
Pet-friendly vacation rentals in North Side
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Top-rated pet-friendly home rentals in North Side
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Pet-friendly house rentals

Spacious Full Home Near the Heart of Wrigleyville
We had an amazing stay at Dustin’s place! We had a group of 9 ladies who fit perfectly with plenty of cozy beds and linens. The location was very walkable and we felt safe. We walked over to Barcocina Lakeview on Friday, and then jumped on the train to River North on Saturday to celebrate St. Patrick’s Day. We had a couple of questions during our visit, and Dustin was speedy on the replies! Everyone in the group said the experience was 10 out of 10. We hope to visit again.

Home away from home
Your place was perfect for my needs. It was larger than necessary for just myself but the location was perfect. My son attends BenU and I loved that I could meet up with him in minutes. Lisle and Naperville are great communities. The house was very well equipped and the yard was perfect. If you are going to have the full 6 people staying there is only one bathroom. Not a problem but if you come with a larger group I just wanted to note that as it is sometimes important. I highly recommend this place and I hope to use it again next year when my son graduates from BenU. Thanks for a great place and stay.

Warm and comfortable inviting Suburban home !
Beautiful area and home, wonderfully helpful and responsive host. Very grateful to have stayed here!

The Sunshine Spot
We stayed for a week. The house was spacious and clean, and the neighborhood felt very safe. It was close to the mall and any store you'd ever need. Richard was very responsive and helpful! Washer & dryer were great to have for a longer stay. Wifi and smart tv were great. Also was glad there was even a lead in the backyard for our dog!

Quiet cul-de-sac with huge fenced in backyard
Tom was a very good host very responsive, This was my first time ever in a Airbnb and I was not disappointed at all very clean he made sure we had everything we needed! I didn’t get to meet bear sadly 🥲 I love dogs and wanted to meet the puppy lol, my girlfriend was pleased for her 21st birthday thank you Tom we will definitely be back again!!

Dog Friendly Cozy North Naperville 3 BED/2 BA Home
Great place! Liz was really nice. I had trouble getting into the home. Liz called me, reset lock remotely and helped me get in. The house was pristine, and really cozy. We had a great time and highly recommend this to anyone interested.

Adorable house Madison Street w/ 2 car garage!
Such a great spot and so close to good coffee and on a beautiful tree lined street. Street parking was a breeze and our party of three each felt like we had privacy in our rooms!

House 3BED/2BATH/1PARKING close to Downtown & Lake
Junni is incredibly responsive. This was a great spot for my family to stay for my daughter’s Loyola University graduation. It was close to my daughter’s apartment and the university. The parking spot is KEY, especially if you are busy and don’t return until the evening or later because street parking was usually full. The home was clean and tidy. When we had an issue figuring out how to match the tv chromecast and connect it to our smart phones, Junni was quick to respond, and with some help from google, we got it working so we were able to stream from our phone to the tv. The wifi works great too. The couches and beds were also very comfortable. The showers worked well. There were plenty of towels, extra toilet paper, and the showers had body wash, shampoo, and conditioner. We would definitely stay here again.
Pet-friendly home rentals with a pool

2-Acre Highland Park Retreat with Heated Pool ~ 5*
We had a great stay overall. From start to finish, Kailash was extremely helpful, friendly and responsive. We needed a long-term stay with 2 big dogs, and this house worked great for us. We didn't get to use the pool much because the weather didn't cooperate, but the pool and patio area are gorgeous. The location is great, close to everything - grocery stores, restaurants, etc. There is a trail behind the house (accessible through a gate in the back yard), and it leads to a beautiful and huge forest preserve - beautiful for walks/hikes in the woods! The kitchen was a great space for us, and it had everything we might need for cooking, etc. The house was very comfortable for our family, and we would come again. Thank you, Kailash!

Level ◆ Brand New Luxe One Bedroom
What isn’t to like about this place? Amazing building, incredible views (from the unit I was in), beautiful unit, great amenities, perfect location, friendly staff. I will be staying here whenever I visit Chicago in the future.

