Apartment holiday rentals in Northwest Side

Find and book unique apartments on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Northwest Side apartment rentals

Weekly apartment rentals

Top guest favourite
Flat in Chicago
5 out of 5 average rating, 30 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

ElizabethRating, 5 stars5 days ago
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
Guest favourite
Flat in Chicago
4.94 out of 5 average rating, 96 reviews

Cozy Jefferson Park 2BR Apt

DietrichRating, 5 stars1 day ago
clean house in cute neighborhood, walkable to multiple breakfast spots, and with responsive, kind hosts.
Superhost
Flat in Oak Park
4.89 out of 5 average rating, 28 reviews

Modern NEW Deluxe Studio in Oak Park

AshlynRating, 5 stars3 weeks ago
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!
Superhost
Flat in Chicago
4.91 out of 5 average rating, 70 reviews

"Great Totally Rehab Apartment in Portage Park

JullietteRating, 5 stars2 weeks ago
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!
Guest favourite
Flat in Chicago
5 out of 5 average rating, 22 reviews

Cozy Chi-town apartment

AdelRating, 5 stars1 week ago
It was really great place to stay in it. very clean and organize
Guest favourite
Flat in Chicago
4.93 out of 5 average rating, 15 reviews

Cozy Casa by O’Hare Airport

KenilaRating, 5 stars1 week ago
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!
Guest favourite
Flat in Chicago
4.91 out of 5 average rating, 54 reviews

Montrose Gardens

JoyceRating, 5 stars1 week ago
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!
Top guest favourite
Flat in Chicago
4.97 out of 5 average rating, 38 reviews

Cozy Bungalow Getaway

SarahRating, 5 starstoday
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

Guest favourite
Flat in Chicago
4.95 out of 5 average rating, 287 reviews

Cozy and Spacious! Logan Square Apartment

JonathanRating, 5 stars4 days ago
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.
Guest favourite
Flat in Oak Park
4.91 out of 5 average rating, 180 reviews

Lovely, spacious 2bd, 1bath home w/free parking

DouglasRating, 5 stars5 days ago
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!
Guest favourite
Flat in Chicago
4.9 out of 5 average rating, 405 reviews

Sunny Logan Square Artists' home

KatyRating, 5 stars3 weeks ago
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!)
Top guest favourite
Flat in Chicago
4.96 out of 5 average rating, 447 reviews

King Bed, Huge Spa Shower, Dining Destination

JanelRating, 5 stars3 weeks ago
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!
Guest favourite
Flat in Chicago
4.83 out of 5 average rating, 141 reviews

Cozy Avondale apt right by Belmont blue line stop

AzariaRating, 5 stars2 weeks ago
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.
Top guest favourite
Flat in Chicago
4.96 out of 5 average rating, 285 reviews

Spacious 1BR apartment in a central location

MakaylaRating, 5 stars2 weeks ago
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.
Superhost
Flat in Chicago
4.86 out of 5 average rating, 122 reviews

Private Garage+Laundry+Restaurant Row+93 Walkscore

EmilyRating, 5 stars1 week ago
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!
Guest favourite
Flat in Chicago
4.92 out of 5 average rating, 261 reviews

Skylights, King Bed, 2 bedrooms

DianaRating, 5 stars1 week ago
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

Superhost
Flat in Chicago
4.67 out of 5 average rating, 312 reviews

Sentral Premium 2BR Apt South Loop Chicago

SilviaRating, 5 stars1 week ago
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!
Superhost
Flat in Chicago
4.85 out of 5 average rating, 79 reviews

Spacious Beautiful Condo

SophiaRating, 5 stars5 days ago
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!
Superhost
Flat in Chicago
4.83 out of 5 average rating, 54 reviews

Rooftop HotTub As Seen On "Married At First Sight"

KimikoRating, 5 stars8 months ago
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!!
Superhost
Flat in Chicago
4.96 out of 5 average rating, 27 reviews

Skyline Oasis: City & Lake Views

NatalieRating, 5 stars3 weeks ago
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!
Superhost
Flat in Chicago
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars1 month 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
Flat in Chicago
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars1 week ago
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
Flat in Chicago
4.83 out of 5 average rating, 119 reviews

Penthouse Near Fulton: Skyline, Spacious

ValerieRating, 5 stars2 weeks ago
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.
Superhost
Flat in Chicago
4.9 out of 5 average rating, 30 reviews

City Skyline Suite (2BD / 2BA)

NataliaRating, 5 stars6 days ago
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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Northwest Side
  6. Flat rentals