Apartments in Woodlawn Chicago

241 - 270 of 374 Results
15
$1,650 - 2,599
1101 E. Hyde Park Boulevard Chicago, IL
1 - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Dishwasher
Fireplace
Hyde Park
23
3D Tour
$3,695 - 4,095
5100 5120 S. Ellis Avenue Chicago, IL
4 BR | Available Now
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Dog Friendly
Cat Friendly
Virtual Tour
Air Conditioning
In Unit Laundry
39
$1,415 - 2,175
1606 E. Hyde Park Blvd Chicago, IL
Studio - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Fitness Center
Storage
7
$1,300
Chicago, IL
3 BR | Available Now
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Grand Crossing
18
3D Tour
$1,630 - 2,150
5034 5046 S. Woodlawn Avenue Chicago, IL
1 - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Virtual Tour
Dishwasher
Fireplace
16
$1,490
5049 S. Drexel Ave Chicago, IL
1 BR | Available Now
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Dog Friendly
Cat Friendly
Fireplace
Hyde Park
25
$1,265 - 1,760
5043 S. Drexel Ave Chicago, IL
1 - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Dishwasher
Hyde Park
14
$1,500
1020 E Hyde Park Blvd Chicago, IL
2 BR | Available Now
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Storage
Kenwood
16
$1,600
Chicago, IL
2 BR | Available Now
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South Shore
1
$1,860
Chicago, IL
3 BR | Available Now
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Storage
Grand Crossing
$1,595
Chicago, IL
1 BR | Available Now
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Dog Friendly
Cat Friendly
Kenwood
$1,000
Chicago, IL
1 - 2 BR | Available Now
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Grand Crossing
0
$1,650
7451-59 S Bennett Ave Chicago, IL
2 BR | Available Now
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South Shore
18
$1,495 - 1,530
918 E. Hyde Park Boulevard Chicago, IL
1 BR | Available Now
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Dog Friendly
Cat Friendly
Dishwasher
Fireplace
Kenwood
59
3D Tour
$1,740 - 3,505
5035 S. East End Dr. Chicago, IL
Studio - 3 BR | Available Now
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Furnished
Dog Friendly
Cat Friendly
Virtual Tour
Luxury
16
$1,530 - 2,055
5300 S. Drexel Blvd. Chicago, IL
Studio - 2 BR | Available Now
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Furnished
Dog Friendly
Cat Friendly
Air Conditioning
Dishwasher
11
$1,750
Chicago, IL
3 BR | Available Now
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Air Conditioning
Storage
Dishwasher
South Shore
1
$1,400 - 1,500
7450 S Maryland Ave Chicago, IL
2 - 3 BR | Available Now
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Grand Crossing
1
$1,700
Chicago, IL
2 BR | Available Now
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Grand Crossing
1
$2,300
6938 S Prairie Ave Chicago, IL
3 BR | Available Now
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House
Grand Crossing
7
$1,100
Chicago, IL
2 BR | Available Now
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Heat Included
Washington Park
1
$1,318
Chicago, IL
3 BR | Available Now
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Air Conditioning
Storage
Washington Park
1
$1,100 - 1,400
6801 - 6811 S Michigan Ave. 101 - 115 E 68th St. Chicago, IL
Studio - 1 BR | Available Now
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Dog Friendly
Cat Friendly
Storage
Grand Crossing
1
$1,500
5838-5850 S Michigan Ave Chicago, IL
2 BR | Available Now
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Cat Friendly
Storage
Disability Access
Washington Park
10
$1,450
Chicago, IL
2 BR | Available Now
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Dog Friendly
Cat Friendly
Grand Crossing
0
$1,450
Chicago, IL
2 BR | Ask for Availability
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Grand Crossing
9
$1,075
Chicago, IL
1 BR | Available Now
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Dog Friendly
Cat Friendly
Grand Crossing
1
$1,100
6820 S Michigan Ave Chicago, IL
1 BR | Available Now
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Grand Crossing
1
$1,395
7213 S Yates Chicago, IL
1 BR | Available Now
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Dog Friendly
Cat Friendly
House
South Shore
1
$1,495
7219 S Yates Blvd Chicago, IL
2 BR | Available Now
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House
Storage
South Shore
241 - 270 of 374 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.