
Luxury Apartments for Rent in Chicago, IL with Swimming Pool (231 Rentals) Page 4 of 5
The most luxurious Apartments in Chicago with high-end amenities, features, and finishes.


Total Monthly Price
837 W Grand Ave, Unit 2

156 W Superior St, Unit 3

839 W Washington St, Unit 3

461 W Chicago Ave, Unit 2003

1390 W Randolph St, Unit 3

347 W Chestnut St, Unit 1313

461 W Chicago Ave, Unit 1502

1356 W Randolph St, Unit 2003

501 N State St, Unit 2203

525 N State St, Unit 2

200 N Wells St, Unit 2201

190 E Illinois St, Unit 3005

1205 N Wells St

347 W Chestnut St, Unit 711

510 S Damen Ave, Unit 1015

513 S Damen Ave, Unit 809

513 S Damen Ave, Unit 1312

513 S Damen Ave, Unit 1205

513 S Damen Ave, Unit 2109

513 S Damen Ave, Unit 1416

513 S Damen Ave, Unit 916

513 S Damen Ave, Unit 1906

513 S Damen Ave, Unit 2009

513 S Damen Ave, Unit 401

513 S Damen Ave, Unit 702

123 N Desplaines St, Unit 2

347 W Chestnut St, Unit 2112

447 W Huron St, Unit 447 W Huron

740 N Aberdeen St, Unit 321

347 W Chestnut St, Unit 911

210 E Illinois St, Unit 1204

14 N Peoria St, Unit 506

1350 W Randolph St, Unit 1113

7890 N Kingsbury St, Unit 1103

735 N Aberdeen St

1637 W Chicago Ave

Luxury spectacular view

211 E. Ohio St.

R+D659

Illume

600 N Lake Shore Dr

55 E Erie St

400 E Ohio St

Luxury condo unit

1850 N. Clark St.

The Duplex Tower

The Grove - Encore

The Reserve

Buckingham
Chicago, IL Local Guide

How much does it cost to rent an apartment in Chicago?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chicago Studio Apartments | $1,988 | $600 | $9,940 |
| Chicago 1 Bedroom Apartments | $2,490 | $650 | $10,000+ |
| Chicago 2 Bedroom Apartments | $3,091 | $850 | $10,000+ |
| Chicago 3 Bedroom Apartments | $3,854 | $883 | $10,000+ |
| Chicago 4 Bedroom Apartments | $3,443 | $970 | $10,000+ |
| Chicago 5 Bedroom Apartments | $7,474 | $2,600 | $10,000+ |
| Chicago 6 Bedroom Apartments | $6,142 | $750 | $10,000+ |
Explore Chicago
Chicago, IL Area Reviews
Nicole • 4+ years in Chicago
April 10, 2026Big 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

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.

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.

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.

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

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.

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.

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.

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.