
Alquileres vacacionales en apartamentos en South Side
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Apartamentos vacacionales con mejores calificaciones en South Side
Los huéspedes concuerdan en que estos apartamentos tienen excelentes valoraciones, entre otras cosas, por su ubicación y limpieza.

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.

Sunny Penthouse - Oakwood Beach
Bright top-floor 2-bedroom, 2-bath condo in the heart of Bronzeville with soaring ceilings and abundant natural light. Relax in the in-unit jacuzzi jetted tub after a day exploring Chicago. The fully equipped kitchen has everything you need to cook at home, or enjoy nearby restaurants. 🌊 Just a 18-minute walk to Oakwood Beach & the lakefront. Within a 20-minute drive of Downtown, Soldier Field, Guaranteed Rate Field, the Field Museum, the Art Institute, Chinatown, Hyde Park, Pilsen & more!

Modern Soul Retreat: 3BR in Bronzeville/HydePark
Experience a modern sanctuary where design meets history in the heart of Chicago’s legendary Bronzeville. This spacious 3-bd, 2-ba flat blends art, minimalist comfort, and cultural warmth. Steps from Hyde Park, Lake Michigan, and local cafes, the space invites you to unwind, reflect, and reconnect with the soul of the South Side. Featuring curated decor, luxury finishes, and a nod to Bronzeville’s Soulful Metropolis legacy, this home offers a one-of-a-kind stay—equal parts style and heritage.

University Retreat
Lovely 3 bedroom apartment in Hyde Park location. Within one block of the U of Chicago; close to the science museum, Metra, restaurants, parks, and less than 1 mile from the proposed Obama Library and the lake. Updated unit has nearly 1,300 SF of livable space to enjoy: vintage hardwood floors throughout, separate living/dining rooms, kitchen with new stainless steel appliances, new furnace, new hot water tank, and a new porch with large fenced yard. Permit parking for guests only!

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.

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)

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.

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.

LIVN West Loop Chicago Classic 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.

Stylish Hyde Park/Kenwood Brownstone Garden Apt
Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.

The Posh Apt. Mins to Downtown & Hyde Park
This spacious garden apt in a 12 yrs old building is sitting in the heart of a historical Bronzeville neighborhood. The unit is setup with all necessary amenities/supplies that will make you comfortable and a memorable trip for you. It is modern, contemporary and a most stay place for a guest like you! I bet you will like it.....

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
Comodidades populares de los apartamentos vacacionales en South Side
Apartamentos vacacionales por semana

Luxurious Bronzeville Apartment with RoofTop

Lux New Hyde Park Apt by UChicago, Museum of S&I

3BR • Massage Chair • 5 Min to UChicago • Sleeps 6

Beautifully Remodeled 2B in Historic Hyde Park

Cozy Coach House Apartment-Near Downtown Chicago

Modern Eco Stay • UChicago • Parking • Backyard

Ingleside Oasis

Beautiful Penthouse (Near Obama Center, UChicago)
Apartamentos vacacionales privados

Comfortable and Cozy Apartment

Spacious 1BR Garden Apt & Parking

Designer Garden Unit in Bridgeport

Classic Chicago Apt in Hyde Park Near UofC

Spacious Parkside 3BR Retreat

Quaint 3BR Home Near Attractions

Vintage Ambience

Stay Above Chicago's Post-Punk Museum - 4BR Loft
Apartamentos vacacionales con jacuzzi

Checkerboard Studio, Private Outdoor Hot Tub, Yard

33rd-Floor Penthouse with Breathtaking Views

Comfy Near Downtown Chicago

DuSable House cerca de la librería Obama

420 friendly apt with 2 queens,1 full,1 twin bed

Level Two Bedroom Suite | Fulton Market

Luxury 3BD Penthouse – Private Patio+Skyline Views

South Loop Suite (Indoor Pool • Fitness Center)
Destinaciones para explorar
- Chicago Alquileres vacacionales
- Indianápolis Alquileres vacacionales
- Columbus Alquileres vacacionales
- San Luis Alquileres vacacionales
- Louisville Alquileres vacacionales
- Cincinnati Alquileres vacacionales
- Detroit Alquileres vacacionales
- Milwaukee Alquileres vacacionales
- Traverse City Alquileres vacacionales
- Downtown Chicago Alquileres vacacionales
- Ann Arbor Alquileres vacacionales
- Windsor Alquileres vacacionales
- Bed and breakfasts South Side
- Condominios vacacionales South Side
- Alojamientos con desayuno South Side
- Alojamientos con acceso al lago South Side
- Alojamientos frente al mar South Side
- Alojamientos vacacionales para familias South Side
- Suites privadas vacacionales South Side
- Alojamientos con acceso a la playa South Side
- Alojamientos vacacionales que admiten mascotas South Side
- Casas adosadas vacacionales South Side
- Casas vacacionales South Side
- Alojamientos con jacuzzi South Side
- Alojamientos vacacionales con piscina South Side
- Apartamentos vacacionales Chicago
- Apartamentos vacacionales Cook
- Apartamentos vacacionales Illinois
- Apartamentos vacacionales Estados Unidos
- Wrigley Field
- Soldier Field
- Parque Lincoln
- United Center
- Grant Park
- Muelle de la Marina
- Parque del Milenio
- Parque Estatal de las Dunas de Indiana
- Estación Naval Great Lakes
- 875 Avenida Michigan Norte
- Six Flags Great America
- Universidad de Chicago
- Museo Field
- Acuario Shedd
- Humboldt Park
- Universidad Loyola de Chicago
- Guaranteed Rate Field
- Zoo de Lincoln Park
- Union Park
- Beachwalk Vacation Rentals
- Casa y Estudio de Frank Lloyd Wright
- Donald E Stephens Convention Center
- Byline Bank Aragon Ballroom
- Zoológico de Washington Park





