320 E 21st St #809, Chicago, IL 60616
Property image
Property image
OFF MARKET

320 E 21st St #809
Chicago, IL 60616

South Loop
  • 2 Beds
  • 2 Baths
  • 850 sqft

$293,000

Trulia Estimate
as of Aug 23, 2026

$293,000

Trulia Estimate
as of Aug 23, 2026
  • 2 Beds
  • 2 Baths
  • 850 sqft

Home Highlights

Property Type
Apartment
Living Area
850 sqft
Price/Sqft
$345
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 320 E 21st St #809.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Beautiful Sunny Penthouse Corner Unit in the Historic Chess Records Building | South Loop Lakefront
Located in the iconic Chess Records Building, this stunning 2-bedroom, 2-bath penthouse corner unit offers an unbeatable prime South Loop lakefront location with incredible character and modern comfort.
Freshly professionally painted, this home features dramatic 13-foot ceilings, exposed brick walls, concrete ceilings, and oversized windows that flood the space with natural light. Both bedrooms are fully enclosed, including a spacious primary suite with two closets and a private attached bathroom featuring a separate shower and tub.
Luxury finishes include:
 Maple hardwood flooring throughout
 Updated kitchen with new granite countertops and stainless-steel appliances
 Two modern bathrooms
 In-unit washer and dryer
 Central air and heat
 Spacious private balcony with breathtaking views of Lake Michigan and McCormick Place
The building offers excellent amenities including secure entry, a rooftop deck, fitness room, and bike storage. Small pets are welcome (additional fee/deposit applies). This is a non-smoking unit and building.
Rent includes: water, gas, heat, A/C, and assigned heated garage parking.
Available: June 1, 2026
Minimum lease term: 12 months
Just steps from public transportation and minutes from all major expressways this is a rare opportunity to live in one of the South Loop's most historic and desirable buildings.
________________________________________

Minimum 12 month lease; All tenants ages 18 and over must complete an application which is $40 per person; 3 times or higher Income rent ratio; One month rent as security deposit.
Email for an application. Tenant pays for electric and optional cable/internet. Move-in FEES: One month security deposit. Move-in fees to HOA: $200 cost/$250 Deposit; same for move out. Small dog allowed: with/$50/month pet rent + $400 additional deposit and $100 non refundable HOA admin cost. No smoking in unit. Please note that the 2nd bedroom is lofted and open at the top to allow natural light.
320 E 21st St #809, Chicago, IL 60616 is a 2 bedroom, 2 bathroom, 850 sqft apartment in South Loop. It last sold for $218,000 on Feb 29, 2016 (7,686% above the $2,800 asking price). More recently, it was listed as a rental in April 2026 with an asking price of $2,800 per month. That rental listing was removed on May 4, 2026. It is currently off market. The Trulia Estimate is $293,000, with a rent estimate of $2,449/month.

Home Details for 320 E 21st St #809

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Interior Features

Appliances & Utilities
DishwasherDryerWasher
Heating & Cooling
Air ConditioningCooling System: Air Conditioner, Central Air
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Parking & Garage
Parking: Attached, On Site

Comparable Sales for 320 E 21st St #809

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1727 S Indiana Ave #116, Chicago, IL
0.30
Apartment
$220,000
11/03/25
1
1.5
1,150 sqft
1439 S Michigan Ave #405, Chicago, IL
0.62
Apartment
$367,500
07/09/26
2
1.5
1,200 sqft
1720 S Michigan Ave #2305, Chicago, IL
0.38
Apartment
$250,000
03/20/26
1
1
722 sqft
1440 S Wabash Ave #403, Chicago, IL
0.66
Apartment
$405,000
07/13/26
2
2
1,100 sqft
419 W Cermak Rd #2C, Chicago, IL
0.94
Apartment
$283,000
12/05/25
3
1.5
1,000 sqft
1305 S Michigan Ave #709, Chicago, IL
0.78
Apartment
$320,000
06/23/26
1
1
800 sqft
125 E 13th St #GU127, Chicago, IL
0.77
Apartment
$32,500
03/09/26
2
2
1,200 sqft
1115 S Plymouth Ct #109, Chicago, IL
1.12
Apartment
$231,500
11/03/25
2
3
1,400 sqft
1801 S Michigan Ave #402, Chicago, IL
0.29
Apartment
$249,900
05/28/26
1
1
-
1600 S Indiana Ave #1208, Chicago, IL
0.79
Apartment
$2,350
12/27/25
1
2
1,000 sqft
Home facts updated by county records

Nearby homes

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Around this home

Neighborhood Overview

South Loop
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about South Loop

At least 492 Trulia users voted on each feature.

