Pet-friendly Vacation Rentals in Chicago, IL

Located on Chicago's south side, this apartment offers convenient access to Downtown Chicago and Indiana, just a short drive away.
This pet-friendly, three-bedroom apartment includes a bonus lounge area and a kitchenette, with outdoor stairs providing access to the second-floor unit.

This pet-friendly apartment in Alsip offers a private basement entrance and driveway parking, situated on a quiet cul-de-sac just 8 minutes from I-294 and 16 minutes from I-57, with Downtown Chicago approximately 48 minutes away.
Boasting 1G Fiber optic Internet, central air conditioning, and access to a large yard, this dog-friendly two-bedroom apartment comfortably accommodates up to four guests and is ideal for travellers with pets.

This 3-bedroom apartment in Chicago offers a unique blend of historical charm and modern amenities, located just 2.7 kilometres from Sox Stadium and within a few kilometres of McCormick Place and Soldier Field.
Boasting a private backyard retreat with a hot tub and sauna, this pet-friendly accommodation also features a dedicated movie theatre and is conveniently situated for exploring Chicago's attractions.

Offering panoramic lake and city views from a high-floor corner apartment, this 2-bedroom, 2-bathroom flat is located in Chicago's Loop district, a central area within walking distance of Millennium Park, the Art Institute, and the Magnificent Mile, with excellent access to public transport.
This spacious 111 square meter, pet-friendly apartment accommodates up to 6 guests and boasts a fully equipped kitchen, air conditioning, and building amenities including a gym and 24-hour doorman, making it ideal for travellers with pets exploring Chicago.

Located in Chicago's Wicker Park district, this apartment is just two blocks from the 'L' train, offering excellent access to the city and O'Hare Airport.
This pet-friendly apartment boasts 3 bedrooms, 2 bathrooms, and accommodates up to 8 guests, featuring a modern kitchen, air conditioning, and a private back deck for relaxation.

This pet-friendly apartment is perfectly situated in Chicago, offering excellent access to public transport and a wealth of nearby dining, shopping, parks, and beaches for your convenience.
This 1-bedroom, 1-bathroom unit on the 4th floor includes a fully equipped kitchen and reliable Wi-Fi, making it a comfortable and move-in ready option for up to two guests and their furry companions, with dogs and cats welcome for a small fee.

Centrally located in a Chicago neighbourhood, this pet-friendly apartment offers immediate access to parks, cafes, and shops, with precise proximity to local attractions.
This one-bedroom apartment is well-equipped with a modern kitchen, allowing for convenient meal preparation and is suitable for two guests, with cats welcome according to specific guidelines.

Boasting breathtaking cityscape views from 38 stories high, this penthouse apartment is located in Chicago's Gold Coast district, just steps from Michigan Avenue, offering excellent access to dining and shopping.
This dog-friendly apartment accommodates up to 10 guests with 3 bedrooms and a pull-out sofa bed, featuring a chef's kitchen with Viking appliances, a rooftop pool, and a full gym for a comfortable stay.

Located in Chicago, this modern 1-bedroom apartment is situated 5.6 kilometres from Lincoln Park Zoo and 6.1 kilometres from Wrigley Field, offering convenient access to key city attractions.
This pet-friendly apartment boasts a fully equipped kitchen, air conditioning, and a terrace, with space for up to 7 guests and complimentary WiFi.

Just 160 metres from Oak Street Beach, this apartment offers a prime location in Chicago, a short walk to Michigan Avenue and Millennium Park.
This pet-friendly apartment features a full kitchen, in-unit washer/dryer, and high-speed Wi-Fi, with on-site parking available for an additional nightly fee.

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.

Enjoy a pet-friendly stay in Des Plaines, conveniently located just 4 kilometres from Chicago O'Hare International Airport and within 30 kilometres of major landmarks like the United Center and Union Station.
This spacious house offers 4 bedrooms, a fully equipped kitchen, and on-site yoga classes, ensuring a comfortable and engaging experience for up to 19 guests.

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.

