House holiday rentals in Rogers Park, Chicago

It was a chaotic start to our vacation stemming off my daughter's graduation from Northwestern; however, Jennifer immediately took the stress off my shoulders and welcomed our family to a fabulous stay at her home. Words cannot express how grateful my family is and without Jennifer's help it would not have been as successfull. I highly recommend staying at any of her properties. She will go above and beyond to make sure you're stay is wonderful!

Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!

Great getaway place to stay at. Beautiful patio area as well!

I had such a great time at the Hacjenda House! I came here with my dog for a peaceful getaway and it was exactly that. Lena set up the fireplace inside for me and I was cozy all night. Plenty of firewood in their backyard. Super spacious and beautiful inside and out. Their tub upstairs is also so spacious for a bath. Lena was so kind by checking in on me throughout my stay. I didn’t want to leave. I definitely want to come back.

Beautiful home, clean and worked perfect for our family. Elisabeth always responded quickly and it was a seamless check in and check out process.

Beautiful home in a quiet neighborhood with responsive and helpful hosts.

We were a group of four teachers planning a girls get away. Elijah’s place was very nice. We asked if we could get in early and he sent us the code right away.He had put a case of water in the refrigerator which we really appreciated. The sectional in the living room was very comfortable and a great place for conversation. The patio in the back was great to sit outside. Overall, it was a very nice place to relax after busy days of sightseeing!

Faith's place was great! The bed was super comfortable and her place was exceptionally clean! Quiet neighborhood. Easy access to highway, local restaurants and grocery store. The fresh eggs she gave us were a treat! She is an excellent communicator. Highly recommend staying at her place.

We had a truly wonderful stay at Casa22. The home is beautiful, luxurious, and impeccably maintained — everything was clean, spotless and thoughtfully arranged. It had all the essentials we needed for a comfortable extended stay with our family, including a well-equipped kitchen, and spacious layout. The hosts, Narcis and Gabriel, were fantastic — extremely responsive, clear in their communication. They provided detailed instructions that made check-in, check-out, and everything in between seamless. The neighborhood is quiet, safe, and very family-friendly, with easy access to main roads — a great location if you're planning to explore Chicago without the stress of city parking. Having a car made it easy to get around, and the area itself felt peaceful and well-kept. If you're visiting the Chicago area and looking for a clean, elegant, and well-managed place to stay, I highly recommend Casa22. We would absolutely love to return!

We loved Lily’s place and would stay again in a heartbeat. The neighborhood is great. The house looks like the pictures. The beds are comfortable and linens clean. The kitchen is well appointed too. Lily’s communication is excellent and she answered questions promptly.

O espaço da Janice é extremamente aconchegante. A cozinha é super equipada (geladeira, fogao, cafeteira, panelas e demais utensílios... alem de manteiga e temperos básicos). O quarto é lindo e a cama super confortável. O banheiro estava limpo e havia itens de higiene de ótima qualidade, além de um excelente secador de cabelo. A televisão era grande e a sala super confortável. Amamos tudo. Quando voltar à Chicago, será a minha escolha!!

Words can’t describe how beautiful and clean the property and neighborhood is! The house is very spacious and modern. The basement is new, has a big room and bathroom with shower. The masters bedroom has a living room and GORGEOUS bathroom! The host provided cleaning supplies and even personal bathroom supplies for men and woman. The host was very nice and friendly 🥰 We had an incident with our previous AIRBNB and we had to rent this one last minute- The host responded at 1am letting us checked in at 1am. If you plan on staying here, please take care of it lol It’s such a lovely house! 100% Recommend!

We loved this cute little house! Super walkable and close to lots of stuff in Logan Square; although we thoroughly enjoyed the peacefulness of hanging out in the private backyard. Would definitely stay again!

Xavier’s place was great, we felt right at home! We were a family group of six, everyone was able to sleep well during the two nights we stay. We also grilled food in the propane-gas grill in the back patio, it was ready to use. All of the spaces were welcoming and spacious. I highly recommend this stay.

This is the second year in a row we stayed at this Airbnb for an extended 4-week stay. Our second stay was as wonderful as the first. The Airbnb is very clean and comfortable and is located in a great neighborhood. Jesse was a fantastic host and always responsive to any request we had. If we have the opportunity for another extended stay next year, we'd love to return. Thank you, Jessie for helping to make our stay most enjoyable.

This was one of best AirBnbs that I have stayed at this year. Clean, great host, lovely house. Comfortable beds, clean bathroom, big shower, a sauna! Highly recommended.

Excellent stay for nearby Northwestern graduation - plenty of beds for all (note: tall people will want to stay on first floor, but basement is well-finished), plenty of hot water for morning rush, easy check-out instructions and super-responsive hosts. All in all, a perfect choice for our extended family weekend!

We thoroughly enjoyed our stay at Josh’s place in Andersonville. It was perfect for our large gathering with the expansive and well decorated house and a backyard large enough for family lawn games. Great location for the midsummer festival in Andersonville. Very clean and comfortable beds.

Great place to stay- the home is open and easy to access. It’s close to lots of walkable restaurants and parks. We have several kids on our trip and got around easily. David communicated great and was easy to work with. Well stay here again for sure.

Stunning apartment with an incredible host!