Pet-friendly vacation rentals in West Side

Beautiful Chicago Greystone

Experience the best of Chicago from this sprawling, private 4-bedroom condo. Located just 15 minutes west of the City Center, you’re perfectly positioned to explore the culinary scene of the West Loop, the lush Garfield Park Conservatory, and the energy of the United Center Transit: Steps from multiple bus lines, 2 blocks to the Blue Line, and 1 mile to the Pink Line Amenities: On-site laundry (available upon request) Local Experts: We live in the unit below and happy to give recommendations

Near 606 Trail | Free Garage Parking | W&D |LUXTEL

Want to hang with the locals in Chicago and be in foodie heaven? Here's where it's at in vibrant Humboldt Park. You’ll love my place it's immaculately kept, beautifully decorated, and tons of natural light pours in. Minutes to the 606 trail that gives you direct access to the equally vibrant Logan Square corridor of hot spots. Experience the best of both areas here. Walk 1 block to CTA, short ride to Metra. My place is good for couples with kids, solo adventurers, and business travelers.

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Clean, Bright Chicago Apt in Bucktown/Logan Square

The whole group will enjoy easy access to everything from this centrally located place. The Western Blue line stop that takes you to downtown Chicago is 2 blocks away. Downtown is a 15 minute ride away if you decide to rent a car. This is the only apartment in the building and sits right above the BEST Grilled Chicken restaurant in Chicago. The apartment is walking distance to many delicious restaurants and local coffee shops. You can find some of the best food in Chicago just steps away.

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Spacious 3BR • Great for Groups • Fast WiFi • Pets

This pet-friendly, Logan Square apartment is brimming with details to make your stay feel like a home away from home. All 3 bedrooms boast super-comfy queen beds with an abundance of pillows and lots of storage space for your belongings. The third bedroom is made private by a lush velvet curtain. There are two dedicated workspaces in the apartment for your work-from-anywhere lifestyle needs. A very well-appointed kitchen is begging for home-cooked meals.

Fun 2BR with Retro Arcade Near Downtown

Escape to this cheerful, pet friendly 700 sqft Chicago retreat for 4-6 guests! Bathed in natural light, this vibrant apartment features a dedicated workspace, fast Wi-Fi, and a classic Simpsons arcade machine. Perfect for families and professionals, you're just minutes from Sox Park and a 15-minute drive to downtown attractions like Millennium Park. Enjoy a fun, comfortable base for your Chicago adventure! Work while away with 500+ mbps internet!

Designer 3br with Balcony & Elevator on Clark!

My 3 bedroom apartment in Sheridan Park is a stunning place to call home in Chicago - You'll love the neighborhood - its vibrant food and arts scene is uniquely diverse in Chicago. A mile north of Wrigley Field - Just to the east, Montrose Beach is a nice break from the city - if work is what brings to you to town, the nearby Brown line will take you right to the Loop. I provide all the essentials to make your stay easy and comfortable.

Stunning Corner 2BR in the Loop | City & Lake View

Dramatic 1,250+ square foot corner apartment with 12 foot tall ceilings, massive windows, and panoramic city and lake views in multiple directions. This stylish light-filled two bedroom, two bathroom space is perfect for groups looking for a luxurious getaway in the sky in the heart of downtown Chicago. Centrally located in a historic building close to everything you want to visit, this is the best location in the city!

Stylish 2BR stunner w/ unbeatable location

Discover the perfect urban retreat in a newly renovated flat with all the modern amenities. Nestled at the border of Ukrainian Village and Wicker Park, this classic Chicago 2-flat offers modern amenities in a historic setting, tucked away in a peaceful corner just steps away from the vibrant city life of Division and Damen with its countless restaurants, watering holes, and one-of-a-kind shops.

Picture Perfect 3Bed Steps from Train and FLW

Welcome to your beautiful 3 bedroom home-away-from-home! From the Insta-worthy forest room to the cozy fireplace reading nook to the modern ice crusher in the kitchen, we've put so much thought into this home that we're sure you won't ever want to leave. Welcoming and newly updated, this unit is close to restaurants, shopping, the best of Frank Lloyd Wright, and the train to the city.

Cozy and Spacious! Logan Square Apartment

Enjoy the local Chicago comforts of a traditional Logan Square apartment decorated with vintage charm. Home to some of the city's most celebrated food and nightlife, Logan Square is one of Chicago’s most exciting neighborhoods with an energy unlike any other in Chicago. And you're only a quick trip to downtown!