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

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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.

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.

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6700 S Merrill Ave
2 Bedroom Apartments

6700 S Merrill Ave

6700 S Merrill AveChicago, IL 60649
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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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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.

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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
  • Utilities Included

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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6715-6733 S Paxton Ave
2 Bedroom Apartments

6715-6733 S Paxton Ave

6715-6733 S Paxton AveChicago, IL 60649
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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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1131 E 61st St
2 Bedroom Apartments

1131 E 61st St

1131 E 61st StChicago, IL 60637

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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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

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 $2,795. 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$2,795
Oglesby Towers Apartments2 Bedrooms Floor Plan B1B1,200 Sq Ft$1,676
5715-5725 S. Kimbark Avenue5715-2bB1,070 Sq Ft$2,995
Keystone Place Apartments2 Bedroom Market1,057 Sq Ft$1,450
6516 S Stony Island Ave2BR/1.0BA950 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 ListingModel NamePriced From
Keystone Place Apartments2 Bedroom Market$1,450
Oglesby Towers Apartments2 Bedrooms Floor Plan B1$1,676
6516 S Stony Island Ave2BR/1.0BA$1,800
Cloistersclo-2b1c$2,795
5715-5725 S. Kimbark Avenue5715-2bB$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.

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Pet Friendly Lifestyle
Woodlawn, Chicago, IL

Ranked #126

Among cities in Illinois 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 $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.

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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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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.

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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.

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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.