
Holiday houses in West Side
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in West Side
Guests agree: these stays are highly rated for location, cleanliness and more.

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

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.

*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

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.

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!

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.

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.

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.

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.

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.

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.

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
Other great holiday rentals in West Side

Spacious & serene in hip spot. Sleeps 4.

Milagro2720 (2F)

Chic PRVT Room w/ Full Bathroom | Logan Square

Comfortable Room Five Min Walk to Blue Line/ RM 2

O33. Next to Downtown

Private room in Bridgeport. C3

Cloudgate Room, minutes to O'Hare in Safest Area

B0- Room in Basement close to United Center
Destinations to explore
- Chicago Holiday rentals
- Platteville Holiday rentals
- Downtown Chicago Holiday rentals
- Indianapolis Holiday rentals
- Southern Indiana Holiday rentals
- Detroit Holiday rentals
- St. Louis Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Wisconsin River Holiday rentals
- Milwaukee Holiday rentals
- Private suite rentals West Side
- Rentals with beach access West Side
- Rentals with breakfast West Side
- Hotel rooms West Side
- Rentals with a fireplace West Side
- Serviced apartment rentals West Side
- Rentals with a balcony West Side
- Rentals with lake access West Side
- Rentals with an accessible height bed West Side
- Apartment rentals West Side
- Rentals with a fire pit West Side
- Fitness-friendly rentals West Side
- Waterfront rentals West Side
- Rentals with an EV charger West Side
- Rentals with a sauna West Side
- Guesthouse rentals West Side
- Townhouse rentals West Side
- Loft rentals West Side
- Rentals with outdoor seating West Side
- House rentals West Side
- Family-friendly rentals West Side
- Rentals with pools West Side
- Condo rentals West Side
- Rentals with a hot tub West Side
- Rentals with a washing machine and dryer West Side
- Pet-friendly rentals West Side
- Smoking-friendly rentals West Side
- Rentals with a patio West Side
- Rentals with a home theatre West Side
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Oak Street Beach
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- The Beverly Country Club
- Museum of Science and Industry
- Brookfield Zoo
- Wilmot Mountain Ski Resort
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- The 606
- Things to do West Side
- Tours West Side
- Nature and outdoors West Side
- Food and drink West Side
- Art and culture West Side
- Things to do Chicago
- Food and drink Chicago
- Art and culture Chicago
- Nature and outdoors Chicago
- Sightseeing Chicago
- Tours Chicago
- Sports activities Chicago
- Things to do Cook County
- Food and drink Cook County
- Sports activities Cook County
- Tours Cook County
- Nature and outdoors Cook County
- Art and culture Cook County
- Sightseeing Cook County
- Things to do Illinois
- Sightseeing Illinois
- Tours Illinois
- Art and culture Illinois
- Nature and outdoors Illinois
- Sports activities Illinois
- Food and drink Illinois
- Things to do United States
- Tours United States
- Entertainment United States
- Sports activities United States
- Nature and outdoors United States
- Wellness United States
- Food and drink United States
- Sightseeing United States
- Art and culture United States




