Holiday rentals in West Side

Dwntown Mins Away/Relax & Stay! Bus/Train Friendly

Take it easy in this peaceful and cozy sleeper, central to everything Chicago has to offer and only minutes from downtown. Take advantage of all of the amenities while your here and enjoy the city night life with all of the great entertainment and restaurants Chicago has to offer. Newley rehabbed with high end appliances and fixtures that you, your significant other or family can enjoy. This relaxing vibe is one that will make it feel like a home away from home with all that it has to offer.

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

Studio Apartment in Oak Park

Nestled in Oak Park's historic district, this charming studio apartment is within walking distance of cafes, shops, restaurants, a movie theater, and the CTA/Metra for city and suburban excursions. Featuring a comfortable queen-sized bed, a newly updated full bathroom, and a kitchenette, it sits mere steps from Ernest Hemingway's childhood home and a few blocks from Frank Lloyd Wright's residence and studio. Enjoy the serenity of this historic home and its hidden garden oasis.

Private room(s) at a great home in Little Italy .

For single Guests: You will enjoy a nice cozy room with its own private bathroom) in a beautiful home . For two people traveling together There is an additional room adjacent to that room, which is offered for an additional fee. The bathroom will be shared among the two travelers. The house is in Little Italy, conveniently close to downtown, the West Loop, UIC, Rush and Cook County . Only 12-minute away to the CTA Blue line. A stop for Bus #7 is half a block away.

Bright Boho Haven free parking

Welcome to our bright, newly constructed 1-bedroom, 1-bath Airbnb in the heart of Oak Park. Enjoy a sunny, modern space with a beautiful bathroom, free parking, and all the essentials. Just steps from grocery stores, coffee shops, and the Oak Park Blue Line stop—reach downtown Chicago in under 30 minutes. Perfect for a cozy getaway or work trip, with fast Wi-Fi, smart TV, kitchenette (no oven!) and a peaceful, walkable neighborhood. We can’t wait to host you!

Cozy Apt+Steps to Train+10 mins to Downtown

Welcome to your stylish retreat in Chicago’s vibrant Little Village neighborhood! -4 Minute Walk to Train -2 Stops from Pilsen on Train -10 Minute Drive to Downtown -Walking distance to local eateries, taquerías, and coffee shops. -Entertainment including an arcade cabinet and board games -Less than 15 minutes from Rush, University of Illinois and Mount Sinai Hospitals Enjoy a seamless blend of cozy vibes, fun, and local flair in this Little Village gem!

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Loft-Inspired Retreat | Stylish Stay Near 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!