Holiday Rentals in Chicago, IL

Located in Chicago's West Loop Gate, this apartment offers excellent access to Michigan Avenue, Navy Pier, Millennium Park, and Grant Park, all within a 2-kilometer radius.
This dog-friendly apartment is fully furnished and features in-apartment laundry, a fully equipped kitchen, high ceilings, and building amenities including a swimming pool and fitness centre, making it ideal for travellers with pets.

Located in Chicago's historic Beverly area, this apartment offers a unique, tree-lined community setting.
This spacious, pet-friendly apartment comfortably accommodates six guests, featuring two large bedrooms with TVs and soundbars, a 65-inch living room TV, and a fully equipped modern kitchen.

This South Loop apartment is located just 2.4 kilometres from the Field Museum and within 2.9 kilometres of Grant Park and DePaul University.
This pet-friendly apartment offers 84 square metres of space with two bedrooms and two bathrooms, featuring complimentary WiFi, on-site parking, a terrace with city views, and access to a fitness centre, making it ideal for families and groups visiting Chicago.

Located in the Lincoln Park district of Chicago, this apartment offers convenient free street parking and private access to the entire unit.
This pet-friendly apartment boasts 15ft ceilings, a queen-size bed, a fully equipped kitchen, and accommodates up to four guests, ensuring a comfortable stay for you and your dog.

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 River North, this apartment is a 5-minute walk to Merchandise Mart and The Loop, placing you in Chicago's prime entertainment and shopping district.
This pet-friendly apartment offers 66 square meters of living space for up to two guests, featuring a fully equipped kitchen, air conditioning, and access to a swimming pool and doorman services.

A short drive from Sox Park and just 15 kilometres from downtown Chicago attractions such as Millennium Park, this apartment offers a convenient base for exploring the city.
This pet-friendly apartment boasts a dedicated workspace with over 500 Mbps internet, a classic Simpsons arcade machine, and a shared, fully fenced backyard, comfortably accommodating up to six guests.

Discover this pet-friendly apartment in Chicago's Historic Old Town Triangle, just steps from diverse dining, shopping, Lincoln Park Zoo, and Lake Michigan, with the Brown Line public transport readily accessible.
This one-bedroom apartment offers a budget-friendly stay with included utilities, complimentary 1G internet, on-site laundry, and two bicycles for guest use, making it ideal for short-term visitors and those relocating with their pets.

This spacious 1,500 sq ft, two-bedroom, two-bathroom condominium in Chicago Ridge is a pet-friendly haven, offering a fantastic family-friendly environment with excellent user, location, and cleanliness ratings.
Conveniently located just a short drive from local parks and attractions in Chicago Ridge, this apartment boasts in-unit laundry and flexible parking, making it an ideal choice for travellers seeking a comfortable and dog-friendly stay.

Conveniently located in Chicago's South Loop, this pet-friendly 2-bedroom apartment is just 2.25 kilometres from the Field Museum, offering easy access to McCormick Place and downtown Chicago.
Enjoy this spacious, naturally lit corner unit apartment, boasting 74 square metres, two bathrooms, a fully equipped kitchen, complimentary WiFi, and an on-site fitness centre, perfect for families and those travelling with pets.

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 Chicago's South Shore, this apartment offers a pet-friendly stay just a short distance from Lake Michigan's shores and within a 20-minute drive of McCormick Place and Soldier Field.
This spacious 139 square metre apartment, suitable for up to 8 guests, boasts air conditioning, a microwave, and yes, pets are allowed, making it an ideal base for exploring attractions like the Museum of Science & Industry and the Obama Library.

This two-bedroom apartment in Chicago offers excellent walkability and bikeability, being just 28 minutes by train or 22 minutes by bike from downtown Chicago, and is located in a safe, working-class neighbourhood.
Perfect for travellers with pets, this dog-friendly apartment boasts a fully stocked kitchen, air conditioning, a private patio, and ample parking, ensuring a comfortable stay for up to four guests.

Relax in your private outdoor hot tub in a leafy, fenced-in yard, a perfect feature for this pet-friendly studio apartment in a Chicago neighbourhood offering easy access to attractions.
This dog-friendly apartment boasts an industrial-chic aesthetic with high ceilings and eclectic decor, providing a comfortable king-size bed, a well-equipped kitchen, and a jetted tub, with optional garage parking available for an additional nightly fee.

Offering excellent transit links, this pet-friendly apartment in Chicago's West Town district provides convenient access to the Loop via the Blue or Green Line, with Wicker Park and River North also easily reachable within approximately 2.5 kilometers.
This apartment features in-unit laundry, fast Wi-Fi, and a kitchen with a fridge, freezer, microwave, and dishwasher, making it ideal for longer stays and relocations, with one dog permitted per stay.

