
Apartment vacation rentals in West Side
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Top-rated apartment rentals in West Side
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Popular amenities for West Side apartment rentals
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Condo Near Downtown Chicago
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.

Sunny garden apartment in West Logan Square
Cozy and great place! The neighborhood is quite safe and very close to 606. The rooms are spacious and clean.

Kasa | Spectacular City Views | Chicago
Great place. Super clean. Prime location- easy to walk to restaurants and shops. Loved my stay would do it again!

Logan Square Oasis
Really liked the neighborhood. Was a short walk to the blue line. The place was perfect and will come back again.

Humboldt Park Retreat: Skylights & Queen Beds
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!

Flor de Luna ~ Little Village Chicago Retreat
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!!

Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
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.

Bold Bohemian Splendor | 2BR | Pilsen
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

Chic retreat near the best of Lakeview & Wrigley
Great place to stay in a fantastic location! Will stay here again while in Chicago.

Logan Square 2nd Floor Chicago Victorian
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!

Hidden Gem:Artsy Speakeasy in Historic Bronzeville
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

Designer Avondale Attic
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!

Explore Lincoln Park from a Polished Apartment
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!

Charming loft style suite
McKinley Park is a safe beautiful neighborhood near the Orange Line. Joyce’s place is spacious, clean and well-appointed.

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

The Grotto of Logan Square
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

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

Spacious Beautiful Condo
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.

Sentral Premium 2BR Apt South Loop Chicago
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! :)

Skyline Oasis: City & Lake Views
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!!

Large Studio Apartment with no cleaning fee
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.

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop
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.

Lincoln Park Haven: Balcony, Walk to Whole Foods
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.

Belmont Pleasures - hot tub / arcade gaming room
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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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Wicker Park
- Willis Tower
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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