Pet-friendly Vacation Rentals in Chicago, IL

Located in Chicago's downtown area, this apartment is conveniently situated 2.25 kilometres from the Field Museum and 2.73 kilometres from Grant Park, with DePaul University also nearby.
This pet-friendly, 200 square meter apartment boasts three bedrooms, accommodating up to ten guests, and features a fully equipped kitchen, on-site parking, and complimentary WiFi, ensuring a comfortable stay for families and their pets.

Located in the prime Gold Coast district, this apartment is just a short walk from Oak Street Beach, the Magnificent Mile, and Navy Pier, offering excellent access to public transport.
This dog-friendly apartment boasts a fully equipped kitchen, air conditioning, and a fitness centre, making it ideal for families and pets seeking a comfortable stay in Chicago.

Located in Chicago, this apartment is just a minute's walk from the Irving Park Blue Line station, offering excellent connectivity and positioning you 6.9 kilometres from Wrigley Field and 11.4 kilometres from Lincoln Park Zoo.
This pet-friendly apartment boasts on-site recreational facilities including a garden and tennis court, alongside a fully equipped kitchen and air conditioning for a comfortable stay.

Located in Chicago's Irving Park neighbourhood, this apartment offers convenient access to downtown attractions like the Chicago Theatre and the Art Institute of Chicago, as well as shopping on Michigan Avenue and at Navy Pier, making it a pet-friendly base for exploring the city.
This 70 square meter, 1-bedroom apartment accommodates up to 4 guests and features a fully equipped kitchen, a dedicated workspace, on-site laundry, and parking, with pets welcome for an additional fee.

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.

This spacious 3-bedroom, 2-bathroom apartment in Chicago is perfectly situated for exploring the city, offering excellent user, location, and cleanliness ratings for a comfortable stay.
Enjoy a fully equipped kitchen, central air conditioning, and an in-unit washer/dryer, with this pet-friendly accommodation also welcoming your furry companions.

Located in a famed, historic Chicago pink brick building dating back to 1890, this expansive 1300 sq ft loft-style apartment offers excellent access to public transport, placing popular neighbourhoods and dining within a 1.6-2.4 kilometre reach.
This pet-friendly apartment welcomes pets with prior approval and boasts a full kitchen, air conditioning, and free fitness classes, making it ideal for families or groups of up to six guests.

Just 40 metres from Garrett Popcorn and the Nike Outlet, this pet-friendly apartment offers excellent access to Chicago's METRA, CTA, and Red Line, with downtown just 17.7 kilometres away.
This spacious quad-level apartment, accommodating up to 7 guests, boasts two living areas with fireplaces, an outdoor entertaining space with a fire pit and grill, and a complimentary wine cellar for a unique stay.

This spacious 3-bedroom apartment in Chicago offers a fantastic pet-friendly base, just 5.6 kilometres from Downtown and a 15-minute drive to Millennium Park, Soldier Field, and Sox Park, with excellent public transport links.
Boasting 950 sqft, this family-friendly apartment accommodates up to 10 guests with a fully equipped kitchen, laundry facilities, free street parking, and a shared fenced backyard, plus an impressive arcade with 10,000 games for endless entertainment.

Conveniently located in a safe Chicago neighbourhood, this private one-bedroom apartment offers easy access to the Chicago Outlet Mall and Harlem Irving Plaza Mall, with numerous dining and shopping options within 500 meters.
This pet-friendly apartment, allowing pets with an additional fee, features secure building access with an elevator, on-site laundry facilities, and complimentary street parking, making it an excellent choice for travellers with dogs.

Just 700 meters from Montrose Beach and the Lakefront Trail, this pet-friendly studio apartment offers prime North Side Chicago accommodation between Uptown and Lakeview.
This dog-friendly aparthotel provides a convenient base for exploring Wrigley Field and Ravenswood, with easy access to downtown via the CTA Red & Brown Lines, and allows pets with prior approval and a fee.

This pet-friendly apartment is located in Chicago's Lincoln Square, just 400 meters from the Western Brown Line station for easy access to the city centre.
Boasting a professionally designed interior with unique art, this sunny, second-floor unit offers 2 bedrooms, 1 bathroom, and in-unit laundry, accommodating up to 4 guests with pets allowed.

Located in the well-known Waveland neighbourhood of Chicago, this apartment offers convenient access to local attractions.
This excellent, pet-friendly apartment boasts a fully equipped kitchen, air conditioning, and parking, with space for up to 4 guests.

