Vacation rentals in West Side

5 out of 5 average rating, 9 reviews

A modern kitchen area includes sleek cabinetry and stainless steel appliances. A wooden dining table surrounded by black metal chairs invites shared meals. A colorful abstract artwork decorates the wall, adding visual interest to the space. Natural light streams through a nearby window.

Guest suite in Chicago

ENC-Chi Arts Suite Near United Center & Downtown

Enjoy a cozy stay in our garden level artist apartment below our private home as we embrace life as empty nesters. Centered in the East Garfield Park community. We’re just a 12-minute commute to downtown Chicago and 7 minutes to the West Loop, IL medical district, and United Center and three blocks from the popular Garfield Park Conservatory. Plus, conveniently located half a mile from essential amenities like grocer, fast-food, Chase bank, and Walgreens. Experience comfort and value with us!

4.94 out of 5 average rating, 199 reviews

A tree-lined street in a quiet neighborhood is visible, with well-maintained lawns and charming homes featuring brick exteriors. A single green chair is positioned on a grassy area, inviting relaxation amidst the landscaped surroundings.

Private room in Evanston

Welcoming Evanston Home

We have a newly renovated suite awaiting your stay, perfect for one guest. This dedicated entry, private room + bathroom, and tree-lined street are in our quiet neighborhood in beautiful Evanston, just north of Chicago. As international travelers ourselves, we love hosting others from near or far! Enjoy a short walk to cafes, stores, mall shopping, parks, and restaurants. Easy free parking, convenient Uber / Lift rides, and public transportation are also here to make your stay enjoyable.

The exterior of a modern high-rise building is visible, featuring large glass windows and a curved architectural design. Surrounding trees line the street, creating a blend of urban and natural elements. The image showcases the building's height against a clear blue sky.

4.8 out of 5 average rating, 304 reviews

Kasa | Studio, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Top guest favorite

A bright hallway is illuminated by natural light, showcasing a mix of art and plants. Shelves with various glassware and plants line one wall, while framed artwork featuring mountains and landscapes adds character. Light wooden flooring runs throughout the space.

4.99 out of 5 average rating, 143 reviews

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.

4.82 out of 5 average rating, 509 reviews

Private room in Chicago

Florence Room - 3min to CTA, Free Parking, Roomy

The Florence room is one of three rooms in the grotto. The room has a king size bed and full size sofa sleeper for a maximum guest count of 4. You will have access to the kitchen for the microwave, toaster, and stove, along with free Keurig coffee. There are multiple common areas on the 1st, 2nd, and 3rd floors including Dining, Living, TV, and Recreation rooms.There is a private mini fridge in your room for food storage. The house is one block from the Kedzie Green line rail station.

A bright living space features a dark brown sofa adorned with orange cushions. A stylish coffee table sits on a patterned area rug, while two large windows allow natural light to fill the room. A corner mirror reflects the sofa and a cozy bed is visible in the background.

4.74 out of 5 average rating, 331 reviews

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.

A spacious living area features a large projector screen displaying a vibrant image. Comfortable seating surrounds a modern electric fireplace, while a potted plant and decorative artwork add subtle touches to the space. Natural light is invited through nearby sliding glass doors.

Home in Chicago

5 out of 5 average rating, 7 reviews

LUXURY - Movie Theater + Spa House

Your vacation is HERE: With the projector tv being as easy to use as a regular flat screen, just turn it on and stream from the abundant premium channels. Relax and unwind...step out to the amazing back yard patio, and enter the enclosed Spa House for access to the hot tub open 24/7. One main bedroom + an open bedroom nook off the family rm. This suite will level your sense of amenities design. Note: Hot tub access privileges are reserved for your suite and the suite above.

A light-filled living area features large windows with green curtains and a view of the courtyard. A comfortable sofa with decorative cushions is positioned next to a wooden coffee table, which holds a book and a small plant. A TV is set on a stylish console.

4.86 out of 5 average rating, 367 reviews

Renovated Designer Flat in Heart of Lincoln Square

Kick back with a fresh coffee and enjoy the designer touches of this renovated apartment, including marble worktops, wood floors and 1920s exposed brickwork. There are great courtyard views, while the memory foam mattress and super-sized sofa add real comfort. Lincoln Square is a quaint, family-friendly neighborhood. There's abundant German influence here, and great shops, restaurants, and bars line Lincoln Avenue. Downtown is 20 mins by train. Wrigley Field is close too.

4.99 out of 5 average rating, 114 reviews

A modern living space features a light-colored sofa with decorative pillows and a woven throw. A warm-toned wooden accent wall complements a sleek electric fireplace below a mounted television. A patterned area rug anchors the room, while shelves in the background display decorative items.

Loft in Chicago

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

4.82 out of 5 average rating, 203 reviews

Private room in Chicago

ChicagoRiver Double Room

Nicely decorated Private (10x11 sq ft) Room w/designated work station, well-lit, *shared common bathroom* (other guests may be in the premises). This is NOT a full condo rental; just 1 room. Quiet & clean, 2 miles from downtown, walking distance to dozens of restaurants in Taylor Street & Little Italy. Perfect location in a quiet neighborhood, but still close to the city to enjoy food& music festivals, free concerts in Grand Park, Museums, Broadway shows, etc

A cozy living area showcases a mix of modern and rustic design elements. Exposed brick walls enhance the character of the space, while natural light filters through the windows. A comfortable sofa and a wooden coffee table are positioned atop a geometric-patterned rug.