Waterfront holiday rentals in Cook County

Amy is an excellent host! She was so proactive about reaching out ahead of time and checking in on us. The unit was extremely clean! Easiest check in I have had with Airbnb—clear/specific directions. Amy was also super accommodating with our checkout time—we had a late flight (7:45pm) and we were able to check out at 5pm instead of noon which allowed us to maximize the last day of our trip! SO close to Loyola beach and has easy access to public transit. There are just a few improvements that would make this a perfect Airbnb: 1) the mattress is uncomfortable (extremely firm), 2) there is a beautiful kitchen but it is not well stocked with the basics (strainer, cooking utensils, pots, etc)—we made do by getting a little creative! Not a problem if you plan on eating out the whole time. 3) A few end tables would be nice for setting a glass of water/coffee etc, 4) needs a few more towels for being so close to the beach! Nonetheless, I would love to stay again and highly recommend!!

I absolutely loved my stay at the wine down! The place was decorated beautifully and was equipped with everything I needed. James even went out of his way to give me a couple of courtesy calls during my stay just to make sure everything was going smoothly. I would definitely stay here again in the near future. Thank you for a great experience.

Very walkable to public transit, super comfortable sleeping arrangements, and beautiful apartment in general!

The apartment was extremely clean!!! I loved the attention to detail. Very quiet street for sleeping at night and easily walkable to beach, restaurants, and attractions.

Clean, comfortable, and beautifully appointed apt. Emily and Roya are helpful and communicative, and all the instructions and photos made things very easy. Would happily stay there again!

Great 1st floor town home on the boarder between Rogers Park and Evanston, right on the waters of Lake Michigan. Lots of sunlight (and able to watch the sunrise over Lake Michigan in the morning) and a couple of parks next door. The bathrooms (especially the showers) were great--full size, nice water pressure. I was able to work remotely while I was there without any issues. As others have noted, parking is on the street; but if you're proactive or book with Spot Hero or similar, it's very manageable. I really enjoyed my stay!

We loved this stay!! It’s a beautiful apartment and is walking distance to a great coffee shop called charmers, as well as almost ON Jarvis beach! The hosts are very friendly and preach over communication and make sure that you have all of the information you need! They allowed us very early check-in had we needed it (I believe by 2pm!) and the apartment was spotless! Very comfortable bed and living area, plus an office if you’re visiting for work. This is a great part of Chicago, with most Ubers we took ending up around $20! There is ample street parking on Jarvis, especially with the beach entrance at the end of the street. We would recommend this space and these hosts to anyone and everyone visiting Chicago. They were so kind and organized and really made for a wonderful trip!

super cute apartment. loved working with the host, very responsive and helpful. Definitely worth a visit!

Rasheed was very attentive. His home is in an excellent location, walking distance to resturants and shopping. The rooftop provided a spectular view of the city. I would definitely recommend Rasheed's home on a trip to Chicago!

Super kind and responsive

Stephanie was a wonderful host, home was squeaky clean. She was incredibly responsive and attentive. Photos matched the description of the house and we would stay here again in the future :)

Beautiful home layout and very spacious! Location was a quick drive to the city, which was convenient. Host was also very kind and attentive. Thank you Ms. Lilly for our stay!

Hugo was a great host. The house was just like the listing, ideal for a weekend with friends. We were five couples with children, an ideal family atmosphere. It has games and equipment to enjoy the lake and garden, such as a small pool, life jackets, sport balls... It was a great weekend thanks to the space and the house, highly recommended!

The return trip was even better than the first! We enjoyed the balcony, the woods across the street add to the relaxation. The uncrowded beach made the sunset even better

Simply beautiful! My daughter ( 7 year old) and my goddaughter ( 5 year old) enjoyed themselves! We loved the layout, beautiful scenery, spacious rooms, the updated amenities, the spa bathtub and the outdoor patio swing is amazing! This house is somewhere you can relax and rewind, enjoy yourself and feel safe at! Angie, is the best! I recommend you stay at Angie’s beach house! You will love this house!!!!!!

We had seven people in town for a family wedding, three couples and a single. They all had their own bedrooms and with bathrooms, no one was waiting to do business, so to speak. The lake and water toys were great. The back deck was very relaxing. Also, compared to most airbnbs, Shon had a lot of things available, such as aluminum foil, Saran wrap and more things in the kitchen. Shon was very responsive when we had questions. If I ever have another reason to visit the area and have a big group, I'd want to use Shon's place again. Oh, one other thing. You're right off Ogden, which has everything you'd need ... groceries, drug store, tons of restaurants and more.

This condo was super-clean. We loved the balcony, where we could relax after climbing dunes with our grandkids! Good mattresses (our daughter & husband took the upstairs bedroom) and we appreciated the king-sized beds. There is quite a tall stairway to climb to get to the 2nd floor. Otherwise, easy access (we used the August app) from the parking lot.

Ashley was a great host! She provided clear instructions for check-in/check-out, had nice local recommendations, and was extremely responsive. I also appreciated that she was willing to accommodate my travel dates near the last minute due to a death in my family. The unit was very clean and well-stocked. I loved the beautiful views from each window and the quiet, serene environment. Although I could hear the train at night, it was not super loud - kinda just like background noise. I actually found it to be peaceful (maybe because I’m from the city lol). Would love to visit again! :)

Spacious with many amenities! Great place to relax with friends.

This was truly one of the best Airbnb experiences I’ve ever had. From the moment I arrived, everything felt warm, welcoming, and thoughtfully prepared. The space was not only beautiful and impeccably clean, but it also had so many special touches that made it feel like a true home away from home. What made this stay exceptional, though, was the host. They were incredibly kind, attentive, and genuinely cared about making my visit as perfect as possible. Every question I had was answered so promptly, and they offered wonderful local recommendations that made my trip even more memorable. It’s rare to find someone who goes above and beyond with such sincerity, but that’s exactly what this host did. I left feeling not just like a guest, but like a friend. I am so grateful for this experience and would return in a heartbeat. Highly, highly recommended to anyone considering this stay — you will be in the very best hands!

This place is near so many spots it was awesome! to go down and get food right below or just walking across the street and grabbing some food. the place was very well cleaned, had great spots just to sit and chill. beds very comfortable, rooms very spacious. water pressure can be very in and out sometimes but water was warm/hot and lasted a full shower.

Peaceful and great location. My husband and I went for leisure and our first time staying at this specific place. We would definitely recommend this condo to anyone thinking about staying. Kristin was very responsive and friendly when talking to her. Thank you again for allowing us to stay. We hope to stay here again.

William paid attention to detail and was responsive. Quick and informative Great location

very nice place, comfortable and only 15 min from downtown chicago.