Which are the best luxury, amenity-packed apartment buildings in Chicago?

I've only been to a few but The Sinclair is pretty good

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Apartments for Rent in Chicago, IL

2,649 rentals available

5350-5358 S. Maryland Avenue
$1,900
5350-5358 South Maryland Avenue, Chicago, IL 60615
(773) 831-4402
2 units available
2 bed • 3 bed
Amenities
On-site laundry, Hardwood floors, Dishwasher, Pet friendly, Recently renovated, Bike storage + more
Pet-Friendly Haven
Walkable charm in vibrant and historic location
Nestled in Chicago's vibrant South Side, 5350-5358 S. Maryland Avenue offers an attractive location in a pet-friendly neighborhood. The area is known for its historical charm, with Washington Park just a short stroll away, providing excellent opportunities for outdoor leisure. Residents laud the convenient transport links and walkable access to dining and shopping options.
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5118 S. Greenwood
$3,750
5118-5120 South Greenwood Avenue, Chicago, IL 60615
(773) 570-2321
1 unit available
4 bed
Amenities
In unit laundry, Patio / balcony, Hardwood floors, Dishwasher, Pet friendly, Parking + more
Architectural Charm
Unique design, walkable neighborhood, pet-friendly lifestyle.
5118 S. Greenwood stands out with its Arts and Crafts architecture, featuring a charming Mission-style rooftop. Residents love the expansive bay windows offering views of Sycamore Park, and the street's walkable neighborhood includes convenient restaurants and public transport. Cats and dogs are welcome, making it a delightful choice for pet owners.
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The Blackwood
$1,760
5200 South Blackstone Avenue, Chicago, IL 60615
(773) 825-6910
8 units available
1 bed • 2 bed
Amenities
In unit laundry, Granite counters, Hardwood floors, Dishwasher, Pet friendly, Parking + more
Historic Elegance
Luxurious living in vibrant Hyde Park neighborhood
The Blackwood boasts a unique blend of Art Deco charm and modern convenience, perfectly situated in the bustling heart of Hyde Park. Delight in exquisite amenities like in-unit laundry, a 24-hour gym, and plush resident lounge. Cats and dogs are welcome, adding to the appeal of these beautifully renovated apartments in a sought-after area.
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5401-5403 S. Woodlawn Avenue
$3,195
5401 South Woodlawn Avenue, Chicago, IL 60615
(773) 570-2681
1 unit available
3 bed
Amenities
In unit laundry, Hardwood floors, Pet friendly, Recently renovated, Range, and Oven
Prime Location
Minutes from Lake Michigan and Washington Park
Experience luxurious urban living at this prime South Side location. Minutes from Lake Michigan and Washington Park, residents enjoy easy access to outdoor activities and scenic views. The building's charming architectural details and top-notch amenities, including hardwood floors and in-unit laundry, create an inviting home environment. Professional management adds to the excellence, ensuring resident satisfaction and comfort.
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5535 S Kimbark
$2,295
5535 South Kimbark Avenue, Chicago, IL 60637
(773) 492-8336
2 units available
2 bed
Amenities
On-site laundry, Hardwood floors, Pet friendly, Gym, Air conditioning, Playground + more
Historic Charm
Prime spot in vibrant Hyde Park neighborhood
Located in the lively Hyde Park, 5535 S. Kimbark offers easy access to a thriving community rich with history and modern conveniences. Residents appreciate the excellent public transport links, making commuting a breeze, and the managing team's responsiveness ensures a seamless living experience. And with a vibrant community atmosphere, it’s an ideal spot for those who value both history and modernity.
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Woodlawn Terrace
$1,175
4726 South Woodlawn Avenue, Chicago, IL 60615
(773) 974-6062
4 units available
Studio • 2 bed
Amenities
On-site laundry, Patio / balcony, Hardwood floors, Dishwasher, Pet friendly, 24hr maintenance + more
Hyde Park
Charming Hyde Park retreat with vibrant community features.
Woodlawn Terrace in popular South Side offers a charming retreat with award-winning courtyard gardens. Residents are delighted by the property's tranquility, alongside the vibrant Hyde Park community offerings. Conveniently positioned, this location allows easy access to essential amenities, ensuring a smoothly integrated lifestyle.
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The Pepperland
$2,445
1509-1517 East 57th Street, Chicago, IL 60637
(773) 570-7757
1 unit available
3 bed
Amenities
On-site laundry, Hardwood floors, Pet friendly, and Bike storage
Vibrant Locale
Eclectic charm in a lively, pet-friendly community.
The Pepperland is nestled in a vibrant neighborhood on Chicago's South Side, celebrated for its eclectic mix of architecture and design. Enjoy the airy interiors with unique bay windows and the convenience of nearby Jackson Park and Lake Shore Drive. Residents love the location's walkability, proximity to dining and shopping, and the warm community vibe.
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5415 S. Woodlawn Avenue
$1,795
5415 South Woodlawn Avenue, Chicago, IL 60615
(773) 985-1080
1 unit available
1 bed
Amenities
On-site laundry, Hardwood floors, Pet friendly, Bike storage, Courtyard, and Range
Prime Location
Charming design near University and Park.
Experience the charm of 5415 S. Woodlawn Avenue with its remarkable design and prime location on Chicago's South Side. Enjoy the ease of access to the University of Chicago and the stroll through Washington Park. Residents appreciate the delightful features like convenient on-site laundry, bike storage, and the welcoming pet policy that includes dogs and cats.
