Pet-friendly Vacation Rentals in Chicago, IL

Just a few blocks from the CTA Pink Line offering direct routes to Chicago, this newly renovated studio apartment is conveniently located in Cicero, directly across the street from a Dollar General.
This pet-friendly studio sleeps up to 3 guests and boasts a fully equipped kitchen, on-site laundry, and a large smart TV with complimentary Wi-Fi, making it an excellent choice for travellers with pets.

This spacious 5-bedroom house in Chicago is a truly pet-friendly option, located just 6.5 kilometres from the Museum of Science and Industry and 7.6 kilometres from Guaranteed Rate Field.
With a generous floor area of 362 square meters, this dog-friendly accommodation boasts multiple living spaces, a fully equipped kitchen, a fitness centre, and entertainment options like billiards and table tennis, ensuring a comfortable stay for up to 16 guests.

Just a 3-minute walk from the Red Line CTA, this 1-bedroom apartment in Chicago offers excellent access to public transport, shops and restaurants, placing you a mere 12-minute ride from Wrigley Field.
This pet-friendly apartment welcomes your furry companions and provides essential amenities including a fridge, freezer, microwave, and air conditioning, ensuring a comfortable stay.

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.

Just 700 meters from Montrose Beach and the Lakefront Trail, this pet-friendly studio apartment offers prime North Side Chicago accommodation between Uptown and Lakeview.
This dog-friendly aparthotel provides a convenient base for exploring Wrigley Field and Ravenswood, with easy access to downtown via the CTA Red & Brown Lines, and allows pets with prior approval and a fee.

Located in the northwest corner of Chicago, this renovated private second-story apartment offers convenient proximity to O'Hare Airport, just 12 kilometers away, and is close to various restaurants, coffee shops, and grocery stores.
This dog-friendly apartment, boasting 93 square meters of floor area, accommodates up to 10 guests and features a well-equipped kitchen, air conditioning, a garden, a spa, and free high-speed fibre Wi-Fi, making it an ideal choice for travellers with pets.

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.

North Park, close to Lincolnwood, offers convenient access to O'Hare Airport (32 kilometres away) and downtown Chicago via public transport, with numerous restaurants, supermarkets, malls, and parks nearby.
This spacious, newly renovated 3000 sq ft apartment is dog-friendly and features ample living space, a fully equipped kitchen, and a garden, making it ideal for families and travellers with pets.

Located in the safe Beverly district of Chicago, this renovated cottage is a convenient 20-kilometre drive from downtown's dining and entertainment.
This pet-friendly apartment offers air conditioning, a garden, and accommodates up to six guests, providing a tranquil atmosphere with essential amenities.

Located in a quiet district of Chicago, this apartment offers a peaceful retreat after a day of exploring, ensuring a comfortable and clean shower experience.
This pet-friendly apartment, which welcomes pets, features a kitchenette and provides linens, making it a practical choice for budget-conscious travellers seeking a quiet night's rest in Chicago.

Centrally located in Chicago's River North district, this apartment is just under 800 metres from Water Tower Chicago and 1.8 kilometres from Oak Street Beach.
This pet-friendly apartment offers a fully equipped kitchen, air conditioning, free WiFi, and access to building amenities including a gym, making it ideal for those travelling with their dogs.

This pet-friendly apartment in Chicago's East Lakeview district is just a 1.6-kilometre walk from Wrigley Field and Boystown, and conveniently located 500 meters from the Sheridan Red Line station for direct downtown access.
This stylish apartment offers a guest capacity of five, boasting a fully equipped kitchen, air conditioning, high-speed WiFi, and an in-unit washer and dryer, ensuring a comfortable stay for you and your dog.

Located in Chicago's Little Italy, this furnished one-bedroom apartment is a short distance from the Art Institute of Chicago and Field Museum, and close to Michigan Avenue and Navy Pier.
This pet-friendly apartment boasts 72 square meters of living space, a fully equipped kitchen, and building amenities including a swimming pool and doorman, perfect for a comfortable stay with your dog.

This duplex apartment is located in Chicago's Rogers Park district, a short 500-meter walk from Loyola Park and approximately 8 kilometers from Wrigley Field, offering a pet-friendly base for your visit.
With two bedrooms and 1.5 bathrooms accommodating up to four guests, this apartment boasts a fully equipped kitchen, in-unit laundry, and central air conditioning, making it ideal for families or small groups travelling with pets.

Centrally located in Westchester, this apartment offers convenient access to major roads, restaurants, and shopping, with Oak Brook Golf Course and Garfield Park just a short drive away.
This pet-friendly apartment is ideal for extended stays and corporate housing, boasting 3 bedrooms, 2 bathrooms, and Smart TVs in every bedroom, alongside ample parking for 2-3 cars and keyless entry for your convenience.

This pet-friendly apartment in Chicago offers a modern, professionally designed interior with a fitted kitchen, a plush sectional sofa, and entertainment amenities including large flat-screen TVs.
Located in a Chicago walk-up building, this ground-floor, basement unit requires a descent of six steps and includes one reserved outdoor parking spot, making it ideal for travellers with pets.

