About Uptown

A surprisingly affordable pocket of Chicago’s North Side, Uptown has a reputation as a laid-back entertainment destination where homeowners can get a lot of square footage for their money. Located conveniently alongside the Red Line train, Uptown offers easy access to downtown while still maintaining its quiet neighborhood charm and local flavor. Uptown’s historic music venues, once the preferred hangouts of famous gangsters like Al Capone and John Dillinger, are still maintained by a community determined to protect the neighborhood’s intriguing identity.

Quick Facts

Current Prices: $94,900 to $3,650,000

Closed Prices: $59,900 to $1,500,000

Median Sale Price: $322,500

Average $ per sq ft: $204

Association Fee Ranges: $0, $35 to $2269/mo

Type: Attached Home (Condo, Townhouse, Loft, etc.), Single-Family Home

Age: 1889 to 2022

Sq. Ft.: 1 to 6555 Sq. Ft.

Bedrooms: 0 to 7 Bedrooms

Bathrooms: 1 to 6 Bathrooms

Around Uptown

From homes to entertainment, Uptown screams affordability, especially when taken into the context of the North Side. Featuring a wide range of home styles, the neighborhood mostly offers townhomes and mid-rise condos, with a few single-family homes sprinkled in. Closer towards the lake are newer condo units, offering a more luxurious side of Uptown. If you are looking for lakeside living at an attainable price, look no further than Uptown.

The main transportation hubs of Uptown are the two Red Line stations at Lawrence Avenue and Wilson Drive. This line runs north/south along the coast of Lake Michigan and will take you (almost) anywhere in Chicago. There are bus routes running east/west on Foster Avenue and Lawrence Avenue that will carry you to the beach or nearby Ravenswood. If you need to travel Downtown, hop on a north/south route along Marine Drive, Sheridan Road, North Broadway, or Clark Street. Close proximity to Lake Shore Drive makes traveling by car a breeze (but actually, look out for those high winds rolling off the lake) and parking is relatively easy to come by this far north.

The southernmost portion of Uptown has a decidedly urban feel, with vintage penthouses offering plenty of space and modern condominiums integrated with shopping districts and corner stores. Further north, near Andersonville, the neighborhood has a slightly more suburban feel with fenced-in yards, spacious gardens, and plenty of street parking. A variety of Vietnamese, Thai, and Chinese establishments can be found in the northeast section of Uptown, known as Asia on Argyle. The Red Line train cuts through the center of the neighborhood, stopping at Argyle, Lawrence, and Wilson. Residents living further east are within walking distance of lakeside amenities such as the Lakefront Trail and Montrose Beach.

With Uptown's rich history as an immigrant neighborhood and cultural melting pot, inhabitants of this area can experience cuisines from all over the world. The Asia on Argyle district offers plenty of spots to get a great bowl of pho — start with Tank Noodle — and the Peking duck at Sun Wah BBQ is a culinary adventure you’ll remember fondly. Further south on Broadway Street, Demera serves up some of the finest Ethiopian cuisine that you’ll find in Chicago. Old-school diners and late-night Mexican restaurants also abound, and thanks to Uptown’s working-class sensibility, you won't break the bank heading out for a bite to eat.

With affordably priced housing and quiet residential areas, Uptown is an ideal spot for everyone from families to college students to artists. The neighborhood’s historic venues still host some of the biggest names in music, so expect to see fans lining up outside the Riviera Theatre, Aragon Ballroom, and Green Mill. Near the lake, you’ll find Uptown’s residents taking a quiet respite from the city with a walk through the park or perhaps taking a furry friend to Montrose Dog Beach.

Uptown’s entertainment district is known far and wide as a guaranteed good time. Party with your favorite rapper while they’re in town performing at the Aragon Ballroom or rock out to your favorite band at the Riviera Theatre. For a more mellow night, grab a drink at the famous Green Mill Cocktail Lounge and listen to world-class jazz musicians play in an intimate setting.

Meet some friends at Montrose Beach for a pickup game of beach volleyball followed by a picnic by the lake. Let the local bike shop give your bike a tune-up while you rest at a coffee shop, then hit the Lakefront Trail to take in views of Lake Michigan. Head west to explore Graceland Cemetery, where visitors from all over come to pay their respects to some of Chicago's most famous residents.

Locals Love

  • Spacious apartments and homes at a reasonable price
  • Representation of cultures from all over the world
  • Easy to find and often free street parking
  • Convenient access to public transit

Locals Don't Love

  • The lack of neighborly interaction in some pockets of Uptown
  • Shopping options are few and far between
  • Closed storefronts dotting main stretches of the neighborhood

Neighborhood Reviews

3 Reviews

Low-key Awesome

Riley U
I moved to the north end of Uptown last summer and I think it's an underrated Chicago neighborhood that doesn't get a lot of hype. On foot or by bike, I can reach awesome restaurants and shops in the Asia on Argyle area or in Andersonville. The red line is also easily accessible, and between the Green Mill, Aragon, and Riviera, you can always catch some live music when you're in the mood. More than anything, I like how friendly and easygoing the community is. Some parts of the neighborhood could still use some love, but overall, Uptown offers an experience that feels very Chicago without the intensity and high price tags of Downtown or Lincoln Park.

The definition of "up and coming"

Samantha R
While there are certain areas of Uptown where I wouldn't be psyched to walk around alone at night, it's really an up and coming area. Tons of new businesses are moving in and the homes are the right price to buy now and reap the benefits of your foresight later.

Uptown Funk You Up

Brandon O
I have lived in the Uptown area for two-and-a-half years now and I would definitely recommend it. Uptown is up and coming and perfect for any families or young professionals, although act quick because the neighborhood is up and coming. There is plenty to do within walking distance from the beach to great music venues. The streets are tree-lined and give you that out of city feel while still maintaining an urban vibe.
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