Pet-friendly Vacation Rentals in Chicago

Located just 1.6 miles from the United Center, this pet-friendly house offers convenient access to downtown Chicago attractions, including Water Tower Chicago (2.7 miles) and Union Station (2.8 miles).
This 160 square foot house features two bedrooms, one bathroom, air conditioning, free WiFi, and a fully equipped kitchen, making it ideal for a group of up to 9 guests.

This pet-friendly apartment in a Chicago neighborhood offers a secure and comfortable stay for up to 2 guests, featuring a fully equipped kitchen and complimentary Wi-Fi.
Located on the second floor, this one-bedroom apartment provides a private retreat with a queen-size bed and a bathtub, perfect for unwinding after exploring Chicago.

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.

This newly renovated 3-bedroom apartment in Chicago offers a peaceful, centrally-located stay, just a 15-minute drive from Midway Airport and a 10-minute drive to Ford City Mall.
Enjoy modern amenities in this pet-friendly apartment, featuring a full kitchen, air conditioning, and a garden, with public transportation only 30 steps away for easy exploration of Chicago.

This 2-bedroom apartment in a Chicago neighborhood offers a fantastic pet-friendly stay for up to 6 guests, with a cat-friendly policy and associated fee.
Enjoy a fully equipped kitchen, complimentary WiFi, and a dedicated living area perfect for relaxation after exploring Chicago's attractions, all within this conveniently located unit.

Conveniently located just 2.5 miles from Midway International Airport, this pet-friendly apartment offers easy access to the CTA train for exploring Chicago.
This 750 square foot, 1-bedroom apartment comfortably accommodates up to 7 guests and features a fully equipped kitchen, air conditioning, and free WiFi.

Centrally located in a historic Chicago neighborhood, this spacious 1300 sq ft loft-style apartment offers a unique architectural experience in a pink brick building dating back to 1890, providing quick access to public transportation and a 6-10 minute commute to popular districts and dining spots.
This pet-friendly apartment welcomes up to 6 guests and features 2 bathrooms, a full kitchen, air conditioning, and FREE fitness classes at The Barre Code, with the added convenience of FREE street parking and a dedicated overnight spot.

Located in Chicago's South Loop, this apartment is 1.4 miles from the Field Museum of Natural History and offers easy access to McCormick Place, Shedd Aquarium, and Navy Pier.
This pet-friendly apartment features 2 bedrooms, 2 bathrooms, a patio with city views, a full kitchen, and access to a fitness center, with optional on-site parking available.

Located in historic Bronzeville, this pet-friendly apartment is just a 9-mile drive from downtown Chicago and steps from the Green Line transit, offering excellent access to attractions like Museum Campus and Navy Pier.
This spacious apartment accommodates up to 7 guests with 2 bathrooms, a fully equipped kitchen, central air conditioning, and is conveniently located 0.3 miles from 31st Street Beach, making it ideal for dog-friendly stays near the water.

This apartment is located in a prime Chicago neighborhood, just one block from Lake Shore Drive, offering easy access to numerous dining, entertainment, and recreational options.
This pet-friendly apartment features two bedrooms and accommodates up to four guests, boasting modern furnishings, a dedicated workspace, and is conveniently located near Lincoln Park Zoo and parks.

This pet-friendly apartment offers a prime location in Chicago, just a 28-minute train ride or a short 15-minute drive to Downtown Chicago.
Enjoy a fully stocked kitchen, private workstations, and convenient access to dining and bars with a Walk Score of 93, making this a perfect dog-friendly getaway.

Enjoy a private garden and a King Bed in this pet-friendly Berwyn apartment, offering excellent highway access for a quick commute to Downtown Berwyn.
This comfortable apartment includes a full kitchen with a fridge, freezer, and microwave, plus air conditioning and is conveniently located near local shopping and diverse dining options.

