Holiday houses in West Side

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Top-rated holiday rentals in West Side

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Guest favourite
Private room in Chicago
4.84 out of 5 average rating, 482 reviews

Sunny full floor (Sleeps 4+ guests)

A whole floor to yourself — the floor is entirely/ exclusively yours! Full floor finished basement w/ light from glass sliding doors, 1.5 private bedrooms, and 2 desks. Spic & span - steamed cleaned after every guest! New memory foam regular queen size bed w/ 2 more queen size airbeds (per request). 7 mins by car to downtown or 2 blocks to train station/ bus stop that both go into downtown. Street level parking available. Masks are optional, not required. Chicago Registration #: R21000069179

Guest favourite
A small sleeping area features a twin bed with a light-colored blanket and a neatly placed towel. A window with blinds allows natural light to filter in. An air conditioning unit is positioned above the bed, and a small wastebasket is visible nearby.
Private room in Chicago
4.9 out of 5 average rating, 60 reviews

Private Room in Rogers Park

Keep it simple at this peaceful and centrally-located place. Highlights: - Loyola University (~2 miles, 6 min drive) - Northwestern University (~3 miles, 10 min drive) - Public transportation nearby (CTA red line, buses) - Lake Shore Dr (1 mile, 5 min drive) - St Francis Hospital about a mile away (5 min drive) All common areas (dining room, kitchen, bathroom) are shared. Only one guest allowed per room. No exceptions! All guests will be asked to leave if multiple guests are present.

Superhost
A modern kitchen area features a compact island with a sleek sink and metallic fixtures. A round dining table with black-and-white polka dot chairs sits against a light pink floral accent wall. Warm lighting enhances the inviting ambience of the space.
Apartment in Chicago
4.83 out of 5 average rating, 372 reviews

*Entire City Apartment 1 block to Train Park Free

Perfectly private - large & comfortable with full kitchen. FREE & EASY street parking One block to (Green Line) train stop to United Center - Concerts, Bulls & Blackhawk games. Two stops to trendy West Loop Randolph bars, restaurants and shops. 10 minute ride downtown Chicago. Kitchen has cooking utensils & coffee, cream, sugar, spices. Shampoo/conditioner/towels/linens are provided. Free wifi. PLEASE NOTE No visitors No smokers no exceptions and agree per message to confirm reservation

Top Guest favourite
Private room in Chicago
5 out of 5 average rating, 142 reviews

Urban Oasis Pilsen - guest room in townhouse

Experience the charm of Pilsen, one of Chicago's trendiest neighborhoods. Your private bedroom features a queen-size bed and an en-suite bathroom with a tub/shower. The room includes a small desk, ample storage space, and a TV with streaming services. Triple-paned windows provide plenty of natural light while minimizing noise from the nearby I-90/94 freeway. The room is located on the third floor (40 steps)! The second floor offers access to the kitchen, living room, TV den, and balcony.

Superhost
A modern galley kitchen features green cabinetry and white countertops. A decorative backsplash with a floral pattern complements the design. Appliances include a gas stove, dishwasher, and coffee maker, while ample shelving showcases houseplants and decorative items.
Apartment in Chicago
4.85 out of 5 average rating, 179 reviews

Funky & newly remodeled 1 bed in Hip Logan Square

Recently remodeled 1 bedroom garden apartment with a fun aesthetic in hip Logan Square. Walking distance to top bars, restaurants and coffee shops such as Sugarmoon, Park & Field, Best Intentions, Lou Malnatis, Damn Fine Coffee Bar and many more. Blocks from the 606 Trail, 90/94 & public transportation. Lovely shared front yard landscaped with florals + garden beds. We will pass along a welcome guide with a list of all our favorite places in the neighborhood!

Superhost
Private room in Chicago
4.82 out of 5 average rating, 17 reviews

A8- 6 min Walk to Pink Line

Located at Pilsen which is one of the 12 Coolest Neighborhoods around the world (by Forbes) this is a Private bedroom with a full size bed bed in a share apartment close to Downtown Chicago (around 15 min by car). Great gastronomy around. Accesible public transportation just 6 min far by walk to the train (Damen Pink Line) We made a very detailed listing so you can know exactly what to expect, don’t book before reading the whole advertisement.

Guest favourite
A private room features a wooden bed with a neatly arranged blanket and a folded towel. A dresser with multiple drawers stands nearby, and a window allows natural light to enter. The walls are painted a soft gray, creating a calm environment.
Private room in Chicago
4.86 out of 5 average rating, 49 reviews

B: Spacious bedroom with private workspace.

Fantastic private room with a workspace. Very convenient location to restaurants and close to public transportation. Downtown is 45 minutes via public transportation. Please note that this is on the second floor and will require you to climb stairs. IMPORTANT: The other room in this apartment is shared with another guest- you cannot reserve the entire house. Kitchen, bathroom, living room are shared spaces.

Top Guest favourite
The bright living area features a blue sofa with decorative pillows, a wooden coffee table, and a desk chair facing a small workspace. Natural light enters through multiple windows, showcasing the hardwood flooring and modern decor elements, including a framed cityscape artwork.
Condo in Chicago
4.99 out of 5 average rating, 668 reviews

Urban Comfort in the Heart of Chicago

This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and a newly remodeled en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.

Superhost
Private room in Chicago
4.77 out of 5 average rating, 338 reviews

Chicago River Room, near Med Ctr

R+ My other listings can be found through my profile page. 7 minutes to O'Hare Airport See below for details. Highway entrance 1 block away, so you can easily drive anywhere. Walking distance to pharmacy, shopping mall (including grocery store), health club, train station, restaurants and a library. 0.6 miles to Harlem Blue Line. Prices are subject to change.

Top Guest favourite
A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.
Condo in Chicago
4.97 out of 5 average rating, 854 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Top Guest favourite
An open living space is visible, featuring a cozy seating area with a brown couch and two green armchairs. A large area rug adds warmth beneath the coffee table. A kitchenette area with wooden counter space and modern appliances is present, while bookshelves display various books and decor.
Apartment in Chicago
4.9 out of 5 average rating, 132 reviews

Garden on Warren

Near West Side / West Loop location, less than 10 minute walk to United Center for Blackhawks, Bulls, music, concerts, shows, and events. Close proximity to CTA Pink & Green lines, Union Park, Randolph & Fulton Street dining districts, University of Illinois at Chicago and Rush Medical District. Private entry, very secure and quiet apartment.

Top Guest favourite
A welcoming living room features a large wooden table surrounded by plants and comfortable seating. Natural light floods the space through expansive windows, enhancing the earthy tones of the decor. A cozy sofa and a vintage armchair create an inviting atmosphere for relaxation.
Private room in Chicago
4.96 out of 5 average rating, 526 reviews

Private room w/bath in urban canopy

Private bedroom w/attached private bath in a gorgeous 3-bedroom/2-bath apt on the only curvy street in Hyde Park. Common entrance and living spaces, shared with an artist who uses two bedrooms - one as studio. Enjoy the lush light-infused top floor of a turn-of-the-century urban tree house.

Popular amenities for West Side holiday rentals

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