Apartment vacation rentals in West Side

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Popular amenities for West Side apartment rentals

Weekly apartment rentals

Superhost
A stylish studio features a spacious bed adorned with colorful pillows. A cozy seating area with a dark sofa is positioned near large windows that allow natural light to fill the room. A small dining table with chairs sits beside the sofa, enhancing the open layout.
Apartment in Oak Park
4.88 out of 5 average rating, 26 reviews

Modern NEW Deluxe Studio in Oak Park

DominiqueRating, 5 stars2 weeks ago
The place was spotless, easy to find, and convenient. I felt right at home, and would definitely recommend to a friend or stay again myself.
Top guest favorite
A comfortable seating area features a plush sectional sofa adorned with soft throw pillows. Light beige cushions contrast against the deep green walls. A large television is mounted opposite the seating, while sheer curtains frame the window beside a door that leads outside.
Apartment in Chicago
5 out of 5 average rating, 11 reviews

Designer Garden Unit in Bridgeport

ChristineRating, 5 stars1 day ago
Beautiful trendy place in the heart of Bridgeport. Went home to visit family and felt at home! Loved our stay and will definitely return. Thank you Wood
Guest favorite
A spacious living room features a large sectional couch in green, accompanied by a round coffee table. A wooden console table supports a flat-screen TV. Light from several windows illuminates the space, complemented by decorative art and houseplants. A staircase leads to the upper floor.
Apartment in Chicago
4.96 out of 5 average rating, 26 reviews

Midcentury, comfy 2bed/2bath

MarkRating, 5 stars4 weeks ago
Diana was great. She was immediately responsive to any question or if I needed anything. She was also very friendly and just made staying at her place very comfortable. The place has a lot of space, which is really nice. The 608 walkway is 2 blocks away and is a great walk, and allows you to exit at various points and visit the Logan Park area, and get food, etc... Getting to Wrigley or thr Frank Lloyd Wright house is a quick drive (arnd 5/6 miles). I didnt want to leave and really enjoyed my stay at Diana's place.
Superhost
A stylish living area is featured, showcasing a green sofa arranged with a round glass coffee table atop a black and white patterned rug. A wall-mounted TV is present, alongside a dining table with two chairs. Large windows allow natural light to fill the space.
Apartment in Chicago
4.84 out of 5 average rating, 63 reviews

Renovated LittleVillage Retreat

KalebRating, 5 stars2 days ago
Leo and Alex’s place was very nice and it looked exactly like the pictures. It was about a 15 minute walk to the nearest train station, which was a HUGE plus because it took you straight into the city. The neighborhood around it wasn’t bad for city standards, but was a little old and had a pretty high cop presence. There’s free street parking which was easy to find every day as long as you stay near the front side of the building. We did have an issue with the shower, but we told them and they quickly checked it out and fixed it. Another issue is that the people upstairs walk very loudly and will make noise all night, but that is out of the host’s control, just something to note. Overall, we had a very nice stay at Leo and Alex’s place and would recommend it to anyone visiting Chicago!
Superhost
The open-concept living area features a fully-equipped kitchen with gray cabinets and granite countertops. A cozy seating area includes a sofa and a patterned area rug, complemented by a coffee table and a decorative side table, creating a functional and comfortable space.
Apartment in Chicago
4.73 out of 5 average rating, 11 reviews

Cool spot in cool neighborhood

JulietteRating, 5 stars3 weeks ago
Next to the trains, a apartment with separate bedroom, living room, kitchen and bathroom, even a laundry room available if necessary and a host who responds quickly and does not hesitate to give advice on Chicago. I highly recommend!
Guest favorite
A modern kitchen is showcased, featuring sleek cabinetry in dark tones and stainless steel appliances. An island with a light countertop provides ample space for meal preparation. Natural light enters through large windows, brightening the inviting atmosphere of the open layout.
Apartment in Chicago
4.94 out of 5 average rating, 49 reviews

