Holiday Rentals in Chicago, IL

Conveniently located in Franklin Park, this apartment is just 3.1 kilometres from Chicago O'Hare International Airport and within a 20.9-24.1 kilometre radius of major Chicago landmarks including the United Center and Union Station.
This pet-friendly apartment, managed by a private host, offers air conditioning, free private parking and a capacity for up to 7 guests, making it ideal for mid and extended stays with your dog.

Located in Chicago's Avondale district, this top-floor apartment is a mere 2.4 kilometres from Wrigley Field and a 7-minute walk to the CTA Belmont Blue Line, offering excellent access to downtown and O'Hare Airport.
This stylishly furnished, pet-friendly 2-bedroom, 2-bathroom apartment accommodates up to 4 guests and boasts a fully equipped kitchen with brand new stainless steel appliances, in-unit laundry, and high-speed WiFi.

Centrally located in a peaceful Chicago neighbourhood, this newly renovated apartment is conveniently situated just 24 kilometres from Midway Airport and 16 kilometres from Ford City Mall.
This pet-friendly apartment offers a comfortable stay for up to 8 guests with its 3 bedrooms, fully equipped kitchen, and air conditioning, and is just steps from public transport and a large public park.

This pet-friendly apartment is located in a Chicago district, accessible solely by stairs, offering a convenient basement-level stay.
Boasting two bedrooms, two bathrooms, and a fully equipped kitchen, this apartment accommodates up to four guests and features an in-unit washer/dryer, making it ideal for longer stays with your cat.

This pet-friendly apartment in Chicago's Back of the Yards neighbourhood is conveniently located 3.2 kilometres from the University of Chicago and 12.8 kilometres from downtown landmarks.
With 5 bedrooms and 1.5 bathrooms, this spacious apartment accommodates up to 9 guests and offers a private garden, free WiFi, and street parking for up to 4 vehicles.

Located in Chicago's Tri-Taylor/Near West Side, this modern loft is a short 5-minute drive to the United Center and within 800 meters of the Illinois Medical District.
This pet-friendly, newly renovated 2nd-floor apartment offers 13-foot ceilings, a gourmet kitchen, and accommodates up to 12 guests, making it ideal for families and groups travelling with their dogs.

Located in Chicago's Rogers Park district, this apartment is just a short walk from the shores of Lake Michigan and offers convenient Red Line access to downtown, making it an ideal base for exploring the city.
This spacious, pet-friendly apartment comfortably accommodates up to 13 guests across 5 bedrooms and 2 bathrooms, featuring a fully equipped chef's kitchen and a dedicated office space.

Located in Belmont-Cragin, this apartment is conveniently situated for exploring local parks, shops, and dining options, with excellent access to public transport.
This spacious, pet-friendly apartment boasts a private theatre, arcade room, and a home gym, alongside a fantastic outdoor lounge with a grill and firepit, comfortably accommodating up to 11 guests.

Just a 5-minute walk from the beach, this pet-friendly apartment is perfectly situated in Chicago's central River North neighbourhood, mere steps from Magnificent Mile shopping.
This spacious 3-bedroom apartment offers excellent amenities including air conditioning and a fully equipped kitchen, accommodating up to 10 guests for a comfortable and quiet stay, with towels, hair dryer and linens provided.

This pet-friendly apartment in Chicago's Wicker Park district is just 150 meters from the Damen Blue Line station, offering easy access to downtown and O'Hare International Airport, and is close to Big Star restaurant.
With four bedrooms accommodating up to eight guests, this spacious apartment features a fully equipped kitchen, in-unit laundry, central air, and keyless entry, making it ideal for families or groups travelling with their pets.

Located just steps from the Magnificent Mile and the high-end boutiques of Oak and Rush Street, this apartment offers a prime Chicago location.
This pet-friendly, 815 sqft one-bedroom apartment welcomes dogs and features a gourmet kitchen, spa-like bathroom, and a working fireplace for a comfortable stay.

This spacious, pet-friendly artist loft offers a unique, private living experience in Brookfield, a western suburb of Chicago, with excellent public transport links including trains and buses just a short walk away, facilitating an easy commute to downtown Chicago.
Boasting a wide-open layout, this apartment accommodates up to 4 guests, features air conditioning, a full kitchen with a dishwasher and Sub-Zero fridge, and a private garden, making it an ideal choice for travellers with pets seeking comfort and convenience.

Located in Chicago, this pet-friendly house is conveniently situated 1.6 kilometres from the United Center and 2.8 kilometres from Union Station, offering easy access to major attractions like 360 Chicago and the Chicago Museum of Contemporary Art.
This 2-bedroom, 1-bathroom house accommodates up to 9 guests, boasting a fully equipped kitchen with a dishwasher and coffee machine, air conditioning, free WiFi, and a garden with patio views, making it an ideal choice for families travelling with pets.

Located in Chicago's River North district, this apartment is just south of the Old Town neighbourhood and close to the CTA Red & Brown Lines for easy city access.
This pet-friendly apartment offers a queen bed, in-unit laundry, and full access to building amenities including a swimming pool, Jacuzzi, and fitness centre.

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 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.

Near McCormick Place, this pet-friendly apartment is conveniently located within 2.4 kilometres of Grant Park and 2.4 kilometres of the Art Institute of Chicago.
This 88 square metre, two-bedroom apartment welcomes pets and offers a fully equipped kitchen, private patio, and on-site parking, ensuring a comfortable stay for families.

