Vacation rentals in Chicago

Lovely place in a good location.

Great location! Felt safe and easy to get around. Close to the Vic Theater and the El. The space was very comfortable for 3 of us. Once we figured out the codes/keys, it was easy enough. I would definitely stay again. Cathy is super easy to talk to and very responsive. Thank you, Cathy!

Craig was extremely nice and accommodating when it came to my birthday weekend. He responds quickly to all questions asked and makes sure we’re comfortable at all times. This home was clean, accurately described, and had the perfect “home feeling”. Overall, when visiting the area I will be booking here again !

This location exceeded our expectations. The location was great. Restaurants, bars, groceries, etc were really close by. We weren’t able to take advantage of the location as much as we wanted only due to the cold, windy weather. We would have done more on the lakefront and on their rooftop.

This was a beautiful place with an excellent view of Lake Michigan. Both rooms had comfortable beds and setup with everything you need. Kitchen is well stocked, but we mostly ordered Grub Hub, lol. Loved spending time here and great place to hangout and chat with friends. It is right on the water and we really enjoyed watching the waves crash against the barrier. It is on the 2nd floor, but the stairs are not bad at all. Felt very safe and having the parking space is a great perk. Very commutative and checked in with us to make sure everything was fine. Would definitely stay here again!

a really awesome place. I highly recommend this place.

Loved staying here! Super cozy, easy to find, and Matt was always responsive and gracious letting me check in early and check out late. There’s a bathtub, a desk by a window perfect for working, and lots of great books. The hosts even left a complimentary bottle of wine and bag of chips! 10/10

We were in town for a show at the Casino, this place was tremendous. Very easy to find, super close to the Casino and the room was quite nice. Would definitely book again if we find ourselves in that area again 😁

Great spot to stay and James was awesome, would highly recommend this place to any of my friends, thanks again!

Jamie’s place was a perfect spot to stay in Chicago. There is access to the L within a few miles (with parking structure), and there are many walkable places locally. We highly recommend Caesar Pierogis on West Irving (offers gluten free pierogis). The neighborhood is charming and safe for walking. After long days of exploring, we came back to Jamie’s place and enjoyed watching Netflix and relaxing in the living room. The kitchen is stocked with utensils, and there is a grocery store within walking distance. Jamie is a very thoughtful host, and her home is quite accommodating. We had a lovely get away. Thank you, Jamie!

Alex was great at communicating and following up. We had some questions and she was responsive. Also goes beyond expectations on things like forgetting coats :0) - thank you! The location is great. Short walk to a Main Street of bars and restaurants, kid friendly too - happy campers pizza joint was a great reco! Also close to the brown line train station and not too far into town - we walked it with children and it was fine. House is really large, spacious. I know some have mentioned about hearing the train, but that is part of city living, it was more than fine. Enjoyed the stay, would recommend it and would go back again if visiting Chicago. Thanks Alex!

I had a wonder stay at this charming flat in Chicago. Danny's home is a beautiful historical building full of character, and the interior was clean, comfortable and well maintained. One of my favorite parts was the cozy backyard-such a peaceful spot to relax on a warm morning or unwind in the evening. You're right in the center of activity, but have plenty of privacy. Danny was friendly, responsive and made everything super easy. I'd definitely stay here again and highly recommend it to anyone, and their dog, visiting Chicago!

We loved our stay here. The place was very comfortable and spacious. The area was close to restaurants either walking distance or a short drive. Parking was super easy and Susan was very accommodating with us having 2 cars. Would highly recommend this place!

This home was absolutely beautiful and exactly what I wanted. I was looking for a large backyard to allow my dogs to run in while I stayed there. The yard is probably 3/4 of an acre and was excellent for the dogs. The driveway even extends beyond the privacy gate where you can pull your car right into it and let the dogs right out. It was perfect for loading the guys up early in the morning and letting them out late at night. I double checked the fence and she definitely reinforced a lot of it. There’s chicken wire on the bottom so the dogs can’t dig underneath it. The home itself is absolutely beautiful with a king size bed in the main bedroom, which has a window right to the backyard. It’s exactly what I needed for my 10 day stay Liz was also super responsive and super helpful for any questions that I had. I’m definitely gonna be able to stay here again.

Very friendly and responsive hosts, thank you so much for accommodating us with our cat! Beautiful house and great location.

The townhouse was amazing. We could have spent the whole time looking at the art and collectibles on the shelves and walls. The location couldn't have been more convenient to Wrigleyville and was a great neighborhood to walk the dogs around in.

We loved our stay. Amy was an excellent communicator. The space was clean, open and very inviting. I loved the location. I would definitely stay there again!

John was a very kind and responsive host. Answered any questions we had very quickly. Home was exactly as pictured and described. Very comfortable place to stay. Everything was clean. Appreciated the family and kid friendliness of the home--not a lot of decorative items in reach that could be broken, no tables with sharp edges, low bed in the upper guest room that was easy to get in and out. Location was close to several restaurants and grocery stores, and not too far a drive from all the major tourist attractions.

The place was clean and well kept .Letitia was very helpful and personable with local recommendations. I checked in late and there was a banana and apple waiting for me which really helped as it was too late for dinner but I was hungry. The kitchen is well equipped and the place is exactly as described. I had a wonderful stay.

Host is very accommodating and responsive. Felt just like home. We’ll be back!!

This was a beautiful place! it had everything we needed. Oak Park downtown is walkable and has everything you could want. It is an upstairs unit so be prepared for some steps. Parking was easy. Michelle was great! Downtown Chicago is only 15m (if there's no traffic.). We would definitely come back!

Thank you for sharing your wonderful space. It was perfect to spend time as a family while moving our daughter in Logan Square. The park nearby was so easy to manage for our dog who joined us. Paul was responsive and helpful. Got to meet his pup who was adorable. Will definitely stay here again

The hosts were very responsive to any questions. They live in the same building and helped with any concerns right away. The space was very homey and comfortable, with convenient bus stops nearby. There were plenty of books, movies, and games if you have time to kill at the apartment. You can hear a lot of footsteps from upstairs neighbors, but usually it wasn't too loud and the provided earplugs were helpful. The neighborhood felt safe and family-friendly. It felt like we were staying with good friends. We highly recommend this place and would stay there again.

Holly and Mark are great hosts. Very responsive and went above and beyond to offer additional help and recommendations for travel, food, etc during our stay.