Holiday rentals in West Side

4.86 out of 5 average rating, 118 reviews

Flat in Forest Park

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

4.83 out of 5 average rating, 71 reviews

Home in Chicago

Brand New Spacious Duplex

ZERO CLEANING FEE, NO EVENTS/NO PARTIES NO CHICAGO RESIDENTS This stylish place to stay is perfect for group trips. Minutes away from downtown Oak Park and downtown Chicago. Great open floor plans to accommodate groups of any size. Walking distance from public transportations. Plenty of parking near facility. Great backyard space with fire pit for nice summer nights. In unit laundry, bar, and projector in the lower level space for entertainment. Plenty of space for small to mid sized groups.

4.97 out of 5 average rating, 310 reviews

Flat in Cicero

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

5 out of 5 average rating, 6 reviews

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!

4.95 out of 5 average rating, 63 reviews

Home in Chicago

Private Logan Square Garden Apt

Welcome to our cozy West Logan Square/West Humboldt Park/Hermosa garden apartment! Perfect for tradeshow/business travelers, solo travelers, &couples. Enjoy a comfy queen-size bed, workspace, fast Wi-Fi, and huge Smart TV w Roku. Plenty of power outlets to keep your devices charged. Get ready in bathroom w/ ample counter space & large mirror. Cook in the well-equipped kitchen with full-sized appliances, spices/oil, microwave & coffee/tea bar. Note: Hosts occupy first floor of the home.

4.75 out of 5 average rating, 327 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.

Guest suite in Chicago

4.82 out of 5 average rating, 272 reviews

Vintage Suite Home Chicago by Sox/Park/Transit

Walkout basement studio in a ca.1890 home built for laborers in the Chicago Stockyards - Please read entire listing before booking. This quiet, tree-lined neighborhood is a respite from city buzz. Get downtown in 4 stops by train or any of 5 nearby buses. Your space has great natural light, 2 comfy beds (1 folds to couch), private bath, flexible work/dining area, super-fast WiFi, and kitchen with all the essentials. Private entry via back door Free street parking Se habla español

Top guest favourite

4.97 out of 5 average rating, 536 reviews

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

Home in Chicago

New place to stay

LUXE - 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.

Top guest favourite

4.99 out of 5 average rating, 83 reviews

Humboldt Park Retreat: Skylights & Queen Beds

Experience the charm of Desert Skylight, a chic second-floor retreat in Chicago's vibrant Humboldt Park neighborhood. This thoughtfully designed space features two cozy queen beds, ultra-fast fiber internet, and a newly renovated kitchen and bathroom. Unwind on the private seasonal patio, perfect for al fresco dining. Just steps from lush Humboldt Park and local eateries, it's an ideal haven for couples, families, or business travelers seeking both comfort and urban adventure.

4.84 out of 5 average rating, 63 reviews

Renovated LittleVillage Retreat

Welcome to our newly renovated retreat in Little Village, Chicago! This stylish unit blends modern amenities with classic charm. Features include a cozy living area with a smart TV, a fully equipped kitchen with stainless steel appliances, a comfortable bedroom with a work desk, and a pristine bathroom with contemporary design. Enjoy in-unit laundry and a secure entry. Convenient street parking and close to local attractions and dining. Perfect for early birds and explorers

5 out of 5 average rating, 4 reviews

Flat in Berwyn

NEW Jade Haven in Berwyn/Riverside

Step into Jade Haven, where tranquility meets modern elegance. This serene one-bedroom, one-bath suite offers a peaceful retreat, inspired by the calming essence of jade. The space features a sleek, airy design with thoughtful touches to make you feel right at home. Fully equipped kitchen, cozy living area, the bedroom invites restful nights, while the spa-like bathroom offers a moment of quiet indulgence. Perfect for a restful getaway or a productive stay.

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Popular amenities for West Side holiday rentals

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Other great holiday rentals in West Side

4.95 out of 5 average rating, 19 reviews

Private RM 1st FLR BDRM|12”Memory Queen BD|TV|Fan

LiRating, 5 stars1 week ago

I really liked it here and would choose to stay again the next time I pass through Chicago.

4.72 out of 5 average rating, 39 reviews

Bees Knees - Room 3

MikaylahRating, 5 stars3 weeks ago

I really enjoyed my stay here . Genova place is very affordable, well kept for a shared space . I like that everything was organized . Toiletries such as body soap , hair conditioner was provided as well as towels and linens . Genova was able to accommodate me as well with some plans that didn’t quite work out with my airfare . I was very grateful and appreciative of that as well . Very good and timely with communication on whatever I needed . I’m sure a future stay here will be planned out . Maybe sooner than later . Great host . Until next time …

4.86 out of 5 average rating, 22 reviews

Bohemian Retreat Room – Near Downtown & UC!

수빈Rating, 5 stars1 month ago

CTA와 가까워서 이동이 편리합니다 호스트와의 소통이 빨라서 좋아요 혼자 여행 와서 6일동안 지냈는데 대체적으로 만족합니다

4.66 out of 5 average rating, 38 reviews

Chicago Prince’s Quarters

JeetRating, 5 stars10 months ago

Hello everyone! I was here for 4 weeks for my rotation at Loretto hospital. The stay was wonderful. Helen was always responsive and friendly. All the amenities provided were functional and well-maintained. All the airbnb mates were friendly, too. The neighborhood is somewhat questionable when comes to safety, however, I encountered no problems during my stay. I would avoid going out on foot after dark. Thank Helen for this beautiful stay!

4.85 out of 5 average rating, 33 reviews

Private King Room in Prime Logan Square

JoeRating, 5 stars4 weeks ago

Perfect base camp to explore Chicago

5 out of 5 average rating, 9 reviews

Private room in Oak Park

DT Oak Park LUXE Private BR C | Queen Bed Sleeps 2

YanitRating, 5 stars2 weeks ago

I had a great stay at this place! The location was absolutely perfect—close to grocery stores and everything I needed was easily accessible. The bedroom was definitely my favorite part: super comfy bed and a spacious closet that fit all my luggage with ease. Everything was clean and well-maintained, which made the stay even more enjoyable. Parking is on the street and not included, but there was plenty of space and could park right in front whenever I needed which was a huge plus. Would definitely stay here again!

4.89 out of 5 average rating, 65 reviews

Private Bedroom in Chicago (North Park)

KyleRating, 5 stars2 days ago

Clean, safe, quiet, cheap. Victor is a responsive host and the home is a good value. Be warned, this is a no frills Airbnb, but the bathrooms were kept clean, the street is in a safe and quiet neighborhood, and there are hundreds of businesses within easy walking distance. I parked my van full of art inventory for a week on the street with no incident or worry. I had room number 5, which has rear building access with a separate key from an outdoor wooden porch. My room had another door to the interior of the house with access to two bathrooms, the kitchen, and laundry in the basement. Two other rooms are for rent in the same house. Everyone was clean, quiet, and respectful of privacy. Thank you Victor.