Pilsen Modern Chic Retreat

SorooshRating, 5 stars5 days ago
The place was very nice and modern. Close walking distance to a nice Vietnamese american fusion place. Could reach downtown chicago and riverwalk in 10 to 15 minutes by uber or you could walk for 20 minutes and catch the metro to downtown. Chinatown was 25 minutes walk
Top guest favorite
A welcoming living area features a leather sofa paired with a decorative throw, complemented by a glass coffee table atop a patterned area rug. Natural light filters through the bright windows, illuminating the bookshelf filled with various books and houseplants adorning the space.
Apartment in Chicago
4.99 out of 5 average rating, 79 reviews

Humboldt Park Retreat: Skylights & Queen Beds

RebekahRating, 5 stars2 weeks ago
I loved this place. Christine was such a great communicator , took initiative and very prompt to respond to text and resolve any issues, which we had none. She contacted me a day before stating they had HVAC issues but would try hard to resolve it Before we arrived and it was! Loved the location, loved the decor, 2 bedrooms so my brother and I enjoyed our separate spaces . Easy and accessible. No issues with parking. Low key , chill. Never saw Christine but she responded within 15' of text through the airbnb app, Chicago is chilly right now, the unit had extra blankets, floor heaters and a wall booster to circulate the heat and great instructions in the house manual for working the wall thermostat. Great coffee bar/area. Would recommend! My impression of the space was Bohemian Chic and felt like home. Thank you! Her neighbors were also very considerate . I was a bit disappointed it was raining because we never got to utilize the outside patio/balcony!!!!!
Guest favorite
A bright living area features large windows allowing natural light to fill the space. A light brown leather sofa and a cozy armchair are accompanied by a wooden coffee table. A decorative rug adds warmth, while shelves with potted plants and books enhance the inviting atmosphere.
Apartment in Chicago
4.95 out of 5 average rating, 64 reviews

Flor de Luna ~ Little Village Chicago Retreat

CameronRating, 5 stars1 week ago
This place was so cute and felt like home. Had everything you would need! She provided places to eat, visit & more! would recommend for a group of 2-4 friends or even a smaller family! Loved it here!!

Private apartment rentals

Guest favorite
A dining area is highlighted by a round table adorned with a lace tablecloth and a small vase of flowers. Light filters through large windows, illuminating the wooden floor. Adjacent, a living space features a couch, chairs, and decorative pieces that create a welcoming environment.
Apartment in Chicago
4.96 out of 5 average rating, 297 reviews

Logan Square 2nd Floor Chicago Victorian

JaspreetRating, 5 stars2 weeks ago
We had an amazing stay at Kitty’s place! From the moment we arrived, she made us feel so welcome. She even decorated the house for my fiancée’s birthday and left us treats, which was such a sweet touch. Her recommendations were super helpful and made our trip even better. The house was full of books and art that made it feel really special, and the beds were super comfy. The separate entrance was great for privacy, and street parking was easy to find, which was a big plus. Thank you so much for all the little things that made our stay unforgettable. We would love to stay here again very soon!
Superhost
The kitchen area showcases wood cabinetry, a sink, and a stove with an oven. A microwave is mounted above the counter, and utensils are neatly arranged in a holder. Colorful tiles add a decorative touch to the backsplash, while natural light illuminates the space.
Apartment in Chicago
4.85 out of 5 average rating, 123 reviews

*A Happy (City) Glamping- walk to train FREE park

LauraRating, 5 stars1 week ago
Perfect location on a quiet street. Super close to the L and a quick ride to the loop. We used both the L and ride share to get to and from without any issues. Other guests at the wedding we went to said we were lucky to be so close to downtown. We liked how the host had great communication and made sure we knew to reach out with any questions. The check in instructions were extremely clear. The kitchen was well equipped for light cooking and there is both refrigerator and freezer. Remember it is a camper, wouldn't be comfortable for someone that has back/joint problems, but otherwise a super cute space. It has both heating and cooling, as well as windows that can be opened for ventilation, so it was easy to adjust the temperature to be comfortable. Perfect for young people who want to get a Ventra pass and see the city via mass transit. We loved making coffee and tea in the morning and enjoying it in the dining nook!
Guest favorite
The exterior of a two-story house is shown, featuring a dark grey facade with white trim. Large windows are adorned with flower boxes displaying colorful blooms. Steps lead to a covered porch, inviting entry into the home.
Apartment in Oak Park
4.89 out of 5 average rating, 161 reviews

