Vacation rentals with a patio in West Side

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Top-rated patio rentals in West Side

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Guest favorite
An elegant 1890 Greystone building is presented, showcasing a symmetrical façade with decorative stonework. A tiered front staircase leads to a charming entryway, flanked by well-maintained landscaping. Large windows enhance natural light, while a vibrant green shrub adds a touch of color to the exterior.
Home in West Side
4.94 out of 5 average rating, 146 reviews

Beautiful Chicago Greystone

Experience the best of Chicago from this sprawling, private 4-bedroom condo. Located just 15 minutes west of the City Center, you’re perfectly positioned to explore the culinary scene of the West Loop, the lush Garfield Park Conservatory, and the energy of the United Center Transit: Steps from multiple bus lines, 2 blocks to the Blue Line, and 1 mile to the Pink Line Amenities: On-site laundry (available upon request) Local Experts: We live in the unit below and happy to give recommendations

Top guest favorite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Apartment in West Rogers Park
4.99 out of 5 average rating, 108 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Top guest favorite
A vibrant living area features two orange armchairs positioned around a decorative wooden table. A floral wallpaper adorns the wall behind a wall-mounted television, while a rich area rug anchors the space. Natural light filters through sheer curtains, highlighting the room's colors.
Apartment in Wicker Park
4.97 out of 5 average rating, 182 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit. Bright top floor unit with a private patio to just chill and unwind or walk downstairs and your literally in the heart of Wicker Park. Super easy access to downtown nightlife/lake/museum all within 15 minutes and super easy commute to O'hare. CTA busses all around and a 2 minute walk to the Blue Line.

Top guest favorite
A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.
Condo in Wicker Park
4.98 out of 5 average rating, 163 reviews

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Guest favorite
A spacious bed with a dark wood frame is positioned against a teal wall, flanked by matching nightstands and elegant lamps. A round mirror above the bed reflects soft light, while a textured blanket rests at the foot. Rich curtains frame the windows, adding depth to the room.
Apartment in West Loop
4.95 out of 5 average rating, 133 reviews

Fulton House #1 - Studio Only (Nightly)

Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced studio has the business-travel amenities you want: ultra speed wifi, work station, top tier dining options within steps, Nespresso coffee maker, bottled water and more. Paid parking next door $20/day, subject to avail - inquire in advance.

Guest favorite
A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.
Condo in Little Italy
4.94 out of 5 average rating, 278 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Guest favorite
The living area features a mix of modern and industrial design, with exposed brick walls and hardwood flooring. A cozy sectional sofa, accented by colorful pillows, complements a stylish area rug. A kitchen area with dark cabinetry and stainless-steel appliances is visible in the background.
Condo in Wrigleyville
4.81 out of 5 average rating, 283 reviews

Can't Beat This 2min Walk to Wrigley!

My home is a half block from Wrigley Field. You can be to the ballpark in 2 minutes (or Murphy's)! Enjoy your pregame afternoon feeling the buzz of the neighborhood from the private deck. Room for 6 to sleep comfortably in a Queen, 1 Twin plus a Twin over Full Bunk Bed and a Murphy Bed. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea! I have extensive information for you - let's chat!

Superhost
The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.
Condo in North Side
4.95 out of 5 average rating, 164 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Top guest favorite
A stylish living space is highlighted by a brown leather sofa and a large area rug, with natural light streaming through the window. The modern kitchen is equipped with sleek black cabinetry and stainless steel appliances. Potted plants add a touch of greenery to the setting.
Home in Wicker Park
4.96 out of 5 average rating, 298 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Top guest favorite
The exterior of a historic two-story building is presented, featuring a contrasting mix of white and blue facades. A striking red door serves as the focal point, framed by elegant architectural details. A wrought iron fence surrounds the property, enhancing its charming curb appeal.
Home in West Side
5.0 out of 5 average rating, 153 reviews

3 bed/2 bath by United Center w/ private parking

Welcome to the Windy City White House – a spacious, historic 150-year old home 3 blocks from the United Center & mins from downtown. 3 bedrooms feature luxury bedding. 2 bathrooms – 1 newly redone w/ a large rainfall shower head. Private deck w/ seating. Spacious living room w/ work space. Fully equipped kitchen. Private parking. It's the perfect place for friends, families, & business travelers to relax in ultimate comfort after a day exploring the city.

Guest favorite
A well-lit bedroom features a spacious bed with white bedding against a backdrop of light grey walls. A wooden nightstand with a lamp is positioned beside the bed. Mirrored closet doors reflect the space, while a tall plant adds a touch of greenery.
Apartment in Bridgeport
4.88 out of 5 average rating, 106 reviews

Bridgeport Place -free parking, McCormick-Sox Park

Experience the charm of the Bridgeport neighborhood in this cozy 1 bedroom private apartment located on a peaceful tree-lined street. The apartment accommodates up to 4 guests with a sofa sleeper. Enjoy free street parking in an un-zoned area, as well as easy access to public train and bus stops nearby. Explore popular nearby attractions such as downtown, Chinatown, Sox Park, and McCormick Place and many other local neighborhood gems.

Guest favorite
A modern living area features a contemporary design with a stylish gray sofa and brown leather chairs. A sleek, geometric area rug sits beneath a coffee table, while framed black-and-white photographs line the walls. Large windows allow natural light to illuminate the space.
Home in Humboldt Park
4.96 out of 5 average rating, 119 reviews

Rooftop Skyline | 5 Ensuites | Games | DT 14 mins

The Monticello ~ Rooftop deck, skyline views, game room, 5 bedrooms w. ensuite bath! ★ "Beautiful, well appointed, and has thoughtful details." ☞ Fully equipped + stocked kitchen ☞ Game room w/ ping pong + arcades ☞ Dedicated workspace + 1 Gig WiFi ☞ Parking → garage (2 cars) ☞ Indoor electric fireplace ☞ Multiple smart TVs (5) ☞ 3 separate bar areas 14 mins → Downtown Chicago 22 mins → Chicago Midway International Airport ✈

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