House holiday rentals in West Side

Cool Quiet Coach House, Private Access + Patio

Retreat to the brick patio of this lovingly renovated home after a long day traversing the neighborhood. The interior is an expression of creativity, greyscale walls, rustic accents, and a varied selection of art and wall hangings tie in the decor. Split Level Floor plan. 1st floor = Living, Eat in Kitchen, bedroom 1 and bathroom. 2nd Floor = 2nd bedroom , bath and an additional sleeping area and desk area. Also features a gorgeous shared yard. The entire coach house is yours!! The coach house is set back behind a 2 unit building and the yard is shared between both. We are available via text or airbnb messaging and try to respond quickly. Please reach out anytime if you need anything at all. Extra supplies, neighborhood recommendations or tips in the neighborhood. The home is located on the border of Wicker Park and Bucktown which is Chicago's original hub of cool. It is a vibrant enclave of culture and commerce, explore vintage finds, record stores, and plenty of indie shopping in this trendy part of town The 24 hour Blue Line EL train is just a 5 minute walk. Door to Door it's only 25 minutes to Millennium park. (5 min walk to the blue line, 10 min ride on the train, 10 minute walk to the Park). The neighborhood is pedestrian and bike friendly , the 606 trail is just a few blocks away also.

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

United Center Compound w/Rooftop, Hot Tub, Sauna

Welcome to the Chicago Mid-Century Gem, an extraordinary urban retreat. With easy access to the CTA Green Line and Madison 20 bus stop, explore the United Center, West Loop, Fulton Market, and downtown with ease, then return to a home designed for gathering and entertaining. Featuring 4 spacious bedrooms, a chef's kitchen, a rooftop deck with a bar, a game-ready lower level, a luxurious primary suite, and a rare heated 3 car garage, this home is the perfect place to relax after every adventure.

NEW! 3BR/2.5B Duplex in Noble Sq

Welcome to our stunning 3 bedroom, 2.5 bath duplexed condo with free parking and ample outdoor space in the heart of the vibrant Noble Square neighborhood. This open, bright and spacious unit is a true urban oasis that will make you feel right at home in the epicenter of Chicago. Our condo is close to some of the city's best restaurants, cafes, and bars, as well as several beautiful parks. With its unbeatable location, modern design, luxurious amenities, and SuperHost service - look no further!

Charming 3-BED in Lincoln Park/ Old Town & Parking

Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

The Full House

A tranquil space surrounded by natural light and embraced by lush greenery. This entire house, with a backyard and parking garage, is in a peaceful neighborhood with tree-lined streets. Just 3 miles from downtown Chicago. A 2-minute walk from public transportation. For local delights, Wicker Park/Humboldt Park beckon with excellent dining/cultural experiences at your doorstep. "When you're lost out there and you're all alone, a light is waiting to carry you home..." Welcome to the Full House!

Chicago Home (1st floor) by Midway near Downtown

Hello, Welcome in 1st floor apt, where 3 rooms are available with newly remodelled kitchen, bathroom and livingroom. LOCATION, convenient location, walking distance to grocery store and few restaurants near by, also walking distance to public transportation bus 62 and 62 H. 5 min driving to Midway airport and 15 min driving to downtown Chicago. Easy access to public transportation to get to Chicago downtown. In addition to convenient location, apt offers access to yard and free parking

Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!

No cleaning fees! Gorgeous gem 10 miles from Downtown, Airport, Lake Michigan, and United Center! 15 miles from Wrigley Field and the Zoo. Next to CTA! 6 bedrooms 2 bathrooms, 10 beds. Sleeps 18 comfortably. Perfect for large groups! Modern smart home with air hockey, pool table, video games, 2 ping pong tables, foosball, 9 big screen TVs including 85" Samsung QLED with surround sound, outdoor dining, charcoal grill, cornhole, dining room, game room, 2 living rooms, and full kitchen.

Entire 3 BR+2 office areas & deck, top floor condo

Welcome! This gorgeous spacious top floor unit of a 3 flat provides ample daylight and easy access to many of Chicago’s great neighborhoods. Parking is easy and permit free. There is central AC and heat that’s controlled by a smart unit which will provide you with the perfect indoor temp at all times. This is a 3 bedroom 1 bath plus 2 office desks that has high speed internet, perfect for working from home as well. We are not on site but please let us know how we can best serve you!

Sophisticated Twnhm in Prestigious Lincoln Park

Welcome to our awesome townhome, nestled in a peaceful residential neighborhood, offering both convenience and serenity. Located with easy access to public transportation, you can explore all that Chicago has to offer. There are multiple levels to this townhome with stairs. A bedroom and bathroom on the ground floor, kitchen and living/dinning room on the middle floor, and the master bedroom with master bathroom on the top floor. A mini roof top to enjoy Chicago nights as well.

Casa Pilsen-HOUSE| Location | Entire Home | Garage

Modern and luxurious new construction design showcasing a spacious living area featuring high ceilings natural light . No detail was spared with all the thoughtful details. Kitchen and living room have open concept with beautiful cabinetry and all new stainless steel appliances and granite counter tops. The place is a single family house, safe with secured entry and outside video surveillance. Back entrance can facilitate handicap entrance with only one short step.

A Comfortable Stay While You are Away in Oak Park

Welcome to this Oak Park home, conveniently minutes from the main expressway, train station, downtown Chicago, and the Medical Center. This entire Oak Park house is ideal for travelers seeking a tranquil and welcoming space to unwind in after a long day, medical professionals, visiting patients at the Medical Center, and families needing long-term housing. The residence is minutes from downtown Oak Park and the historical landmarks of Frank Lloyd Wright's home and studio.