Apartments in Woodlawn Chicago

151 - 180 of 415 Results
15
3D Tour
$1,950 - 1,999
1018 E 54Th St Chicago, IL
2 BR | Jun. 19, 2026
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Dog Friendly
Cat Friendly
Virtual Tour
Balcony/Deck/Patio
Hyde Park
15
3D Tour
$1,285 - 2,050
5337 S Hyde Park Blvd Chicago, IL
Studio - 2 BR | Jun. 30, 2026
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Dog Friendly
Cat Friendly
Virtual Tour
In Unit Laundry
Hyde Park
16
3D Tour
$1,180 - 1,375
5336 5338 S. Hyde Park Blvd. Chicago, IL
Studio - 1 BR | Jul. 12, 2026
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Dog Friendly
Cat Friendly
Virtual Tour
Storage
Fireplace
20
$1,245
1367 E. 53rd, Unit A803 Chicago, IL
Studio | Available Now
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Heat Included
Cat Friendly
Storage
Hyde Park
$1,250
1367 E. 53rd, Unit A012 Chicago, IL
Studio | Available Now
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Heat Included
Cat Friendly
Storage
Hyde Park
11
$1,300
Chicago, IL
2 BR | Available Now
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South Shore
8
$1,200
Chicago, IL
1 BR | Available Now
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Hyde Park
20
$1,250 - 1,400
Chicago, IL
2 - 3 BR | Available Now
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Heat Included
Covered Parking
South Shore
21
$1,830 - 4,150
5326 5336 S. Greenwood Avenue Chicago, IL
1 - 4 BR | Jun. 11, 2026
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Dog Friendly
Cat Friendly
In Unit Laundry
Storage
Dishwasher
17
3D Tour
$2,395 - 3,095
5325 S. Hyde Park Boulevard Chicago, IL
2 - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Virtual Tour
Air Conditioning
Hyde Park
1
$1,395
6929 S. Paxton, Unit F-4 Chicago, IL
2 BR | Available Now
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Cat Friendly
Surface Parking
Storage
South Shore
1
$1,686
Chicago, IL
2 BR | Available Now
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Surface Parking
Storage
South Shore
12
$1,899 - 2,325
5400 5406 S. Maryland Avenue Chicago, IL
2 - 4 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Dishwasher
Hyde Park
1
$1,395
6929 S. Paxton, Unit R-5 Chicago, IL
2 BR | Available Now
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Cat Friendly
Storage
South Shore
36
$1,999 - 2,395
5400 5408 S. Ingleside Chicago, IL
1 - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Dishwasher
Hyde Park
37
$2,175 - 3,335
5237 5245 S. Kenwood Avenue Chicago, IL
2 - 4 BR | May. 23, 2026
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Dog Friendly
Cat Friendly
In Unit Laundry
Balcony/Deck/Patio
Hyde Park
25
$1,980 - 2,090
1350 E 53rd Chicago, IL
2 BR | Jul. 16, 2026
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Dog Friendly
Cat Friendly
In Unit Laundry
Balcony/Deck/Patio
Storage
6
$1,175 - 1,658
5254 S. Dorchester Ave. Chicago, IL
Studio - 1 BR | Available Now
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Cat Friendly
Luxury
Section 8
Air Conditioning
Fitness Center
14
$2,265 - 2,660
1330 E 53rd St Chicago, IL
Studio - 1 BR | Jul. 11, 2026
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Air Conditioning
In Unit Laundry
Fitness Center
Disability Access
Dishwasher
52
3D Tour
$1,975 - 2,399
5401 5409 S. Cottage Grove Avenue Chicago, IL
2 - 3 BR | Jul. 13, 2026
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Dog Friendly
Cat Friendly
Virtual Tour
Air Conditioning
Dishwasher
40
$1,950
Chicago, IL
1 BR | Jun. 1, 2026
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Air Conditioning
In Unit Laundry
Dishwasher
Hyde Park
2
$1,860
7144 S Jeffery Blvd Chicago, IL
3 BR | Ask for Availability
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Surface Parking
Storage
South Shore
8
$1,800
Chicago, IL
3 BR | Available Now
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South Shore
19
3D Tour
$1,899 - 2,099
5350 5358 S. Maryland Chicago, IL
2 BR | Available Now
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Dog Friendly
Cat Friendly
Virtual Tour
Dishwasher
Hyde Park
48
$1,240 - 1,850
5300 5308 S. Hyde Park Boulevard Chicago, IL
Studio - 2 BR | Jun. 27, 2026
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Dog Friendly
Cat Friendly
Hyde Park
48
$1,550 - 2,899
5320 5326.5 S. Drexel Boulevard Chicago, IL
1 - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Storage
Dishwasher
Hyde Park
34
$1,690 - 2,400
5307 South Hyde Park Boulevard Chicago, IL
Studio - 2 BR | Available Now
Contact
Dog Friendly
Cat Friendly
Air Conditioning
In Unit Laundry
Balcony/Deck/Patio
1
$1,686 - 1,860
7147 S Jeffery Blvd Chicago, IL
2 BR | Available Now
Contact
Surface Parking
Storage
South Shore
1
$1,100
6747 S Oglesby Ave Chicago, IL
1 BR | Available Now
Storage
Disability Access
South Shore
15
3D Tour
$1,795 - 1,995
5355 5361 S. Cottage Grove Chicago, IL
2 - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Virtual Tour
Air Conditioning
Dishwasher
151 - 180 of 415 Results
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Chicago:
May Rent Report

