View All South Loop Chicago IL Homes with Guest House Listings

3 Beds ⋅ 2 Baths ⋅ 12699009 MLS ⋅ ACTIVE Status ⋅ Prairie House At Central Station BLDG.

Stunning, bright and spacious NW corner home at the Prairie House in South Loop with spectacular skyline views. Open floor plan with huge living room flooded with light and featuring a gas fireplace, built-ins and motorized shades. Cooking will be a pleasure in the chef's kitchen with white cabinetry, quartz counters, stainless steel appliances (yes, a gas stove!) and a pantry. Dining area right off the kitchen leads to an awesome deck for grilling, cocktails and soaking in the unobstructed panoramic views. Hardwood floors throughout the living areas, great storage with custom closets and front loading LG in-unit washer and dryer. The primary suite features a large bedroom with a private, west facing balcony, huge bath with a tub and a separate shower and a walk-in-closet. The two additional bedrooms are spacious and can work as guest rooms or an office. Brand new carpeting installed in all 3 bedrooms. Two premier, side-by-side parking spaces are included in the price with room for your bikes. Excellent location in a super quiet enclave of townhomes east of Indiana Ave with easy access to the lakefront, Burnham Harbor, Museum Campus, Soldier's Field, Mark Twain Park and downtown. Walking distance to shopping, dining and nightlife. Meticulously maintained, full-amenity building with 24-hour doorman, sundeck, community room and fitness center, additional storage. $1.7M in reserves, no rental cap. Truly a remarkable property, living here will feel like a vacation retreat!

1515 S Prairie Avenue Unit #1214, Chicago

$1,170,000

4 Beds ⋅ 3 Baths ⋅ 12005485 MLS ⋅ CLOSED Status

Light pours into all four levels of this south-facing end-unit 4 bedroom / 2.5 bath townhome on a quiet tree lined street. With unobstructed views looking southwest, this townhome has the best views in the complex. The front gate leads you to a fully fenced in newly built stone patio and garden space perfect for entertaining. Upon entering the home, you're greeted by a gracious foyer and versatile living or home office space. The second floor is an open and light-filled space with wood flooring throughout, tall ceilings and exposure from almost all directions. Your generously appointed kitchen comes with sleek SS appliances, freshly painted white cabinets, kitchen island and plenty of space for a smaller eat-in kitchen table. The kitchen flows seamlessly into your formal dining room and oversized living / family room with wood burning fireplace. A powder room just off the kitchen is perfect for guest use while entertaining. The third level features an expansive primary suite that flows into a hallway flanked with newly updated closet space. The spa-like ensuite bath comes with a soaking tub, double vanity and large marble walk-in shower. Connected to the bath is a flexible den / bedroom or office space. The top level features a full bath and two additional large bedrooms one with a lofted play or reading space. Capping off this floor is a western facing deck with skyline views. The attached 2 car garage is perfect for additional storage. This home offers the best of South Loop living on one of its premier tree lined streets. Easy access to public transportation, the lakefront path and Soldier Field. Don't miss out on this light filled home with uneatable light.

1472 S Prairie Avenue, Chicago

$397,500

3 Beds ⋅ 3 Baths ⋅ 11936873 MLS ⋅ CLOSED Status

You wont believe the massive amount of space in this one-of-a-kind extra wide townhome in the South Loop! Enjoy the benefits of townhome living while having the security and amenities found in a high rise condo! Enter the home through a welcoming courtyard on the buildings 4th floor and enjoy this exclusive opportunity, only 1 of 8 townhomes in the building! Gracious foyer with 2 sets of closets flows nicely into the main level with features oak hardwood floors and an open layout. South facing living area with floor to ceilings windows, a fireplace and large deck, perfect for relaxing, grilling and entertaining. Designated dining area can house a large table. Updated kitchen features granite countertops with an island, beautiful 42" dark espresso cabinets and stainless steel appliances, including a newer refrigerator & dishwasher (2022), + pantry with pull out shelves. Powder room with custom vessel sink is also conveniently located on the living level. Newer carpet on the bedroom level which features a huge king-size primary bedroom with walk-in closet. Ensuite bathroom boasts a dual sink vanity with granite counters, separate shower & Jacuzzi tub. The 2nd bedroom and guest bathroom are on the 2nd level along with new washer/dryer (2022). The multifunctional top floor can be used as a family room, den/office, playroom, or 3rd bedroom! Roof deck off of the top floor flex space is ideal for entertaining! Sought after 1st floor garage space available for $25k + storage cage included in price. AC (2017). Water Heater (2016). Assessments include heat, gas, water, cable and internet - only additional bill is electric! Well run building with a newly renovated lobby, door staff, business center and gym. Prime South Loop location just 3 blocks to the EL, and steps to Soldier Field, Museum Campus, dog parks, playgrounds and Millenium Park. Investor friendly building.

1529 S State Street Unit #TH2, Chicago

$337,000

2 Beds ⋅ 2 Baths ⋅ 11867772 MLS ⋅ CLOSED Status

Fabulous 2 bedroom 2 bath at Chess Lofts nestled in the historic Prairie District! Nice foyer area with coat closet, in-unit washer/dryer, and plenty of space for a console table upon entering the unit. Great sized second bedroom off the foyer and guest bathroom opposite of the bedroom. Kitchen features stainless steel appliances, granite countertops, and breakfast bar for seating. Ample space for a dining table/chairs that lead into the living room. Large balcony off the living room with great city views. Primary bedroom features 2 closets, ensuite bathroom with separate shower and tub. Garage parking space #62 (and it's a large space!) included in the price. Building features gym, key-access bike storage in heated garage, and common green rooftop deck with amazing city and Lake Michigan views. Entire unit was just repainted, so it will be a blank slate for the new owners! Building surrounded by history and museums including The Wheeler Hotel next door (designated as a Chicago Landmark in 1998), The Clarke-Ford House Museum (one of Chicago's oldest surviving homes after the fire), and The Glessner House Museum. Close to a plethora of entertainment venues including Soldier Field, McCormick place, and the new Wintrust Arena. Tons of great dining and coffee options nearby including Apolonia, Showroom Food Hall, Spoke & Bird, Teapot Brew Bakery, Il Culaccino to name a handful! Pedestrian access ramp to Lakeshore Path down the street at 18th and Calumet, Prairie District Park and Dog Park & 16th & Prairie Dog Park nearby, and much, much more.

320 E 21St Street Unit #304, Chicago

Start Your Search

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.

South Loop, Chicago IL · Curated MLS Search

Homes with Guest House in South Loop, Chicago IL

An editorially curated view of every active homes with guest house listing in South Loop, Chicago IL. Updated in real time from the local MLS, presented without the noise.

Browse Active Listings

South Loop, Chicago IL Market Snapshot

Inventory here shifts week to week. The listings on this page pull straight from the MLS, so what you see is what's actually for sale right now.

Next Steps in South Loop, Chicago IL

Speak with an Agent

Call (312) 788-7079

Local South Loop, Chicago IL expertise

Data Brief

Full South Loop, Chicago IL Market Report

Pricing trends & absorption

Browse Everything

All South Loop, Chicago IL Listings

Every active property

← Back to South Loop, Chicago IL Homes for Sale