Holiday Rentals in Chicago, IL

Just 160 meters from Broadway's restaurants and shops, this pet-friendly apartment offers excellent access to Hollywood Beach and the lakefront trail in Chicago.
This 3-bedroom, 2-bathroom apartment accommodates up to 8 guests and includes a fully equipped kitchen, on-site laundry, and dedicated garage parking, with three complimentary bikes for exploring the area.

Centrally located in Chicago, this apartment offers convenient access to major tourist attractions and public transport, making exploration effortless.
This pet-friendly apartment accommodates two guests and includes air conditioning, a fridge, and internet, ensuring a comfortable stay for you and your dog.

Enjoy a pet-friendly stay in this updated vintage Chicago apartment, situated in the Avondale neighbourhood, conveniently close to the Green Exchange and Greenhouse Loft, with easy street parking available via permits.
This two-bedroom apartment offers a fully equipped kitchen, air conditioning, and garden access with a fire pit and grill, making it ideal for families and guests travelling with their pets.

Ideally located in Streeterville, Downtown Chicago, this apartment is a 5-minute walk from The Loop and close to Michigan Avenue's shopping and Navy Pier, offering a prime spot for exploring the city.
This pet-friendly one-bedroom apartment boasts 60 square meters of modern living space, featuring a fully equipped kitchen, a private terrace, and in-apartment laundry, perfect for guests and their pets.

Located in Chicago's South Loop, this apartment offers excellent access to major attractions, situated just 2.4 kilometres from Soldier Field and the Field Museum of Natural History, and 2.9 kilometres from Grant Park.
This pet-friendly apartment boasts 88 square metres of living space, featuring two bedrooms and two bathrooms, a fully equipped kitchen, air conditioning, a terrace with city views, and on-site parking, ensuring a comfortable stay for you and your dog.

Boasting a private entrance on Newberry Street, this first-floor condo offers a secluded feel in Chicago, just a short walk from the 18th Street corner and close to the city's attractions.
This spacious, pet-friendly apartment accommodates up to six guests and features soaring 20-foot ceilings, a fully stocked kitchen, a dedicated workspace, and an in-unit washer and dryer for convenience.

Located in Chicago's River North district, this apartment is a short distance from The Magnificent Mile for premier shopping and across the river from the Loop business district, with riverside green space just 800 meters away.
This pet-friendly apartment offers 56 square meters of stylish, modern living space with a fully-equipped kitchen, air conditioning, a swimming pool, and a balcony, perfect for up to four guests.

Situated in the cool Avondale district of Chicago, this apartment offers easy access to downtown and O'Hare International Airport, located just 11 kilometers from each.
This dog-friendly apartment sleeps four and features a fully fenced garden with a fire pit, perfect for enjoying the outdoors with your pets.

Across from a public park and pool, this four-bedroom, three-bathroom apartment offers a prime Chicago location, just a short walk from the city's renowned shopping, dining, and entertainment districts, and is a pet-friendly haven for your holiday.
This spacious apartment boasts a dedicated game room with a fireplace and a home office nook with ultra-fast Wi-Fi, perfect for families or groups of up to 10, with two dedicated parking spaces and a modern living area featuring two kitchens.

This historic 1881 walk-up apartment in Chicago's Gold Coast offers a prime pet-friendly base, just steps from the lakefront and Lincoln Park's free zoo.
Enjoy a spacious terrace, in-unit laundry, and a record player in this 2-bedroom apartment, perfect for a group of four seeking modern comforts with vintage appeal.

This two-bedroom apartment in Chicago offers excellent ratings for location and cleanliness, situated in a district with convenient access to the city's attractions.
This pet-friendly apartment, accommodating up to five guests, features 79 square meters of floor area, modern furniture, a fully equipped kitchen, and unlimited Netflix for your enjoyment.

