2 Bedroom Apartments for Rent in the Woodlawn Neighborhood of Chicago, IL (110 Rentals)

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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.

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6700 S Merrill Ave
2 Bedroom Apartments

6700 S Merrill Ave

6700 S Merrill AveChicago, IL 60649
  • Utilities Included
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6650 S Drexel
2 Bedroom Apartments

6650 S Drexel

6650-6658 S Drexel AveChicago, IL 60637
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6516 S University
2 Bedroom Apartments

6516 S University

6516 S University AveChicago, IL 60637
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Island Terrace
2 Bedroom Apartments

Island Terrace

6430 S Stony Island AveChicago, IL 60637
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Trianon Lofts
2 Bedroom Apartments

Trianon Lofts

803 E 61st StChicago, IL 60637
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Jackson Park Terrace
2 Bedroom Apartments

Jackson Park Terrace

6040 S Harper AveChicago, IL 60637
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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

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Cloisters
2 Bedroom Apartments

Cloisters

5801-5811 S Dorchester AveChicago, IL 60637
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Wooded Isle Apartments
2 Bedroom Apartments

Wooded Isle Apartments

5736-5762 S Stony Island AveChicago, IL 60637
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Woodlawn
2 Bedroom Apartments

Woodlawn

6517 S University AveChicago, IL 60637
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Wolcott Apartments
2 Bedroom Apartments

Wolcott Apartments

6446 S Kenwood AveChicago, IL 60637
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6715-6733 S Paxton Ave
2 Bedroom Apartments

6715-6733 S Paxton Ave

6715-6733 S Paxton AveChicago, IL 60649
  • Utilities Included

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!

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Lakefront Place
2 Bedroom Apartments

Lakefront Place

6730 South Shore DrChicago, IL 60649
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1534 E 65th Pl
2 Bedroom Apartments

1534 E 65th Pl

1534 E 65th PlChicago, IL 60637
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1508 E 67th Pl
2 Bedroom Apartments

1508 E 67th Pl

1508 E 67th PlChicago, IL 60637
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6700 S Clyde Ave
2 Bedroom Apartments

6700 S Clyde Ave

6700 S Clyde AveChicago, IL 60649

Chicago's Best Affordable Neighborhoods

Learn about Chicago and the best places to live with original content written by our Chicago, IL Local Expert Nicole Harms

Woodlawn, Chicago, IL Local Guide

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 $2,895. Here is today’s list of the largest available 2 Bedroom units in the area:

Apartment ListingModel NameSquare FootagePriced From
Cloistersclo-2b1c1,285 Sq Ft$2,895
City Hyde Parkchp-2bT101,179 Sq Ft$3,500
The Del Pradodelp-2PH051,175 Sq Ft$3,599
Regents Park2bs091,130 Sq Ft$2,290
5401 Cornell by 3L Living2BR/1.0BA1,085 Sq Ft$2,069
5715-5725 S. Kimbark Avenue5715-2bB1,059 Sq Ft$2,995
Keystone Place Apartments2 Bedroom Market1,057 Sq Ft$1,336

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 $2,623. Here is today’s list of the cheapest available 2 Bedroom options in the area:

Apartment ListingModel NamePriced From
Keystone Place Apartments2 Bedroom Market$1,450
The Flamingo Apartments2 Bedroom Floor Plan B1$1,634
5401 Cornell by 3L Living2BR/1.0BA$2,069
Regents Park2bn07$2,245
The Del Pradodelp-2b308$2,250
Cloistersclo-2b1c$2,895
5715-5725 S. Kimbark Avenue5715-2bB$2,995
City Hyde Parkchp-2bT01$3,135

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Pet Friendly Lifestyle
Woodlawn, Chicago, IL

Ranked #77

Among neighborhoods in Chicago, IL for Apartment listings with Pet Friendly Amenities

Pet Friendliness Lifestyle Score

3.0
Pet Friendly

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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

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 $2,623.

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 $2,895 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 1,275 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.

decorative image for A Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent in Chicago article

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.

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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.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.

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Navigating the Rental Market: Tips for First-Time Renters

Written by: Sandy Baker

Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.