
Pet-friendly vacation rentals in West Side
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Top-rated pet-friendly home rentals in West Side
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Popular amenities for West Side pet-friendly home rentals
Pet-friendly house rentals

MiniGolfHouse-Chicago Close Warm Indoor Fun!
It was amazing with the kids they enjoyed the mini golf a lot ….spacious bedrooms very good kitchen and cleaned washrooms …overall it was great

Historic Old Town, Fabulous 4 Bedroom Home
We absolutely lived this place-enough room for our family and well appointed. Located in a great walkable area and close to the train! We are looking forward to returning!

The Brookfield Breakaway w/ Game Room
Highly recommended.... House was a really nice spot to stay at.... If ever back in town I'll definitely book back with them....

Private 3rd Floor Apartment
Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.

Casa PLZN Location | Entire Home | Garage Parking
We had a wonderful stay. The place was clean, comfortable, and had enough space for our larger group. It was really nice getting to use the garage parking space and the outdoor area is cozy. After day 1, we did have trouble getting into the place through the front door keypad, there was a battery issue. Thankfully there is access to the home through the back door/garage. Thanks for a great stay!

BoHo House - A Chic, 1903 Chicago Workers Cottage
My family and I had a fantastic stay! The space was exactly as described; clean, stylish, and thoughtfully designed. Check-in was smooth, and Adam was super helpful throughout our visit. We especially appreciated the backyard for our dogs . The location was perfect. It was close to everything we needed but still quiet and peaceful. Would absolutely stay here again and highly recommend to anyone visiting the area!

Quiet cul-de-sac with huge fenced in backyard
A great spot!! A friend and I were in town for a concert and this place was perfect! The patio was really cool and Tom has the cutest dog!!

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.
Pet-friendly home rentals with a pool

South Loop | Rooftop With In & Out Parking | 2
Absolutely loved my stay here! The place was super nice and clean, comfortable, and just as described. The lounge area had such a beautiful view and was a great spot to relax. Everything was well-maintained and felt really welcoming. I’d definitely recommend this place to anyone visiting Chicago and would love to stay here again next time.

Level Junior Two Bedroom Suite | Fulton Market
Had such a great stay! Everything was very clean and all information given was thorough.

Forest Park Oasis - Dog Friendly - Parks - the "L"
Absolutely wonderful stay! The place was spotless, beautifully decorated, and had everything we needed for a comfortable visit. The host was thoughtful in making check-in easy. Although we didn’t travel with children the park across the street would be an added plus for families with children (soccer field, skate board ramp, playground & tennis courts). The neighborhood felt very safe and family-friendly! We felt right at home and would definitely stay here again. Highly recommended!

Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool
This was the best place for our family to stay during our time in Chicago. We decided to pay top dollar for all the amenities that this place had to offer. First of all, the view from the balcony on the 28th (top) floor definitely takes your breath away. A factor thar caused us to go with this Airbnb vs others was the parking that was included in the parking garage. We did not want to risk trying to find parking daily since we were not sure about the parking situation in Chicago. There were A/C units in each room and the living room which kept the place cool during our stay and also created white noise which drowned out the sound of the train that traveled right beside the building. Location of this place was also perfect. We walked to cloudgate 20min. Also there is a Trader Joe’s grocery store 7min walk. There are popular places within a block distance to get your chicago pizza/hot dog fix. I can go on and on about how this place was awesome to create an unforgettable memory

Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!
Kevin and Kayla’s unit on W Diversey Ave was a cozy and convenient spot for our Chicago trip. The space was clean, well-equipped, and had everything we needed, with quick access to buses and the Blue Line. The only minor downside was some occasional dog-walking noise from the unit above, but as it has already been mentioned before, it is to be expected. Mattresses were a bit wobbly for our tastes but it's a matter of preference. Overall a great, cozy place on a very convenient location in Chicagoland. What really stood out was Kevin’s excellent hosting—he went out of his way to make us feel at home, regularly checking if we needed anything, and was quick to help in-person when we had a small hiccup on our last day. Super responsive and friendly and a true host!

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

Modern unit in Bridgeport-Chicago
Great place to stay. Paola was a wonderful host and communicated very well. Would definitely stay here again!

Paradise 4BR w/ Pool & Games
We recently moved backed to the Chicagoland area from Texas. We needed a place to stay while our Chicago home was being renovated. Lily’s place was perfect. It had everything we needed for the duration of our extended stay. It was well appointed. Exceptionally clean. It had all the amenities necessary for our family to live comfortably and it was close to grocery stores, shopping, restaurants, and downtown Chicago. Highly recommend.
Private, pet-friendly home rentals

Near 606 Trail | Free Garage Parking | W&D |LUXTEL
What can I say??? Yolanda’s place was super clean, easy to get to and very comfortable and up to date on every level. We felt right at home and was within walking distance to our son’s apartment. We love Chicago and staying here made it even more enjoyable. Pictures do not do justice to. We will stay here again when we’re in Chicago again.

Bright & Spacious| Free Parking |Trendy Bridgeport
Enjoyed our stay here! The place was really comfortable and close to a lot of places!!

Loft-Inspired Retreat | Stylish Stay Near Downtown
Great location. Near grocery store, great restaurants in the heart of Pilsen, and the green/pink line to get to downtown Chicago.

Logan Square Oasis
Really liked the neighborhood. Was a short walk to the blue line. The place was perfect and will come back again.

Unmatched Urban Retreat Close to 18th Strip & Loop
My only real criticism of the stay would be finding out that you can’t check in until 5pm until a couple weeks before the trip. We booked months in advances had plans earlier in the day that had to be altered because of such a late check in time. Prob would have booked somewhere else or booked a day earlier.

Garden on Warren
Location was incredible and had quick access to almost anything. Area was quiet and peaceful to stroll through. The space was very clean and comfortable. I’d absolutely stay here again!

Private Garden APT/ Cozy/Warm
Louis was very responsive and the place was lovely. Parking was a nightmare but manageable. Would recommend this place to others!
Explore the City from an Elegant, Urban Retreat
Our stay at Marissa’s went seamlessly! She was very responsive and accommodating ! Would stay here again :)
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Lincoln Park
- Lincoln Park Zoo
- Willis Tower
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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