Pet-friendly Vacation Rentals in Chicago, IL

Located in Chicago's Wicker Park district, this pet-friendly apartment offers a unique, art-filled building experience with private parking, just a 5-minute commute to downtown Chicago.
This two-bedroom apartment accommodates up to six guests and features a shared garden, a fully equipped kitchen, and flexible sleeping arrangements, making it ideal for travellers with pets.

Conveniently located in Chicago's West Ridge neighbourhood, this apartment is a short 500-metre walk from Warren Park and minutes from Devon Avenue's shops and restaurants, offering a truly pet-friendly base for exploring the city.
This 2-bedroom apartment accommodates up to 5 guests and features air conditioning, a kitchen with a fridge and freezer, and excellent user, location, and cleanliness ratings, making it a comfortable and hygienic choice for visitors with pets.

Conveniently located in Chicago, this pet-friendly house is just 800 metres from the Green Line CTA station, offering easy access to downtown, and is a short 1.4 kilometre drive to the Garfield Park Conservatory.
This spacious 5-bedroom house welcomes up to 12 guests and includes a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning and a garden, making it ideal for families and groups travelling with their pets.

This spacious 8-bedroom house in Chicago's Avondale district is a fantastic pet-friendly option, located just 15 kilometres from O'Hare Airport and 200 metres from the highway.
With two full kitchens, ample gathering spaces, and parking for two vehicles, this dog-friendly accommodation comfortably sleeps 16 guests and offers a high-touch service from Hosty Co.

Located in Chicago's Loop district, this apartment is a 14-minute walk from Millennium Park and 1.4 kilometres from DePaul University, offering a prime city centre position.
This pet-friendly apartment boasts 136 square meters of living space, air conditioning, a kitchen with a fridge, microwave, and dishwasher, an indoor swimming pool, and on-site parking, ensuring a comfortable stay for you and your pets.

Conveniently located near the University of Chicago Hospitals Heliport, this apartment is 4.6 kilometres from the Museum of Science and Industry and 7.7 kilometres from Guaranteed Rate Field.
This pet-friendly apartment offers air-conditioned comfort for two guests, featuring a private bathroom and parking, making it ideal for travellers exploring Chicago with their pets.

Located in Chicago's West Loop & Fulton Market districts, this apartment offers proximity to renowned dining and entertainment hubs.
This pet-friendly apartment provides access to excellent amenities, including a swimming pool and fitness centre, and is ideal for travellers seeking a well-equipped home away from home.

Located in a trendy Chicago neighbourhood, this apartment is a short walk from Wrigleyville and Boystown, with Target and Starbucks nearby, and downtown reachable in under 20 minutes by train.
This pet-friendly apartment boasts a private, multi-level house with a backyard deck, grill, and private covered parking, offering a luxurious experience for up to 8 guests with three bedrooms and three bathrooms, including a primary suite with a jacuzzi and steam room.

This newly renovated 3-bedroom, 2-bathroom apartment is perfectly situated in Chicago's Chinatown district, just a 5-minute drive from McCormick Place and adjacent to Ping Tom Park.
Ideal for travellers with pets, this dog-friendly accommodation offers ample sleeping arrangements for up to 10 guests, including a dedicated free parking spot and convenient access to public transport for exploring the city.

Located in Chicago's West Town district, this garden apartment is a mere 3-minute walk to the Michelin-starred Kasama restaurant and 9 minutes on foot from Division Street's dining scene, with easy access to bus stops (4-10 minutes' walk) and the Blue Line (16 minutes' walk).
This dog-friendly apartment boasts a private fenced patio, a king and queen bed setup, a height-adjustable desk, and in-unit laundry, making it ideal for guests with pets looking to explore Chicago's culinary hotspots and public transport links.

Located in a peaceful urban district, this apartment offers convenient access to Chicago's attractions, providing a tranquil escape from the city bustle.
This dog-friendly apartment boasts four bedrooms, accommodates up to eight guests, and features essential amenities like air conditioning and parking, ensuring a comfortable and memorable stay for families and their pets.

