Apartment vacation rentals in West Side

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Popular amenities for West Side apartment rentals

Weekly apartment rentals

Guest favorite
A modern kitchen features sleek dark cabinetry and a spacious island with high-backed blue chairs. Stainless steel appliances are visible, alongside a decorative arrangement of plants. The open layout allows natural light to illuminate the area, enhancing the overall ambiance.
Apartment in Chicago
4.91 out of 5 average rating, 45 reviews

Condo Near Downtown Chicago

SaeedRating, 5 stars1 week ago
This air bnb was very nice! It made you want to spend time in it. Location was 10 min Uber or 20 min train into town.
Guest favorite
The living area features a dark couch adorned with decorative pillows, positioned against a wall. A patterned area rug lies beneath, and a colorful armchair is visible in the corner. Two windows allow natural light to enter, framed by curtains, enhancing the room's vibrant art.
Apartment in Chicago
4.83 out of 5 average rating, 46 reviews

Sunny garden apartment in West Logan Square

NatRating, 5 stars6 days ago
Cozy and great place! The neighborhood is quite safe and very close to 606. The rooms are spacious and clean.
Superhost
The spacious bedroom features a large bed dressed in crisp white linens, framed by soft side tables with gold accents. A piece of abstract artwork adorns the wall above the bed, and natural light enters through a large window with unobstructed views.
Apartment in Chicago
4.71 out of 5 average rating, 1,074 reviews

Kasa | Spectacular City Views | Chicago

GustavRating, 5 stars5 days ago
Great place. Super clean. Prime location- easy to walk to restaurants and shops. Loved my stay would do it again!
Superhost
A bright living area is depicted, featuring a dark gray sofa with green accent pillows. A wooden coffee table is positioned in front, with a small decorative item. Light-colored curtains frame the windows, and a mirror hangs on the wall, while a door leads to the bedroom.
Apartment in Chicago
4.79 out of 5 average rating, 48 reviews

Logan Square Oasis

MichaelRating, 5 stars6 months ago
Really liked the neighborhood. Was a short walk to the blue line. The place was perfect and will come back again.
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, 83 reviews

Humboldt Park Retreat: Skylights & Queen Beds

PageRating, 5 stars4 days ago
Such a beautiful, cozy space! Very comfortable beds, the perfect coffee setup and fast WiFi gave us the ability to work and play. Plus our host was incredibly responsive and communicative. Would definitely stay again!
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!!
Top guest favorite
A welcoming living area is highlighted by a green sofa adorned with an assortment of colorful cushions. Above, modern art prints create visual interest on the walls, and a coffee table sits on a textured rug, complemented by natural light streaming through the large windows.
Apartment in Chicago
4.98 out of 5 average rating, 52 reviews

Sunny Cozy Spacious Boho-Chic Condo in Bridgeport

DeirdreRating, 5 stars1 day ago
We loved our stay here. Laura has been a great host. The apartment is clean, quiet, very organized and stocked with some things you may not have thought to bring on your trip but find that you need. We truly felt at home.
Guest favorite
A cozy living area is highlighted by a brown leather sofa adorned with decorative pillows. A low coffee table sits in front, featuring a plant and decorative items. The green accent wall is complemented by framed artwork, and natural light streams through a window dressed with light curtains.
Apartment in Chicago
4.93 out of 5 average rating, 56 reviews

Bold Bohemian Splendor | 2BR | Pilsen

CézanneRating, 5 stars1 week ago
Easy access to Chicago hotspots, spacious and comfortable home atmosphere. Host Nat was responsive to our wonders and gave memorable recommendations. A good find!

Private apartment rentals

Guest favorite
A modern living area features a gray sofa facing a round marble coffee table. Behind, a built-in bookshelf holds various books. Natural light streams through multiple windows, illuminating a dining area with a round table and stylish chairs. Greenery adds a touch of nature.
Apartment in Chicago
4.95 out of 5 average rating, 120 reviews

Chic retreat near the best of Lakeview & Wrigley

KortneyRating, 5 stars6 days ago
Great place to stay in a fantastic location! Will stay here again while in Chicago.
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, 298 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!
Guest favorite
A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.
Apartment in Chicago
4.92 out of 5 average rating, 121 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

