Apartments in Woodlawn Chicago

301 - 330 of 375 Results
20
$1,775 - 2,399
3.7
4850 Drexel Boulevard Chicago, IL
1 - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Fitness Center
Storage
17
$1,170 - 1,825
4726 4740 South Woodlawn Ave. Chicago, IL
Studio - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Dishwasher
Kenwood
23
$1,040 - 1,680
4721 29 St Chicago, IL
Studio - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Dishwasher
Kenwood
0
$1,686
Chicago, IL
2 BR | Available Now
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Washington Park
8
$1,600
Chicago, IL
2 BR | Available Now
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Dishwasher
Grand Crossing
1
$1,600
Chicago, IL
2 BR | Available Now
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Grand Crossing
1
$1,700
7451 -53 S Vernon Ave 430-40 E 75th St Chicago, IL
2 BR | Available Now
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Dog Friendly
Cat Friendly
Storage
Grand Crossing
12
$2,000
Chicago, IL
3 BR | Ask for Availability
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Grand Boulevard
6
$1,350
Chicago, IL
2 BR | Available Now
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Dog Friendly
Grand Crossing
0
$1,400
Chicago, IL
1 BR | Available Now
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South Shore
43
$1,495 - 1,545
4742 S Woodlawn Ave Chicago, IL
1 BR | Nov. 1, 2026
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Dog Friendly
Dishwasher
Kenwood
$1,050
Chicago, IL
1 BR | Available Now
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Kenwood
1
$1,200
2531-41 E 73Rd St Chicago, IL
2 BR | Available Now
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Dog Friendly
Storage
South Shore
$1,550
Chicago, IL
2 BR | Available Now
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Dog Friendly
Cat Friendly
Grand Boulevard
1
$1,295 - 1,395
7263 S South Shore Dr Chicago, IL
1 - 2 BR | Available Now
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Storage
Disability Access
South Shore
0
$1,300
Chicago, IL
1 - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Storage
Dishwasher
3
$1,780
Chicago, IL
2 BR | Available Now
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Heat Included
Dog Friendly
Cat Friendly
Grand Crossing
1
$1,075 - 1,396
4829 S Cottage Grv Chicago, IL
1 BR | Available Now
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Kenwood
26
$1,950
4901-09 S. Champlain Ave. Chicago, IL
2 - 3 BR | Available Now
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Dog Friendly
Air Conditioning
In Unit Laundry
Balcony/Deck/Patio
Dishwasher
5
$1,686
Chicago, IL
2 BR | Available Now
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Storage
Disability Access
Grand Crossing
1
$1,500
7824 S Greenwood Ave Chicago, IL
4 BR | Available Now
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Storage
Disability Access
Grand Crossing
1
$2,850
Chicago, IL
2 BR | Available Now
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Kenwood
20
$1,950
Chicago, IL
3 BR | Available Now
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Dog Friendly
Cat Friendly
Storage
Dishwasher
South Shore
11
3D Tour
$1,750
4851 59 S. Champlain Ave Chicago, IL
2 BR | Available Now
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Dog Friendly
Cat Friendly
Virtual Tour
Balcony/Deck/Patio
Grand Boulevard
1
$2,500
4850 S Champlain Ave Chicago, IL
2 BR | Available Now
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Dishwasher
Grand Boulevard
10
$1,050
Chicago, IL
2 BR | Ask for Availability
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Washington Park
8
$1,086
Chicago, IL
2 BR | Ask for Availability
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Grand Crossing
10
$1,686
Chicago, IL
2 BR | Available Now
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Storage
Disability Access
Grand Crossing
7
$1,035
Chicago, IL
3 BR | Ask for Availability
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Kenwood
12
$2,450
Chicago, IL
5 BR | Available Now
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Grand Crossing
301 - 330 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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Apr. 2026
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Jun. 2026
Jul. 2026
Aug. 2026
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.