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5528-5532 S. Everett Avenue
$1,175
5528-5532 South Everett Avenue, Chicago, IL 60637
(773) 364-6412
1 unit available
Studio
Amenities
On-site laundry, Patio / balcony, Hardwood floors, Pet friendly, Bike storage, and Range
Pet Haven
Convenient access to Lake Michigan and vibrant locales.
Nestled in the historic South Side, this vibrant property offers quick access to Lake Michigan and excellent public transit, making commuting a breeze. With a variety of restaurants and cafes just around the corner, enjoy the urban lifestyle paired with a peaceful environment. The building welcomes all pets, ensuring that every family member is accommodated.
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4859 S. Champlain Avenue
$1,750
4851-59 South Champlain Avenue, Chicago, IL 60615
(773) 980-9931
1 unit available
2 bed
Amenities
On-site laundry, Patio / balcony, Hardwood floors, Pet friendly, Recently renovated, Walk in closets + more
Architectural Charm
Unique charm with easy city access.
This property on South Champlain Avenue boasts stunning early 20th-century architectural details, including hand-laid mosaic floors and carved-wood banisters. Residents enjoy bright, updated interiors complemented by large windows that illuminate with natural light. The community is a welcoming space for cat owners, and access to public transportation makes city commuting a breeze.
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5405-5407 S. Woodlawn Avenue
$1,399
5405-5407 South Woodlawn Avenue, Chicago, IL 60615
(240) 434-0195
3 units available
Studio
Amenities
On-site laundry, Hardwood floors, Pet friendly, Parking, Range, and Oven
Prime Location
Charming property near Hyde Park attractions.
Discover a beautifully renovated gem in Chicago's vibrant South Side. This pet-friendly property, nestled in a popular neighborhood, offers cats a place to call home. Enjoy being steps away from Hyde Park’s cultural treasures and walking distance to Washington Park for easy, tranquil strolls.
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Windermere House
$1,920
1642 East 56th Street, Chicago, IL 60637
(773) 825-5020
11 units available
Studio • 1 bed • 2 bed • 3 bed
Amenities
On-site laundry, Hardwood floors, Dishwasher, Pet friendly, Parking, Recently renovated + more
Historic Elegance
Classic charm with modern amenities and prime location.
Windermere House combines historic charm with contemporary living. Nestled in a popular neighborhood on Chicago's South Side, this residence is within walking distance of the University of Chicago and offers easy access to local dining and shopping options. With practical conveniences like a gym and in-unit laundry, plus the welcoming staff highlighted in reviews, residents enjoy a balanced lifestyle.
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5335-5345 S. Kimbark Ave.
$2,995
5335 South Kimbark Avenue, Chicago, IL 60615
(773) 673-9799
3 units available
3 bed • 4 bed
Amenities
On-site laundry, Patio / balcony, Hardwood floors, Pet friendly, Recently renovated, and Basketball court
Prime Location
Enviable spot in vibrant neighborhood near parks and eateries.
Situated in a popular South Side neighborhood, this property offers proximity to numerous parks and a vibrant dining scene along 53rd Street. Residents can enjoy modern comforts with hardwood floors, renovated spaces, and spacious porches. Plus, it's pet-friendly, welcoming both cats and dogs.
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5222-38 S. Drexel Avenue
$1,600
5222 South Drexel Avenue, Chicago, IL 60615
(773) 985-8999
5 units available
1 bed • 2 bed • 3 bed
Amenities
On-site laundry, Hardwood floors, Pet friendly, Recently renovated, Gym, Air conditioning + more
Ideal Location
Comfort and convenience in vibrant Hyde Park.
Located in the vibrant South Side of Chicago, this property offers tenants a comfortable and convenient living experience. With proximity to the University of Chicago and easy access to public transportation, commuting is a breeze. The building boasts top-notch amenities, including a fitness center, a clubhouse, and positive community vibes bolstered by efficient management.
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5300-5308 S. Hyde Park Boulevard
$1,390
5300-5308 South Hyde Park Boulevard, Chicago, IL 60615
(773) 326-1546
2 units available
1 bed • 2 bed
Amenities
On-site laundry, Hardwood floors, Pet friendly, Parking, Recently renovated, and Bike storage
Elegant Design
Lake views and a vibrant community.
Nestled in the historically rich South Side neighborhood of Chicago, this property offers breathtaking views of Lake Michigan and an elegantly designed facade. Residents love the recently renovated apartments with beautiful hardwood floors and the warm, welcoming community atmosphere. Dog and cat owners will cherish the pet-friendly policies, ensuring comfort for all members of the family.
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Aspire Residences
$2,170
2111 South Wabash Avenue, Chicago, IL 60616
(508) 474-8389
Rent Savings
10 units available
1 bed • 3 bed
Amenities
In unit laundry, Golf room, Patio / balcony, Granite counters, Hardwood floors, Dishwasher + more
Urban Luxury
Luxurious living in vibrant Chicago South Loop.
Aspire Residences offers luxurious living with sweeping city views, sophisticated amenities, and a vibrant urban location. Enjoy a modern lifestyle with a resort-style pool, a top-tier fitness center, and pet-friendly spaces. Residents praise the stylish interiors and excellent management team.
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The average rent for a 1 bedroom apartment in Chicago is $2,260+, while the average rent for a 2 bedroom apartment is $2,808+. Rent rates updated 4 days ago

