Top Rated Apartments for Rent in Chicago, IL with Swimming Pool (100 Rentals)

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Apartments in Chicago with the best features, newest construction, and richest amenities.

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Flora
Rent Specials
$2,249 - $28,969
Total Monthly Price

Total Monthly Price

Base Rent
$2,249 - $28,969
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

Flora

1114 W Carroll AveChicago, IL 60607
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AMLI West Loop
$2,500 - $6,899
Total Monthly Price

Total Monthly Price

Base Rent
$2,500 - $6,899
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Varies
Studio to 2 Bedroom Apartments Available Now

AMLI West Loop

205 S PeoriaChicago, IL 60607
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Spoke
Rent Specials
$2,141 - $5,790
Total Monthly Price

Total Monthly Price

Base Rent
$2,141 - $5,790
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Aug 3

Spoke

728 N Morgan StChicago, IL 60642
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The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago

Chicago may cost more than the national average, but with the right neighborhood, a smart transit strategy, and a few local insider tips, living well in the Windy City is more achievable than you might think. Our local expert breaks down everything from rent and groceries to transportation and healthcare so you can plan your move with confidence.

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AMLI Lofts
$2,342 - $6,489
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Total Monthly Price

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$2,342 - $6,489
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Studio to 2 Bedroom Apartments Available Now

AMLI Lofts

850 S Clark StChicago, IL 60605
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AMLI River North
$2,343 - $9,948
Total Monthly Price

Total Monthly Price

Base Rent
$2,343 - $9,948
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Studio to 3 Bedroom Apartments Available Now

AMLI River North

71 W Hubbard StChicago, IL 60654
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SoNo East
$2,281 - $7,791
Total Monthly Price

Total Monthly Price

Base Rent
$2,281 - $7,791
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Varies
Studio to 2 Bedroom Apartments Available Aug 7

SoNo East

840 W Blackhawk StChicago, IL 60642
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One Superior Place
$2,406 - $4,803
Total Monthly Price

Total Monthly Price

Base Rent
$2,406 - $4,803
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Varies
Studio to 2 Bedroom Apartments Available Now

One Superior Place

1 W Superior StChicago, IL 60654
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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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The Van Buren
Rent Specials
$2,726 - $6,558
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Total Monthly Price

Base Rent
$2,726 - $6,558
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Varies
1 to 2 Bedroom Apartments Available Aug 19

The Van Buren

808 W Van Buren StChicago, IL 60607
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Elevate Lincoln Park
$2,694 - $13,380
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Total Monthly Price

Base Rent
$2,694 - $13,380
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Studio to 3 Bedroom Apartments Available Aug 18

Elevate Lincoln Park

930 W Altgeld StChicago, IL 60614
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Lake and Wells
$2,317 - $4,769
Total Monthly Price

Total Monthly Price

Base Rent
$2,317 - $4,769
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Varies
Studio to 2 Bedroom Apartments Available Now

Lake and Wells

210 N Wells StChicago, IL 60606
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Westerly
Rent Specials
$2,429 - $7,657
Total Monthly Price

Total Monthly Price

Base Rent
$2,429 - $7,657
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

Westerly

740 N Aberdeen StChicago, IL 60642
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Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible

Looking for a rental near Chicago? These five cities offer excellent options! From small-town charm to excellent business options, you can't go wrong!

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Logan Apartments
$2,291 - $8,656
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Total Monthly Price

Base Rent
$2,291 - $8,656
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Studio to 2 Bedroom Apartments Available Now

Logan Apartments

2522 N Milwaukee AveChicago, IL 60647
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The Cooper
Rent Specials
$2,320 - $11,004
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Total Monthly Price

Base Rent
$2,320 - $11,004
Total Monthly Price
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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
$2,841 - $14,536
Total Monthly Price

Total Monthly Price

Base Rent
$2,841 - $14,536
Total Monthly Price
$2,841 - $14,536
Studio to 3 Bedroom Apartments Available Now

465 North Park

465 N Park DrChicago, IL 60611
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727 West Madison
$2,304 - $9,963
Total Monthly Price

Total Monthly Price

Base Rent
$2,304 - $9,963
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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
$2,395 - $14,160
Total Monthly Price

Total Monthly Price

Base Rent
$2,395 - $14,160
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Studio to 4 Bedroom Apartments Available Now

The Sinclair

1201 N La Salle DrChicago, IL 60610
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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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1225 Old Town
$2,405 - $6,656
Total Monthly Price

Total Monthly Price

Base Rent
$2,405 - $6,656
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Varies
Studio to 3 Bedroom Apartments Available Now

1225 Old Town

1225 N Wells StChicago, IL 60610
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100 W. Chestnut
$2,177 - $3,643
Total Monthly Price

Total Monthly Price

Base Rent
$2,177 - $3,643
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Varies
1 to 2 Bedroom Apartments Available Aug 31

100 W. Chestnut

100 W Chestnut StChicago, IL 60610
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OneEleven
Rent Specials
$2,667 - $21,566
Total Monthly Price

Total Monthly Price

Base Rent
$2,667 - $21,566
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

OneEleven

111 W Wacker DrChicago, IL 60601
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Env Chicago
Rent Specials
$2,658 - $7,312
Total Monthly Price

Total Monthly Price

Base Rent
$2,658 - $7,312
Total Monthly Price
Varies
Studio to 2 Bedroom Apartments Available Now

Env Chicago

161 W Kinzie StChicago, IL 60654
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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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Showing Results 1-50, Page 1 of 2

Chicago, IL Local Guide

Best Neighborhoods to Rent in Near Chicago's Top Employers: A Guide for Renters

A Local Expert's Guide to The 10 Best Chicago Neighborhoods near Major Local Employers. Find your perfect Chicago, IL apartment, condo, or rental home today at ApartmentHomeLiving.com

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A Local Expert's Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago

A Local Expert's guide to the Best Student Friendly Neighborhoods Near Colleges in the Chicago, IL metro area for affordable living. Find your perfect Chicago Student apartment, condo, or rental home today at ApartmentHomeliving.com

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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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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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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Chicago, IL Rentals by Map

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See the most popular apartments and homes in Chicago, IL

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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 Midpointe listed at $1,112.

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

The average rent for a Apartment in Chicago with Swimming Pool is $4,170.

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 618 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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The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago

Written by: Nicole Harms

When choosing a place to live, there are many things you must consider. Your employer, your shopping preferences, and even schools are all important to think about. Yet cost of living is also important to know and plan for.

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Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible

Written by: Nicole Harms

I’m Nicole, you’re ApartmentHomeLiving.com Local Expert for Chicago. There’s no denying I love the Windy City. Yet there’s also no denying that rental homes in Chicago can be pricy, small, and hard to find.

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Chicago Relocation 101: Mastering Utilities, Registration, and the CTA

Written by: Nicole Harms

Moving to a new city is always an exciting time, especially one as vibrant and diverse as Chicago. With world-class museums, a breathtaking lakefront, and numerous employment opportunities, there’s much to love about this city.

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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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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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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.