Conveniently located in Chicago, this pet-friendly apartment is approximately 18 kilometres from Midway International Airport and within driving distance of the Museum of Science and Industry (9 kilometres), Willis Tower (19 kilometres), and Buckingham Memorial Fountain (20 kilometres).
This 14 square metre apartment accommodates up to two guests with one bedroom and one bathroom, featuring air conditioning, cable flat-screen TVs, and complimentary on-site private parking, making it ideal for travellers with pets.

Newly remodelled, this 3-bedroom apartment in Chicago's Andersonville district offers historic Greystone charm and is located a mere 3.2 kilometres from the beach and 6.4 kilometres from Wrigleyville, with Downtown Chicago just a 15-minute drive away.
This pet-friendly apartment boasts a fully equipped chef's kitchen, in-unit laundry, and three Roku TVs, accommodating up to six guests with one king and two queen beds, ensuring a comfortable stay for you and your dog-friendly companions.

Located in Chicago's prime West Loop, this pet-friendly apartment is just over 1.6 kilometres from Willis Tower and within a few kilometres of the Art Institute and Navy Pier.
This 58 square meter, one-bedroom apartment welcomes pets and offers a fully equipped kitchen, air conditioning, free WiFi, and access to building amenities including a pool and gym, with city views and proximity to Union Station.

Located in the Giddings Chicago 985 area, this apartment offers excellent proximity to Chicago's key landmarks and attractions, making it a convenient base for exploring the city.
This pet-friendly apartment, managed by LuxuryLodgingSTR, boasts 7 bedrooms, 3 bathrooms, and accommodates up to 15 guests, featuring a full kitchen with a fridge, microwave, and dishwasher, plus air conditioning and on-site parking.

Just 5.5 kilometres from Wrigley Field, this Irving Park top-floor apartment in Chicago offers a convenient base for exploring the city and is a truly pet-friendly choice.
With a generous floor area of 93 square meters, this apartment accommodates up to 10 guests and features two bedrooms, a fully equipped kitchen, air conditioning, and a balcony, ensuring a comfortable stay for you and your pets.

Enjoy a unique coach house apartment experience in Chicago's Little Village, conveniently located approximately 5.4 kilometres from Pilsen and within easy reach of Millennium Park and Soldier Field.
This pet-friendly accommodation offers a classic Pac-Man arcade, a private office with a printer and scanner, and an exclusive patio with a grill, perfect for remote workers and families with pets.

Just 500 meters from the shores of Lake Michigan and a short walk to Loyola University, this pet-friendly apartment in Chicago's Rogers Park offers ideal accommodation for those travelling with their dogs.
This one-bedroom, one-bathroom apartment accommodates up to two guests and features essential amenities including air conditioning, a dishwasher, and convenient on-site parking, making it a comfortable base for exploring the local neighbourhood and its many parks and eateries.

Located in Chicago's Loop district, this apartment is a short train ride from Union Station and within easy reach of Millennium Park, Michigan Avenue, and Navy Pier.
This pet-friendly apartment offers 103 square meters of space with two bedrooms and two bathrooms, featuring a fully equipped kitchen, in-apartment laundry, and building amenities including a swimming pool and BBQ area, perfect for guests and their pets.

Offering panoramic city views from its top-floor private balcony, this 2-bedroom apartment is situated in Chicago's desirable West Loop, just a 5-minute walk from Little Italy and Union Park, making it a perfect pet-friendly base for exploring the area.
This apartment boasts a fully-equipped chef's kitchen, smart TVs, a Sonos sound system, and access to building amenities including a fitness centre and rooftop terrace, with service dogs welcome upon prior approval.

Enjoy city views from the rooftop firepit and outdoor dining area of this spacious 4-bedroom apartment, conveniently located just a 13-minute walk from the United Center and offering a pet-friendly environment for your stay in Chicago.
This expansive 223 square meter apartment boasts 2 living rooms, a private patio with garden views, and barbecue facilities, ensuring a comfortable and well-equipped stay for up to 23 guests, with laundry service also available.

Offering spectacular city views from its huge windows, this spacious 3-bedroom apartment in Chicago is a truly pet-friendly choice for your stay.
Located in a Chicago neighbourhood, this apartment is just 400 meters from acclaimed restaurants like Moody Tongue and a short walk to South Wabash cafes, with excellent public transport links.

