Apartments in Woodlawn Chicago

271 - 300 of 375 Results
6
3D Tour
$4,095
1154 56 St Chicago, IL
2 BR | Available Now
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Dog Friendly
Cat Friendly
Virtual Tour
Air Conditioning
In Unit Laundry
1
$1,495
7219 S Yates Blvd Chicago, IL
2 BR | Available Now
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House
Storage
South Shore
1
$1,350
Chicago, IL
1 BR | Available Now
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Dog Friendly
Cat Friendly
House
South Shore
8
$1,325
Chicago, IL
1 BR | Available Now
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Dog Friendly
Cat Friendly
House
South Shore
9
$1,395
Chicago, IL
1 BR | Available Now
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Dog Friendly
Cat Friendly
House
South Shore
1
$1,686
Chicago, IL
2 BR | Available Now
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Disability Access
South Shore
20
$1,495 - 1,550
Chicago, IL
1 - 2 BR | Available Now
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Dog Friendly
Cat Friendly
House
South Shore
1
$1,350 - 1,400
Chicago, IL
2 BR | Available Now
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Grand Crossing
21
$750
Chicago, IL
Studio | Available Now
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Heat Included
Washington Park
6
$1,100
Chicago, IL
2 BR | Available Now
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Washington Park
0
$1,840
212 E 71st St Unit 3 Chicago, IL
3 BR | Available Now
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Grand Crossing
1
$1,200
Chicago, IL
1 BR | Available Now
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Grand Crossing
1
$1,050 - 1,450
2445 E 72nd St Chicago, IL
Studio - 1 BR | Available Now
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South Shore
10
$1,500
7100 S South Shore Dr Chicago, IL
1 BR | Available Now
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Dog Friendly
Cat Friendly
South Shore
7
$1,395 - 1,450
Chicago, IL
2 BR | Available Now
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South Shore
$1,000 - 1,050
Chicago, IL
2 BR | Available Now
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Grand Crossing
8
$1,795 - 2,395
5320-53265 S Drexel Blvd Chicago, IL
Studio - 3 BR | Available Now
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Dishwasher
Kenwood
7
$1,495
Chicago, IL
2 BR | Available Now
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South Shore
1
$1,395 - 1,450
Chicago, IL
2 BR | Available Now
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South Shore
0
$1,195 - 1,487
7200 S Coles Ave Chicago, IL
1 BR | Available Now
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Heat Included
Dog Friendly
Cat Friendly
Storage
Disability Access
16
$1,195 - 1,487
Chicago, IL
1 BR | Available Now
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Dog Friendly
Cat Friendly
South Shore
3
$850 - 2,200
Chicago, IL
2 - 5 BR | Ask for Availability
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Washington Park
1
$1,700 - 1,750
Chicago, IL
3 BR | Available Now
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Grand Boulevard
17
$1,595
Chicago, IL
4 BR | Available Now
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Dog Friendly
Cat Friendly
Washington Park
19
$1,180
Chicago, IL
1 BR | Ask for Availability
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Kenwood
1
$1,860
125 E 71st St Chicago, IL
2 BR | Available Now
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Storage
Grand Crossing
11
$1,240
500-512 E 75th St Chicago, IL
2 BR | Available Now
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Dog Friendly
Cat Friendly
Grand Crossing
10
$1,150
Chicago, IL
2 BR | Available Now
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Cat Friendly
South Shore
1
$1,095 - 1,195
5.0
7220 S South Shore Dr Chicago, IL
1 BR | Available Now
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Cat Friendly
Storage
Disability Access
South Shore
1
$1,500
Chicago, IL
1 BR | Available Now
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Grand Crossing
271 - 300 of 375 Results
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Chicago:
October Rent Report

Welcome to the October 2026 Chicago Apartment Report. In this assessment of the local rental market, Rentable data scientists and rental experts break down the October 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

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Sep. 2026
Oct. 2026
1 BR       2 BR

Chicago Rent Prices Decrease From September to October

Chicago rent prices decreased over the last month. From September to October, 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 September to October, 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 $.

October 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.

October 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 October 1 BR M/M % Change 2 BR October 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.