Private suite holiday rentals in West Side

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 recreational area features a ping pong table, a large flat-screen TV, and comfortable leather seating. A coffee table sits in front of the couch adorned with a colorful quilt. Exercise weights are positioned on the floor, adding to the diverse amenities of the space.

4.85 out of 5 average rating, 272 reviews

Wrigleyville/Boystown/Entire Private Floor!

1000 sq ft-entire private floor & door access. The perfect Wrigleyville/Boystown/Lake location. Zip to downtown Chicago in minutes via cab or public transportation options. Our friendly neighborhood is packed with fun bars, fabulous restaurants, unique boutiques & great music venues. Enjoy pool, ping pong and pinball and our 65" 4K flat screen TV or a seat at the bar. A Queen bed, 2 single beds in the main room, steam shower and bathroom. We have a mini fridge, microwave, coffee and home gym.

A spacious sleeping area features a layered quilt on a large bed, accented by soft pillows. Two bedside lamps provide gentle illumination beside the bed. The walls are painted dark, with framed artwork hanging above the bed, and natural light enters through small windows.

4.98 out of 5 average rating, 179 reviews

Entire Below Level Studio w/ Private Sauna

Centrally located between Logan Sq., Bucktown, Wicker Park & Ukrainian Village. Easily jump on the 606 walk/bike path or the Blue Line train. Lincoln Park Zoo, N. Ave. Beach & other hot spots are a quick Uber ride away. The Blue Line offers access to downtown, museums, Bears games @ Soldier Field & direct access to O’Hare. Wrigley Field is just across town. The Bulls play at the United Center 2 miles away. There are great local eats/drink on our block! Note that this is a below level unit

A cozy sitting area features a vibrant orange sofa adorned with black cushions and a matching ottoman. A wooden desk with a red chair sits nearby, while a floor lamp casts a warm glow. Bright artwork depicting flowers adds a touch of color to the wall.

4.98 out of 5 average rating, 321 reviews

Stylish Studio in Historic Logan Square

Modern garden studio (4 steps down), located in the heart of the highly desirable Logan Square neighborhood. This luxurious space with heated floors & a spa inspired bathroom and kitchenette is situated on the Historic Logan Boulevard, 2 blocks from the CTA Blue Line which runs between downtown & O'Hare airport. The suite has a private entrance & access to a magical shared backyard space. The owner's treehouse deck can be reserved. An oasis in the city with exciting city easily accessible!

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.

4.91 out of 5 average rating, 515 reviews

A charming house is framed by a lush garden filled with various shrubs and flowering plants. The exterior features a mix of wood siding and prominent windows, while a white picket fence lines the front yard, enhancing the home's inviting presence.

Guest suite in Oak Park

Entire upstairs in Arts and Crafts Oak Park home

You have the use of the entire upstairs (with a separate, lockable private entrance). With two bedrooms, bathroom and a common area with a futon, fridge, microwave, coffee maker and kettle, it is flexible for individuals or small groups of no more than 4 people. Free overnight parking. We're a quick walk to the CTA Blue line, coffee shops and restaurants, parks, musical venues, the Oak Park Arts District, and a quick drive to downtown. Our home is cozy, in a friendly neighborhood.

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 brick bungalow features a welcoming front porch adorned with a US flag. The porch includes a railing and seating area, while flower pots add greenery. Stairs lead up to the front door, which is detailed with a decorative screen.

4.95 out of 5 average rating, 185 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

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.

4.91 out of 5 average rating, 174 reviews

New Bright & Airy Entire Unit in Logan

This new modern unit is located in West Logan, one of the most exciting neighborhoods in Chicago. Close to public transportation, 2 blocks from the 606 Bloomingdale recreation trail, and minutes away from the best restaurants and bars in the city! Wifi, large-screen TV with streaming channels, washer/dryer, kitchenette, mini fridge, coffee/tea, board games, free street parking. You will love this custom designed & converted space!

A dining area features a large table set for meals, surrounded by two green armchairs and a bench. Natural light enters through two large windows, highlighting a softly patterned area rug beneath the table. Artwork lines the walls, adding character to the space.