Pet-friendly Vacation Rentals in Chicago

This pet-friendly attic apartment is located in Chicago's Avondale neighborhood, just a short walk from Milwaukee Avenue's dining and entertainment.
Enjoy a private entrance and the convenience of a full kitchen, air conditioning, and internet in this 1-bedroom, 1-bathroom apartment perfect for two guests seeking an authentic Chicago experience with their pets.

Just under a block from Wrigley Field in the Lakeview district, this apartment offers unbeatable proximity to Cubs games and concerts, with immediate access to numerous restaurants, bars, and shopping.
This pet-friendly apartment, recently updated in 2023, comfortably accommodates up to 4 guests with high-speed Wi-Fi, a 55" Smart TV, and a functional efficiency kitchen, making it a great choice for travelers exploring Chicago with their dogs.

Just 500 feet from Wrigley Field and Montrose Beach, this apartment is located in Chicago's Lakeview East/Wrigley neighborhood.
This pet-friendly apartment offers 1000 square feet of space with 3 bedrooms, accommodating up to 12 guests and featuring 3 classic arcade machines with over 7,000 games.

Experience the Gold Coast from this high-floor, furnished apartment in Chicago, offering expansive city views and immediate move-in convenience for you and your pets.
This pet-friendly apartment boasts a fully equipped kitchen, air conditioning, a swimming pool, and a fitness center, ensuring a comfortable and amenity-rich stay with easy access to Chicago's renowned architectural tours and lakefront activities.

This garden-level apartment in Chicago offers a private entrance and walk-out patio, providing convenient access to the city's renowned landmarks and attractions, just a short distance away.
This pet-friendly apartment comfortably accommodates up to 5 guests across two bedrooms and includes a full kitchen, WiFi, and air conditioning, making it an excellent choice for families and travelers with pets.

Located in Chicago's historic Gold Coast, this apartment is just a 1-minute walk to the Division & State bus stop and a 5-minute walk to the Clark/Division Red Line station, placing you steps from Oak Street Beach and world-class dining.
This pet-friendly one-bedroom apartment, offering 550 square feet of space for up to 2 guests, features a full kitchen with a fridge and microwave, reliable WiFi, and shared laundry facilities, making it ideal for travelers with dogs and cats.

Located in Chicago's Edgewater neighborhood, this garden apartment is just a short walk from the shopping and dining of Andersonville.
This pet-friendly apartment offers a full kitchen, air conditioning, and is conveniently located near public transit, making it easy to explore Chicago with your dog.

This pet-friendly apartment in Alsip offers a unique RV living experience with 4310 square feet of floor area, featuring a kitchenette, air conditioning, and a terrace with a fireplace, located 6.8 miles from Midway International Airport and 14 miles from Guaranteed Rate Field.
Enjoy apartment-style comfort in this Alsip accommodation, perfect for families and dog-friendly stays, providing amenities like free WiFi, a garden, and convenient access to Chicago attractions.

Located in Chicago's River North district, this luxury loft is just two blocks from Michigan Avenue and six blocks from Lake Michigan.
This pet-friendly apartment offers three bedrooms, sleeping up to eight guests, with a fully equipped chef's kitchen and secure parking available a couple of blocks away.

This pet-friendly apartment offers a quiet lower-level living space in a Chicago neighborhood, conveniently located within a 30-minute commute to downtown Chicago and just a short drive from O'Hare International Airport and natural attractions like forest preserves and Lake Michigan.
Enjoy a convenient kitchenette with a fridge and microwave, ample free parking directly in front, and walkability to shopping, parks, and public transportation, making it an excellent choice for travelers seeking a dog-friendly stay.

Located in Chicago's culturally rich Humboldt Park, this apartment offers easy commutes to the Loop, West Town, and University of Chicago campuses, preserving original 1900s architectural charm with a midcentury modern, art-inspired interior.
This pet-friendly apartment boasts 2 bedrooms, accommodates up to 6 guests, and features modern luxuries like in-unit laundry, quality kitchen appliances, and high-pressure shower heads, ensuring a comfortable stay for you and your furry companions.

