1 Bedroom Apartments for Rent in Chicago, IL Under $5,500 (2,747 Rentals) Page 7 of 55

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55 W. Chestnut
$1,838 - $2,436
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$1,789 - $3,323
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1 Bedroom Apartments Available Aug 1

55 W. Chestnut

55 W Chestnut StChicago, IL 60610
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Nicole • 4+ years in Chicago

April 10, 2026

Big city challenges with traffic but also provides the amenities of the city you can't find elsewhere

Frequently Asked Questions about 1 Bedroom Chicago Apartments

What is the Cheapest apartment in Chicago with 1 Bedroom?

Currently the most affordable 1 Bedroom in Chicago is at Westhaven Park II - C listed at $754.

How much is the average rent for a 1 Bedroom Chicago Apartment?

The average rent for a 1 Bedroom Apartment in Chicago is $2,476.

What is the largest available 1 Bedroom Chicago Apartment for rent?

Today's apartment with the most square footage in Chicago is a 1,381 square feet unit starting from $9,987 at The Parker Fulton Market.

What is the average size for Chicago 1 Bedroom Apartments for rent?

The average size for a 1 Bedroom rental in Chicago is currently 995 sq ft.

Expert Rental Resources

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.

Helpful Local Expert Guides

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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Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago

Written by: Nicole Harms

With world-class museums lining its streets, Chicago is a place people go to learn. It’s not surprising, therefore, that it’s also home to multiple colleges and universities with national and global reputations.

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Best Neighborhoods to Rent in Near Chicago's Top Employers

Written by: Nicole Harms

Whenever life takes me into the city, I’m always impressed with the sheer amount of industry and commerce that it holds. With all of that commerce comes a wide range of employment options.

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Explore the Windy City (But Watch for Falling Ice) - An Insider's Guide to Renting in Chicago

Written by: Nicole Harms

From Lake Shore Drive to the O’Hare Airport, the city of Chicago is a study in diversity, resilience, and culture.

Articles, How-To's, and Tips

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.