Welcome to the May 2026 Chicago Apartment Report. In this assessment of the local rental market, Rentable data scientists and rental experts break down the May 2026 key findings and figures for the Chicago rental landscape.

Our experts analyze the pricing trends — one-bedroom, two-bedroom, year-over-year and month-over-month — in Chicago and surrounding areas and provide comparisons to the entire metro area, nearby cities and some of the most desirable and expensive cities in the United States. Take a look at the last 12 months of Chicago average rent prices in the chart below.

Monthly Rent Report

$2,150
$1,610
$1,080
$540
$0
Jun. 2025
Jul. 2025
Aug. 2025
Sep. 2025
Oct. 2025
Nov. 2025
Dec. 2025
Jan. 2026
Feb. 2026
Mar. 2026
Apr. 2026
May. 2026
1 BR       2 BR

Chicago Rent Prices Decrease From April to May

Chicago rent prices decreased over the last month. From April to May, the city experienced a 0% decrease for the price of a one-bedroom apartment. The rent price for a Chicago one-bedroom apartments currently stands at $.

When we take a look at the two-bedroom comparison from April to May, Chicago experienced a 0% decrease for the price of a two-bedroom apartment. The rent price for a Chicago two-bedroom apartments currently stands at $.

May Prices: Chicago vs. Surrounding Areas

Rent Prices in Chicago and Surrounding Areas

Rent prices have decreased in Chicago over the last month. But how have the surrounding areas fared when it comes to the recent volatility in apartment prices? Rent prices in 0 of the Chicago suburbs increased last month. On the other hand, 0 local areas experienced a decrease in the price of a one-bedroom apartment.

More key findings include:

  • Rents did not increase in any of the Chicago suburbs

  • Rents did not decrease in any of the Chicago suburbs.

May 2026 Pricing Trends: Chicago vs. National Comparisons

Chicago Rent Prices More Affordable Than Major Cities

Rent growth in Chicago over the past year has been declining. When compared to major cities nearby, along with some of the most expensive cities in the country, Chicago average rent prices appear to be relatively affordable for local residents.

The price for a Chicago one-bedroom apartment remains vastly more affordable than four of the largest cities in the United States — New York City, Washington, D.C. San Francisco and Los Angeles. And pricing compares quite similarly to nearby Midwest cities.

For more information about Chicago and surrounding area rent prices, take a look at the complete data set below.

Data set for Chicago and suburbs

1 BR May 1 BR M/M % Change 2 BR May 2 BR M/M % Change

Methodology

Each month, using over 1 million Rentable listings across the United States, we calculate the median 1-bedroom and 2-bedroom rent prices by city, state, and nation, and track the month-over-month percent change. To avoid small sample sizes, we restrict the analysis for our reports to cities meeting minimum population and property count thresholds.