Vacation rentals in West Side

Upscale High-Rise Apt · Rooftop Pool + Views

Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

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.

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.

Private King Room in Prime Logan Square

Come stay at this affordably priced private bedroom in an apartment. Your bedroom has a very comfortable queen size bed and a desk and monitor to work from. The apartment has a recently renovated, fully equipped kitchen. Apartment has a free washer and dryer for laundry You will be steps away from Blue Line train and busses and some best restaurants, coffee shops, cocktail lounges and bars in Chicago This is a private room in a shared apartment. Shared bathroom and apartment.

10 Mins to Downtown Luxurious Cozy Boho - Sleeps 5

Luxurious 550 sqft 1BR 1BA located 10 min from Downtown!! Stand up shower, games for adults & kids 2 Smart TVs, free wifi (600 mpbs speed) Sleeps 4 comfortably, 1 queen bed, 1 futon, 1 air mattress Street parking can be very difficult!! - permits provided Walking distance from famous 26th street, plenty of restaurants 3 miles from Little Italy and Chinatown Walking distance to bus and train 10-15 min drive from Millenium Park and Soldier Field Great for professionals and travelers

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.

Loft Style Private Apt 3 (1 Room- 420 Friendly)

Please do not book unless you read the entire listing, including all house rules & amenities. No refunds will be given if you book without first reading the house rules Near Loyola University. 420 friendly environment. No Cleaning Fee, Full Kitchen, Living Room, 1 Shared Bathroom, Internet, Heat, Air Conditioning Redline, CTA, Beach, Groceries, Gyms, Multiple Bars & Diverse Cuisine within 5-15 min walking

Spacious & serene in hip spot. Sleeps 4.

Located in the heart of Pilsen, a vibrant neighborhood rich in Mexican arts/ culture, and an emerging hipsterville. Check out art gallery crawls, award winning restaurants and local taquerias. Thalia Hall (3 blocks away) w/ indie and major musicians. 7 mins via car to downtown or 2 blocks to train/bus. Mask wearing is optional. Guests are not required to wear masks. Chicago Registration #: R21000069179

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.