The Loop Homes under $500,000

The Loop Homes under $500,000

Welcome to The Loop, Chicago's vibrant heart that perfectly marries urban energy with a touch of historic charm. Nestled in Cook County, this iconic neighborhood is renowned for its stunning architecture, bustling business district, and cultural landmarks. Whether you're a young professional, a growing family, or a savvy investor, The Loop offers a dynamic lifestyle and a diverse array of homes, including fantastic options under $500,000.

Imagine residing in a neighborhood where every day feels like an adventure. The Loop is not just a place to live; it's a hub of activity, with world-class dining, shopping, and entertainment right at your doorstep. Stroll along the picturesque streets and take in the stunning skyline, or enjoy a leisurely afternoon at Millennium Park, where you can relax by the iconic Cloud Gate sculpture and catch a free concert in the summer.

For those seeking affordable homes, The Loop has a variety of options that cater to different tastes and preferences. From chic condos with modern amenities to cozy lofts that boast character and charm, there’s something for everyone. With prices under $500,000, you can find your dream home without breaking the bank.

Living in The Loop means being part of a thriving community that celebrates art, culture, and innovation. With easy access to public transportation, you can explore all that Chicago has to offer, from the trendy neighborhoods of Wicker Park to the historic streets of Hyde Park. Discover your perfect home in The Loop and embrace the exciting urban lifestyle that awaits you!

Newest The Loop Homes under $500,000

65 E Monroe Street Unit #4711, Chicago
$325,000
1 Beds ⋅ 1 Baths ⋅ 12767006 MLS ⋅ NEW Status
Soaring 47th-floor 1 bedroom/1 bathroom residence at The Park Monroe with floor-to-ceiling windows and sweeping skyline views. The open living and dining area flows out to a private balcony, with warm hardwood flooring throughout the main living space and roller shades on every window. The kitchen is made for cooking and entertaining. It has a large granite island with seating for three, abundant storage, and stainless-steel appliances including a gas range. The spacious bedroom offers two double-door closets for excellent storage. The full bath features a tub with frosted glass sliding doors and a stone-topped vanity with generous cabinet space. In-unit washer and dryer. This full-amenity building offers 24-hour door staff, a sundeck with firepit and grills, an outdoor hot tub, an indoor lap pool, a fitness center, a theater room, a party room, and a dog run. Steps to Millennium Park, the Loop, transit, and dining.

65 E Monroe Street Unit #4711, Chicago
330 S Michigan Avenue Unit #1910, Chicago
$285,000
2 Beds ⋅ 2 Baths ⋅ 12791962 MLS ⋅ NEW Status
Best priced 2bed/2bath at 330 S Michigan. Spacious split true two-bedroom with and in-unit washer/dryer. Loads of light with extra large windows in each room. Plenty of closet space and Full storage cage on the same floor. Great floor plan for home office or roommate situation. 24-hour security, exercise room, on-site engineer. Convenient to all modes of transportation. Enjoy Michigan Avenue living in the historic McCormick building close to Symphony Center, Millennium Park, Theater District, Universities, the Loop businesses and the Cultural Mile. Come home to the elegant marble entry, wide, well maintained corridors with historic architectural details of moldings, tray ceilings, and more. Full-time door staff, cleaning staff. At this great value, this unit is definitely worth checking out. Rental parking options or future parking purchase is available.

330 S Michigan Avenue Unit #1910, Chicago
235 W Van Buren Street Unit #2816, Chicago
$360,000
2 Beds ⋅ 2 Baths ⋅ 12788416 MLS ⋅ NEW Status
Welcome home to high rise living in the heart of it all. This sleek unit features floor-to-ceiling windows, hardwood floors, high ceilings, generous closets, and private outdoor space. Enjoy sweeping city views and conveniences like in-unit laundry, garage parking (included in the price), and on-site grocery. With fresh paint throughout and brand new carpet, all that's left to do is move in!

235 W Van Buren Street Unit #2816, Chicago
400 E Randolph Street Unit #2218, Chicago
$285,000
1 Beds ⋅ 1 Baths ⋅ 12789344 MLS ⋅ NEW Status
BRING YOUR CREATIVE SIDE AND MAKE IT YOUR OWN! This spacious 825 sq. ft. one-bedroom offers a wonderful opportunity to create a home that reflects your personal style. Do as much-or as little-as you want! Enjoy a generous floor plan, huge private terrace, and beautiful views in a fantastic location. The home is priced with its current condition already considered, giving you the flexibility to update, renovate, or simply move in and make changes over time. A great opportunity to add your own finishing touches without paying for someone else's renovation choices. GREAT LOCATION, GREAT BUILDING & GREAT VIEWS! The building offers strong reserves and solid finances, along with an impressive array of amenities. Enjoy a full-service lifestyle with a health club and spa, indoor pool, fitness facilities, sundeck and more. Whether you're looking for a primary residence, in-town home, or a property you can personalize over time, this is an opportunity to get a large one-bedroom with exceptional outdoor space in a highly desirable building and location. Bring your ideas, bring your style, and make this one your own!