Conveniently located in Chicago, this pet-friendly apartment offers excellent access to McCormick Place, Soldier Field, and Grant Park, with the Field Museum just 2.2 kilometres away.
This 88 square metre apartment features two bedrooms and two bathrooms, a fully equipped kitchen with a dishwasher, and is ideal for families and business travellers, with on-site private parking and a fitness centre available.

Located in Chicago's West Town neighbourhood, this apartment offers easy access to the Blue Line, connecting you to O'Hare and the Loop, with Merchandise Mart and Michigan Avenue just a short journey away.
This pet-friendly apartment welcomes one dog and features three bedrooms, two bathrooms, and a capacity for seven guests, boasting a kitchen with a fridge, microwave, and dishwasher, plus air conditioning and a terrace.

This South Loop apartment in Chicago offers a pet-friendly stay, conveniently located just 1.4 kilometres from the Field Museum and 1.7 kilometres from Grant Park, making it ideal for exploring the city with your dog.
Boasting 800 square meters of floor area, this apartment features 2 bedrooms, 2 bathrooms, a full kitchen with a dishwasher, and on-site parking, ensuring a comfortable and convenient visit for up to 15 guests.

Located in Chicago's Gold Coast and Old Town districts, this newly renovated 2-bedroom loft is just 200 meters from Michigan Avenue and Lake Michigan, offering spectacular city views and prime access to the city's renowned shopping and dining.
This pet-friendly apartment boasts a professionally designed open-concept living and kitchen area, comfortably accommodating up to 8 guests with a king bed, two full beds, and a sofa bed, alongside a state-of-the-art chef's kitchen and access to a well-equipped gym and rooftop sundeck.

Centrally located in the transitioning North Lawndale neighbourhood, this newly renovated, stylish 3-level apartment is just 3.2 kilometres from downtown Chicago and offers convenient access to the medical district, Pilsen, and Chinatown.
This spacious, pet-friendly apartment accommodates up to 12 guests and features a fully finished basement with a game room, a private gated backyard with grilling space, and private parking for 3 cars, ensuring a comfortable stay for you and your dog.

Conveniently situated in Chicago's McCormick Place district, this pet-friendly apartment offers easy access to Soldier Field (2.25 kilometres), Grant Park (2.74 kilometres), and the Field Museum (2.25 kilometres).
This spacious 84 square meter, 2-bedroom apartment welcomes pets and features a fully equipped kitchen, air conditioning, and on-site private parking, making it ideal for families or groups of up to six guests.

This apartment in Chicago offers excellent pet-friendly accommodation, located approximately 12.55 kilometres from Wrigley Field and 12.23 kilometres from Lincoln Park Zoo, with the United Center also around 11.94 kilometres away.
Boasting a generous 1000 square meters of floor area, this dog-friendly apartment comfortably accommodates up to 9 guests with 2 bedrooms, a dedicated workspace, a fully equipped kitchen, and access to a garden, ensuring a pleasant 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.

Located in the Near North Side, this apartment offers direct access to Old Town, Lincoln Park, and the Clybourn Corridor, just a short distance from the New City shopping plaza and Second City Theater.
This spacious 116 square meter apartment, perfect for up to 10 guests, boasts five bedrooms and three bathrooms, alongside a fully equipped kitchen and is a pet-friendly option for your Chicago visit.

Offering stunning city views from its South Loop location, this modern loft-style penthouse apartment is situated directly across from Grant Park and Lake Michigan, placing you within easy walking distance of The Bean and Soldier Field.
This pet-friendly apartment boasts 31 square meters of living space, accommodates up to 4 guests with 1 bedroom and 1 bathroom, and features en-suite laundry, a fully equipped kitchen, and fast WiFi, with the Red Line subway just 480 meters away for convenient city exploration.

Ideally situated in Chicago's West Loop, this apartment offers direct access to public transport and iconic landmarks, being a mere 12-minute walk from Union Station and 1.4 kilometres from the Willis Tower.
This pet-friendly apartment boasts a 58 square meter floor area, features a kitchen with a microwave and dishwasher, air conditioning, a swimming pool, a terrace/balcony, a fitness centre, and on-site parking for up to 3 guests.

