Apartments for Rent in Chicago, IL Under $5,500 with Swimming Pool (278 Rentals) Page 2 of 6

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1225 Old Town
$2,405 - $7,210
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$2,405 - $7,210
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Studio to 3 Bedroom Apartments Available Now

1225 Old Town

1225 N Wells StChicago, IL 60610
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State and Grand
Rent Specials
$2,894 - $7,170
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$2,894 - $7,170
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1 to 3 Bedroom Apartments Available Now

State and Grand

505 N State StChicago, IL 60654
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Lake and Wells
$2,420 - $4,370
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$2,420 - $4,370
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Studio to 2 Bedroom Apartments Available Now

Lake and Wells

210 N Wells StChicago, IL 60606
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Chicago Relocation 101: Mastering Utilities, Registration, and the CTA

Moving to Chicago? This essential relocation guide offers a complete checklist for new residents, covering finding the right neighborhood, setting up utilities (ComEd, People’s Gas), and mastering high-rise moving logistics and vehicle registration.

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Westerly
Rent Specials
$2,535 - $7,549
Total Monthly Price

Total Monthly Price

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$2,535 - $7,549
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Studio to 3 Bedroom Apartments Available Now

Westerly

740 N Aberdeen StChicago, IL 60642
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Logan Apartments
$2,546 - $10,216
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$2,546 - $10,216
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Studio to 2 Bedroom Apartments Available Jul 3

Logan Apartments

2522 N Milwaukee AveChicago, IL 60647
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The Cooper
Rent Specials
$2,148 - $12,687
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Total Monthly Price

Base Rent
$2,148 - $12,687
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Studio to 3 Bedroom Apartments Available Now

The Cooper

720 S Wells StChicago, IL 60607
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465 North Park
$3,190 - $14,818
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Total Monthly Price

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$3,190 - $14,818
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Studio to 3 Bedroom Apartments Available Jul 5

465 North Park

465 N Park DrChicago, IL 60611
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Explore the Windy City (But Watch for Falling Ice) - An Insider's Guide to Renting in Chicago

Learn about the best things about living in Chicago from a local in the Insiders Guide to Renting in Chicago. Find your perfect Chicago apartment today!

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727 West Madison
$2,582 - $13,762
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$2,582 - $13,762
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Studio to 3 Bedroom Apartments Available Now

727 West Madison

727 W Madison StChicago, IL 60661
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The Sinclair
$2,788 - $14,473
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$2,788 - $14,473
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Studio to 4 Bedroom Apartments Available Now

The Sinclair

1201 N La Salle DrChicago, IL 60610
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1133 N. Dearborn
$1,869 - $4,064
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$1,869 - $4,064
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Studio to 2 Bedroom Apartments Available Jul 1

1133 N. Dearborn

1133 N Dearborn StChicago, IL 60610
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100 W. Chestnut
$2,177 - $3,643
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$2,177 - $3,643
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1 to 2 Bedroom Apartments Available Aug 1

100 W. Chestnut

100 W Chestnut StChicago, IL 60610
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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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OneEleven
Rent Specials
$2,708 - $20,461
Total Monthly Price

Total Monthly Price

Base Rent
$2,708 - $20,461
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Studio to 3 Bedroom Apartments Available Now

OneEleven

111 W Wacker DrChicago, IL 60601
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Env Chicago
Rent Specials
$2,738 - $6,931
Total Monthly Price

Total Monthly Price

Base Rent
$2,738 - $6,931
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Studio to 2 Bedroom Apartments Available Now

Env Chicago

161 W Kinzie StChicago, IL 60654
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1120 N. LaSalle
$1,615 - $3,616
Total Monthly Price

Total Monthly Price

Base Rent
$1,615 - $3,616
Total Monthly Price
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Studio to 2 Bedroom Apartments Available Jul 1

1120 N. LaSalle

1120 LaSalle DrChicago, IL 60610
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750 N. Rush
$2,424 - $7,983
Total Monthly Price

Total Monthly Price

Base Rent
$2,424 - $7,983
Total Monthly Price
$2,424 - $7,983
1 to 3 Bedroom Apartments Available Jul 1

750 N. Rush

750 N Rush StChicago, IL 60611
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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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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

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April 10, 2026

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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 $4,241.

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

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

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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.