This pet-friendly apartment in Chicago's North Center neighbourhood is a mere 3.2 kilometres from Wrigley Field and 9.7 kilometres from Lake Michigan, offering excellent access to local attractions.
Boasting 65 square metres of space, this apartment comfortably accommodates up to six guests with two bedrooms, one bathroom, and features a fully equipped kitchen, air conditioning, and in-unit laundry facilities.

Conveniently situated in Chicago's Washington Park, this apartment offers excellent proximity to the University of Chicago, just 500 meters away, and easy access to Downtown Chicago and both O'Hare and Midway Airports.
This pet-friendly apartment welcomes up to 6 guests, boasting a fully equipped kitchen, modern furnishings, and free street parking, making it an ideal choice for longer stays and dog-friendly holidays.

Located in Chicago's Pilsen neighbourhood, this modern apartment offers exceptional access to the city centre, being just 200 metres from the train station for swift journeys.
This pet-friendly apartment boasts a spacious open-plan living area, a fully equipped kitchen, and accommodates up to 11 guests, making it ideal for families and groups travelling with their dogs.

This spacious row home in Chicago offers a prime location, just 3.4 kilometres from Union Station and 2.1 miles from the United Center, ensuring easy access to transit and downtown attractions.
Perfect for families and dog-friendly holidays, this four-bedroom house boasts 260 square metres of living space, a fully equipped kitchen, three bathrooms, and a balcony, with free private parking and WiFi included.

Industrial-chic loft accommodation in Chicago offers a pet-friendly stay, just a short walk from Lake Michigan and Montrose Beach.
This dog-friendly loft boasts 16ft ceilings, a fully equipped kitchen with a Nespresso machine, and access to a rooftop deck and dog park, all within easy reach of Aragon Ballroom and local jazz clubs.

This pet-friendly apartment in Chicago's historic Gold Coast offers a sophisticated urban retreat, located adjacent to Lake Michigan and within easy reach of the upscale shopping and dining of Oak and Rush Streets.
Boasting 65 square meters of living space, this one-bedroom apartment accommodates two guests and features a fully equipped kitchen, in-apartment laundry, a balcony with city views, and access to building amenities including a BBQ area and doorman.

Located in Chicago Ridge, this apartment is situated 10.3 kilometres from Midway International Airport, with Guaranteed Rate Field and the Museum of Science and Industry both 22.5 kilometres away.
This pet-friendly apartment offers a spacious 102 square meter layout with one bedroom and two bathrooms, accommodating up to 7 guests and featuring a balcony, air conditioning, and free WiFi.

This apartment is located in Chicago's Loop district, within 800 meters of the city centre and close to landmarks like the CIBC Theatre and Willis Tower, offering a prime spot for exploring downtown Chicago.
Boasting a rooftop swimming pool and a garden, this pet-friendly apartment accommodates up to 9 guests, with fully equipped kitchens, air conditioning, and complimentary WiFi, ensuring a comfortable stay for you and your pets.

Located in Chicago's Near West Side, this apartment offers easy access to Millennium Park and Grant Park, just a short distance from major entertainment venues like the United Center and Soldier Field.
This pet-friendly one-bedroom apartment, spanning 64 square meters, features a fully equipped kitchen, in-apartment laundry, and building amenities including parking, making it ideal for guests travelling with their dogs.

Centrally located in Bensenville, this apartment offers easy access, just a few minutes from O'Hare Airport and a short drive to downtown Chicago.
This spacious 4-bedroom apartment welcomes pets and features a basement suite with a pool table and a 75-inch Roku TV, alongside a fenced backyard with patio seating for a truly pet-friendly stay.

