Holiday Rentals in Chicago, IL

This apartment in Chicago offers a spacious private yard with patio furniture, ideal for outdoor entertaining and BBQs, and is a truly dog-friendly accommodation.
Guests can enjoy an expansive open-plan living and kitchen area, a large basement family room with a 65-inch TV and surround sound, and the convenience of two bathrooms, all accommodating up to 10 people.

Experience a unique B&B stay in this pet-friendly apartment, offering daily breakfast from a highly-rated Irish restaurant downstairs and located just 800 meters from the iconic Wrigley Field and the scenic Chicago Riverwalk.
This dog-friendly apartment provides two bedrooms, a modern bathroom, a fully equipped kitchen with stainless steel appliances, an in-unit washer/dryer, and an office space with an air mattress, comfortably accommodating up to six guests with pets allowed.

Bucktown's entertainment district is easily accessible from this unique house, located just 1 kilometre from the lakefront.
This expansive, pet-friendly estate boasts 8 bedrooms, 4 bathrooms, and a private cabaret theatre, Tiki Bar Saloon, and Cloud Spa, offering an unforgettable experience for large groups and celebrations.

This pet-friendly apartment in Chicago offers a private ground-floor entrance and garden views, located just 4 kilometres from Midway International Airport and within easy reach of Guaranteed Rate Field (9 kilometres) and the Museum of Science and Industry (10 kilometres).
Boasting 70 square meters of floor area, this dog-friendly apartment comfortably accommodates up to 7 guests with its 1 bedroom, 1 bathroom, and a sofa bed, featuring a fully equipped kitchen with a dishwasher and microwave, plus complimentary WiFi.

North of Boystown in Lakeview, this pet-friendly studio is a 2 kilometre walk from Wrigley Field and close to Lake Michigan, the Red Line, and numerous dining and entertainment options.
This fully equipped apartment offers a queen-size bed, fast Wi-Fi, and air conditioning, making it ideal for two guests seeking a comfortable stay with their pets in Chicago.

This pet-friendly 1-bedroom apartment is conveniently located in a Chicago district, offering easy access to key landmarks.
Guests can enjoy a fully furnished space with a king-size bed and a well-equipped kitchen, perfect for up to two people and their cats upon approval.

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.

Directly opposite Lake Opeka, this Des Plaines house offers fishing, boating, and picnic areas, with O'Hare Airport, Allstate Arena, and Rivers Casino just 5 minutes away.
This pet-friendly house boasts a newly remodelled kitchen, two 75-inch TVs, a finished basement, and ample parking for up to six cars, comfortably accommodating ten guests with three bedrooms and two bathrooms.

This pet-friendly apartment is perfectly situated in Chicago's Greektown, just 0.7 kilometres from Willis Tower and a 9-minute walk to Union Station.
Enjoy city views from the private balcony of this 65 square metre, 1-bedroom apartment, which comes complete with a microwave, dishwasher, and barbecue, and welcomes pets.

This 2-bedroom apartment in Chicago offers a highly walkable and bikeable neighbourhood, situated just 24 kilometres from downtown Chicago, accessible by a 28-minute train ride or a 15-minute drive.
This pet-friendly apartment boasts a fully equipped kitchen, in-unit laundry, and dedicated workstations, providing a comfortable stay for up to 4 guests with a private patio and multiple parking options.

Boasting a prime location between Chicago's most sought-after neighbourhoods, this two-bedroom apartment offers immediate access to dining and nightlife, with the Blue Line transit just a 10-minute walk away for swift connections to downtown and O'Hare.
This pet-friendly apartment comfortably accommodates up to five guests and features a fully updated kitchen with brand-new appliances, a cozy living space with a queen pullout sofa, and a large screen TV, ensuring a pleasant stay for you and your dog.

Prime Wicker Park, Chicago, this pet-friendly apartment is located at North Ave & Ashland, offering a convenient 16-minute commute to downtown.
This spacious, stylishly updated 3-bedroom apartment boasts free on-site parking and accommodates up to 6 guests, with a fully equipped kitchen and air conditioning.

Located in a Chicago neighbourhood, this pet-friendly studio is conveniently situated 4.3 kilometres from Wrigley Field and 17.7 kilometres from O'Hare International Airport.
This spacious 74 square metre studio apartment welcomes pets and features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, along with air conditioning, free WiFi, and parking for a comfortable stay.

Experience a sun-drenched duplex in Chicago's Pilsen district, offering a unique "urban treehouse" feel with floor-to-ceiling windows, just a short walk from the National Museum of Mexican Art and Pilsen's renowned street art.
This pet-friendly apartment boasts a sleek chef’s kitchen, a primary suite with a skylight, and a rare private parking spot, providing comfortable accommodation for up to seven guests with convenient access to the Pink Line for city exploration.

Just a 4-minute walk from Wrigley Field, this 3-bedroom apartment in Chicago's Wrigleyville neighbourhood offers a fantastic location for baseball fans and is exceptionally pet-friendly.
Enjoy 111 square meters of living space with a fully equipped kitchen, air conditioning, and a private terrace, making it an ideal base for exploring attractions like Lincoln Park Zoo, just 4.1 kilometres away.

Just a 3 to 5 kilometre drive from Fulton Market, downtown, Wicker Park, and the United Centre, this pet-friendly apartment offers prime access to Chicago's popular districts and the Randolph Street culinary scene.
This one-bedroom apartment, accommodating up to four guests, boasts excellent ratings for location, cleanliness, and user experience, featuring a private terrace, shared backyard, and luxurious bathroom amenities including floor warmers and Bluetooth mirrors.

