Holiday rentals in West Side

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

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.

Cozy Private Room in a unique Chicago Penthouse

Our three bedroom Penthouse apartment has a cozy guest room with detached private bathroom. It fits two and is centrally located on a quiet street near Du Paul University. Enjoy a gourmet kitchen, roof access and easy access to major subway lines, coffee shops, restaurants and movie theater are all in walking distance. You will share the apartment with us and our two cats. Your room is totally private and the bathroom is only used by you. The apartment is a walk up on the fourth floor.

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

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!

Egyptian Room - Free Parking, 1 block to CTA

Comfortable lower level bedroom with a pillow top king bed, granite topped desk, and smart tv makes this room a super cozy retreat, You will have full access to the kitchen cooking and free Keurig coffee. You have a private mini fridge in your room for food storage. There are multiple common areas on the 1st, 2nd, and 3rd floors including Dining, Living, TV, and Recreation rooms. Easy unmetered street parking is readily available for those coming by car.

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.

Springfield Serenity

Welcome to Springfield Serenity, a modern two-bedroom retreat designed for calm and connection. Unwind in the serene meditation corner, enjoy a movie night or a round of Pac-Man in the cozy entertainment room, and relax in a space filled with soft tones of greenish-blue and gold. Whether you’re here to rest, reset, or explore, Springfield Serenity offers a peaceful, stylish escape that feels like home.

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.

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.

Cloudgate Room, minutes to O'Hare in Safest Area

My other listing can be found through my profile. This room is just next to the washroom. My place is only 1 mile/1.6km to USMLE Center; 10 minutes driving to O'Hare, 0.6 miles to CTA Blue Line station. Early check in is available for an additional fee. Prices are subject to change.

The Blue Room

A spacious single-family home; minutes away from Midway Airport (train station), within walking distance from gorgeous and dog-friendly parks, and walking distance of plentiful of supermarkets and convenience stores. Downtown Chicago is just about 40 minutes away from a train ride.