Private suite holiday rentals in West Side

A cozy living area features a plush green sofa adorned with patterned throw pillows. A textured rug covers the floor, while a wooden staircase leads to the lofted sleeping area. Natural light filters through the window, illuminating the space.

4.96 out of 5 average rating, 372 reviews

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

A cozy bedroom is presented with warm wood flooring and soft lighting. A spacious bed is adorned with neutral bedding, complemented by a decorative bench at the foot. A dresser and artwork decorate the walls, while natural light filters in through small windows.

4.91 out of 5 average rating, 137 reviews

Cozy 1BR + Futon • Deck • Laundry • Private Entry

Located at the geographic center of Chicago with plenty of FREE street parking. The area is very safe and about a 10-min walk to the 35th/Archer Orange Line and just 3 blocks from the Archer bus—both take you downtown within minutes. This lower-level 1BR has a private entrance, spacious queen bedroom, living room with full futon, full kitchen, and private bath. Perfect for solo stays, couples, small families, or work trips. Enjoy your own space with access to a back patio, grill, and laundry.

The living area features a comfortable sofa adorned with colorful cushions, positioned beside a unique wooden coffee table. A striking piece of wall art adds visual interest, while a dining area with modern chairs is visible in the background, complemented by potted plants.

4.94 out of 5 average rating, 459 reviews

Peaceful Portage Park Apartment

You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night

The living room features two teal sofas arranged for comfort, complemented by a purple ottoman. Natural light filters through sheer curtains, illuminating the wood flooring. A small plant and framed artwork adorn the walls, enhancing the inviting atmosphere of the space.

4.85 out of 5 average rating, 103 reviews

Logan Square Chicago 2BR cottage, close to it all!

Beautifully restored 2 bed/ 1 bath apartment in a 100+ year old workman’s style cottage in the heart of Logan Square. Relax in your private first floor unit on a quiet tree-lined residential street. The living & dining rooms are furnished with brand new sofas & multiple vintage pieces perfect for spreading out & relaxing or cooking dinner in the updated kitchen. To keep costs down, a cleaning fee has already been included in the nightly rate. Excessive mess will result in an additional fee.

A spacious living area features a comfortable dark sofa with decorative red and blue pillows. A soft area rug lies beneath a wooden coffee table. Natural light fills the room from large windows, illuminating the cozy sleeping area with a neat bed dressed in light linens.

4.92 out of 5 average rating, 103 reviews

Renovated basement studio w/ independent entrance

Make this newly renovated studio located near the heart of Chicago your home away from home. Set at the vibrant Noble Square/Eckhart park neighborhood within West Town where you are walking distance to restaurants, bars, park and public transportation that takes you straight to downtown. Luxe & comfort throughout- stocked kitchen, new king size memory foam bed and gel-infused pillows, queen bed sofa & a work area. Great for city explorers, couples with or without kids and business travelers.

A spacious bed layered with a colorful patterned blanket is positioned near large glass doors that open to a private deck. Sheer curtains frame the entrance, allowing natural light to fill the room while offering a view of the greenery and flowers on the deck.

4.93 out of 5 average rating, 153 reviews

Entirely Private Suite - Urban Oasis - Pilsen/UIC

Pilsen - McCormick Place - Soldier Field - Thalia Hall - UIC - Chinatown - South Loop - Radius Welcome to a brand new, entirely private, spacious and peaceful oasis in Pilsen-UIC with a smartlock system and self check in. Central location near some of the hottest neighborhoods, restaurants, concert and tourism venues, and minutes from the Loop! Full bath with a luxurious spa shower, cable, wifi, flatscreen tv, refrigerator, iron, desk, coffeemaker, toiletries and a lovely private deck.

A charming brick two-story home is framed by lush greenery and colorful flower beds. The entrance is adorned with light fixtures, and steps lead up to a welcoming porch. The well-maintained garden features a variety of blooming plants, enhancing the inviting ambiance.

4.94 out of 5 average rating, 412 reviews

Luxe, Private Suite w/Own Entrance-2023 Renovated

Newly remodeled private city oasis! Professionally designed suite with private keyed courtyard entry & small lighted covered patio w/table and chairs (work outside!) New ensuite bathroom w/heated floor, bespoke vanity & fab water pressure. Quiet tree-lined street with free parking, great restaurants, old pubs, shops & transport walkable. Great launch to all Chicago has to offer while enjoying charming Bucktown. Close to Downtown, Wrigley, DePaul, Zoo, Lincoln Pk, United Ctr, Lakefront.

4.81 out of 5 average rating, 196 reviews

A spacious living area showcases a light brown sectional sofa positioned around a coffee table. Two large televisions are visible in the background, framed by dark curtains. A decorative rug and plants add warmth to the room, which is illuminated by natural light.

Guest suite in Oak Park

Private 2 BR Oak Park Garden Apt

This spacious 2 BR garden apartment is fully furnished, private Kitchen and Bathroom ! In a safe, quiet neighborhood, stay cool and comfortable while you rest. 1 block from the Austin Blue line and the 290/ Eisenhower express way. Approx 20 minutes to Downtown Chicago or Midway Airport and 30 mins to O'hare Airport. Oak Park is a wonderfully diverse community and holds the largest collection of Frank Lloyd Wright homes. It is also the childhood home of Ernest Hemingway.

Superhost

A cozy kitchen area features light blue cabinetry and essential appliances, including a microwave. A dining table is set for four, with white bowls arranged neatly. The space is illuminated by natural light, revealing a warm atmosphere complemented by a patterned rug.

4.81 out of 5 average rating, 307 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, 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

A lounge area features a curvy orange sofa, complemented by a black circular coffee table resting on a textured cream rug. Natural light filters through large windows, illuminating framed wall art with subtle hues. Minimalist decor creates a cozy and inviting atmosphere.

4.94 out of 5 average rating, 162 reviews

Logan Square Garden Suite

Creative and quiet light-filled garden unit with lots of books, accompanied by comfortable lounge furniture and touches of nature for cozying up and relaxing after long travel or late nights. This is a perfect space for solo travelers or couples. This is also a great space if you are traveling with a small child or infant. The place is set up much like a hotel room in that it does not have a kitchen but we do provide a mini fridge and Nespresso machine.

A living area features exposed brick walls and polished hardwood floors. A comfortable sofa along with two wooden side tables, each topped with a lamp, is positioned for relaxing. Large windows allow natural light to fill the space, providing views of the outdoors.

4.87 out of 5 average rating, 177 reviews

The Huron Haven

A beautiful, one-of-a-kind, hidden gem in the heart of River West. Private entry. Front & Back Patios. Full office space. Large Living Room. Exposed brick walls, 11.5’ tall ceilings. Large barn doors lead from the living room / office to a large master bedroom with large modern bathroom. The bedroom has French doors which open to private balcony with a beautiful back patio, dining space, and thriving garden. On Property Parking

An open living area features a comfortable sectional sofa upholstered in neutral tones, accented by colorful cushions. A large-screen TV is positioned on a simple console, while natural light from a window brightens the space. A potted plant and decorative elements add charm.