Studio: $1,898+Trending up
1 Bed: $2,260+Trending up
2 Beds: $2,808+Trending up
3+ Beds: $3,544+Trending up

* Averages are based on the rental prices of properties listed on Apartment List that don’t include fees

Top neighborhoods in Chicago

Downtown Chicago
View 171 listings
What it’s like to live in Downtown Chicago
Skyline energy pulses through The Loop's canyon-like streets. Renters in converted office towers enjoy rooftop pools but face 2AM garbage truck noise. Winter wind tunnels off Lake Michigan test cold tolerance.
Great for
Young Professionals
Tech Workers
Nightlife Enthusiasts
Commuters
Investors
Neighborhood vibe
Urban
Bustling
Walkable
View 171 listings
Northwest Side
View 158 listings
What it’s like to live in Northwest Side
Family-friendly character defines Chicago's Northwest Side, where communities like Portage Park and Jefferson Park maintain authentic neighborhood identity with European influences throughout. Rental options include bungalows, two-flats, and apartment buildings with more space than similarly priced properties in trendier districts. While the area offers excellent access to both O'Hare Airport and the Blue Line to downtown, the residential character means fewer entertainment options within walking distance despite good transportation connections. Well-suited for families, city employees, and professionals seeking genuine Chicago neighborhoods with more space and parking who don't require extensive nightlife options beyond local taverns and restaurants with established community character.
Great for
Working-Class Residents
First-Time Renters
Investors
Commuters
Neighborhood vibe
Mixed-Use
Peaceful
Mixed-Use & Commercial
View 158 listings
Far Southeast Side
View 142 listings
What it’s like to live in Far Southeast Side
Far Southeast Side offers significantly more affordable housing options than northern or central Chicago neighborhoods. Many homes feature surprisingly large lots with actual yards – a rarity in much of Chicago. While downtown commutes require longer transit times and some commercial areas need investment, residents enjoy genuine community connection, substantially more living space, and excellent access to Lake Michigan beaches with less crowding than northside shorelines.
Great for
Working-Class Residents
First-Time Renters
Investors
Commuters
Neighborhood vibe
Mixed-Use
Peaceful
Mixed-Use & Commercial
View 142 listings

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Finding Apartments for Rent in Chicago, Illinois

Chicago is a vibrant city filled with must-see attractions. From visiting Millennium Park's "Bean" sculpture to walking the scenic Lakefront Trail, there's no shortage of entertaining activities in the Windy City.

Whether you’re a first-time renter moving to one of Chicago’s many affordable neighborhoods or a long-time resident trading up to a downtown Chicago apartment with a lake view, search for your new home with Apartment List. With so many rentals in Chicago to choose from, you need a better apartment-hunting strategy than Googling “apartments for rent near me.”

Start by taking our quiz, and let our AI-powered algorithm find your dream Chicago apartment. The search function considers multiple factors to showcase the ideal apartments in Chicago, including neighborhood preferences and public transit access.

With just a few clicks, you’ll find the perfect apartment rentals in Chicago, Illinois.

FAQs answered by renters in Chicago, IL

Which are the best luxury, amenity-packed apartment buildings in Chicago?
Wolf Point West and East
Answered on Feb 22, 2025 by Ellyse H.
westmore apartment
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Apartments for Rent in Chicago, IL

Average rent in Chicago, Illinois

Top neighborhoods in Chicago

Downtown Chicago

What it’s like to live in Downtown Chicago

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Northwest Side

What it’s like to live in Northwest Side

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Far Southeast Side

What it’s like to live in Far Southeast Side

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Finding Apartments for Rent in Chicago, Illinois

FAQs answered by renters in Chicago, IL

Which are the best luxury, amenity-packed apartment buildings in Chicago?