Apartment holiday rentals in North Side

clean house in cute neighborhood, walkable to multiple breakfast spots, and with responsive, kind hosts.

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!

Wonderful stay! The place was very comfortable, clean, and convenient. The neighborhood is great! The hosts were always responsive and helpful and went out of their way to make sure we had everything we needed. Would definitely stay again!

At first I couldn’t believe so many 5 star reviews—and now I know why. Because you can’t give a 6. We were between business trips and have a child who lives Chicago so we thought we’d make a weekend of it rather than flying home. Lovely, homey, classy, unique, comfortable, warm and very cool all in one place. You need only to roll out of the door to find great food, great people and great fun. Thank you for opening your home to us.

We wanted to park and walk the area, attend a Cubs game, go to dinner. We could do it all without moving our car! Note though that we got SpotHero parking right behind our place. It is an extra expense but worth never moving. I do recommend this lovely Air BnB!

Hubby and I were in Chicago for 5 nights to visit our son. The studio was the perfect environment to return to at the end of each day and we very much enjoyed our stay. It is clean, stylish and very comfortable. The neighborhood is quiet and we felt safe when out walking. There are numerous good restaurants and stores that are within walking distance, and we were able to easily secure ride-share when needed. Nick was a great communicator and was always quick to respond to questions. Also he was very kind and accommodated our late afternoon flight and request for a late checkout. Would definitely stay here again.

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!

Cosy and clean apartment in a peaceful and well connected neighbourhood, walking distance to buses, the L, share bikes and plenty of cafes and restaurants. Without a car it takes about 40 minutes to get downtown, but the location and apartment are worth the little extra time. Micheal and Georgia were kind and communicative hosts—definitely recommend staying here!

Nice and clean place! Would recommend a stay here if you are looking for somewhere outside the business of downtown

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!

Lovely basement studio in very nice neighborhood. Easy drive to nearby neighborhoods or downtown area. Highly recommend if you’re looking for a comfortable stay!

Great location, nice unit. Older building but nice updates. You can definitely hear the tenant upstairs so bring headphones or earplugs if that bothers you.

Exactly what we were looking for. We wanted somewhere within walking distance to Wrigley Fielf

Hugh’s place was great! Hugh and Susan were great communicators and always quick to respond. I very much appreciated them accommodating my requests, we’ll definitely look to stay here again when in town for a Cubs game.

Great location! Safe, clean, clear check-in/out instructions, perfect for our weekend in Chicago.

Lovely neighborhood, street parking can be challenging dependent on the day and time of day. It is on the end of the street making it a quieter location.

Loved our stay. Right in the middle of everything we wanted to do in Chicago. If we couldn't walk to it, public transportation was readily available. Stephanie was always friendly and responsive. Would definitely stay here again.

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!

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!

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!

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.

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.

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.

The host is very helpful. The house next door seems to be abandoned; therefore, there is a lot of trash and broken glass on the floor next to this building. The place is very chic and fun. My favorite part was the bath bar and back yard. There are no dishes only cups and coffee mugs no paper towels and no plates. I liked the fact that the host asked questions before approving our reservation. I will definitely reserve again.