
Apartment holiday rentals in Northwest Side
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Top-rated apartment rentals in Northwest Side
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Popular amenities for Northwest Side apartment rentals
Weekly apartment rentals

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
This is a charming and very comfortable unit. All the amenities are thoughtful and more generous than most other AirBNBs that I’ve stayed. We found the location very convenient to family and Northwestern U, and even getting downtown. The unit was spotless, clean and organized. And exceeded our expectations. Being able to park in the garage was a huge benefit for us. We had a busy schedule with leaving in the morning and not getting back until later evening. It was so nice not to have to search for street parking and not have that worry. We very much enjoyed our stay. This will be our “place” when we return. Elizabeth

Cozy Jefferson Park 2BR Apt
clean house in cute neighborhood, walkable to multiple breakfast spots, and with responsive, kind hosts.

Modern NEW Deluxe Studio in Oak Park
This was the perfect spot for our weekend trip! Oak Park was the cutest little town and very easy to get to downtown Chicago. The listing was just like the pictures, and the check in/out process was one of the easiest we’ve ever had! Would definitely stay here again😊 Only thing to note is you are able to hear the street noises, and if the sun is something that will wake you up in the morning, be aware that it is shining through those beautiful big windows! Overall, an amazing experience!

"Great Totally Rehab Apartment in Portage Park
Martha’s place was a real gem. It was a great apartment that was well decorated and ft very comfortable. The location felt very safe and there were great restaurants around!

Cozy Chi-town apartment
It was really great place to stay in it. very clean and organize

Cozy Casa by O’Hare Airport
We found this place after canceling a sketchy place we were originally planning to stay at. The place was very clean and clutter free. Everything was within 20-40 minute drive with Chicago’s traffic. He had very clear instructions and rules. Great place at a great price!

Montrose Gardens
This was a very cute one bedroom apartment. It was perfect for my husband, myself and my daughter. Extremely clean. So sweet they left treats and snacks! Host was very nice and accommodating. Would definitely stay again!

Cozy Bungalow Getaway
Lisa is such a wonderful host! She made it such an easy process checking in and out and was so helpful and kind giving recommendations of places nearby. Lisa's place is such a a great find, it's a great location and it really makes you feel like you're in a home away from home. Lisa made our time in Chicago much more enjoyable knowing we had somewhere so comfortable to come back to. Tober is great too!
Private apartment rentals

Cozy and Spacious! Logan Square Apartment
Just had a fun stay with my wife and kids. Unit is comfortable, kitchen is fully stocked, and Charles was super responsive and accommodating. Would definitely rebook.

Lovely, spacious 2bd, 1bath home w/free parking
This cute home is situated in a nice neighborhood and was clean when we arrived. Tiffany was helpful and left great instructions. We really appreciated it!

Sunny Logan Square Artists' home
We loved our stay at Kyle’s place - it was decorated SO cute (I went with two girlfriends and I’m pretty sure we all squealed with joy when we first opened the door). The location was perfect - just a quick walk to all the shops and restaurants Logan Square had to offer - and to public transportation (which we used the whole time in Chicago). The neighborhood was very peaceful and quiet; we all felt very safe. When I come back to Chicago, I will absolutely be staying here again. Thanks for sharing your space with us, Kyle! We loved it! (Side note: you gave me so many ideas for house decor, your style is impeccable!)
King Bed, Huge Spa Shower, Dining Destination
We had a wonderful stay at Kristin’s place! She was a generous host and very responsive communicator. We traveled with our toddler and Kristin was great about providing everything we’d need, including a few toys. The primary bedroom and bathroom were both amazing, as everyone else has mentioned in their reviews. We had a very busy trip and it was great to come home to a spa-like bathroom and extremely comfortable bed each night. We will definitely be back!

Cozy Avondale apt right by Belmont blue line stop
Great spot in Logan Square. Close to the Belmont Blue line, easy to get around, and quiet neighborhood within walking distance to food and coffee. Very quiet and clean place, it was a nice little home away from home spot. Enough space for my boyfriend and I both to work from home.

Spacious 1BR apartment in a central location
Great experience! I stayed at Alex’s place for a concert and it was perfect for what we needed. Close to public transit, good food, and fairly quiet neighborhood do Chicago. Highly recommend.

Private Garage+Laundry+Restaurant Row+93 Walkscore
Another great stay! Eva is a great host and ensured that everything was well stocked and ready for my stay. The location was great for outdoor running, just a block from an entrance to the popular 606 Trail. 5 stars!
Skylights, King Bed, 2 bedrooms
had a great last-minute stay here! tara was so easy to communicate with and the space was extremely comfortable. its a bit of a walk to the L (train) so i'd recommend a car but street parking is ample and free. another note is it up about fifteen stairs if there are any accessibility concerns. but we were so pleased and i would absolutely stay here again!!
Apartment rentals with a hot tub

Sentral Premium 2BR Apt South Loop Chicago
Fantastic stay in Chicago! The location was perfect and easy to find, with a spectacular view of Lake Michigan and the Sears Tower. It’s an amazing starting point for sightseeing on foot with the family. Check-in and check-out were super easy, and the host was very responsive with great tips for the area. We would absolutely come back anytime!

Spacious Beautiful Condo
We came for our daughter’s graduation and stayed a few extra days to tour the city. This place was perfectly located for both occasions. It was much more spacious than we expected, and everything was very clean. We especially appreciated the fresh towels and beddings. Our only wish is that the beds were a bit larger, especially the double bed, which would be more comfortable for a couple if it were at least a queen size. That said, the beds were very comfortable. Overall, we had a wonderful stay - definitely one of our best Airbnb experiences!

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
Perfect weeklong stay in Chicago! The apartment is well equipped and makes you feel right at home. The building is connected via sky bridge to Jewel making it easy to grab groceries. The location cannot be beat - easy access to West Loop, Wicker Park, River North. The hosts were fantastic and flexible with our check in times. Looking forward to coming back!

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.

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.

Penthouse Near Fulton: Skyline, Spacious
SPECTACULAR!! This space is how you should visit Chicago. Breath taking views from this 33rd floor luxury penthouse apartment lives up to the hype. Our family of six were extremely comfortable in this 3 bedroom/3 bath unit. And for a person that likes cooking, the kitchen is spacious. Don’t pass on seeing Chicago from the views in this beautiful apartment.

City Skyline Suite (2BD / 2BA)
We loved this apartment and our trip to Chicago. We felt safe when coming home late at night and we walked everywhere, even though train stations are pretty close. The views from 17th floor are spectacular in 3 directions, including Lake Michigan and Willis Tower. The place is very clean and comfortable. I wish we could stay longer.
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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
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Moraine Hills State Park