Loft vacation rentals in North Side

We had a girls trip and stayed at this Airbnb and we absolutely loved it! Very clean and it looks better than the photos :) we felt safe inside, it’s spacious, clean and a great deal! If I ever come back with a big group, I’ll consider staying here again.

GuruNischan’s place felt right at home. Friendly, communicative, respectful, both her and her roommate Jose, made my stay a very relaxing experience. The place is clean and quite, I would happily recommend and book again !

5 stars isn’t enough! This fifth-story penthouse was truly next level. The rooftop patio has the most incredible views I’ve ever seen of downtown Chicago—day or night, it’s stunning. The space itself is super artsy, thoughtfully designed, and had everything I needed for a comfortable, relaxing stay. It strikes the perfect balance between privacy and connection, and the location? Unbeatable. You can walk to everything—restaurants, sights, riverwalk—you name it. The host was honestly the best I’ve ever had: responsive, kind, and made me feel genuinely welcome. This place was perfect in every way. I’d recommend it to absolutely anyone visiting the city, and I’ll 100% be back.

The unit was just as described. Centrally located and walkable. The penthouse is a great space for a larger group to socialize. The private rooftop deck was larger than expected and provided a cool view above Old Town. The space was well-stocked and freshly cleaned on arrival and the host was kind enough to give us a late checkout on request.

Lovely space for a small family. Nice to be by a park, quiet area and close to major streets as well. Peaceful and nice stay!

Great Airbnb with a responsiveness host and very convenient location. Would definitely stay here again.

Perfect place in Pilsen. Comfortable, stylish- just a great place to stay.

Great place to stay! Adamm was very responsive to every question I had. Also, it’s a very close drive/walk to a lot of places so you can truly experience a Chicago vibe. Highly recommend!

Everything described and more! Clean, under a 5 min walk to 4 coffee shops, train and bus station and shopping options. Michael was very warm, welcoming and responsive. This Airbnb made a birthday trip to Chicago really special! 🥰

I planned a small get together of six people to celebrate my best friend’s bachelor weekend. I decided to choose Jose’a Airbnb and I’m glad I did! The place was spacious and it had everything we needed! He had a 55” TV so we can hook up our switch console to play video games. We used the pool table, the dart board, and his poker set! We also cooked up some breakfast at his place too. He had a place to sleep for all six of us and he had towels and pillows/blankets for us to use. We didn’t use the CTA line to go to downtown Chicago but the line was a short walking distance from the Airbnb. I’m glad Jose was comfortable letting us use his Airbnb to celebrate and everything was perfect! Definitely recommend others to use his Airbnb! Thank you Jose!

Our group had a great stay! Spacious and plenty of sleeping space for 15 of us. Hosts were very responsive when we had an issue with the keypad malfunctioning to access the unit. Appreciate their help and attentiveness!

Great location, walkable to many restaurants, a couple of blocks from the Millennium park. Up to 15 min drive to pretty much anywhere within the Loop. The apartment looks just like the pictures, large living area with very high ceilings, natural light from the roof windows. Everything was clean. Towels, shower gel and shampoo provided. 1.5 baths. Two comfortable large beds upstairs. Easy access to the unit via the Latch app. The host is proactive and responds within minutes. Thanks for having me, would definitely stay again.

Very spacious and close to lots of entertainment! We loved the large rooftop patio!

O was very accommodating with checking in early! Very responsive host. The loft was in the absolute PERFECT location! Super close to anything & everything. Right around the corner to the L, we were able to quickly get to & from everything. The beds were comfortable. The loft is incredibly spacious with neat little quarks all over. Slightly noisy at night due to a downstairs bar, but nothing that kept us up all night. 10/10 will stay here again with a big group!