Waterfront vacation rentals in North Side

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.

Perfect space for a girls weekend. Host prepared the apartment to our needs with special little extras set out for us to enjoy. Also the two full bathrooms were clean and well designed.

Great place to stay! Can get anywhere in the city, its right off the "L". Not far from Michigan Ave, either. Would highly recommend this place to anyone who is traveling to Chicago.

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.

Loved our stay in Rogers Park, the apartment is 2 blocks from the lake and 1 block from the Morse redline station! Super walkable area with coffee shops, restaurants and bars - stay was just as described and host was very responsive whenever there were questions or concerns.

I loved this stay. The hosts were very responsive and friendly. The beach being nearby was so nice. We took nightly walks to the beach and it was very peaceful and beautiful. The apartment is spacious, cozy, has bright natural lighting during the day, and has all the amenities you’ll need. It felt luxurious and very homey. The bed was very comfortable and had a goose down blanket. It felt like I was sleeping on a marshmallow or a cloud! Only thing is parking can get a little complicated if you’re leaving and coming back often, but for the most part it was okay. Overall, I would stay here again and recommend this to anyone wanting to book!

This place was PERFECT. We rented it for Graduation Weekend as it was just a 13-minute walk from Loyola University AND a quick walk to the beach. The apartment was beautifully renovated with pristine bathrooms and an amazing kitchen FULL of amenities (pans, baking dishes, plastic containers, toaster, coffee maker with filters, even a fondue pot). There was a beautiful front porch that overlooked the lake and a cute backyard complete with heaters if needed. The apartment had plenty of extras like blankets, towels, pillows, and more. It even had a working gas fireplace that was wonderful to turn on in the evenings. The beds were so comfortable, and the neighborhood was quiet. The host, Diane, was communicative, helpful, and willing to meet your needs. I HIGHLY recommend this place. Would rent again in a heartbeat.

Great home and location. Safe neighborhood, walkable to restaurants, shopping, beach. Home was clutter free, clean and well maintained. Beds were comfortable and we had plenty of supplies for duration of stay (fresh towels, blankets, paper products, soap, shampoo, conditioner, etc.) Rooftop deck with nice view. Host was very responsive with any questions and communicated well. House was perfect size for our group of 6. We appreciate Rasheed making our stay perfect! Will stay here again in the future.

Great stay for me and my friends. Very spacious and beautiful outside space. Plenty of beds and top of the notch kitchen.

Highly recommend this Airbnb. The owner has truly made it a home away from home. She has everything you need in the kitchen, plentiful pillows, extra towels and blankets. The house is very private as it is at the end of a cul de sac in a quaint neighborhood. There is a walking trail and field directly behind the house where you see families and people with their dogs. Though very tranquil, the house is very close to stores and restaurants. It was very clean and rivaled most hotels in that regard. The beds were comfortable and the showers were perfect. Nice that it had two sitting areas and TVs in every room! The most amazing thing about her property is Stephanie herself. She takes great pride and was always readily available. I felt like I had a friend while away from home. She helped with whatever she could.

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!

The place was amazing. We had a great time hosting friends and family.

This place was amazing... They layout was terrific. quiet neighborhood, safe, and had everything we needed. we were celebrating my birthday (pre) My friends 🧡 Even set up a Bday table for me down stairs and we had our in vip golden girlz(ladies) celebrations 🍾 😀 😄 ❤️

Stay went very smoothly and I would recommend for anyone seeing an event at Allstate arena(walking distance) or needing a place to stay flying thru O'Hare. Target and a wide variety of fast casual dining 1 min away. The listing mentioned a grill and that was unavailable, you may want to check with the host in advance if you are planning to use any amenities.

What a wonderful stay. We rented the entire unit, it was perfect for our 8 people including kids, and could probably fit more. It was clean, easy to get inside and plenty of street parking available. Close to cafe’s and bakeries, a lovely morning stroll. Kai and Beca were responsive to our messages. My only thing was that the basement was super cold compared to upstairs, but I usually like my space toasty. Would suggest space heaters in the future 😅 but otherwise a really lovely stay and close enough to the city to get around. I would stay again.

The Airbnb was clean, exactly as described, and in a great location. Check in was easy and we were able to get settled right away. William was very proactive in communicating instructions well before our arrival. Overall, we had a lovely time visiting Chicago and would recommend staying here!

everything was extremely nice, unfortunately the knob to change from shower to faucet was detached so we could not utilize the very large beautiful bathtub. The front porch light also needs to be replaced, we opted to leave the front door open to be able to see outside after dark. Other than that everything was extremely nice. Still worthy of a five-star review.

WWWWOOOWWW!! This host team was EXCEPTIONAL! I’ve stayed in plenty of AirBnBs, and I’ve NEVER encountered a host that was so EXTREMELY accommodating, responsive, and kind! Other hosts should take a page out of their book! The only thing I would change, and it’s not a bad thing (just a matter of preference); I would have some type of blinds or drapes over the living room windows. This will allow for privacy when you’re sitting in the living/dining room areas at night with the lights on inside. Hands down, we would without a doubt book with this team again! Thank you Wendy, Matt, and your co-hosts for helping to make our time in Chicago wonderful!

If you're looking for a place in Chicago that is gorgeous to stay in with easy access to public transit, this is it! The hosts were super helpful with recommendations and quick to answer with any questions. I would definitely stay there again!

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.

William’s house is precious and our stay was amazing! Thank you for letting us experience Chicago from the heart of downtown. The place was clean and William was extremely helpful with all my questions. I will definitely recommend this place. The parking had clear instructions and just a 4 mins walk away. The only issue was no elevator, we had to carry our heavy bags up 2 floors. But that shouldn’t stop you, the 2 mins of effort is all worth it.

Richard was a great host and very responsive! The air bnb looked exactly like the photos, very beautiful home.