A Little Slice of Heaven in Oak Park, IL

RichardRating, 5 stars6 days ago
excellent apartment, very comfortable . Thoughtful snack and extras in kitchen. Rachael is a delightful host. Had a wonderful granddaughters graduation and only two blocks away.. Would stay here again.
Guest favorite
A living area features a large television mounted above a white fireplace with an electric insert. Decorative elements include a vintage mirror and a clock on the wall. A black tufted ottoman is positioned beside the fireplace, with illuminated warm tones from a nearby hanging light.
Apartment in Chicago
4.86 out of 5 average rating, 312 reviews

Charming loft style suite

KellyRating, 5 stars4 weeks ago
McKinley Park is a safe beautiful neighborhood near the Orange Line. Joyce’s place is spacious, clean and well-appointed.
Guest favorite
A light blue sofa is positioned against a textured brick wall, complemented by three framed artworks above. A small, round white coffee table sits in front of the sofa. The adjacent area reveals a glimpse of the dining space and kitchen, featuring natural light from the window.
Apartment in Chicago
4.91 out of 5 average rating, 159 reviews

Cozy 1BR in the heart of Logan Square

JulietRating, 5 stars1 day ago
Amazing host, very responsive. Would come stay again!
Guest favorite
A cozy living area features a sectional sofa with a vibrant throw pillow, complemented by a mid-century armchair. A colorful area rug adds warmth to the hardwood floor. Large windows with blinds provide ample natural light, while a decorative lamp and a globe accent the space.
Apartment in Chicago
4.96 out of 5 average rating, 252 reviews

Spacious apartment in Logan Square

AlanRating, 5 stars3 weeks ago
Joanne was a great host. It’s an older home with a modern touch. I would recommend changing the locks if that doesn’t take a way from the charm. I will definitely try to book here anytime I travel to Chicago.
Guest favorite
A spacious living area is highlighted by a black sofa facing a light-colored coffee table. A vibrant area rug adds color underfoot. The walls are adorned with colorful vinyl records and framed artwork, while original woodwork details frame the open layout leading to the dining area.
Apartment in Oak Park
4.86 out of 5 average rating, 650 reviews

Rockin' 2Bed steps to shops/food/train

BrianRating, 5 stars2 weeks ago
Great stay and location was very nice
Guest favorite
The living area features exposed brick walls and wooden beams, complemented by a gray sectional sofa and a dark blue armchair. A flat-screen television is mounted on the wall. A coffee table sits atop a patterned rug, and a workspace is located in the corner with a desk and lamp.
Apartment in Chicago
4.96 out of 5 average rating, 121 reviews

Garden Unit Getaway-Bucktown

JensRating, 5 stars2 weeks ago
Keith’s place in Bucktown is a great find. The place itself is just as described- a spacious lower level apartment with a separate sitting area and well-stocked kitchen. The location is in a very walkable area among beautiful townhouses and plenty of restaurants, coffee shops and bars. Conveniently located to public transit to get to downtown and the airport. Would definitely stay here again!

Apartment rentals with a hot tub

Superhost
A bright living area features floor-to-ceiling windows, offering views of the city. A comfortable sofa is positioned beside a round coffee table, with a decorative vase. A dining table with four chairs is visible, complemented by a textured area rug that adds warmth to the modern space.
Apartment in Chicago
4.86 out of 5 average rating, 91 reviews

Quiet but in the Heart of City walk Everywhere

TomRating, 5 stars1 week ago
Nice appartment in West loop, well equipped and the access to a gym & pool is a plus. Cloud9 staff was responsive and helpful.
Superhost
An elevated outdoor space features multiple levels, including an upper deck with railing. Lush greenery and carefully arranged seating areas create an inviting atmosphere. The exterior of the structure is painted in soft hues, and large windows allow for ample natural light.
Apartment in Chicago
4.98 out of 5 average rating, 102 reviews