Located in Chicago's Wrigleyville, this apartment is just 300 metres from the iconic Wrigley Field, offering an excellent base for exploring the area and attending Cubs games.
This dog-friendly, three-bedroom apartment comfortably accommodates up to eight guests and features a full kitchen, a wet bar, and two private parking spots, making it ideal for families and groups with pets.

Situated near Chicago's Museum Campus, this apartment is approximately 2.4 kilometres from the Field Museum and 2.9 kilometres from Grant Park and DePaul University.
This pet-friendly apartment offers 88 square metres of living space for up to 10 guests, featuring a fully equipped kitchen, on-site parking, and an outdoor fireplace, making it ideal for families and those travelling with their dogs.

Located in Chicago's West Town district, this apartment is conveniently situated within 3.2 kilometres of Millennium Park and Lake Michigan, with the United Center and Lincoln Park Zoo also within reasonable reach.
This excellent-rated, pet-friendly apartment offers two bedrooms for up to five guests, featuring a kitchen with a fridge, microwave, and dishwasher, plus a terrace/balcony, garden, parking, and an in-unit washer/dryer for a comfortable stay.

Located in Chicago's historic Bronzeville district, this apartment offers proximity to Lake Michigan and Grant Park, with Michigan Avenue and Navy Pier just a short distance away.
This pet-friendly apartment boasts two bedrooms, two bathrooms, and a jetted bathtub, providing private parking and an outdoor space ideal for travellers with pets.

This apartment is located in Chicago's Wicker Park district, just 1.6 kilometers from The Robey Rooftop Bar and 320 meters from Small Cheval Burgers and the Wicker Park Dog Park.
This spacious 185 square meter apartment is pet-friendly and features a design-forward interior with lush greenery, offering an open-concept layout ideal for groups, along with a shared, reservable outdoor patio for entertaining.

This apartment is located in Chicago's Old Town district, just a 3-5 minute drive from Lincoln Park and North Avenue Beach.
This dog-friendly apartment offers ample space for up to 12 guests with five bedrooms, two living areas including a lounge with arcade games, and a full kitchen.

Located in Chicago's Old Town district, this 8-bedroom duplex apartment is just a short walk from the lakefront and a variety of shops and eateries.
This spacious, pet-friendly apartment offers ample room for large families or groups, featuring modern furnishings, two living areas, and a fully equipped kitchen, ensuring a comfortable stay with your dog.

Located in the trendy Wicker Park/Bucktown district, this private, luxuriously designed three-storey farmhouse coach house is just 1.6 kilometres from Chicago's Elevated Park & Trail, the '606', and a 10-minute walk to the Western Blue Line station.
This pet-friendly apartment offers exclusive access to the entire coach house, accommodating up to 9 guests with 4 bedrooms, 2 bathrooms, a fully equipped modern kitchen, and a dedicated basement area perfect for entertainment.

Located in Chicago's East Garfield Park, this 1883 row home offers a rare spacious garden and is just a 4-minute walk to the CTA green line for quick downtown access.
This pet-friendly apartment boasts over 2800 sq ft across three floors, featuring 4 bedrooms, 2.5 bathrooms, 3 living areas, and capacity for 16 guests, with a 2-car garage and ample street parking.

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.

Boasting high-floor city views, this studio apartment is situated in Streeterville, a prime Chicago district, just a 5-minute walk from The Loop and close to Michigan Avenue's luxury shopping.
This pet-friendly studio, offering a king-sized bed and a fully equipped kitchen, is perfect for two guests and features on-site amenities including a swimming pool and fitness centre.

Located in Chicago's Irving Park, this apartment is a 10-minute walk from the Addison Blue Line subway and offers convenient access to the 90/94 expressway, with Wrigley Field just a short distance away.
This pet-friendly apartment provides 93 square meters of private living space with two bedrooms, accommodating up to five guests, and features in-unit laundry and parking.