TammyRating, 5 stars2 weeks ago
Absolutely loved the stay I didn’t not realize this space was spacious but still quite cozy and very well equipped for just about anyone coming to Chicago to visit. Very clean loved that it’s hassle free to park and no stairs is always a win in my book. Love the artwork and the games available I didn’t spend too much time inside but I enjoyed the time I did spend and I’m definitely recommending this location and will be back again once I discover a few other side of Chicago I think this is by far my best stay since using Airbnb
Guest favorite
A bright and airy attic space is characterized by soaring white shiplap walls and rustic wood flooring. A comfortable sectional sofa and lounge chair are positioned around a glass coffee table. Natural light floods in through multiple skylights, illuminating the cozy bedroom area visible in the background.
Apartment in Chicago
4.97 out of 5 average rating, 160 reviews

Designer Avondale Attic

ChristopherRating, 5 stars3 weeks ago
One of our favorite Airbnbs in Chicago, it has a great central location and great street parking (with a permit). It's cute. clean, and quiet. I highly recommend!
Top guest favorite
Apartment in Chicago
5 out of 5 average rating, 263 reviews

Explore Lincoln Park from a Polished Apartment

KatieRating, 5 stars1 week ago
You can believe the hype of the great reviews. Beth’s place has everything I want in an Airbnb. The decorations were thoughtful, there’s coffee and a full kitchen and a great shower and so many windows - all with black out blinds for night. Plus, the area is fantastic. I went on great neighborhood runs and it’s a quick straight shot to the lake too. Plus, the bus downtown is on the corner and really easy to navigate. Oh! And she left cookies for me! Thank you thank you, Beth!
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 stars1 month ago
McKinley Park is a safe beautiful neighborhood near the Orange Line. Joyce’s place is spacious, clean and well-appointed.
Guest favorite
The living room features a spacious teal sofa paired with a simple black coffee table in front. A window with sheer curtains allows natural light to fill the area, complemented by a floor lamp and potted plants. Hardwood floors add warmth to the room.
Apartment in Berwyn
4.9 out of 5 average rating, 301 reviews

The Green Bungalow: Charming 1-BR apt. with patio

MoniqueRating, 5 stars3 days ago
Only got to stay one night but it was a great hidden gem right outside the city! Needed a break from all the hustle and bustle. Had everything I needed, and the bed was so cozy! Christine and Dan always responded to me very quickly. Would stay again!
Guest favorite
An inviting studio space features warm wooden paneling and a dark couch. A coffee table with magazines and guidebooks is centrally positioned. Soft lighting is provided by wall sconces, and a bed is visible in the background, accented by a colorful wall art piece.
Apartment in Chicago
4.91 out of 5 average rating, 425 reviews

The Grotto of Logan Square

CassandraRating, 5 stars2 weeks ago
Ben and Karen's place is tucked into a quiet, beautiful block of the city. The space was a clean and nicely decorated retreat. They made check in and getting into the apartment super easy.

Apartment rentals with a hot tub

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, 103 reviews

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

BriantRating, 5 stars1 week ago
We stayed on the third floor of the complex and enjoyed Matthew's attention to detail. He gave a lot of thought to all components of his property.
Superhost
An open-concept living and dining area is showcased with a gray sectional sofa and a wooden coffee table. A modern ceiling fan hangs above, and natural light fills the space. A dining table with six chairs is positioned nearby, adjacent to a sleek kitchen.
Apartment in Chicago
4.84 out of 5 average rating, 77 reviews

Spacious Beautiful Condo

KristinRating, 5 stars1 week ago
Perfect location for a family to stay that’s close to everything. We did days in the city and a game at Wrigley. Very clean and perfect for our long weekend in Chicago.
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, 311 reviews

Sentral Premium 2BR Apt South Loop Chicago

YvetteRating, 5 stars2 weeks 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 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
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 starstoday
David and his co-host were excellent. Our family enjoyed our stay. We used to live in the Bronzeville area and love the new additions to the neighborhood. Everything met or exceeded our expectations.
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 stars3 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
A hot tub is positioned on a rooftop terrace, with views of the Chicago skyline in the background. The space is framed by glass railings, allowing for an unobstructed vista of the city. Soft light reflects off the water, creating a serene atmosphere.
Apartment in Chicago
4.92 out of 5 average rating, 37 reviews

Lincoln Park Haven: Balcony, Walk to Whole Foods

HoustonRating, 5 stars1 month ago
We had a great stay at this apartment in Lincoln Park. The view was excellent, and the building amenities were a nice bonus. The location was convenient too--Whole Foods was right across the street, with other shops like REI nearby. It was easy to get downtown and explore other parts of Lincoln Park. We were traveling with a toddler and a newborn, and the host helped by providing a pack 'n play. Communication was clear and timely. Overall, a smooth experience.
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, 117 reviews

Belmont Pleasures - hot tub / arcade gaming room

LizRating, 5 stars5 days 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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