a room in Uptown with expectations of that old swingin' class — most of these rooms are used by transients and homeless people getting back on their feet, and should only be considered by travelers as rock-bottom budget options. Nearby Edgewater has a few nice, gay-friendly B&Bs, though.


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

Routes through Uptown

END Rogers Park  N  S  Lakeview-North Center The Loop

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