  • 93 % Say there are sidewalks

  • 92 % Say it's dog friendly

  • 85 % Say it's walkable to restaurants

  • 80 % Say it's walkable to grocery stores

  • 79 % Say streets are well-lit

  • 65 % Say there's holiday spirit

  • 56 % Say kids play outside

  • 56 % Say people would walk alone at night

  • 55 % Say they plan to stay for at least 5 years

  • 50 % Say neighbors are friendly

  • 49 % Say parking is easy

  • 43 % Say car is needed

  • 42 % Say it's quiet

  • 39 % Say there are community events

  • 37 % Say yards are well-kept

  • 22 % Say there's wildlife

Sourced by Trulia users. Learn more about our methodology.
  • Bob
    "The people are all friendly and there is lots of diversity. The homes architecture is wonderful and a major attraction. The proximity to the lake, bike trails, sports, music and museums is so appealing."
    0
    Flag
  • Dejonee Oakley
    "Great place to live very good area nice people but Chicago is a city not a neighborhood so when you look at it as a whole then you will see it’s more than just that! "
    0
    Flag
  • F4fgwmv4n8
    "I’m in rural Alaska with no public transportation. Everyone has their means of transportation. If not, we have taxis. Commute is very short. "
    0
    Flag
  • Adrianalaurahernandez
    "I’ve lived in the neighborhood for 14 years. It feels like a small town community in the middle of the heart of the city."
    0
    Flag
  • Jordanhaye07
    "I’ve lived in the neighborhood for 4 years. It’s a great place to single,over 30 and under 50 people"
    1
    Flag
  • Trulia User
    "Bookfest lalapalooza skatepark volleyball and other fun stuff. Pizza time is great as well. The South Loop is just really neat."
    0
    Flag
  • Trulia User
    "This area is very low-key and quiet at times. Family oriented, as well as young professionals. Sense of community with the local businesses and soldier field being local"
    6
    Flag
  • Trulia User
    "Nice neighborhood and wonderful parks and lake front. Public transportation is abundant. Restaurants and grocery stores are close by as well. Colleges, and students abound. "
    2
    Flag
  • Trulia User
    "Little grass but tree spots that compensate for that. There are a lot of parks close by however that make up for not having grass everywhere. "
    2
    Flag
  • Trulia User
    "Good School system and decent neighborhood. Diverse for the most part. Would definitely stay here if I found another home. "
    1
    Flag
  • Trulia User
    "Roosevelt Station and bus service can get you anywhere in the city. I can get from my apartment to Midway in less than 30 minutes. "
    0
    Flag
  • Trulia User
    "I know some one that live in the Neighborhood And I’ve visited and everything seems to be pleasant high and quiet"
    0
    Flag
  • Trulia User
    "Neighborhood with a lot of beautiful real estate & high end shops along with essential commissaries & department stores."
    1
    Flag
  • Trulia User
    "They have a few doggie parks in and around the area. It’s been many people able to walk their dogs up and the down the streets! "
    1
    Flag
  • Trulia User
    "great place for walking your dog . dog park located on 14th & wabash. friendly community, city life, everything is walking distance "
    1
    Flag
  • Trulia User
    "It’s a very knit community, Great stores nice parks for your children everything‘s in walking distance, Awesome views of Lake Michigan"
    0
    Flag
  • Trulia User
    "Very dog friendly! Close proximity to dog parks, people pick up after their dogs, and lots of pet shops and veterinarians nearby."
    0
    Flag
  • Trulia User
    "Great people & food Amazing places to shop, I love the scenery I can look out my window and see the lakefront. & the Neighborhood as well police"
    0
    Flag
  • Trulia User
    "There are at least 1/2 dozen dog parks here and plenty of quiet streets with light traffic which makes it easy to walk dogs without worrying about cross traffic"
    0
    Flag
  • Trulia User
    "As long as you have a parking spot in the garage everything’s great closest soldier Field close to the shed aquarium bike paths very dog friendly for the most part I feel pretty safe"
    0
    Flag
  • Trulia User
    "It’s all concrete no grass or trees and dog poop everywhere. Heavy traffic all day and night. There is a vet on every other block though. "
    0
    Flag
  • Trulia User
    "Lots of parks nearby as well as good food and Resturant joints. Best is the access to grant park and high ways."
