2 Bedroom Apartments for Rent in the Uptown Neighborhood of Chicago, IL (456 Rentals)

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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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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Looking for the perfect new rental? Learn great ways to spot the perfect apartment for you, identify common red flags, and avoid rental issues and scams with these expert provided actionable tips.

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4337 N Dayton St, Unit 2
$3,131

Total Monthly Price

Base Rent$3,131
Total Monthly Price$3,131
2 Bedroom Apartment Available Sep 30

4337 N Dayton St, Unit 2

4337 N Dayton StChicago, IL 60613
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1421 W Cuyler Ave, Unit 2
$2,550

Total Monthly Price

Base Rent$2,550
Total Monthly Price$2,550
2 Bedroom Apartment Available Oct 15

1421 W Cuyler Ave, Unit 2

1421 W Cuyler AveChicago, IL 60613
Affordability

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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1604 W Berwyn Ave, Unit 02
$3,150

Total Monthly Price

Base Rent$3,150
Total Monthly Price$3,150
2 Bedroom Apartment Available Now

1604 W Berwyn Ave, Unit 02

1604 W Berwyn AveChicago, IL 60640
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1329 W Wilson Ave
$2,500

Total Monthly Price

Base Rent$1,450 - $2,500
Total Monthly Price$1,450 - $2,500
2 Bedroom Apartment Available Now

1329 W Wilson Ave

1329 W Wilson AveChicago, IL 60640
Affordability
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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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938 W Carmen Ave
$3,200

Total Monthly Price

Base Rent$2,550 - $3,200
Total Monthly Price$2,550 - $3,200
2 Bedroom Apartment Available Now

938 W Carmen Ave

938 W Carmen AveChicago, IL 60640
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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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Uptown, Chicago, IL Local Guide

Largest Available Uptown 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in the Uptown area of Chicago, IL is found at 900 W Montrose Ave and is listed at 1,250 square feet priced from $2,500. Here is today’s list of the largest available 2 Bedroom units in the area:

Apartment ListingModel NameSquare FootagePriced From
900 W Montrose Ave905 Agatite - 2 bed den1,250 Sq Ft$2,500
4180 Marine Terrace Apartments2BR/1.0BA1,200 Sq Ft$3,275
The DraperPH011,196 Sq Ft$4,895
Reside 707B61,155 Sq Ft$3,211
The Carmen2BR/2.0BA1,123 Sq Ft$3,200
1250 W Grace St1253-11,100 Sq Ft$3,000
3765 N Lakewood Ave1253-11,100 Sq Ft$3,195
Eight Eleven UptownB11,075 Sq Ft$3,566
The Eagle Building - 3833 N Broadway2BR/2.0BA1,014 Sq Ft$3,850
Tidemark2 bd / 2 ba827 Sq FtCall for Rates

Cheapest Available Uptown 2 Bedroom Apartments

Currently the lowest priced 2 Bedroom apartment unit Uptown of Chicago, IL is the 2 Bedrooms Floor Plan B3 Model starting from $2,179 at Times Square Apartments. The average price for all 2 Bedroom apartments in Uptown is currently $3,073. Here is today’s list of the cheapest available 2 Bedroom options in the area:

Apartment ListingModel NamePriced From
Times Square Apartments2 Bedrooms Floor Plan B3$2,179
Sheridan-Gunnison Apartments2 Bedroom$2,250
Sheridan Plaza - 4607 N Sheridan RdTwo Bedroom$2,308
1101-11 W. Grace St.Two Bedroom$2,495

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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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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Best Local Schools in
Uptown, Chicago, IL

School data provided by Great Schools

Lifestyle Ratings

ApartmentHomeLiving brings you our detailed rental search system called 'Lifestyle ratings', composed of rentals and neighborhoods across the USA, and customized analysis for Northern Chicago. Our Lifestyle Ratings help you zero-in on the perfect place to call home. This takes in many factors including rankings of the best places for the best proximity to parks and outdoor amenities, luxury amenities, transit availability, pet-friendly communities, places to raise kids, walking, and biking. Find Lifestyle Search in the filter options (above). Happy Searching!

Frequently Asked Questions about 2 Bedroom Uptown Apartments

What is the Cheapest apartment in Uptown with 2 Bedroom?

Currently the most affordable 2 Bedroom in Uptown is at Times Square Apartments listed at $2,179.

How much is the average rent for a 2 Bedroom Uptown Apartment?

The average rent for a 2 Bedroom Apartment in Uptown is $3,073.

What is the largest available 2 Bedroom Uptown Apartment for rent?

Today's apartment with the most square footage in Uptown is a 1,250 square feet unit starting from $2,500 at 900 W Montrose Ave.

What is the average size for Uptown 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Uptown is currently 1,700 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

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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

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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

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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.

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