Apartments for Rent in Chicago, IL Under $5,500 with Swimming Pool (277 Rentals) Page 4 of 6

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601 N State St
$2,545 - $4,448
Total Monthly Price

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Base Rent
$2,545 - $4,448
Total Monthly Price
$2,545 - $4,448
Studio to 2 Bedroom Apartment Available Aug 27

601 N State St

601 N State StChicago, IL 60654
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3611 W Wolfram St, Unit 2
$2,590
Total Monthly Price

Total Monthly Price

Base Rent
$2,590
Total Monthly Price
$2,590
2 Bedroom Apartment Available Aug 1

3611 W Wolfram St, Unit 2

3611 W Wolfram StChicago, IL 60618
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17 N Ada St, Unit 701
$3,243
Total Monthly Price

Total Monthly Price

Base Rent
$3,243
Total Monthly Price
$3,243
1 Bedroom Apartment Available Now

17 N Ada St, Unit 701

17 N Ada StChicago, IL 60607
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720 W Gordon Terrace, Unit 5C
$3,000
Total Monthly Price

Total Monthly Price

Base Rent
$3,000
Total Monthly Price
$3,000
2 Bedroom Apartment Available Aug 1

720 W Gordon Terrace, Unit 5C

720 W Gordon TerraceChicago, IL 60613
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620 N State St
$2,894 - $4,472
Total Monthly Price

Total Monthly Price

Base Rent
$2,894 - $4,472
Total Monthly Price
$2,894 - $4,472
1 to 2 Bedroom Apartment Available Jul 17

620 N State St

620 N State StChicago, IL 60654
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4653 N Major Ave, Unit 2S
$1,400
Total Monthly Price

Total Monthly Price

Base Rent
$1,400
Total Monthly Price
$1,400
1 Bedroom Apartment Available Now

4653 N Major Ave, Unit 2S

4653 N Major AveChicago, IL 60630
Affordability
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Showing Results 151-200, Page 4 of 6

Chicago, IL Area Reviews

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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 Chicago Apartments with Swimming Pool

What is the Cheapest Swimming Pool apartment in Chicago?

Currently the most affordable Apartment in Chicago with Swimming Pool is at 3548 S Western Ave, Unit 1R listed at $1,095.

How much is the average rent for Chicago Apartments with Swimming Pool?

The average rent for a Apartment in Chicago with Swimming Pool is $4,260.

What is the largest Chicago Apartment for rent with Swimming Pool?

Today's Apartment with Swimming Pool and the most square footage in Chicago is a 4,425 square feet unit starting from $2,258 at 369 Grand by Onni.

What is the average size for Chicago Apartments for rent with Swimming Pool?

The average size for a rental with Swimming Pool in Chicago is currently at 590 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

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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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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

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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

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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.

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Creative Ways Developers Reimagine Retail Spaces as Residential Units

Written by: Robin Stewart

Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.