
Apartment vacation rentals in West Side
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Top-rated apartment rentals in West Side
Guests agree: these apartments are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for West Side apartment rentals
Weekly apartment rentals

Chic retreat near the best of Lakeview & Wrigley
Nice and clean 1 bed unit for a week of comfortable stay. Thank you for hosting us!!

*The Belltower Haven*Large*Family Friendly*Wi-Fi
Great spot to stay and James was awesome, would highly recommend this place to any of my friends, thanks again!

Bright two bedroom garden apartment
My family and I stayed for a few days and really enjoyed the unit. The place was really clean, well equipped, and was just as described. Parking was very easy to find, the neighborhood was beautiful, and within walking distance of several restaurants and coffee spots. Carol was very responsive to questions and gave excellent guidance on accessing the place. She was even kind enough to return a forgotten item to us. I would highly recommend this space and would absolutely come back again for another stay.

Comfortable Vintage North Side Retreat for 8
Great place in Chicago. Close to the brown line for loop access. Walkable and beautiful area

Cool and Modern Chicago Apartment near Transit
Our stay at Afsha's was perfect! From the booking through checkout, communication and instructions were proactive and clear. The space was incredibly clean and there were prestine linens and towels available. The kitchen had everything we needed and was organized beautifully. The location is in a thriving neighborhood and the off-street parking space was great to have in an area where parking is hard to find.

*Comfortable & Spacious Home Close to Downtown*
This was a very spacious and clean apartment that comfortably hosted our family of 6 for several days. Having two separate living areas was very useful and allowed our group to spread out a bit. The full-size crib in the extension area off the master bedroom was also much appreciated as we had a 2-year-old with us. The building is on a quiet street just one block from Humboldt Park and two blocks from restaurants and shops on North Avenue. There was a grocery store within 2 blocks. Dubbs was a very responsive host, and we appreciate his flexibility with checkout time. We would happily stay here again.

Oasis Collection's Mid-Century 3 Bd Wicker Park.
This is a very clean and comfortable unit. The beds are very comfy, the comforts are wonderfully soft. Basic toiletries and kitchen essentials are provided. The location is excellent for us, as we have young grandchildren and a dog, both enjoyed wicker park. Many restaurants are close enough for walking.

BERNARD CHATEAU - LOGAN SQUARE
it was my first Airbnb experience and it was very pleasant. The location is perfect to get to the place, but perfectly peaceful in the night.
Private apartment rentals

Modern 3BR with Private Rooftop & Free Parking
A great place to stay for a family to explore downtown Chicago. The location is convenient, with easy access to major attractions, and restaurants. The home was clean, cozy, and well-equipped — we truly felt like we were at our own home. The host was responsive and thoughtful, which made our stay even more comfortable. Highly recommended!

Private Garden Apartment GATED FREE Parking
Highly recommend. Peaceful, well equipped unit with a homey feel. Bed extremely comfortable, with many pillows and comfortable mattress. Elena represents the unit well. I will rent again the next time I am in Chicago.

Lovely 2bedroom 1bath Apt and outdoor seating.
A very nice and welcoming place to stay!

Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
Shaun and Christina's place was exactly what we were looking for. Lots of cool restaurants nearby and they were extremely helpful and communicative. Highly recommend!

North Side Pied-à-terre
We needed a place to stay in the Roscoe Village area, and this was perfect from a location and size standpoint. It is urban-on a well traveled street, close to the metro stop, lots of coffee shops and places to eat. Appreciated the white noise machine in the bedroom and the bathroom towels were very nice. Communication was excellent and easy to understand. Highly recommend!

Adorable 1BR apartment near Northwestern
The place was exactly as shown and described. Very lovely in a very peaceful part of town. Responses to questions were always prompt and clear. One of the best. Thank you for the pleasant stay.

New apartment
Loved the walkability and great access to transit and chinatown restaurants. amazing stay! thank you!

Stylish & Modern 2 Bedroom Lincoln Square Condo
Eric’s place was quiet, homey, attractive and comfortable, good neighborhood, close to our granddaughter’s, good restaurants nearby. He responded quickly when we couldn’t get in (the door code was my old phone number, which I hadn’t changed on airbnb and didn’t remember - my bad).
Apartment rentals with a hot tub

Quiet but in the Heart of City walk Everywhere
This place was incredible. My kids and I loved staying here. My young daughter had asked to stay in a "fancy hotel" on our trip, and this blew her mind with the views over the city, how nice the space was, and the pool and hot tub that we pretty much had to ourselves every evening. The kitchen had the things we needed to make our own meals. And we were within easy reach of every place we wanted to go. The included parking spot really took things over the top to make this a great deal and an amazing stay for our family.

Minutes to Wrigley Amazing Location - Sleeps 6
Freddy was an incredibly friendly and responsive host, really went above and beyond to ensure a good trip. The location is perfect, just a few minute walk to everything you could want while still maintaining a quiet residential feel.

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!!

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!!

Large Studio Apartment with no cleaning fee
What a great stay! The boat was even better. He was immediately responsive and accommodated extra when caught in a pinch. He was very communicative and helpful. The place was very comfortable for both us and the dogs. It felt like home! Would recommend to anyone.

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop
Avantika’s penthouse apartment was absolutely lovely. The space was comfortable and well-designed, with beautiful bedrooms and impeccably clean bathrooms. The kitchen was modern, spacious, and had everything we needed. Avantika was incredibly kind, helpful, and very responsive throughout our stay. We had a fantastic experience and will definitely be back!

Sentral 2 Bedroom Apt in South Loop Chicago
Very easy for a local who needed a different place to stay during a remodel

Belmont Pleasures - hot tub / arcade gaming room
What could I say… the place was amazing!! My grandson and his friends had a terrific time. Me and my family enjoyed the couple for days we stayed here, the amount of things you can do in the house was amazing, will definitely will be booking all my grandkids parties here.
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Six Flags Great America
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Flossmoor Golf Club
- Museum of Science and Industry
- Willis Tower
- Lincoln Park
- Wicker Park
- Chicago History Museum
- Skokie Country Club
- Illinois Beach State Park
- Washington Park Zoo
- Promontory Point
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