Located in Chicago, this apartment offers vintage charm and is conveniently situated between 6.9 kilometres and 9.3 kilometres from popular attractions such as Lincoln Park Zoo, Wrigley Field, and the United Center.
This pet-friendly apartment boasts a fully equipped kitchen, air conditioning, and on-site parking, making it an excellent choice for travellers with pets.

Boasting proximity to Fullerton Beach (3058 metres) and Lincoln Park Zoo (2.6 kilometres), this pet-friendly apartment offers a prime Chicago location.
This spacious 2-bedroom, 2-bathroom apartment accommodates up to 7 guests and features a fully equipped kitchen, air conditioning, free WiFi, and access to a fitness centre and barbecue facilities.

This spacious West Town apartment is located just 1.9 kilometres from the United Center, with convenient access to attractions such as Water Tower Chicago and Willis Tower.
Enjoy a truly pet-friendly stay with a private terrace, fully equipped kitchen, and free WiFi, perfect for families and those travelling with their dogs.

Located in Chicago's Ukrainian Village within West Town, this pet-friendly apartment is a short 3.2 kilometre distance from the United Center and a manageable drive to downtown attractions.
This spacious three-level, 316 square meter apartment offers ample room for up to 8 guests, featuring a fully equipped oversized kitchen with two sinks and dishwashers, a private deck with a pergola and gas grill, and a finished lower level for recreation, making it an ideal dog-friendly choice.

Offering privacy and an entire unit to yourself, this spacious garden-level apartment is located in Chicago's Albany Park, just a 5-minute walk from the Brown Line and a short drive from Lincoln Square, making it a very pet-friendly choice.
This newly rehabbed apartment boasts a fully equipped kitchen with brand-new appliances, a dedicated sunroom perfect for an office or yoga, and convenient access to shared laundry facilities, ensuring a comfortable stay for you and your pets.

Boasting stunning city views, this apartment is perfectly positioned in downtown Chicago, just a short walk from Lake Michigan and Millennium Park.
This spacious 3-bedroom apartment, ideal for up to 8 guests, offers a fully-equipped kitchen, air conditioning, and is wonderfully pet-friendly, ensuring a comfortable stay for you and your dog-friendly companions.

This spacious 2-bedroom apartment in Chicago offers excellent access to major attractions, situated approximately 6.9 kilometres from the United Center and within a 10.3-kilometre radius of landmarks such as Water Tower Chicago and Lincoln Park Zoo, making it a convenient base for exploring the city.
A truly pet-friendly apartment, this accommodation provides a fully equipped kitchen, air conditioning, and free WiFi, along with free private parking, ensuring a comfortable stay for families and their beloved pets.

This family-friendly 3-bedroom, 2-bathroom apartment in Chicago welcomes pets and is conveniently located just over 32 kilometres from the city centre, situated in a quiet neighbourhood with easy access to public transport.
Offering excellent ratings for cleanliness and location, this dog-friendly accommodation provides a fully furnished and well-maintained space for up to six guests, complete with essential kitchen appliances and air conditioning for a comfortable stay.

This apartment in Oak Park is conveniently located just 800 meters from local dining, cafes, and shops, and within walking distance of the iconic Frank Lloyd Wright Home & Studio and the Ernest Hemingway Birthplace Museum.
Boasting five bedrooms and three bathrooms, this pet-friendly accommodation comfortably sleeps up to 12 guests and features a fully equipped chef's kitchen, a private backyard, and a 2-car garage, ensuring a seamless stay for families and their pets.

This pet-friendly apartment in Chicago's West Town district is conveniently located approximately 3.2 kilometres from Michigan Avenue and Navy Pier, offering easy access to Lincoln Park Zoo and the Field Museum.
With 2 bedrooms and space for 4 guests, this apartment includes essential amenities such as WiFi, air conditioning, and a kitchen with a fridge, microwave oven, and dishwasher, making it a great choice for families and dog-friendly holidays.

Located in Chicago's McCormick Place area, this pet-friendly studio is just 2.25 kilometres from the Field Museum of Natural History and 2.74 kilometres from Grant Park.
This studio offers a fully equipped kitchen, complimentary WiFi, on-site parking, and barbecue facilities, accommodating up to 7 guests with pets allowed.

Directly across from Chicago's Horner Park, this pet-friendly garden apartment is conveniently located in the North Center neighbourhood.
This two-bedroom, one-bathroom apartment accommodates up to five guests and offers a private patio, making it ideal for families and their pets.