Quiet but in the Heart of City walk Everywhere
Nice appartment in West loop, well equipped and the access to a gym & pool is a plus. Cloud9 staff was responsive and helpful.

Luxury Designer Penthouse NW | Pool | Gold Coast
Couldn’t find a better spot for me. I’m from LIlINCOLN PARK Chicago. I go every year for my birthday, right in the heart of things with a great view, very clean. The set up in the apartment was awesome. Will be back.

South Loop | Rooftop With In & Out Parking | 1
This spot is in a great location — just a short, easy walk to and from Soldier Field, and convenient for grabbing an Uber to explore other parts of Chicago. The split master bedrooms with private bathrooms are a great feature, especially for groups wanting a bit of privacy. A couple of suggestions: it would be nice to have TVs in the bedrooms (just a personal preference), and the living room could use either a larger couch or an extra chair to comfortably seat four adults. Communication with TAIMS was excellent — they were quick to respond to all our messages. The only hiccup was parking: it was a bit confusing because the street address didn't match the address listed on the parking garage sign. Once we figured it out, it was fine, but clearer instructions would definitely help future guests.

DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool
Great location and convenient to explore the city. Walkable to restaurants and public transport. Unit is very spacious and view from patio during night time is breathtaking. Matches the description accurately. AC is controlled by city so living area can get cold during night time and no way to adjust the temperature. Finding the location can be tricky as google maps shows duplicate address inside federal building on w Jackson st.

Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!
The location was perfect for us and our kids with the park right across the street, a grocery store, coffee and restaurants all within very close walking distance! The house was very clean, everything we needed and Kevin was very quick to respond and helpful when we thought one of the kids locked us out of the house! Would definitely recommend Kevin as a host and this was a great stay!

Luxury 3 Bed w/ Gym, Pool, Parking, Game Rm & More
Great place. Great location. Patty was great at communicating whenever we needed anything.
Private, pet-friendly home rentals

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
The living room was very comfortable and provided a great space for all our group to hangout after a wedding. The extra bedding and coffee was a nice plus!

Downtown Elegance ✨ Private Yard Parking
We were a party of 8 humans and 2 dogs, staying for the weekend. Our family had plenty of space, and the outdoor patio was a nice bonus. The kitchen was well-equipped with coffee and tea, nice new appliances, lots of dishes and utensils (we did not need a melon baller, but she had one in case we needed it!). We found it really easy to get to the L, and also convenient for walking. It was such a relief to park once and not have to drive at all. The street was nice and quiet (I mean, there were trains, because Chicago ☺️). It felt very safe, so we were comfortable taking the dogs on walks anytime. Alexandra communicated with me really well leading up to our stay, and stayed in touch throughout. We made a lot of memories, and the lovely accommodations were part of that.

Newly-renovated historic home in Logan Square
Danny's place in Logan Square is very charming and in a great location (~10 minute walk to Blue Line). It had everything we needed as a family with two young children. Their place is very clean and they are responsive hosts. There are also a few good restaurants right around the corner, which was great after a long day of walking around Chicago!

Less is more! Pet friendly Tiny Home near Chicago!
what a cute and thoughtful stay! Was a great spot to stop during my cross country move.

The Country Life! Entire House.
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.

a SIMPLE place
Place was just as described. Easy instructions to enter and house manual was clear. Steve checked in to ensure all was well upon arrival

Susie's Space. 2BR easy parking & pet friendly
Really liked it, nice location, plenty of room, comfortable, good kitchen. Getting around using buses and the subway was also very easy.

Downtown Wilmette Micro Studio
I enjoyed staying at Anna’s place this last weekend. The location is great and I had everything I needed for my short stay.
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
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- Shedd Aquarium
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- Lincoln Park Zoo
- Willis Tower
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- Illinois Beach State Park
- Flossmoor Golf Club
- Brookfield Zoo
- The 606
- Washington Park Zoo
- Wilmot Mountain Ski Resort
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