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What started as a 19th century playground for affluent Chicagoans is now one of the city’s most desirable entertainment destinations. Charlie Chaplin, Gloria Swanson, Wallace Beery and Francis X. Bushman used to walk the streets of Argyle when the historic Essany Studios was still in full-swing as a silent movie house in this northern section of Chicago.

It’s hard to find mention of Uptown without a reference to jazz. This Chicago neighborhood is, after all, home to the famous Green Mill Jazz Club. Back in the day, Al Capone used to frequent this once smoky joint with his henchman when big jazz names graced the stage, and even Frank Sinatra slung back a few through a couple of sets.

Aragon Ballroom

Today, locals head to Uptown’s main thoroughfare, Broadway, for wide-ranging dining choices and late-night noshing. Rather than being dominated by a particular ethnic cuisine, as many Chicago neighborhoods are (e.g. Mexican fare in Rogers Park and Indian food on Devon Avenue), this area has something to satiate the most discerning palate. Within the span of two blocks you can feast on regional dishes from Italy, India, Japan and Ethiopia, to name a few. Venture a few blocks north to Argyle Street and you can choose from several authentic Vietnamese restaurants, so many in fact that this small section of Uptown is often referred to by locals as “Little Vietnam.”

When local Uptowners aren’t eating out at the local cafés and storefront restaurants, you can find them taking subdued strolls along the neighborhood’s lakeside walking paths or indulging in a picnic at one of its many parks. Uptown has some of the most unique parks in the city including Wilson Avenue Skatepark with plenty of rails, curbs, spines and pyramids for showing off your inner daredevil. There’s also Montrose Harbor for off-pier fishing and Montrose Beach provides a serene spot to soak up some rays.

The residential pockets of Uptown are made up of landmark condos and apartment complexes, many of which have been converted into affordable housing. Recently this Chicago neighborhood has made way for newer condos and small-scale high-rises, but still remains one of the cheaper areas in the city. One bedroom lofts and condos start as low as $188,000 while single-family detached homes sell for about $800,000. And just like every other Chicago neighborhood, there are several stately properties listed in the millions.  

Interested in Uptown real estate? Uptown Restaurants & Bars
Uptown Resources Uptown Shopping
Uptown Entertainment Uptown Schools

Dining in Uptown

Joanne & Sons
1775 W Sunnyside Ave
Cuisine: American
Cafe Nhu Hoa
1020 W Argyle St
Cuisine: Asian
4936 N Broadway St
Cuisine: Asian
Hai Yen Restaurant
1055 W Argyle
Cuisine: Asian
Hing Wang
1111 W Wilson Ave
Cuisine: Asian
Nha Trang Restaurant
1007 W Argyle St
Cuisine: Asian
Uptown Pizza & Barbecue Rest
1031 W Wilson Ave
Cuisine: Barbecue/Pizza
Julie Mai's Le Bistro
5025 N Clark St
Cuisine: French
Andies Restaurant
1467 W Montrose Ave
Cuisine: Greek
3911 N Sheridan Rd
Cuisine: Middle Eastern
Silver Seafood
4829 N. Broadway
Cuisine: Seafood
Siam Cafe
4712 N Sheridan Rd
Cuisine: Asian

Resources in Uptown / Sheridan Park

Columbia Chicago Lakeshore
4840 N. Marine

Columbus Maryville Clinic
810 W. Montrose

Thorek Hospital
850 W. Irving Park
Post Office
1343 W. Irving Park

4850 N. Broadway

Entertainment in Uptown / Sheridan Park

Black Ensemble Theater
4520 N. Beacon
Riviera Theatre
4746 N. Racine
The Green Mill Jazz Club
4802 N. Broadway
Big Chicks
5042 N. Sheridan
Black Ensemble Theater
4520 N. Beacon St.
Chase Park
4701 N. Ashland
Frankie J's on Broadway / MethaDome Theatre
4437 N. Broadway
The Neo-Futurarium
5153 N. Ashland
O'Rourke Center for the Performing Arts
1145 W. Wilson
Profiles Theatre
4147 N. Broadway
Aragon Ballroom
1106 W. Lawrence
Holiday Club
4000 N. Sheridan
Lakeview Lounge
5110 N. Broadway
Old St. Andrew's Inn
5938 N. Broadway

Shopping in Uptown / Sheridan Park

Tai Nam Market
4925 N. Broadway
Wilson Broadway Mall
1114 W. Wilson
Universal Music & Entertainment
4423 N. Broadway
Beck's Book Store
4520 N. Broadway
Me Too Accessories
4541 N. Clark
Unique Findings
1218 W. Wilson

Schools in Uptown / Sheridan Park

Mc Cutcheon School-Branch
4850 N Kenmore Ave
1109 1/2 W Lawrence Ave
St Augustine College
1345 W Argyle St
Mc Cutcheon Elementary School
4865 N Sheridan Rd
Goudy Elementary School
5120 N Winthrop Ave
Jose Marti Bilingual Education
5126 N Kenmore Ave