
Apartments for Rent in the Uptown Chicago Neighborhood of Chicago, IL with Swimming Pool (29 Rentals)


The Sally

Eight Eleven Uptown

Solverre

The Winnie

The Draper

The Lawrence House
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.

Total Monthly Price
4315 N Hazel St, Unit 104

655 W Irving Park Rd, Unit 04113

655 W Irving Park Rd, Unit 811

720 W Gordon Ter, Unit 9B

1131 W Winona St

4250 N Marine Dr, Unit 0828

4643 N Clark St, Unit 01
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.

655 W Irving Park Rd, Unit 5303

5100 N Marine Dr, Unit 22A

4334 N Sheridan Rd, Unit M06R

5050 N Sheridan Rd, Unit 410

4607 N Sheridan Rd, Unit 903

4180 N Marine Dr, Unit 612

4180 N Marine Dr, Unit 1002
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!

1136 W Wilson Ave, Unit 210

1136 W Wilson Ave, Unit 307

The Waterford

Park Place Tower

4343 N Clarendon Ave

Lake Park Plaza

Metropolitan
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.

5100 N Marine Dr
Uptown Chicago, Chicago, IL Local Guide

How much does it cost to rent an apartment in Uptown Chicago?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Uptown Chicago Studio Apartments | $1,567 | $595 | $2,516 |
| Uptown Chicago 1 Bedroom Apartments | $2,144 | $640 | $3,785 |
| Uptown Chicago 2 Bedroom Apartments | $3,012 | $762 | $4,995 |
| Uptown Chicago 3 Bedroom Apartments | $3,577 | $2,550 | $5,380 |
| Uptown Chicago 4 Bedroom Apartments | $4,250 | $4,250 | $4,250 |
Browse Apartments in this Neighborhood
There are currently 29 rentals with your search options within a 2 mile radius of the Uptown Chicago Neighborhood of Chicago, IL.
See all Apartments in ChicagoExplore Chicago
Uptown Chicago, Chicago, IL Local Guide
- Nearby Chicago neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
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
Read ArticleA 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
Read ArticleReal 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.
Read ArticleQuick 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.
Best Local Schools in Uptown Chicago, Chicago, IL
McCutcheon Elementary School
Lake View High School
Walt Disney Magnet School
School data provided by Great Schools
Frequently Asked Questions about Uptown Chicago Apartments with Swimming Pool
What is the Cheapest Swimming Pool apartment in Uptown Chicago?
Currently the most affordable Apartment in Uptown Chicago with Swimming Pool is at The Winnie listed at $1,234.
How much is the average rent for Uptown Chicago Apartments with Swimming Pool?
The average rent for a Apartment in Uptown Chicago with Swimming Pool is $3,053.
What is the largest Uptown Chicago Apartment for rent with Swimming Pool?
Today's Apartment with Swimming Pool and the most square footage in Uptown Chicago is a 2,250 square feet unit starting from $2,020 at Eight Eleven Uptown.
What is the average size for Uptown Chicago Apartments for rent with Swimming Pool?
The average size for a rental with Swimming Pool in Uptown Chicago is currently at 431 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

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.

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.