Holiday Rentals in Chicago, IL

This pet-friendly apartment in Chicago's South Loop is conveniently located 2.25 kilometres from the Field Museum and 2.73 kilometres from Grant Park, offering easy access to McCormick Place and downtown attractions.
Boasting 104 square metres of living space, this family-friendly apartment features three bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, and on-site parking, ensuring a comfortable stay for up to 19 guests.

This Berwyn apartment is conveniently located for exploring Chicago's major attractions, situated approximately 21 kilometres from the United Center and 26 kilometres from McCormick Place.
This pet-friendly apartment accommodates up to 8 guests and offers essential amenities including air conditioning, linens, and on-site laundry facilities.

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.

Located in East Lakeview, this apartment is just 320 meters from Lake Michigan and within easy reach of Lincoln Park Zoo and Wrigley Field.
This spacious 232 square meter apartment is a pet-friendly haven, offering three bedrooms, two bathrooms, and dedicated work-from-home spaces, perfect for families and groups of up to 20 guests.

Conveniently located in Chicago's West Town district, this detached house is just 1 block from the METRA, offering swift access to the United Center, Millennium Park, and downtown Chicago.
This pet-friendly 3-bedroom house accommodates up to 6 guests and features a private yard, free street parking, and a kitchen equipped with a fridge, ensuring a comfortable stay for you and your dog.

Conveniently located in Cook County, this apartment offers easy access to O'Hare Airport and is just a short distance from the Blue Line for exploring Chicago.
This pet-friendly apartment is ideal for families and features a full kitchen with high-end appliances, complimentary private parking, and free Wi-Fi, accommodating up to 4 guests with 2 pets allowed for a fee.

Boasting a large whirlpool hot tub, this two-bedroom apartment in Berwyn is a truly pet-friendly option for your stay.
Conveniently located just over 32 kilometres from downtown Chicago, this spacious apartment offers a separate living and dining area, air conditioning, and allows pets.

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.

Located in Chicago's Lakeview district, this apartment is just 700 meters from the entertainment hub of Southport and close to Wrigley Field, offering a prime spot for exploring.
This pet-friendly apartment accommodates up to six guests with two bedrooms, featuring a private patio garden and essential amenities, ensuring a comfortable stay for families and their pets.

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.

Located in Bridgeview, this apartment is a 20-minute drive from downtown Chicago, offering a peaceful stay in a southwest suburban neighbourhood.
This pet-friendly apartment boasts a private, fenced garden with a fire pit and accommodates up to six guests across three bedrooms, including a self check-in option for convenience.

Located in Chicago's Avondale neighbourhood, this apartment is housed within a classic 1896 Greystone building, offering historic architectural details and excellent access to public transport, including Blue Line stations less than 1 kilometre away.
This pet-friendly apartment features a fully furnished interior with two queen-size beds, a full kitchen, and a garden patio, providing ample space for up to four guests and a dog-friendly environment near popular Logan Square eateries.

Boasting a private urban entrance in Chicago, this coach house offers a unique city feel with excellent ratings for location and cleanliness, ensuring a peaceful stay thanks to its noise detection device.
This pet-friendly apartment sleeps six across three bedrooms, each with a private en-suite, and features a fully-equipped kitchen, a 65" HD TV, and a sofa bed for extra guests, making it ideal for families or groups travelling with their dogs.

Located in a historic Chicago neighbourhood, this apartment offers an authentic city experience, placing you less than 32 kilometres from summer beaches, Lollapalooza, Bears football, golf, and museums.
This pet-friendly apartment provides ample space for larger groups and features a dedicated back porch area, ensuring a comfortable and convenient stay for you and your dog-friendly companions.

Located in Chicago's Pilsen neighbourhood, this newly renovated studio is 3.4 kilometres from the United Centre and 5.9 kilometres from Union Station, Willis Tower, and Guaranteed Rate Field.
This dog-friendly studio offers 65 square metres of space for up to three guests, featuring a fully equipped kitchen with a fridge and microwave, air conditioning, and complimentary WiFi.

This pet-friendly apartment in Chicago's Old Town district is just an 11-minute walk from Lincoln Park Zoo and a 13-minute stroll to North Avenue Beach, with 360 Chicago and Water Tower Chicago also nearby at 2.7 kilometres away.
Offering air conditioning and a fully equipped kitchen with a dishwasher, this apartment provides free WiFi and a private entrance, ensuring a comfortable stay for you and your dog.

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.

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 Ridge, this apartment is situated 10.3 kilometres from Midway International Airport, with Guaranteed Rate Field and the Museum of Science and Industry both 22.5 kilometres away.
This pet-friendly apartment offers a spacious 102 square meter layout with one bedroom and two bathrooms, accommodating up to 7 guests and featuring a balcony, air conditioning, and free WiFi.