Centrally located in Chicago's historic Bronzeville neighbourhood on a quiet street, this pet-friendly apartment is just over 3 kilometers from the University of Chicago and a mere 10-minute commute to Downtown Chicago.
This one-bedroom apartment offers a newly remodelled bathroom with a Jacuzzi tub, a well-equipped kitchen, and a large screen TV, comfortably accommodating up to two guests.

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.

This spacious apartment in Chicago welcomes pets and offers modern smart home features with ultra-high-speed WiFi, located conveniently near the CTA for easy access to Downtown, Lake Michigan, and attractions like the United Centre, which is 16 kilometres away.
Boasting 6 bedrooms and 2 bathrooms, this dog-friendly accommodation comfortably sleeps up to 18 guests and features an impressive game room with arcade games, shuffleboard, and a convertible game table, alongside outdoor entertainment options.

Located in Chicago's Irving Park neighbourhood, this pet-friendly apartment is just 11 kilometres from downtown and offers excellent access to the Blue Line and Metra trains for easy travel.
This spacious 111 square metre apartment sleeps up to six guests and boasts a newly renovated en-suite bathroom with a walk-in rainfall shower, a second bathroom with a jacuzzi tub, and a fully equipped kitchen, making it ideal for families and dog-friendly holidays.

Located in Chicago's Wicker Park district, this apartment is just a short Uber ride from downtown and within walking distance of numerous restaurants, shops, and nightlife.
This pet-friendly apartment boasts a private back porch and a shared garden, offering comfortable accommodation for up to 5 guests with a newly renovated bathroom and a fully equipped kitchen.

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.

Perfectly situated just north of downtown Chicago, this pet-friendly apartment is a mere 100 metres from Oak Street Beach and a short walk to Michigan Avenue and Millennium Park.
This one-bedroom apartment, accommodating up to three guests, offers a full kitchen, in-unit laundry, ultra high-speed Wi-Fi, and on-site parking for an additional nightly fee.

Just 965 meters from the Metra station, this apartment offers a quick 15-minute journey to downtown Chicago and is a pet-friendly haven for travellers exploring the city.
This newly renovated one-bedroom apartment accommodates up to four guests with a queen bed and sofa bed, featuring a fully equipped kitchen, air conditioning, parking, and is only 965 meters from Lake Michigan.

Located in Chicago's Albany Park, this luxury 6-bedroom house is just 24 kilometres from downtown, 16 kilometres from Wrigley Field, and 16 kilometres from O'Hare Airport, offering a pet-friendly base for exploring the city.
This spacious and recently refurbished apartment boasts a gourmet kitchen with a 5-person island, central air conditioning, a finished walk-out basement, and a private two-car garage, ensuring a comfortable stay for up to 12 guests and their pets.

Located in Chicago's West Town, this pet-friendly apartment is a short walk from Wicker Park and West Loop, offering easy public transport access to downtown.
This 51 square meter apartment features two bedrooms, a well-equipped kitchen, a private patio, and is ideal for up to six guests, with a work desk and fast internet for remote workers.

This apartment is situated in Chicago's historic Printers Row district, just a short walk from Grant Park and the Museum Campus, offering excellent transit access.
With 116 square meters of space and a private balcony boasting cityscape views, this pet-friendly loft provides ample room for up to 7 guests and includes access to a ground-floor gym.

Boasting a prime location, this four-bedroom house is just a 19-minute walk from Oak Street Beach, 1.9 kilometres from 360 Chicago, and 2.2 kilometres from Water Tower Chicago.
This pet-friendly holiday home offers ample space for families, featuring a private patio with barbecue facilities, a garden, and access to on-site spa and fitness centre amenities.

Located in Chicago's River North district, this hotel is 2.4 kilometres from Oak Street Beach and close to the Shops at Northbridge, Water Tower Chicago, and Willis Tower.
This pet-friendly hotel offers guests a swimming pool, fitness centre, sauna, and hot tub, with complimentary WiFi and on-site parking.