400 E Randolph Street Unit #2218, Chicago
60 E Monroe Street Unit #1905, Chicago
$339,900
1 Beds ⋅ 1 Baths ⋅ 12789912 MLS ⋅ NEW Status ⋅ The Legacy At Millennium Park BLDG.
Enjoy elevated downtown living in this move-in-ready 1-bedroom, 1-bathroom condo with the convenience of an in-unit washer and dryer, floor-to-ceiling windows, and a private balcony overlooking the city. Spanning 875 SF on the 19th floor, this inviting residence feels bright and open, with hardwood floors throughout the living room and kitchen. The modern kitchen pairs dark cabinetry with granite countertops and stainless steel appliances, while a cozy nook in the living room offers the perfect spot for a home office. Retreat to a generously sized bedroom with ample room for a king-sized bed and a walk-in closet. The spacious bathroom includes a bidet-equipped toilet and grout updated in 2026. Beyond the unit, The Legacy at Millennium Park offers full-service living in the heart of Chicago's Loop, with 24-hour door staff, on-site management and maintenance, an indoor pool and whirlpool, fitness center, steam rooms, landscaped terrace, multiple skydecks and lounges, and a secure outdoor dog run. Other conveniences include an assigned storage cage, bicycle rooms, EV charging, and garage parking (spaces may be available for purchase from other residents). Skybridge access to the University Club of Chicago and resident clubs, committees, and social activities add to the sense of community. Located directly across from Millennium Park and near Grant Park, Buckingham Fountain, the Art Institute, Chicago Symphony Center, Riverwalk, Lakefront Path, dining, entertainment, and public transportation, this address puts the best of downtown Chicago within easy reach.

60 E Monroe Street Unit #1905, Chicago
235 W Van Buren Street Unit #2314, Chicago
$375,000
2 Beds ⋅ 2 Baths ⋅ 12790092 MLS ⋅ NEW Status
Experience the height of Loop luxury in this rare, sun-drenched 2-bedroom, 2-bathroom corner unit perched on the 23rd floor of the iconic Perkins + Will-designed 235 W Van Buren. Boasting a highly coveted north and west dual exposure, this turnkey home offers sweeping, unobstructed views of the Willis Tower, the Chicago River, and stunning western sunsets. Spanning a smart 900+ square feet The interior has been completely revitalized with brand-new flooring and a freshly painted modern palette. The open-concept kitchen is fully upgraded with an entirely new stainless steel appliance suite, including a brand-new dishwasher, refrigerator, microwave, and an upgraded premium stove. Privacy windows in the second bedroom. Enjoy optimal privacy with a split-bedroom floor plan and seamless access to public transit, world-class dining, and the downtown financial district. Move right in and watch the city come alive from your private urban oasis!

235 W Van Buren Street Unit #2314, Chicago
400 E Randolph Street Unit #1515, Chicago
$425,000
1 Beds ⋅ 1 Baths ⋅ 12788521 MLS ⋅ ACTIVE Status ⋅ New Eastside BLDG.
Gorgeous world-class LAKE views for life! Great large condo with sunny South views of the lake, harbor, park, and skyline. Large private terrace. Full-sized 1-bedroom with 825 sqft. Financially strong building. Newer windows, new risers, newer health club, new elevators and more! This is a great unit in the heart of Chicago's New Eastside (60601). Come see the exciting "New Eastside" neighborhood. The building, Outer Drive East, is almost new again, with numerous renovations and strong financials. All-new lobby with glistening white terrazzo floors. New windows, new 5-star resort-like health-fitness spa. Racquetball, basketball, free weights, machine weights, cardio, massage therapy, children's playroom, and a famous geodesic domed year-round sunny pool. Hospitality/party room, business center with resident computers and a printer, library, community BBQ grills, and a bi-level sun deck. HOA includes heat, a/c, gas, cable, cable with TiVo 6 DVR, 24/7 lobby desk, security, and door attendants. 3 bike rooms and 3 car-washing stalls. A restaurant bar/grill, a beauty and nail salon, and several other businesses are located on the 7th floor. There are two grocery shopping options: either Bockwinkel's Harbor Market (across the street) or a 2-story Mariano's grocery store with good prices and a wide selection for your daily shopping needs. Very friendly building with lots of social activities and events, including a book club, world affairs club, bingo, summer picnic, children's Halloween party, children's holiday party, and a resident holiday party, to name a few. Great Outer Drive East community in the New Eastside neighborhood. Nestled in the New Eastside neighborhood is Lakeshore East Park. This 6-acre oasis in the neighborhood's nucleus includes large grassy areas, a children's playlot, and a dog park. Maggie Daley Park is across Randolph Street to the south and incorporates tennis courts, a children's activity area, park district facilities with programming, the famous ribbon ice skating rink, mini-golf, and professional outdoor climbing walls. Millennium Park is a block away from all the world-famous music venues, including the Grant Park Orchestra, Saturday morning exercise classes, and outdoor movies in the summer. 30-minute free parking for showings, guests, and deliveries. Located in the New Eastside neighborhood, this prestigious condo is just moments away from fine dining, upscale shopping, the lake and harbor, and cultural landmarks.