This pet-friendly house in Chicago is located in a neighbourhood with easy access to public transport and dining, just 2.7 kilometres from Wrigley Field and 5.3 kilometres from Loyola University Chicago.
Offering 186 square metres of space with three bedrooms and two bathrooms, this accommodation comfortably sleeps eleven guests and features air conditioning, a patio, and free WiFi, making it ideal for groups travelling with their pets.

Boasting breathtaking panoramic views of Chicago and the lake from its 38th floor perch, this penthouse apartment is located in the Gold Coast district, mere steps from Michigan Avenue.
This pet-friendly apartment offers 139 square meters of space, accommodating up to 10 guests across 3 bedrooms with a rooftop pool and gym, and is conveniently situated just 150 meters from the beach.

This pet-friendly apartment in Chicago's Uptown district is situated just 4 minutes on foot from the Lawrence Red Line station and a short stroll from Montrose Beach, Aragon Ballroom, and Riviera Theatre.
Boasting a fully stocked kitchen with modern appliances, a dedicated workstation, and an in-unit washer/dryer, this one-bedroom apartment offers comfortable accommodation for two guests, with a rooftop area providing city views and access to a fitness centre.

Boasting unparalleled lake views, this downtown Chicago penthouse is just 640 metres from Grant Park and a 11-minute walk from DePaul University, making it a prime location for exploring the Art Institute of Chicago and the Chicago Symphony Orchestra.
This pet-friendly, three-bedroom apartment offers 102 square metres of space, accommodating up to eight guests with a kitchen, air conditioning, a balcony, and access to an on-site fitness centre, ensuring a comfortable stay for you and your dog.

This pet-friendly apartment in Chicago offers a private patio with outdoor seating and a fire pit, ideal for guests travelling with pets.
Conveniently located 3.9 kilometres from the United Center and 6.1 kilometres from Water Tower Chicago, this 51 square metre apartment sleeps up to six guests and includes free WiFi and private parking.

Located on Michigan Avenue, this apartment is conveniently situated 2.25 kilometres from the Field Museum and close to Soldier Field and Grant Park.
This pet-friendly apartment offers 84 square metres of living space with two bedrooms, two bathrooms, and a fully equipped kitchen, plus on-site parking and a fitness centre.

Located in the River North & Gold Coast districts, this apartment is just 160 meters from Michigan Avenue and 640 meters from Lake Michigan, offering a prime spot near Oak Street Beach and Navy Pier.
This dog-friendly apartment boasts a chef's kitchen with state-of-the-art GE appliances and comfortable sleeping arrangements for over 10 guests, making it ideal for families and groups travelling with their pets.

Directly opposite Wrigley Field in Chicago's Wrigleyville, this recently renovated apartment offers prime access to the iconic stadium.
This dog-friendly apartment boasts three bedrooms accommodating up to six guests, featuring in-unit laundry, a fully equipped kitchen, and on-site parking, with baby equipment available upon request.

Boasting a prime location in Chicago's West Town district, this apartment is less than 2 kilometres from iconic attractions like the Willis Tower and Skydeck Chicago.
This dog-friendly apartment offers a spacious 4-bedroom, 2-bathroom layout accommodating up to 10 guests, complete with a fully equipped kitchen, a garden, and a patio featuring a firepit and smoker for enjoyable outdoor living.

Apartment for up to 3 guests with an excellent rating of 99% based on 126 reviews. You will be in Chicago.
Services and facilities: a dish washer, an iron and a fridge. Take advantage of the air conditioning in this apartment in Chicago.

This pet-friendly apartment in Chicago's Lakeview district is conveniently located just 560 meters from Lake Michigan and 800 meters from the Diversey Brown/Purple Line, with Boystown and Wrigley Field also a short walk away.
Boasting 38 square meters of space with one bedroom and a full-size futon, this apartment comfortably accommodates up to three guests and features a well-equipped eat-in kitchen, a private deck, and in-unit laundry facilities for a hassle-free stay.

Located in Chicago's McCormick Place district, this studio is conveniently situated near Soldier Field and Downtown, with the Field Museum, Grant Park, and the Art Institute of Chicago all within 2.9 kilometres.
This pet-friendly studio offers 51 square metres of living space, featuring a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus complimentary Wi-Fi and on-site parking.

Set in Chicago's Fulton Market district, this penthouse is perfectly positioned for exploring the city's renowned dining and nightlife, with private parking included for your convenience.
This dog-friendly apartment offers 3 bedrooms, 2 bathrooms, and sleeps up to 10 guests, featuring a fully equipped kitchen, air conditioning, and access to a building gym and rooftop with city views.