Luxury Apartments for Rent in Chicago, IL with Swimming Pool (231 Rentals) Page 2 of 5

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

The most luxurious Apartments in Chicago with high-end amenities, features, and finishes.

close
View Me
Lake and Wells
$2,315 - $4,370
Total Monthly Price

Total Monthly Price

Base Rent
$2,315 - $4,370
Total Monthly Price
Varies
Studio to 2 Bedroom Apartments Available Now

Lake and Wells

210 N Wells StChicago, IL 60606
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour

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.

Read Article
close
View Me
Westerly
$2,359 - $7,722
Total Monthly Price

Total Monthly Price

Base Rent
$2,359 - $7,722
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

Westerly

740 N Aberdeen StChicago, IL 60642
Affordability
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
The Cooper
Rent Specials
$2,281 - $11,139
Total Monthly Price

Total Monthly Price

Base Rent
$2,281 - $11,139
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

The Cooper

720 S Wells StChicago, IL 60607
Student Housing
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
465 North Park
$2,727 - $15,151
Total Monthly Price

Total Monthly Price

Base Rent
$2,727 - $15,151
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

465 North Park

465 N Park DrChicago, IL 60611
Luxury
  • Verified
  • Customer Reviewed
  • 3D Tour

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!

Read Article
close
View Me
727 West Madison
$2,491 - $11,603
Total Monthly Price

Total Monthly Price

Base Rent
$2,491 - $11,603
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

727 West Madison

727 W Madison StChicago, IL 60661
Luxury
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
The Sinclair
$2,624 - $6,425
Total Monthly Price

Total Monthly Price

Base Rent
$2,624 - $6,425
Total Monthly Price
Varies
Studio to 4 Bedroom Apartments Available Now

The Sinclair

1201 N La Salle DrChicago, IL 60610
Pet Friendly
  • Verified
  • Customer Reviewed
  • Utilities Included

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.

Read Article
close
View Me
OneEleven
$2,709 - $18,703
Total Monthly Price

Total Monthly Price

Base Rent
$2,709 - $18,703
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

OneEleven

111 W Wacker DrChicago, IL 60601
Luxury
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
Env Chicago
Rent Specials
$2,443 - $7,407
Total Monthly Price

Total Monthly Price

Base Rent
$2,443 - $7,407
Total Monthly Price
Varies
Studio to 2 Bedroom Apartments Available Now

Env Chicago

161 W Kinzie StChicago, IL 60654
Luxury
  • Verified
  • Customer Reviewed
  • 3D Tour

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.

Read Article

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

Read Article
Showing Results 51-100, Page 2 of 5

Chicago, IL Area Reviews

  • Parks
  • Entertainment
  • Local Vibes
  • Restaurants
  • Location
  • Traffic
  • Public Transportation
  • Outdoor Access
  • Cost of Living
  • Safety

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 $1,081.

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

The average rent for a Apartment in Chicago with Swimming Pool is $4,245.

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 584 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.

decorative image for Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago article

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.

decorative image for Best Neighborhoods to Rent in Near Chicago's Top Employers article

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.

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

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 Creative Ways Developers Reimagine Retail Spaces as Residential Units article

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.

decorative image for Neighborhood and Market Insights: How to Choose the Right Area to Rent article

Neighborhood and Market Insights: How to Choose the Right Area to Rent

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.

decorative image for A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back article

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Written by: Lauren Harrington

I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

decorative image for Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts article

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.