Centrally located in Oak Park, this apartment offers convenient access to Chicago's numerous sightseeing opportunities, just a short distance from the city's attractions.
This pet-friendly apartment boasts a spacious 4-room layout, including a separate bedroom with a king-sized bed and a sofa sleeper, accommodating up to four guests with private off-street parking and a garden.

This pet-friendly apartment in Chicago offers a prime location, situated just 1.9 kilometres from the United Center and 4.9 kilometres from Union Station.
Enjoy a spacious 223 square metre apartment featuring three bedrooms, three bathrooms, a private balcony with outdoor seating, and a fully equipped kitchen, making it ideal for families and offering a convenient hot tub amenity.

Perfectly situated in Wrigleyville, this apartment is a 7-minute walk from the iconic Wrigley Field and a 5-minute walk west to the Southport Corridor's shopping and dining.
This pet-friendly apartment accommodates up to six guests, offering a private terrace and complimentary linen, soap, and a Nespresso machine for your convenience.

This apartment in Chicago's Loop district is conveniently located a short train ride from Union Station, with the Willis Tower and Millennium Park within easy reach.
This pet-friendly apartment offers a BBQ area, swimming pool, and fitness centre, ensuring a comfortable stay for you and your dog.

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 Oak Park, this apartment is approximately 11.3 kilometres from the United Center and 14.6 kilometres from Willis Tower, offering convenient access to Chicago landmarks.
This pet-friendly apartment boasts a private terrace and on-site tennis court, with 84 square metres of space accommodating up to five guests and featuring complimentary WiFi and parking.

Centrally located in Chicago's West Loop, this historic 2-story Greystone apartment is just 4.8 kilometres from downtown and 4 blocks from the United Center, offering a pet-friendly base for exploring the city.
This spacious apartment accommodates up to 12 guests with 4 bedrooms, two living rooms featuring a fireplace and PlayStation, a backyard oasis with a firepit, and a rooftop deck, ensuring a comfortable and entertaining stay for you and your pets.

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.

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.

Discover an urban spa-inspired retreat in Chicago's Wicker Park, just a 5-minute walk from the Damen Blue Line, offering a pet-friendly haven with a private steam room and oversized jetted tub.
This 2-bedroom apartment accommodates up to 6 guests and boasts a garden, terrace, and parking, ensuring a comfortable stay near cultural highlights like the Chicago History Museum and entertainment venues such as the United Center.

This apartment in Chicago's Avondale/Logan Square district is a 24-minute drive from Downtown Chicago and conveniently located near the California Blue Line train stop, with easy access to Interstate 90.
Offering 5 bedrooms and 4 bathrooms across 232 square meters, this pet-friendly accommodation boasts a private garden, a detached garage, and a driveway, making it a rare find for families or groups of up to 10 guests.

This newly renovated penthouse apartment in Chicago's Gold Coast and Old Town offers exceptional city views and is just steps from Michigan Avenue, Lake Michigan, and Wells Street, providing a prime location for exploring.
Boasting a full gym and a rooftop sundeck, this pet-friendly luxury loft apartment comfortably accommodates up to 8 guests, with a high-end chef's kitchen and one complimentary secured parking space a few blocks away.

This pet-friendly apartment in Oak Park offers a unique duplexed layout with a whimsical third-floor cabin-like children's bedroom, ideal for families travelling with their furry companions.
Conveniently located just 240 meters from the Oak Park Av. CTA 'L' Blue Line stop and I-290, this dog-friendly accommodation provides easy access to downtown Chicago (a 15-minute drive) and a wealth of local amenities including shops, dining, and parks.

Centrally located in Old Town, this apartment is just a few blocks from Michigan Avenue, the Gold Coast, and River North, offering a prime spot for exploring Chicago's popular districts.
This spacious, pet-friendly apartment building boasts six bedrooms and five bathrooms, accommodating up to 14 guests with two entire units exclusively for visitors, and features newly finished, high-end kitchens and hospital-grade disinfectant cleaning for a comfortable, seamless stay.

This studio in Downtown Chicago offers a pet-friendly stay, just a 6-minute walk from Oak Street Beach and 0.9 kilometers from the city centre.
Enjoy a fully equipped kitchen with a dishwasher and air conditioning in this 56 square meter studio, complete with a patio for outdoor dining.

Located in downtown Chicago, this house is just 720 meters from Grant Park and 0.6 miles from the Art Institute of Chicago, placing you moments from Millennium Park and Buckingham Fountain.
This pet-friendly house offers 2 bedrooms, 2 bathrooms and a fully equipped kitchen, with complimentary WiFi and a fitness centre available for 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.

Explore this expansive 7-bedroom apartment in Chicago, offering a unique private fun house experience and a dedicated office space, perfect for families and groups of up to 15, with the added bonus of being pet-friendly.
This dog-friendly apartment boasts extensive entertainment, including an arcade and theatre room, alongside a fully equipped kitchen and on-site laundry, ensuring a comfortable and engaging stay for all guests.

Located 1.5 kilometres east of Lincoln Park Zoo, this historic 1883 Chicago apartment boasts original woodwork and offers direct train access to Wrigley Field, making it an ideal pet-friendly base.
This spacious, family-friendly apartment accommodates up to six guests and features air conditioning, a full kitchen including a dishwasher, and complimentary street parking.