400 E Randolph Street Unit #1515, Chicago
330 S Michigan Avenue Unit #1601, Chicago
$439,900
2 Beds ⋅ 2 Baths ⋅ 12786433 MLS ⋅ ACTIVE Status
Exquisite East view with breathtaking lake shoreline views, Buckingham fountain, Adler Planetarium, Chicago Museum, Grant Park, Millennium Park, Monroe Harbor and much more. New flooring throughout, Open concept layout kitchen with island, fully updated with elegant quartz countertops, gold and marble backsplash, with Viking oven range, island vent hood with charcoal filters, new recess lights, SS Refrigerator, Dishwasher and Microwave. Beautiful custom built-in mounted electric FP, with designed shelves add to the elegance of the L/R. Updated modern vanity in MB en suite, 2nd bedroom offers more space for additional bed, divider can be removed. In-unit laundry. Furnitures can be included. Step to Metra, CTA, Walk to Millennium Park, Chicago Cultural Mile, Art Institute, Symphony Center, Auditorium Theatre, Chicago Theatre District, Museum Campus. Residents enjoy the perfect blend of historic character and modern city living, with professional door staff, fitness facilities, private storage, and investor-friendly ownership options. Situated in the heart of the Loop, you'll be steps from world-class dining, shopping, cultural attractions, lakefront recreation, public transportation, and everything downtown Chicago has to offer. Whether you're seeking a primary residence, in-town retreat, or investment opportunity, this rarely available home delivers exceptional views, an unbeatable location, and the exclusivity of being the only active listing in the building. Secure indoor parking is available for lease, sellers leasing 1 pkg space #20 for 250/month, can be transferred to the new owner at same rate.

330 S Michigan Avenue Unit #1601, Chicago
222 N Columbus Drive Unit #2209, Chicago
$459,000
2 Beds ⋅ 2 Baths ⋅ 12785269 MLS ⋅ ACTIVE Status
Move-in-ready southeast corner two-bedroom, two-bath condo with a private balcony overlooking Lakeshore East Park and the surrounding skyline. Thoughtful updates, continuous wide-plank luxury vinyl flooring, motorized window treatments, and custom California Closets throughout make this home especially comfortable and easy to move into. | OPEN LIVING + DINING: The split-bedroom floor plan features a spacious living room with large windows and sliding glass doors to the balcony. The dining area is conveniently located off the kitchen, with room for a full dining table. | KITCHEN: The open kitchen features black granite countertops, breakfast-bar seating, a custom mosaic tile backsplash, stainless steel appliances, and newer kitchen appliances. | TWO BEDROOMS + TWO BATHS: The primary bedroom includes a walk-in closet with a custom California Closets system and an ensuite bathroom. The second bedroom is located on the opposite side of the condo, with a nearby full bathroom. Both bathrooms are clean and well maintained, with a tub/shower combination. | CUSTOM STORAGE + EVERYDAY COMFORT: Every closet has been fitted with California Closets organizers, making excellent use of the available storage. Wide-plank flooring continues throughout the home, complemented by white baseboards, neutral paint, motorized window treatments, a blackout shade in the bedroom, and an in-unit washer and dryer. | PRIVATE BALCONY + SOUTHEAST VIEWS: Enjoy outdoor space with views of Lakeshore East Park, Aqua's landscaped amenity deck, and the surrounding New Eastside skyline. | RECENT BUILDING IMPROVEMENTS: Park Millennium has completed its multi-year elevator modernization project, along with a newly renovated elevator area and updates to several common spaces. | FULL-SERVICE AMENITIES: 24-hour door staff, on-site management, indoor pool, hot tub, sauna, steam room, fitness center, yoga studio, renovated party room, business center, game room with a new golf simulator and pool table, outdoor sundeck with grilling areas, dog walk, and on-site dry cleaning. Cable and internet are included in the monthly assessments. | EVERYDAY CONVENIENCE: Direct access to Chicago's Pedway system, Bockwinkel's grocery nearby, and rental parking available in the attached garage. Enjoy easy access to Lakeshore East Park, Millennium Park, the Riverwalk, Michigan Avenue, shopping, dining, and public transportation.

