
2 Bedroom Apartments for Rent in the Woodlawn Neighborhood of Chicago, IL (105 Rentals)


Academy at Drexel

Oglesby Towers Apartments

5715-5725 S. Kimbark Avenue

1140 E Marquette Rd, Unit 2D
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

6219 S Kenwood Ave

6223 S Kenwood Ave

6150 S University Ave

6620 S Cottage Grove Ave

6411 S Evans Ave
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
Woodlawn - One of the Best Affordable Neighborhoods in Chicago
Named as one of the Best Affordable Neighborhoods to rent in Chicago by our Chicago, IL Local Expert Nicole Harms. See how it ranks!
Woodlawn, Chicago, IL Local Guide

How much does it cost to rent an apartment in Woodlawn?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Woodlawn Studio Apartments | $1,176 | $726 | $1,958 |
Woodlawn 1 Bedroom Apartments | $1,616 | $1,150 | $2,675 |
Woodlawn 2 Bedroom Apartments | $1,934 | $1,000 | $3,299 |
Woodlawn 3 Bedroom Apartments | $2,026 | $1,665 | $2,999 |
Woodlawn 4 Bedroom Apartments | $1,750 | $1,750 | $1,750 |
Browse Apartments in this Neighborhood
There are currently 105 rentals with your search options within a 2 mile radius of the Woodlawn Neighborhood of Chicago, IL.
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Woodlawn, Chicago, IL Local Guide
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Largest Available Woodlawn 2 Bedroom Apartments
The largest available 2 Bedroom apartment unit in the Woodlawn area of Chicago, IL is found at Cloisters and is listed at 1,285 square feet priced from $2,795. Here is today’s list of the largest available 2 Bedroom units in the area:
Apartment Listing | Model Name | Square Footage | Priced From |
---|---|---|---|
Cloisters | clo-2b1c | 1,285 Sq Ft | $2,795 |
Oglesby Towers Apartments | 2 Bedrooms Floor Plan B1B | 1,200 Sq Ft | $1,676 |
5715-5725 S. Kimbark Avenue | 5715-2bB | 1,070 Sq Ft | $2,995 |
Keystone Place Apartments | 2 Bedroom Market | 1,057 Sq Ft | $1,450 |
6516 S Stony Island Ave | 2BR/1.0BA | 950 Sq Ft | $1,800 |
Cheapest Available Woodlawn 2 Bedroom Apartments
Currently the lowest priced 2 Bedroom apartment unit Woodlawn of Chicago, IL is the 2 Bedroom Market Model starting from $1,450 at Keystone Place Apartments. The average price for all 2 Bedroom apartments in Woodlawn is currently $1,934. Here is today’s list of the cheapest available 2 Bedroom options in the area:
Apartment Listing | Model Name | Priced From |
---|---|---|
Keystone Place Apartments | 2 Bedroom Market | $1,450 |
Oglesby Towers Apartments | 2 Bedrooms Floor Plan B1 | $1,676 |
6516 S Stony Island Ave | 2BR/1.0BA | $1,800 |
Cloisters | clo-2b1c | $2,795 |
5715-5725 S. Kimbark Avenue | 5715-2bB | $2,995 |
Quick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
Pet Friendly LifestyleWoodlawn, Chicago, IL
Ranked #126
Among cities in Illinois for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.0Pet Friendly
Best Local Schools in Woodlawn, Chicago, IL
Carnegie Elementary School
Hyde Park Academy High School
Wadsworth PreK-8th STEM School
School data provided by Great Schools
Getting Around the Woodlawn Neighborhood in Chicago, IL
Walk Score®
69 / 100
Somewhat Walkable
Some errands can be accomplished on foot
Bike Score®
71 / 100
Very Bikeable
Biking is convenient for most trips
Transit Score®
71 / 100
Excellent Transit
Transit is convenient for most trips
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about 2 Bedroom Woodlawn Apartments
What is the Cheapest apartment in Woodlawn with 2 Bedroom?
Currently the most affordable 2 Bedroom in Woodlawn is at Keystone Place Apartments listed at $1,450.
How much is the average rent for a 2 Bedroom Woodlawn Apartment?
The average rent for a 2 Bedroom Apartment in Woodlawn is $1,934.
What is the largest available 2 Bedroom Woodlawn Apartment for rent?
Today's apartment with the most square footage in Woodlawn is a 1,285 square feet unit starting from $2,795 at Cloisters.
What is the average size for Woodlawn 2 Bedroom Apartments for rent?
The average size for a 2 Bedroom rental in Woodlawn is currently 1,185 sq ft.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

A Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent in Chicago
Written by: Nicole Harms
I’m Nicole, your ApartmentHomeLiving.com Local Expert for Chicago, IL. As a resident of the Chicago area for over 20 years, I’ve learned which neighborhoods are great and which are best avoided.

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.