    0
    Flag
  • Trulia User
    "What’s not to like! If you want a more rural atmosphere then not here but the parks and local amenities are great!"
    0
    Flag
  • Trulia User
    "Lots of dogs and people out walking their dogs. Most of us have gotten to know each other over the years just by walking at the same time. "
    0
    Flag
  • Trulia User
    "It’s accessible, people are kind, there are great local spots and it gives you the feel of a city and a neighborhood at the same time"
    0
    Flag
  • Trulia User
    "The laSalle bank marathon, the stores and bars , close by the lake , Solderfeild, the hotels ,, having a police station in such a close proximity that the officer’s know the neighborhood."
    0
    Flag
  • Megan W.
    "My neighborhood is close to CTA lines, bike shares, and walkable to the loop. I’m able to walk to my office in the loop when the weather is nice"
    2
    Flag
  • Brikozlowski
    "the easiest commute I've ever had. just walk down Polk to the other entrance for Harrison red line stop. go north 4 stops and I'm at work! "
    0
    Flag
  • Efrain D.
    "I walk everywhere within the Loop, or bike if the weather is nice enough. Public transit is quite frequent and feels safe."
    1
    Flag
  • Brikozlowski
    "printers row literary fest, close to the loop and museums and the lake, easy to access, not overly crowded, not overly expensive "
    1
    Flag
  • DeVonte D. .
    "It’s a safe neighborhood and it’s a lot of places to shop at as fair grocery stores, and retail. Police is always patrolling the area. "
    0
    Flag
  • Trulia User
    "Festivals are done year round here in south loop. Book festivals, music festivals and live events at the millennium park."
    1
    Flag
  • Darnell G. J.
    "My commute is 5 mins on the orange line to the loop. Living close to the Roosevelt station, I have easy access to the red, orange and green lines making it easy to get anywhere in the city"
    0
    Flag
  • Jorge M.
    "Great neighborhood. And is currently evolving to be even better. More restaurants and stores appear all the time. Very close to all museums, parks and touristic attractions of the City. "
    0
    Flag
  • Rgazzimd
    "We are close to Lake Michigan, grant park and field museum. Friendly neighborhood.No better place to be! "
    1
    Flag
  • Bianca R.
    "Lots of soccer games and team sports for kids and adults at Kelly park. During the summer time McKinley park has the neighborhood pool open summer camp for kids. Pond for adults to take their kids fishing or even just for a nice walk around the park "
    1
    Flag
  • M5150v
    "The book fair is nothing short of amazing. The lake, skate park, Millennium park, simply beautiful incredible and full of amazing energy!"
    0
    Flag
  • Abigail C.
    "Love the south loop. So great for kids. Easy to get around with the train and bus. Dog friendly. Super cute!"
    0
    Flag
  • Kristyharvey13
    "There are lots of kids in our area. The parks are a great place for the kids to play. Our building works to welcome families and pets. "
    0
    Flag
  • Ndallensworth
    "I hardly see any kids in the neighborhood only 1 kid in my 50 unit building. There are playgrounds for children in the neighborhood. "
    0
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
May 4, 2026
Source: Zillow Rentals
ListingRemoved
$2,800
Apr 7, 2026
Source: Zillow Rentals
Listed For Rent
$2,800
Oct 14, 2024
Source: Zillow Rentals
ListingRemoved
$2,500
May 25, 2024
Source: Zillow Rentals
ListingRemoved
May 10, 2024
Source: Zillow Rentals
PriceChange
$2,500
Price decreased by 6%

Frequently asked questions about 320 E 21st St #809

  • What is 320 E 21st St #809 estimated to be worth?
    Trulia's estimated value for 320 E 21st St #809 in Chicago, IL is $293,000.
  • What is the price history for 320 E 21st St #809?
    320 E 21st St #809 in Chicago, IL last sold for $218,000 in February 2016.
  • Is Chicago a buyer's or seller's market?
    Chicago is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Chicago?
    The median sale price in Chicago is $384K. That is roughly unchanged from the prior month.
  • Does 320 E 21st St #809 have air conditioning?
    Yes, 320 E 21st St #809 in Chicago, IL has air conditioning.
  • Does 320 E 21st St #809 have laundry facilities?
    Yes, 320 E 21st St #809 in Chicago, IL has in-unit laundry.

Homes for rent near 320 E 21st St #809

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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