Located in Chicago's prime South Loop, this apartment offers excellent access to downtown, being just 1.7 miles from Grant Park and 1.8 miles from the Art Institute of Chicago.
This spacious 3-bedroom apartment is pet-friendly, featuring 1190 square feet of living space, a fully equipped kitchen, and private on-site parking, making it ideal for families and business travelers visiting McCormick Place.

This pet-friendly apartment is located in a working-class neighborhood, just a 10-minute drive from downtown Chicago attractions like McCormick Place and Soldier Field, and a 5-minute drive to Chinatown and Pilsen nightlife.
This spacious 3-floor, 4-bedroom home accommodates up to 10 guests with a chef's kitchen, two living rooms, and secure off-street parking for 2 cars, making it ideal for families or groups traveling with pets.

Just 500 feet from McCormick Place Convention Center, this pet-friendly house in Chicago's South Loop offers excellent access for convention attendees and easy commutes to downtown via the green line.
This house welcomes pets and features a full kitchen with a fridge, freezer, microwave, and dishwasher, along with air conditioning, a garden, and garage parking for up to 5 guests.

Discover a rare private outdoor deck with a fire pit in this West Town Chicago apartment, a peaceful boutique hideaway tucked behind a historic home, offering keyless entry and no shared spaces for a secure, private experience.
This 550 square foot, pet-friendly apartment sleeps up to 6 guests and features a fully stocked kitchen, in-unit washer/dryer, and air conditioning, all within a walkable neighborhood renowned for its dining scene and just a 12-minute commute to downtown Chicago.

This pet-friendly apartment in Oak Park offers easy access to downtown Chicago attractions, with Navy Pier and Millennium Park approximately 10-15 miles away.
With two bedrooms, two bathrooms, and space for up to eight guests, this dog-friendly apartment features a fully equipped kitchen, free on-street parking, and high-speed Wi-Fi, making it a convenient choice for families and remote workers.

Located in the historic Bronzeville neighborhood, this apartment offers convenient access to downtown Chicago attractions and is just 0.5 miles from Lake Michigan.
This pet-friendly apartment complex features three independent units with separate entrances, accommodating over 30 guests and boasting full kitchens, bathrooms, and living areas perfect for large groups and events.

This pet-friendly apartment in Chicago's South Loop offers skyline views and is conveniently located 1.4 miles from the Field Museum of Natural History and 1.7 miles from Grant Park.
Enjoy 800 square feet of living space with 2 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, and an on-site fitness center, with private parking available.

Located in Chicago's West Loop, this apartment is a 15-minute walk from Union Station and 1.1 miles from Willis Tower.
This pet-friendly apartment offers 1080 square feet of space, accommodates up to 9 guests, and features a full kitchen, air conditioning, a balcony, and on-site parking for your convenience.

Located in Chicago's West Loop, this apartment is just a 12-minute walk from Union Station and 0.9 miles from Willis Tower, offering convenient access to downtown attractions.
This pet-friendly apartment features 620 square feet of living space, including a full kitchen and a rooftop pool, perfect for travelers with pets.

Prime Wrigleyville, this apartment is an 8-minute walk from Wrigley Field and within 3.9 miles of downtown Chicago landmarks like Water Tower Chicago.
This pet-friendly apartment offers 1400 square feet with 2 bedrooms, a kitchenette, a private balcony, and on-site parking, ensuring a comfortable stay for you and your dog-friendly companions.

Located in Chicago's trendy West Town neighborhood, this 2-bedroom apartment is just 1.2 miles from the United Center and a few miles from Water Tower Chicago and 360 Chicago.
This pet-friendly apartment offers a well-equipped kitchen with a dishwasher and microwave, air conditioning, an outdoor seating area, and on-site private parking for your convenience.

This pet-friendly apartment in Westchester offers easy access to downtown Chicago, just a 25-minute drive away, and is conveniently located within 3 miles of attractions like Brookfield Zoo and Oakbrook Center shopping.
Boasting 2250 square feet, this apartment comfortably accommodates up to 10 guests with 4 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, a terrace, garden, and parking, all within walking distance of local restaurants, coffee shops, and Gladstone Park.