Prime Wrigleyville location offers direct views of Wrigley Field, with the lake and Boystown just a short distance away, making this a truly pet-friendly apartment.
This apartment features a chef's kitchen, a spa-like bathroom, a large private deck, and off-street parking, perfect for accommodating up to six guests with their pets.

This River West townhouse in Chicago is located 1.6 miles from Union Station, 1.7 miles from the United Center, and 1.9 miles from Willis Tower.
This pet-friendly house offers 2250 square feet of space with 4 bedrooms and 4 bathrooms, featuring a fully equipped kitchen, air conditioning, and a private barbecue for outdoor enjoyment.

Located in Chicago's McCormick Place district, this apartment is conveniently situated 1.4 miles from the Field Museum and 1.7 miles from Grant Park.
This pet-friendly 2-bedroom apartment offers 900 square feet of living space, accommodates up to 15 guests, and includes a full kitchen, air conditioning, and on-site parking.

Enjoy a pet-friendly Forest Park apartment conveniently located just an 8-minute walk from the Blue Line, offering a quick 20-mile drive to downtown Chicago without the congestion.
This apartment features a full kitchen with a fridge and microwave, air conditioning, and a backyard, making it an excellent choice for travelers seeking a dog-friendly escape with easy access to Chicago's attractions.

This pet-friendly apartment on Michigan Avenue offers easy access to Chicago attractions, located 1.4 miles from the Field Museum of Natural History and near Soldier Field.
Enjoy 900 square feet of living space in this family-friendly apartment, featuring a full kitchen, air conditioning, a garden, and a fitness center, with pets allowed.

Located in Chicago's West Loop, this apartment is just a 5-minute walk to Union Park and a 10-minute walk to Fulton Market, offering easy access to public transportation for exploring Little Italy and Randolph Street Market.
This pet-friendly apartment boasts 6 bedrooms and 6 bathrooms, accommodating up to 15 guests with rollaway beds available, and features a fully-equipped chef's kitchen, private balconies, and access to a 24/7 fitness center and sky lounge.

This pet-friendly apartment is located in Chicago's River North district, offering easy access to major attractions and situated 1.1 miles from Oak Street Beach and Shops at Northbridge, as well as close to 360 Chicago and Willis Tower.
Enjoy a relaxing stay in this 830 sq ft apartment with a private balcony offering city views, a fully equipped kitchen, in-unit laundry, and access to an on-site spa, sauna, and fitness center.

This spacious 4-bedroom house in Chicago is a pet-friendly haven, located just a 19-minute walk from Oak Street Beach and conveniently situated 1.2 miles from 360 Chicago and 1.4 miles from Water Tower Chicago.
Enjoy a fantastic stay with amenities like a private balcony, terrace, garden with barbecue, spa access, fitness center, and free private parking, making it an ideal choice for families and pet owners alike.

Enjoy unmatched skyline views from this pet-friendly apartment in Chicago's Lincoln Park district, located just 1.8 miles from North Avenue Beach and 2.1 miles from Water Tower Chicago.
This 2-bedroom, 2-bathroom apartment accommodates up to 4 guests and features on-site parking, complimentary WiFi, air conditioning, and a seasonal outdoor swimming pool, making it ideal for travelers with pets.

This Oak Park apartment is conveniently located near the Frank Lloyd Wright Home & Studio and the Ernest Hemingway Birthplace Museum, offering easy access to shops and restaurants.
This spacious, pet-friendly apartment comfortably sleeps up to 12 guests with 5 bedrooms, a fully equipped kitchen, private backyard, and garage parking for 2 cars, making it ideal for families or groups traveling with their dogs.

