
Apartments for Rent with Specials in Chicago, IL with Swimming Pool (86 Rentals) Page 2 of 2
Apartments in Chicago with special offers and discounts available right now - opportunities to save money or get a month or more of free rent.


Total Monthly Price
620 N State St

Total Monthly Price
233 S Halsted St

Total Monthly Price
444 N Orleans St

Total Monthly Price
651 W Washington Blvd

Total Monthly Price
1240 W Randolph St

Total Monthly Price
944 W Madison St

Total Monthly Price
601 N State St

Total Monthly Price
215 N Clinton St
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!

Total Monthly Price
942 W Huron St

Total Monthly Price
158 W Division St

Total Monthly Price
1415 W Randolph St

Ovaltine

The Reserve

Total Monthly Price
District 1860

Total Monthly Price
The Henry at Harms Woods

ReNew Des Plaines North & South

Huntington Square
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

Total Monthly Price
Optima Old Orchard Woods

Glen Oaks Commons

The Monarch

The Element

Arbor House

Total Monthly Price
Uptown La Grange

Green Oaks Apartments

The Eclipse at 1450

Total Monthly Price
Orion Prospect
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

Novu Apartments

Tanglewood

Ashton Arlington Heights

Forest Cove Apartments

Mont Clare

Welkin Apartments

Manchester Court Apartments

The Residences at Sawmill Station

The Bennington
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.
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 | $2,073 | $595 | $9,999 |
| Chicago 1 Bedroom Apartments | $2,462 | $640 | $9,075 |
| Chicago 2 Bedroom Apartments | $3,058 | $762 | $10,000+ |
| Chicago 3 Bedroom Apartments | $3,702 | $883 | $10,000+ |
| Chicago 4 Bedroom Apartments | $4,306 | $1,025 | $10,000+ |
| Chicago 5 Bedroom Apartments | $5,453 | $2,995 | $10,000+ |
| Chicago 6 Bedroom Apartments | $19,280 | $7,000 | $10,000+ |
Browse Top Apartments in Chicago
See all Apartments in ChicagoExplore 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 $1,115.
How much is the average rent for Chicago Apartments with Swimming Pool?
The average rent for a Apartment in Chicago with Swimming Pool is $4,222.
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 626 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

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.

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.

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.

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

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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.

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.

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.