
Apartment vacation rentals in West Side
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Top-rated apartment rentals in West Side
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Weekly apartment rentals

Modern NEW Deluxe Studio in Oak Park
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.

Designer Garden Unit in Bridgeport
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

Midcentury, comfy 2bed/2bath
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.

Renovated LittleVillage Retreat
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!

Cool spot in cool neighborhood
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!

Pilsen Modern Chic Retreat
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

Humboldt Park Retreat: Skylights & Queen Beds
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!!!!!

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!!
Private apartment rentals

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!

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

A Little Slice of Heaven in Oak Park, IL
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.

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

Cozy 1BR in the heart of Logan Square
Amazing host, very responsive. Would come stay again!

Spacious apartment in Logan Square
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.

Rockin' 2Bed steps to shops/food/train
Great stay and location was very nice

Garden Unit Getaway-Bucktown
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

Quiet but in the Heart of City walk Everywhere
Nice appartment in West loop, well equipped and the access to a gym & pool is a plus. Cloud9 staff was responsive and helpful.

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

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! :)

Rooftop HotTub As Seen On "Married At First Sight"
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!!

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
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!

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.

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
- Garfield Park Conservatory
- Lincoln Park
- Lincoln Park Zoo
- Willis Tower
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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