Located in Chicago's historic Gold Coast district, this apartment is just north of downtown and adjacent to Lake Michigan, offering proximity to upscale shopping on Oak and Rush Streets and celebrated restaurants.
This pet-friendly apartment boasts 730 square feet, a fully equipped kitchen, and stunning balcony views over the city, with building amenities including a BBQ area, doorman, and laundry facilities, making it ideal for stays of one month or longer.

Located in Chicago's Avondale/Logan Square neighborhood, this 5-bedroom apartment is a 15-minute drive from Downtown Chicago and just steps from Restaurant Row on Diversey Avenue.
This pet-friendly apartment offers 2550 sq ft of space for up to 10 guests, featuring a full kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, a terrace, garden, and parking.

Located in Chicago's North Center neighborhood, this apartment is a 5-7 minute walk from the Irving Park Brown Line Station, offering a 20-minute commute to the Loop.
This pet-friendly apartment boasts a spacious 1450 sq ft layout with 3 bedrooms and 2 bathrooms, accommodating up to 6 guests, and features a furnished back deck and private garden.

This downtown Chicago penthouse offers a prime location, just an 8-minute walk from DePaul University and 0.6 miles from Grant Park, placing you moments from the Art Institute of Chicago and Willis Tower.
This pet-friendly apartment features 3 bedrooms, 1110 square feet of living space, a private balcony with city views, and complimentary WiFi, ensuring a comfortable stay for up to 12 guests.

Just a 15-18 minute walk from Foster and Montrose Beaches, this pet-friendly apartment in Chicago offers convenient access to the lakefront and is located approximately 1.9 miles from Wrigley Field.
This spacious apartment welcomes pets and features 3 bedrooms, 3 living rooms, and a fully equipped kitchen, making it ideal for families and groups.

This penthouse loft apartment in Chicago's Gold Coast and Old Town districts offers stunning city views and immediate access to Michigan Avenue and Wells Street, just steps from Lake Michigan.
This spacious, pet-friendly apartment boasts 1190 square feet, a gourmet kitchen, and sleeping arrangements for up to 8 guests, with building amenities including a rooftop sundeck and gym.

Located in Chicago's Wicker Park, this apartment is just one block from the Blue Line L train, offering a 10-minute commute to downtown and a 30-minute commute to O'Hare Airport.
This pet-friendly apartment boasts 2,000 sq ft of tropical-themed space, accommodating up to 23 guests with amenities like a kitchen, air conditioning, and a shared backyard patio, making it ideal for group stays and bachelorette parties.

Vacation house to rent for 4 people. You will stay in Forest Park.
Facilities and services: an iron, a freeze and a washing machine. Take advantage of the air conditioning in this house!

Apartment to rent for 4 people with an excellent rating of 97% based on 188 reviews. Your accommodation will be located in Chicago.
Services and facilities: a dish washer, an iron and a fridge. Take advantage of the air conditioning in this apartment!

Located in Chicago's Avondale/Logan Square neighborhood, this apartment is just a 5-minute walk from the Logan Square CTA Blue Line stop, offering excellent access to the city.
This pet-friendly apartment welcomes dogs with prior permission and a fee, and features a fully stocked kitchen, free laundry, a dedicated workspace, and shared backyard access for a comfortable stay.

Located in Chicago's South Loop, this apartment is just 1.6 miles from Guaranteed Rate Field and conveniently close to Soldier Field and McCormick Place.
This pet-friendly, 4-bedroom apartment offers 180 square feet of living space, accommodates 19 guests, and features a full kitchen, air conditioning, on-site parking, and a fitness center.

Located in Chicago, this renovated house is 1.5 miles from Oakwood Beach and 1.7 miles from Guaranteed Rate Field, offering easy access to downtown Chicago within a 10-minute drive.
This spacious 3200 square foot, pet-friendly house is perfect for families, featuring 6 bedrooms, 5 bathrooms, a full kitchen, a kids pool, an indoor play area, outdoor play equipment, and a patio, with free private parking and free WiFi.