
Apartment holiday rentals in South Side
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Top-rated apartment rentals in South Side
Guests agree: These apartments are highly rated for location, cleanliness and more.

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.
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Hidden Gem:Artsy Speakeasy in Historic Bronzeville
Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TV, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles), Navy Pier, Obama Library, Millennium Park, Beach (1 mile), Museum, & Sports arenas.
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Best Location in Hyde Park apartment
Lovely 2 bedroom apartment in Hyde Park. Within one block of the U of Chicago. The lake is within a 10min walk. Ample Street Parking available in safe street patroled by UChicGo police. Close to the science museum, Metra, restaurants, parks, and famous Japanese garden. Updated unit was remodeled last year for you to enjoy. Separate living/dining rooms. Extra cleaning fee for 2nd bedroom. Great view to the park and tennis courts and porch on the kitchen to enjoy breakfast outside.
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Spacious 1BR Garden Apt & Parking
Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. This is our home, so we are mostly upstairs or nearby if needed. Access is private via back gate just off the parking lot with reserved parking space.
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1BR South Loop Loft I SuperHost + Top Rated!
Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!
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Blue Brick Apartment in Bridgeport - Park for Free
• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 2nd floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)
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Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.
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Pilsen Modern Chic Retreat
Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.
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LIVN West Loop Chicago Queen Studio Apartment
Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.
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Travel To Chicago New City
You'll fall in love with this Cozy Modern Home on your visit to bustling Chicago! - 10mins to downtown - Short walk or drive to hip breweries - Near supermarkets - Modern appliances in the open kitchen - Full size comfy memory foam mattresses - Huge backyard patio with pergola and string lights for relaxing
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Hyde Park/ Bronzeville Apartment 3E
Simply your home away from home. This beautiful three bedroom living quarters has a lovely peaceful atmosphere. Minutes from downtown Chicago, Hyde Park as well as President Obama's home! When you stay here, you will be centrally located to enjoy great eatery, night life, museums and much more!
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Beverly Area Boutique -Central (South) Location
In the historic Beverly area this quaint space was built in 1880! Peaceful, quiet and safe! Located 3-5 mins from both major highways. Minutes from Downtown Chicago… aboard Metras safe and comfortable rail. This special place is close to everything, making it easy to plan your visit.
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Popular amenities for South Side apartment rentals
Weekly apartment rentals

Designer Garden Unit in Bridgeport
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Roomy and Comfortable Apartment with everything UN
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Sunny Penthouse - Oakwood Beach
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Cozy Hyde Park Apartment | Near Lake & UChicago
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Lux New Hyde Park Apt by UChicago, Museum of S&I
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Stylish Hyde Park/Kenwood Brownstone Garden Apt
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Modern Eco Stay • UChicago • Parking • Backyard
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Simply Sleek & Uneek: Mins To/Fr D'Town Chicago
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Private apartment rentals

Beautifully Remodeled 2B in Historic Hyde Park
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Windy City Escape- 2 queen BR
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Relaxed Hyde Park Studio Getaway Near Downtown
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Chicago stay Near Midway Airport • CTA • Downtown
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Comfortable and Cozy Apartment
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La Casita Norte
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Chic Studio in Historic Hyde Park – Walk to Campus
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Penthouse, Lux stay near Downtown, McComick & Lake
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Apartment rentals with a hot tub

Spacious and Ideally located in the Lakeview area
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Luxury 3BD Penthouse – Private Patio+Skyline Views
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Luxury South Loop Apt
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33rd-Floor Penthouse with Breathtaking Views
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420 friendly apt with 2 queens,1 full,1 twin bed
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DuSable International House Near The Obama Library
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Checkerboard Studio, Private Outdoor Hot Tub, Yard
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South Loop Suite (Indoor Pool • Fitness Center)
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- Wrigley Field
- Soldier Field
- United Center
- Lincoln Park
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- University of Chicago
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Donald E Stephens Convention Center
- Union Park
- Beachwalk Vacation Rentals
- Washington Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park





