Overview
Listings
Map
Lifestyle
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Demographics
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LUXESQUIRE

Uptown
Chicago's original entertainment district. Reborn.

THE NEIGHBORHOOD STORY

Uptown is one of Chicago's most fascinating neighborhoods — a community with a Golden Age entertainment heritage (the Aragon Ballroom, the Green Mill, the Riviera Theatre all date to the 1920s when Uptown was Chicago's most glamorous destination) and a contemporary identity that is simultaneously diverse, evolving, and genuinely interesting. The neighborhood's architectural legacy — large courtyard buildings, grand theatres, and commercial buildings from the Jazz Age — creates a physical environment of unusual grandeur.

WHY RESIDENTS LOVE IT

•   Green Mill CocktailLounge — Al Capone's favorite bar still operates, serving jazz and cocktails inan irreplaceable atmospheric setting.

•   Aragon Ballroom — thelegendary 1926 ballroom continues as a concert venue and remainsarchitecturally extraordinary.

•   Immediate Lake Michiganaccess — Montrose Beach and the Lakefront Trail are neighborhood amenities.

•   Red Line access —multiple stops provide direct downtown connectivity.

•   Architectural grandeur —Uptown's 1920s commercial and residential buildings are among the North Side'smost visually impressive.

•   Price point opportunity— Uptown remains more affordable than Lakeview and Edgewater with comparablelakefront proximity.

HOMES & ARCHITECTURE

Uptown's housing stock is defined by the scale of its Jazz Age courtyard buildings — grand limestone and brick multi-unit structures from the 1910s-1930s with formal entries, shared courtyards, and architectural details that reflect a period of genuine ambition in apartment design. High-rise residential towers from the mid-century period add density along the lakefront corridor.

PROPERTY TYPES AT A GLANCE

Property Type Description
Jazz Age Courtyard Buildings The neighborhood's most distinctive residential type — grand 1920s-30s multi-unit buildings with architectural character.
Lakefront High-Rise Condominiums Mid-century towers with lake views along the Sheridan Road corridor.
Vintage Two-Flats & Three-Flats Classic Chicago residential stock with strong rental demand from the neighborhood's diverse population.
New Construction Condominiums Infill development responding to sustained demand from buyers pursuing the neighborhood's trajectory.

POCKETS & DISTRICTS

Pocket / District Character & Vibe
Argyle Street/Asian District Cultural vibrancy, excellent dining, community identity rooted in Southeast Asian heritage
Broadway Corridor Entertainment heritage, commercial activity, active redevelopment
Sheridan/Lakefront Premium lakefront positioning, highest values, best lake access

HOW TO MOVE AROUND

Red Line at Wilson, Sheridan, and Argyle stations. Multiple bus routes. Lakefront Trail access at Montrose Beach. Local Tip: The Wilson station is undergoing a major renovation — when complete, it will be the best-equipped transit station on the North Side. The surrounding real estate already reflects awareness of this improvement.

DINING & NIGHTLIFE

Fine Dining

•   TAC Quick ThaiKitchen — Acclaimed Thai restaurantthat is a destination from across the city

•   Demera EthiopianRestaurant — One of Chicago's mostcelebrated Ethiopian restaurants, anchoring the neighborhood's diverse culinaryscene

Casual & Neighborhood Favorites

•   Argyle Street diningcorridor — A concentration ofauthentic Vietnamese, Thai, and Chinese restaurants that draws diners fromacross Chicago

Late Night

•   Green Mill Jazz Club — Live jazz until 4 a.m. — one of Chicago's mostbeloved nightlife institutions

GREEN SPACE & OUTDOORS

•   Montrose Beach — One of Chicago's most beloved beaches — a widesandy expanse with a dog beach and the Montrose Point bird sanctuary

•   Montrose Point BirdSanctuary — A remarkable urban naturepreserve that is one of the best birding locations in the Midwest

•   Lakefront Trail — Connects through the neighborhood, linking MontroseBeach to beaches north and south

Uptown Signature Listings

For Sele

$2,500,000

654 Ocean Dr, Miami, FL 33101

4 BA
5 BD
MLS# 345678
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Active Under Contract

$950,000

321 Trendy Blvd, Chicago, IL 60601

1 BA
1 BD
MLS# 210987
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Active Under Contract

$450,000

789 Rustic Rd, Austin, TX 73301

1 BA
2 BD
MLS# 789012
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Active Under Contract

$850,000

456 Elegant Ave, Los Angeles, CA 90001

3 BA
4 BD
MLS# 654321
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For Sale

$1,200,000

123 Luxury St, New York, NY 10001

2 BA
3 BD
MLS# 123456
Explore All Lincoln Park Homes

Lifestyle & Points of Interest

01
Dining
02
Coffee
03
Grocery
04
Bars / Nightlife
05
Fitness
06
Parks
08
Schools
07
Dog Parks
09
Hospitals
10
Transit
Dining
Coffee
Grocery
Bars / Nightlife
Fitness
Parks
Schools
Dog Parks
Hospitals
Transit

EDUCATION LANDSCAPE

School Type Grades Notes
Uplift High School CPS Public 9-12 Community high school with specialized programs
Stewart Elementary CPS Public PK-8 Neighborhood elementary school
Senn High School CPS Public 9-12 Comprehensive high school with IB program serving the broader Far North Side
High School
Mixed Schools
type
Name
Category
Grades
School rating
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
Private
9th - 12th
1/5
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5
type
Name
Category
Grades
School rating
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5

WHO LIVES HERE

Population Median Age Avg. Household Income
52,000 33 $68,000
Population Density Gender Split Education
Very High 49% Male / 51% Female 48% Bachelor's or higher
High School
Mixed Schools
type
Name
Category
Grades
School rating
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
Private
9th - 12th
1/5
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5
type
Name
Category
Grades
School rating
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5

WALKABILITY & ACCESS SCORES

88
Walk
Walk Score
76
Bike
Bike Score
80
Transit
Transit Score

THE LUXESQUIRE INSIDER TAKE

Uptown is where Chicago's most interesting next chapter is being written. The architectural bones — the Aragon, the Green Mill, the Jazz Age courtyard buildings — are extraordinary. The lakefront is right there. The Red Line is excellent. And the price point still reflects enough uncertainty about the trajectory that genuine value exists. The buyers who arrive before the trajectory is universally recognized will be pleased with how this reads in ten years.

Get in Touch

Have questions or want to book a tour? Contact us today and our team will guide you every step of the way.

Contact Us

A Chicago luxury real estate brokerage guided by Realtor-Lawyers.

Strategic. Discreet. White-Glove.

Contact

122 S Michigan Ave, Suite 1390
Chicago, IL 60603

Phone:

312.912.7262

Fax:

312.912.7255

Email:

info@luxesquire.com
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