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis

JessicaRating, 5 stars2 weeks ago
Thank you so much, Matthew! The beds were comfortable, the BNB was extremely clean, but still felt the coziness of Home. The hot tub definitely was the highlight of our wind down at night. We will be booking again!
Superhost
A spacious indoor garden lounge features abundant natural light streaming through large windows. Modern white furniture is arranged around a central coffee table, surrounded by lush greenery and decorative plants. The airy atmosphere is enhanced by hanging light fixtures, creating a serene and inviting space.
Apartment in Chicago
4.67 out of 5 average rating, 309 reviews

Sentral Premium 2BR Apt South Loop Chicago

YvetteRating, 5 stars1 week ago
It was a great place to stay definitely felt like home! I went for the weekend and the restaurants around there were great. They communicated very well when I had questions and responded with good time. Thank you and I’ll see you next year! :)
Superhost
A private hot tub is set on a rooftop deck, featuring bubbling water and a city skyline backdrop. Plush seating with soft cushions is arranged nearby, creating a comfortable space for relaxation. The view includes various high-rise buildings against a colorful sky.
Apartment in Chicago
4.83 out of 5 average rating, 54 reviews

Rooftop HotTub As Seen On "Married At First Sight"

KimikoRating, 5 stars8 months ago
I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!
Superhost
A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.
Apartment in Chicago
4.96 out of 5 average rating, 25 reviews

Skyline Oasis: City & Lake Views

NatashaRating, 5 stars3 months ago
Let me just say, the pictures don’t do this cute, cozy place justice! I’m big on hospitality and customer service, and Johana and Akos were beyond accommodating and communicative. I would dare to say this is the most accommodating place I’ve experienced so far! The space has such a good energy and flow to it — cozy, inviting, and with a beautiful sunset view from the kitchen window that you can enjoy right from the living room sofa. The views are stunning, and the building itself is upscale, clean, and even smells great! I enjoy playing some of the games that were pervaded( Uno and Jenga) and I appreciated that the TVs had all the apps, HBO, Disney, prime, Netflix etc. It’s in a great location, and I felt very safe throughout my stay. The only con would be some city noise, but it didn’t bother me at all. There’s a nearby train that doesn’t pass often, and again, it wasn’t an issue for me. I would definitely recommend this place!!
Superhost
A living area features two sofas and a coffee table centered on a colorful area rug. Warm lighting emanates from two table lamps beside the sofas. Artwork adorns the wall, enhancing the cozy ambiance of the space.
Apartment in Chicago
4.87 out of 5 average rating, 15 reviews

Large Studio Apartment with no cleaning fee

ErikaRating, 5 stars2 weeks ago
We had a good stay and David communicated very well with help that was needed. Good place to stay with anyone traveling with a small child. Thank you!
Superhost
The living area features a light-filled open layout with floor-to-ceiling windows. A plush sectional sofa is complemented by two stylish lounge chairs. A low coffee table sits on a modern area rug, with a decorative plant adding a touch of greenery to the space.
Apartment in Chicago
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars2 weeks ago
We stayed with my family for 3 days n loved the place it's ambience, cleanliness, very well equipped with all the necessities.....this place definitely feels like home and the hosts are very kind and quick with there response. Wherever in future I am coming to chicago shall book this place.
Superhost
The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.
Apartment in Chicago
4.98 out of 5 average rating, 116 reviews

Belmont Pleasures - hot tub / arcade gaming room

LizRating, 5 stars1 day ago
Mariam was an amazing host and very communicative with us throughout our stay to ensure check in went smooth and to let us know if we needed anything. The place was just like the pictures and accommodated our bachelorette party perfectly! Plenty of beds and space for everyone! (Party of 10!) The area had plenty of free street parking and a 2 car garage which was very convenient for our stay! Overall we loved our stay and had a great time playing games and enjoying the jacuzzi and patio! Thank you Mariam you were amazing!

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