Located in Chicago's prime Gold Coast, this apartment is just 0.5 miles from Oak Street Beach, offering a desirable urban experience with convenient access to the city's renowned attractions.
This 700 sq ft, one-bedroom, one-bathroom apartment allows pets and features modern decor, a fully equipped kitchen, air conditioning, and a balcony with appealing city views, perfect for travelers seeking a pet-friendly stay.

Enjoy breathtaking skyline views from this top-floor, pet-friendly apartment in Chicago's Fulton Market district, just a 7-minute walk to Union Park and a 10-minute walk to Google HQ.
This 1350 sq. ft. apartment offers 2 bedrooms and 2 bathrooms for up to 5 guests, featuring a fully-equipped chef's kitchen, private balcony, and access to extensive building amenities including a pool, spa, and fitness center, making it a great choice for dog-friendly stays.

Located in Chicago's West Loop, this apartment is a 5-10 minute walk from Union Station and a short distance from downtown landmarks like the Merchandise Mart.
This pet-friendly one-bedroom apartment offers 510 square feet of modern living space with a fully equipped kitchen, in-apartment laundry, and building amenities including a swimming pool and rooftop BBQ, perfect for travelers with pets.

This pet-friendly apartment is located in Chicago's South Loop, just 1.2 miles from Soldier Field and 1.7 miles from Grant Park.
Offering 1120 square feet, this 3-bedroom, 2-bathroom apartment features a kitchen with a fridge, microwave, and dishwasher, plus air conditioning, free WiFi, and a fitness center, and is dog-friendly.

This renovated historic Chicago multi-apartment bungalow in the northwest corner offers a private second-story living space, conveniently located near O'Hare Airport and local amenities.
This pet-friendly apartment boasts 1000 square feet, features a well-equipped kitchen and complimentary breakfast items, and is ideal for families and marijuana users with designated outdoor smoking areas, welcoming up to two dogs.

Located catty-corner to Wrigley Field, this recently renovated 3-bedroom apartment in Chicago's Wrigleyville district offers unbeatable proximity to the stadium, restaurants, and entertainment venues, making it an ideal and pet-friendly choice for baseball fans and explorers.
This apartment comfortably accommodates up to 6 guests with 2 bathrooms, in-unit laundry, a full kitchen with modern appliances, and a Smart TV, plus baby gear is available upon request, ensuring a convenient and enjoyable stay for families with pets.

Just 7 minutes on foot from Lake Michigan's shores, this pet-friendly apartment in Chicago's Lakeview neighborhood is also an 8-minute walk to the Diversey brown/purple line for easy city access.
This 410 sq ft apartment, ideal for up to 3 guests, boasts a unique art-filled interior, a full kitchen, a back deck, and is conveniently located near Wrigley Field and Michigan Avenue.

Located in Chicago's Wrigleyville, this apartment is a 5-minute walk from Wrigley Field and two blocks from the Southport Corridor's shops and restaurants.
This pet-friendly apartment features a private duplex layout with 5 bedrooms, offering ample space and a kitchen equipped with a fridge, freezer, microwave, and dishwasher, ensuring a comfortable stay for families and their furry companions.

Just 500 feet from Schreiber Park and Hartigan Beach Park, this pet-friendly apartment offers easy access to Chicago's lakefront in the Rogers Park neighborhood.
This 3-bedroom apartment accommodates up to 6 guests and features a full kitchen, in-building laundry, and private access, making it ideal for families and longer stays.

Just 4 minutes from the Lawrence Red Line station, this modern apartment is located in Uptown, Chicago, steps from Montrose Beach, Aragon Ballroom, and the Riviera Theatre.
This pet-friendly apartment offers a fully equipped kitchen, a queen-size gel mattress, a futon, and access to a fitness center and a private rooftop with city views.

This South Loop apartment is conveniently located 1.4 miles from the Field Museum, offering easy access to McCormick Place, Soldier Field, and the Shedd Aquarium.
This pet-friendly apartment features 3 bedrooms, 2 bathrooms, a fitness center, and free WiFi, making it an ideal choice for families and travelers with pets visiting Chicago.