Located in Andersonville, a district recognised as one of the world's coolest neighbourhoods, this apartment is just a short walk from Clark Street's dining and shops, and within easy reach of the Argyle Red Line and Ravenswood Metra for travel to Downtown and Wrigleyville.
This pet-friendly, two-bedroom apartment comfortably accommodates four guests and features a modern kitchen with a full island, stainless steel appliances, and in-unit laundry, ensuring a convenient stay for you and your dog.

Located in Chicago's Lincoln Park district, this apartment offers immediate access to McGee's Tavern and Grille and is within 1.5 kilometers of numerous cafes, dining options, pubs, parks, and public transport.
This pet-friendly apartment on the second floor boasts a full kitchen, high-speed internet, air conditioning, and includes free 24-hour street parking, comfortably accommodating up to 4 guests.

Historic Bronzeville offers this five-bedroom apartment, just 800 meters from the Obama Presidential Center and 1.6 kilometers from the University of Chicago, with complimentary two-car parking on a private gated driveway.
This expansive 344-square-meter apartment boasts a chef's kitchen, a spa-like master bathroom, and a heated Flex Studio, making it an ideal pet-friendly haven with a fenced backyard and rooftop deck for enjoying sweeping Chicago skyline views.

Conveniently located in Chicago's Bridgeport district, this apartment is situated just over 3.2 kilometres from Willis Tower and a 10-minute Uber ride to Michigan Avenue, also within walking distance of the White Sox's park.
This expansive 186 square metre pet-friendly apartment offers accommodation for up to 8 guests, boasting 3 bedrooms, 3 bathrooms (one with a jetted tub), a private patio with a grill, and a living area with a sofa bed and office space.

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.

Located in Chicago's prestigious Gold Coast district, this penthouse apartment is a mere stroll from Michigan Avenue's renowned shopping and dining, and just a short distance to the beach, offering a prime position for exploring the city.
This dog-friendly, 139 square meter apartment boasts a professionally designed interior and comfortably accommodates up to 10 guests, featuring a fully equipped chef's kitchen and access to a rooftop pool and gym, making it ideal for families and groups.

Located in Chicago's central district, this expansive loft is just 8 minutes on foot from DePaul University and 0.96 kilometres from Grant Park, placing you near major cultural institutions.
This pet-friendly apartment offers 295 square meters of space with 5 bedrooms and 6 bathrooms, accommodating up to 35 guests with a fully equipped kitchen, private balcony, and fitness centre.

Situated in Chicago's esteemed Gold Coast, this luxury penthouse is mere steps from Lake Michigan and offers unparalleled access to dining and shopping.
This pet-friendly apartment, boasting 167 square meters of space, features three en-suite bedrooms, a chef's kitchen with premium appliances, and two private patios, comfortably accommodating up to 10 guests.

Located in Chicago's East Village, this spacious 4-story apartment is a short subway ride from downtown attractions like the Loop and Michigan Avenue, with convenient access to the I-90/94 expressway.
This pet-friendly apartment offers 223 square meters of living space with four bedrooms and four bathrooms, featuring luxury amenities such as an en-suite spa bathroom, a chef's kitchen with marble countertops, and two terraces with skyline views, accommodating up to 12 guests.

Rare private garage parking is available at this spacious third-floor apartment in Chicago's Avondale neighbourhood, offering a pet-friendly base conveniently located between Logan Square and Avondale with easy access to the CTA Blue Line for downtown travel.
This entire apartment spans 223 square meters and features four true bedrooms, two bathrooms, and accommodation for up to eight guests, complete with a kitchen, air conditioning, and a terrace/balcony for a comfortable stay.

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.

Located in the Streeterville district, this apartment offers a prime position near Chicago's top attractions, with the building itself providing a doorman and laundry facilities.
This pet-friendly apartment, featuring a fully equipped kitchen and smart TV, is perfect for two guests and boasts a comfortable 60 square meters of living space, with a swimming pool and fitness centre available on-site.

Offering an excellent location in Chicago's Avondale/Logan Square district, this recently remodelled first-floor apartment is just a short walk from acclaimed restaurants and coffee shops, with convenient access to major highways and public transport.
This pet-friendly apartment comfortably accommodates up to eight guests and includes complimentary 100 Mbps internet, a dishwasher, and a 4K smart TV, making it ideal for families and those travelling with pets.

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.

Boasting an expansive 1000 sqft rooftop terrace with city skyline views, this luxurious apartment is situated in Chicago's Humboldt Park district, approximately 8 kilometres from downtown.
This dog-friendly apartment offers five spacious bedrooms, each with a private en-suite bathroom, and accommodates up to 16 guests, featuring three distinct living areas, a modern kitchen, and a secure two-car private garage.

This South Loop apartment is conveniently located 2.25 kilometres from the Field Museum and within easy reach of McCormick Place and the lakefront.
Enjoy a spacious 88 square metre, two-bedroom apartment in this pet-friendly South Loop location, offering a fitness centre and city views for a comfortable stay.

Just 5 minutes' walk from the CTA Green Line's Kedzie station, this newly renovated 4-bedroom apartment offers easy access to downtown Chicago and the West Loop, with Garfield Park Conservatory nearby.
This pet-friendly apartment comfortably accommodates up to 10 guests and features a fully stocked kitchen, high-speed Wi-Fi, central air conditioning, and convenient garage and street parking.

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.