Located in Chicago's Pilsen neighbourhood, this expansive 5-bedroom house is just 3.9 kilometres from the United Center and 5.9 kilometres from both the Guaranteed Rate Field and Willis Tower, offering a prime spot near the Medical District.
This pet-friendly house boasts a generous 5000 square metre floor area, accommodating up to 21 guests with 5 bedrooms and 4 bathrooms, alongside a fully equipped kitchen and a relaxing spa bath for a comfortable stay.

Centrally located in downtown Chicago, this spacious penthouse apartment is just an 8-minute walk from DePaul University and 0.6 kilometres from Grant Park, offering easy access to the Art Institute of Chicago and Willis Tower.
This pet-friendly apartment boasts a private balcony with city views, a fitness centre, and air conditioning, making it an ideal choice for travellers exploring Chicago with their dogs.

Located in Chicago's Albany Park district, this apartment offers vintage charm and modern amenities, with the CTA Brown Line and Montrose 78 bus line just steps away, providing easy access to Wrigley Field and the Art Institute.
This pet-friendly, two-bedroom apartment boasts a unique library with over 4,000 titles, a den, dining room, and a bathroom with both a bathtub and shower, along with a rear patio featuring a firepit and skyline views, accommodating up to four guests.

Perfectly situated in East Lakeview, this apartment is just a short 500 meters walk from Montrose Beach, offering a fantastic pet-friendly escape near the water.
This charming 2-bedroom apartment, located on the third floor of a historic home, welcomes pets and provides access to a private garden and laundry facilities upon request.

This apartment in Chicago offers a pet-friendly stay, conveniently located just 2.4 kilometres from the Field Museum of Natural History and near McCormick Place, Museum Campus, Grant Park, and Soldier Field.
With 79 square metres of space, this dog-friendly apartment features two bedrooms, two bathrooms, a fully equipped kitchen, and on-site fitness facilities, ensuring a comfortable visit for up to 11 guests.

Located in Chicago's Portage Park district, this apartment is a convenient base for exploring the city, with Wrigley Field and United Center within a short 10-minute drive.
This spacious 231 square meter apartment boasts seven bedrooms, accommodating up to 15 guests with ease, and is a truly pet-friendly option, allowing your furry companions to join the fun.

Just a few hundred meters from the lakefront and local parks, this Edgewater, Chicago apartment offers excellent proximity to shops and dining, with straightforward public transport links for exploring the city.
This dog-friendly apartment, accommodating up to four guests, features two bedrooms, one bathroom, and a modern kitchen, making it a perfect base for travellers with pets.

Located in Historic Old Town, this apartment is just 800 meters from the lakefront, Lincoln Park Zoo, and the Chicago History Museum, offering excellent access to downtown Chicago via the brown line train, a mere 10-minute journey.
This pet-friendly apartment features a fully equipped kitchen, complimentary high-speed internet, and a washer and dryer, comfortably accommodating up to 4 guests in its two bedrooms, with one queen and one double bed.

Located in Chicago, this apartment offers convenient access to McCormick Place and Soldier Field, with the Field Museum of Natural History 2.25 kilometres away and Grant Park 2.73 kilometres away.
This pet-friendly, allergy-free, non-smoking apartment boasts a spacious 2-bedroom layout sleeping up to 6 guests, complete with a fully equipped kitchen, air conditioning, and on-site private parking for your convenience.

Offering prime South Loop location, this aparthotel is situated just 1.6 kilometres from Grant Park and 1.6 kilometres from the Art Institute of Chicago, providing excellent access to city attractions.
This aparthotel is genuinely pet-friendly, welcoming one dog or cat per unit with applicable daily fees and breed restrictions, whilst boasting fully equipped kitchens, air conditioning, a swimming pool, and a fitness centre for a comfortable stay.

Located in Chicago's Lakeview East/Wrigley district, this apartment is a short distance from Wrigleyville and Montrose Beach, offering a truly pet-friendly stay.
This 3-bedroom apartment accommodates up to 12 guests and features 4 Smart TVs and 3 classic arcade machines with over 7,000 games, ensuring entertainment for everyone, including your dog-friendly family.