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 Dunning, this apartment is a 7-minute drive to Target and within a 24-40 minute drive of O'Hare International Airport, Copernicus Center, and Logan Square.
This 3-bedroom apartment comfortably accommodates 8 guests and is dog-friendly, featuring a full kitchen with a dishwasher, air conditioning, and an on-site gym with a Peloton bike.

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 a Chicago district, this apartment is just 1.4 kilometres from the city centre, offering an 18-minute walk to Oak Street Beach and proximity to Water Tower Chicago.
This pet-friendly apartment, boasting 80 square metres and space for up to 6 guests, features air conditioning, a private balcony with city views, and complimentary Wi-Fi, ensuring a comfortable stay for you and your dog.

This pet-friendly house is located in downtown Chicago, just 965 meters from the Field Museum of Natural History and a 15-minute walk from Grant Park.
With a floor area of 98 square meters, this accommodation offers 2 bedrooms, 2 bathrooms, and a guest capacity of 8, featuring a fully equipped kitchen, air conditioning, and a sun terrace for a comfortable stay with your pets.

Perfectly situated in Chicago's Near North Side, this studio offers prime access to Old Town, Lincoln Park, and the Clybourn Corridor, just a short walk from New City shopping and the Second City Theater.
This pet-friendly studio boasts a generous 65 square meters of space for up to 4 guests, featuring a fully-equipped kitchen with stainless steel appliances, in-unit laundry, and impressive city views.

This apartment in Chicago's Rogers Park neighbourhood is just three blocks from Lake Michigan and the seaside, offering easy access to public transport for downtown attractions.
This pet-friendly apartment accommodates four guests and boasts newly remodelled bathrooms with a jetted tub and bidet, a fully stocked kitchen with unique appliances, and on-site laundry facilities.

Located in Chicago's trendy River North district, this apartment is just a 5-minute walk from the Merchandise Mart and The Loop, with Michigan Avenue shopping and entertainment also nearby.
This pet-friendly apartment offers 77 square meters of living space, accommodating up to 2 guests with a fully equipped kitchen, in-apartment laundry, and access to on-site amenities including a swimming pool and sauna.

This expansive two-storey penthouse apartment in Chicago's Downtown Loop district offers million-dollar views and is situated just 160 meters from the Red Line 'L' subway, within walking distance of Millennium Park, the Art Institute, and The Bean.
This pet-friendly apartment boasts 220 square meters of living space across two levels, accommodating up to 14 guests with five bedrooms and five bathrooms, featuring a private rooftop deck, a gym, pool, and is conveniently located near Soldier Field and the Museum Campus.

This top-floor luxury apartment in Chicago's Fulton Market district offers stunning skyline views and is just a 7-minute walk to Union Park and 10 minutes to Google HQ, making it an ideal base for exploring the city.
Boasting accommodation for up to 22 guests with 9 Queen rooms and 8 bathrooms, this pet-friendly apartment also provides access to 30,000 sq. ft. of building amenities including a pool, spa, and fitness centre, ensuring a comfortable stay for you and your dog.

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.

Located in Chicago's Logan Square district, this pet-friendly apartment is a short trip from downtown and equidistant from two Blue Line stops, offering easy access to O'Hare International Airport and the city centre.
This two-bedroom apartment accommodates up to five guests and boasts a fully equipped kitchen, air conditioning, complimentary toiletries, and a midcentury record player for your enjoyment.

This Lincoln Park apartment, located very close to the North & Clybourn Red Line station, offers immediate access to numerous restaurants, shops such as Whole Foods and Trader Joe's, and the Steppenwolf Theatre.
Pets are welcome in this spacious four-bedroom apartment that accommodates up to 12 guests, featuring multiple private decks and complimentary access to three dedicated parking spots.

Perfectly situated in Chicago's Historic Old Town Triangle district, this apartment is just 160 meters from Wells Street's dining and entertainment, and 320 meters from Lincoln Park, the Zoo, and Lake Michigan's path, offering a truly pet-friendly escape.
Enjoy a luxurious stay with three bedrooms accommodating up to four guests, featuring Carrera marble bathrooms, high-speed internet, and complimentary bicycles for exploring the city, all within this dog-friendly apartment.

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.

Enjoy a family-friendly apartment stay in Chicago, conveniently located just 6.9 kilometres from the United Centre and within 10.1 kilometres of key attractions like Water Tower Chicago and the Lincoln Park Zoo, with complimentary on-site parking and free Wi-Fi making it a great choice for travellers seeking a pet-friendly base.
This 102 square metre apartment offers air conditioning, a full kitchen with a dishwasher, and an outdoor dining area with a garden, ensuring a comfortable stay for up to seven guests and accepting pets.

Prime Wrigleyville offers a pet-friendly apartment experience just a 2-minute walk from Wrigley Field, with Lincoln Park Zoo located 3.9 kilometres away and Loyola University Chicago 6.4 kilometres distant.
This spacious 195 square metre duplex apartment boasts five bedrooms, two bathrooms, two living rooms with a fireplace, a fully equipped kitchen, and private parking, making it ideal for larger groups travelling with their pets.

This luxurious 3-bedroom apartment in Chicago's city centre offers a private 3-story retreat with a 360° roof deck, just a 5-minute drive from Fulton Market's dining scene and the United Center Arena, and within 10 kilometres of Lake Michigan.
This pet-friendly accommodation boasts a King Suite with a steam shower, a Queen Suite with private roof deck access, a full kitchen with a balcony, and a private garage, making it ideal for families and travellers with pets seeking a dog-friendly stay with high-speed WiFi and Smart TVs.