Holiday rentals in West Side

Beautiful Chicago Greystone

Experience the best of Chicago from this sprawling, private 4-bedroom condo. Located just 15 minutes west of the City Center, you’re perfectly positioned to explore the culinary scene of the West Loop, the lush Garfield Park Conservatory, and the energy of the United Center Transit: Steps from multiple bus lines, 2 blocks to the Blue Line, and 1 mile to the Pink Line Amenities: On-site laundry (available upon request) Local Experts: We live in the unit below and happy to give recommendations

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center

Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, girls trips, family gatherings, professionals or large groups seeking cozy comfort Unwind in the spa-style bath tub, gather in the private backyard patio, with fire place for cozy evenings accommodating your group Steps from Metra station with a direct train to Downtown, 4mins away from the Obama presidential center in Jackson pack, museum of science & industry and the lake

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Apartment in Chicago. Just 15 mins from downtown

Escape to your private sanctuary in Chicago near downtown. We have (2) charming one-bedroom apartments next door to each other. The perfect blend of comfort and convenience for your next getaway. A peaceful neighborhood, you'll find a bright and inviting living space, complete with comfortable sofas and smart TVs for relaxing evenings. The fully equipped kitchen has everything you need to whip up a delicious meal, whether it's a quick breakfast or a gourmet dinner. A safe space to unwind.

Pilsen Prism: Sun-Drenched 3BR + Parking

Experience the ultimate Chicago stay in this sun-drenched Pilsen sanctuary. With massive floor-to-ceiling windows and an "urban treehouse" vibe, this modern 3BR/2.5BA duplex is a light-filled retreat for groups. Enjoy soaring ceilings, a sleek chef’s kitchen, and curated minimalist design. Rare bonus: 1 private parking spot included! Nestled in the heart of Pilsen’s world-class art and dining scene. Spacious, stylish, and perfectly located - your luminous urban escape starts here.

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

The Chicago Cozy Brick Retreat

This unit offers a charming blend of modern amenities and historic charm. This thoughtfully designed unit features an open-concept living space with exposed brick walls and stylish furnishings. The fully equipped kitchen boasts new appliances, perfect for culinary adventures. The comfortable bedroom, with a cozy bed and ample storage, ensures a restful stay. The sleek bathroom includes contemporary fixtures and a walk-in shower. Street parking is easily available.

Comfortable and Cozy Apartment

Enjoy this simple and cozy apartment! Located just a few blocks from stores like Walgreens, Aldi, Target, Laundromat and various restaurants. Its conveniently located just a 10 minute walk from the orange line cta train station. Disfrutá de la sencillez de este alojamiento tranquilo y céntrico. Ubicada a dos minutos de tiendas como target, Walgreens, Aldi, Lavandería y restaurantes . Estamos a 10 minutos del aeropuerto midway y 15 minutos del centro de Chicago.

Chicago Row House Garden Apartmt

This stylish urban garden apartment is a comfortable stay just a few blocks from the United Center and 1 mile from the very popular West Loop and Fulton Market areas! Street parking is readily available and free! We are a 3 mile straight shot down to Millennium Park in the Loop. Take the “L”, bike or walk there and hit Greek Town, the Lyric Opera, the Sears (Willis) Tower, the Art Institute and the Bean (Cloud Gate) along the way!

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.

Loft-Inspired Pilsen Retreat | 10 min to Downtown

Unwind in this loft inspired unit with soaring ceilings, ideally located just 10 minutes from downtown Chicago in the vibrant Pilsen neighborhood. Enjoy a fully-equipped kitchen, luxury bathroom with rain shower, cozy queen bedroom, and spacious living area with a pull-out sofa. Features include high-speed WiFi, central heat/air, Smart TVs, and washer/dryer access. Perfect for up to 4 guests–your chic urban retreat awaits!