222 N Columbus Drive Unit #2209, Chicago
431 S Dearborn Street Unit #1603, Chicago
$400,000
4 Beds ⋅ 2 Baths ⋅ 12777033 MLS ⋅ ACTIVE Status
Own a piece of Chicago history! Spacious 4-bed with primary ensuite and walk in closet, 2-bath home in the landmark Manhattan Building (1891), designed by William Le Baron Jenney and Chicago's oldest surviving steel-frame skyscraper. Signature bay windows fill the unit with natural light. Enjoy hardwood floors, stainless steel appliances, abundant closet space, and in-unit laundry. The flexible layout suits roommates, a home office, or room to spread out. Secure Butterfly automated entry and a bike room ($75/year per bike) add everyday convenience. Parking is available nearby through the building's agreement with 314 S. Federal ($15/day or $250/month). Pet friendly and rental friendly (6-month minimum lease), so it's great for owner-occupants or investors. Perfectly set in Printing Row/South Loop, steps from Grant Park, Dearborn Station, the Loop, restaurants, shops, and multiple CTA lines. A rare large floor plan in a true architectural icon. Don't miss it!

431 S Dearborn Street Unit #1603, Chicago
212 W Washington Street Unit #1908, Chicago
$340,000
2 Beds ⋅ 2 Baths ⋅ 12773247 MLS ⋅ ACTIVE Status
Experience downtown Chicago living at its finest in this rarely available and highly coveted 2 bed, 2 bath residence at 212 W Washington, a historical treasure rich in architectural charm. This spacious "soft loft" unit features an expansive open layout with soaring ceilings, hardwood floors throughout, and oversized windows that flood the home with natural light. The renovated kitchen with island is perfect for entertaining, offering ample prep space and open flow to the living space. The living and dining areas - with a gas fireplace - open effortlessly onto a private 15-foot west-facing balcony, ideal for taking in sunsets and the vibrant cityscape below. Both bedrooms in this unit have been fully enclosed for privacy! The primary suite includes an en-suite bath and abundant closet space, while the second bedroom and full guest bath (that opens up to both the hall and the second bedroom) offer flexibility for guests, a home office, or both. In-unit washer and dryer provide everyday convenience, while the building delivers full-service amenities including a 24-hour door staff, remodeled fitness center, sun deck with fireplaces and lounge furniture, community grills, bike room, dog run, on-site manager/engineer, storage, Tide laundry lockers, and an elegant lobby that honors the building's historic architecture. Originally constructed in 1913 and once home to the Illinois Bell headquarters, this beautifully restored Beaux-Arts structure-now known as The City Centre Condominiums-seamlessly blends early 20th-century elegance with modern luxury. Set in the heart of the Chicago Loop, residents are surrounded by the best of city living-the Chicago Riverwalk, Millennium Park, State Street shopping, and the Theatre District are all just steps away. With CTA train lines, Metra stations, and expressway access right outside your door, exploring every corner of the city couldn't be easier. HOA includes all utilities (including internet and cable) except electricity. Don't miss this opportunity to own a piece of Chicago history in a location that truly connects you to everything the city has to offer.

212 W Washington Street Unit #1908, Chicago
222 N Columbus Drive Unit #2207, Chicago
$255,000
1 Beds ⋅ 1 Baths ⋅ 12783585 MLS ⋅ ACTIVE Status
This unit boasts a prime location featuring floor-to-ceiling windows with abundant natural light and stunning balcony views. The spacious layout includes sliding doors leading to the balcony from both the living room and the bedroom, two generous closets, and an in-unit washer and dryer. The building is within walking distance of Millennium Park, the Magnificent Mile, the Chicago Riverwalk, world-class dining and underground pedway. Fully renovated luxury amenities-included in the HOA fees-feature a 25-meter lap pool, Jacuzzi, 24-hour fitness center with sauna, club room with private dining, and a business center. Amenities also include a relaxing tree-lined sundeck with grills, 24-hour door security, an on-site grocery, and dry cleaners. The building is also pet-friendly.

222 N Columbus Drive Unit #2207, Chicago
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