This pet-friendly apartment in Chicago is located a 19-minute walk from Fullerton Beach and 1.8 kilometres from Wrigley Field, offering excellent access to local attractions.
Spacious and dog-friendly, this apartment boasts 4 bedrooms, a fully equipped kitchen, a garden, a tennis court, and a bar, with free Wi-Fi and private parking making it ideal for families and groups of up to 20.

Enjoy a rare private street-facing deck and an enclosed sunroom at this pet-friendly apartment, located just 400 meters from Andersonville's shops and cafes, offering easy access to Chicago's Metra, Red Line, and express bus routes for downtown travel.
This modern 3-bedroom apartment accommodates up to 5 guests and boasts soaring ceilings, south-facing windows, individual mini-split climate control in each bedroom, a fully stocked kitchen with an eat-in breakfast nook, a formal dining room, in-unit laundry, and rare private garage parking.

Located in Chicago's River North district, this ultra high-end apartment offers a private elevator and terrace, just moments from premier nightlife and restaurants, and is a truly pet-friendly choice for your city break.
Boasting 223 square meters of floor area, this apartment comfortably accommodates 12 guests with three bedrooms, three bathrooms, a state-of-the-art kitchen featuring Gaggenau appliances, and floor-to-ceiling windows opening onto an outdoor patio, all complemented by 24-hour doorman service and included secured parking.

Located in Chicago's West Town district, this four-bedroom house is under 10 minutes by car from downtown attractions including Willis Tower and Skydeck Chicago.
This pet-friendly house offers accommodation for up to 10 guests and boasts a spacious patio with a firepit and smoker, plus six Smart TVs and a dedicated game area.

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.

This pet-friendly apartment is located in Chicago's Uptown neighbourhood, just 15 minutes from downtown and a few blocks from the CTA Red Line.
Offering 139 square meters of space, this apartment comfortably accommodates up to 4 guests with three bedrooms, a fully equipped kitchen with brand new stainless steel appliances, and in-unit laundry.

Penthouse living on the 38th floor in Chicago's Gold Coast offers breathtaking cityscape and lake views, just steps from Michigan Avenue's renowned shopping and dining.
This pet-friendly apartment provides a high-end chef's kitchen, elevator access, a rooftop pool, and a full gym, accommodating up to 10 guests with complimentary parking nearby.

This apartment is situated in a Chicago district offering proximity to local attractions, with convenient street parking and a dedicated garage spot, making it a great base for exploring the city.
This pet-friendly apartment boasts flexible sleeping arrangements for up to six guests, with an optional private upstairs suite featuring a third bedroom, office, and second living room for an additional fee.

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.

Conveniently located in Berkeley, this apartment offers excellent access to O'Hare Airport at approximately 43 kilometres and downtown Chicago at around 40 kilometres, making it a practical choice for travellers with pets.
This pet-friendly apartment comfortably accommodates up to six guests with three Queen-size beds and features a well-equipped kitchen, two TVs with Netflix, and on-site coin laundry facilities for a hassle-free stay.

Located in Chicago's Oriole Park neighbourhood, this apartment offers excellent access to O'Hare International Airport, just a 3-kilometre drive away, and is conveniently situated near the Blue and Yellow Line CTA train stations for effortless city exploration, making it a superb choice for travellers seeking a pet-friendly stay.
This family-friendly apartment boasts a chef's kitchen with a dedicated coffee bar, a unique kids' dream room, and sleeps up to six guests across three bedrooms and two bathrooms, ensuring a comfortable and convenient home-away-from-home experience where pets are welcome.

Located in Chicago's Avondale district, this apartment is a 15-20 minute drive from downtown attractions, placing you in a globally recognised area for its dining and street life.
This pet-friendly apartment, suitable for up to 4 guests, boasts a full kitchen, a king bed, and two twin mattresses, offering a fun and wondrous atmosphere within a 1911 building.