Just 8 minutes on foot from the iconic Wrigley Field, this apartment is situated in Chicago's Wrigleyville district, offering convenient access to Fullerton Beach (2.6 kilometres) and Lincoln Park Zoo (3.4 kilometres), as well as downtown attractions like Water Tower Chicago and 360 Chicago (both 6.3 kilometres away).
This spacious, pet-friendly 5-bedroom apartment boasts 60 square meters of living space, featuring air conditioning, complimentary WiFi, and private on-site parking, making it an ideal choice for families and dog-friendly holidays in Chicago.

Conveniently located just 6 kilometres from Chicago O'Hare International Airport, this apartment offers easy access to popular Chicago attractions such as Wrigley Field, 17.7 kilometres away, and Lincoln Park Zoo, 19.3 kilometres distant.
This pet-friendly three-bedroom apartment boasts 98 square metres of living space, accommodating up to 17 guests with two bathrooms, a fully equipped kitchen featuring a dishwasher and microwave, free WiFi, air conditioning, and on-site laundry facilities.

Set in a historic 19th-century building, this pet-friendly apartment in Chicago is a 19-minute walk from Fullerton Beach and 1.7 kilometres from Wrigley Field, also conveniently close to Lincoln Park Zoo.
This spacious apartment offers 4 bedrooms, 2 bathrooms, a fully equipped kitchen with a dishwasher and oven, and features a garden, a tennis court, and a sun terrace, making it ideal for families and offering excellent opportunities for cycling and fishing.

Offering a unique travel experience, this 32' RV in Alsip, a south Chicago suburb, is conveniently located approximately 22-25 kilometres from major Chicago attractions including Guaranteed Rate Field, the Museum of Science and Industry, the Field Museum, and Willis Tower.
This pet-friendly accommodation welcomes your furry companions and features a terrace, free WiFi, and complimentary private parking, ensuring a comfortable stay for up to 7 guests with self-catering kitchen facilities.

This River North apartment is conveniently located just over 0.8 kilometres from 360 Chicago and approximately 1.9 kilometres from Oak Street Beach, offering a pet-friendly base in the city.
Enjoy year-round comfort with air conditioning and make use of the fully equipped kitchen, including a barbecue, in this one-bedroom apartment that accommodates up to two guests.

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.

Just 160 meters from Wrigley Field, this apartment in Chicago's Lakeview district offers an unbeatable location for game days and concerts.
This pet-friendly apartment boasts 84 square meters of space, accommodating up to six guests with a fully equipped kitchen and modern amenities, making it ideal for longer stays or home-style meals.

Ideally situated in Chicago's Humboldt Park, this apartment offers superb public transport links and is just minutes from the popular 606 Trail, making it a truly pet-friendly choice for exploring the city.
This modern, 93 square meter apartment accommodates up to four guests with two bedrooms, one bathroom, and boasts a private terrace, a garden, and a fully equipped kitchen, ensuring a comfortable stay for you and your pets.

Located in Chicago's prime Gold Coast, this apartment offers superb walkability to Oak Street Beach, the Magnificent Mile, and Navy Pier, all within a few blocks, and is just around the corner from the Clark/Division Red Line and several CTA bus routes.
This pet-friendly apartment is ideal for families and boasts excellent ratings for user experience, location, and cleanliness, featuring air conditioning, a full kitchen including a dishwasher, and accommodates up to four guests.

Located in Melrose Park, this top-floor apartment offers a peaceful retreat with excellent access to local dining and a playground just a short walk away, whilst being only an 18-minute drive from O'Hare International Airport and Allstate Arena, and 35 minutes from downtown Chicago.
This dog-friendly apartment comfortably accommodates up to six guests, boasting three bedrooms equipped with white noise machines for a restful sleep, a fully fitted kitchen, air conditioning, and on-site entertainment including board games and a large screen TV, with complimentary designated parking provided.

Newly renovated, this pet-friendly garden apartment in East Lincoln Park, Chicago, offers a private entrance and is a short walk to Lincoln Park Zoo and the Conservatory, with a distinctive red door and Victorian row house charm.
This 58 square meter apartment boasts a fireplace, an outdoor deck, and is conveniently located near Lake Michigan and Millennium Park, with covered parking available and excellent access to public transport for exploring the city.

Located in Chicago, this apartment is situated approximately 2.25 kilometres from the Field Museum and conveniently close to McCormick Place and Soldier Field.
This pet-friendly apartment offers a 74 square metre space with two bedrooms and two bathrooms, featuring a fully equipped kitchen, air conditioning, and on-site parking, making it ideal for families and event attendees.

Perfectly situated in Chicago's Bridgeport neighbourhood, this apartment is just a short distance from the natural beauty of Lake Michigan and Millennium Park, offering easy access to cultural institutions like the Field Museum and the Art Institute of Chicago.
This pet-friendly apartment boasts 111 square meters of living space, accommodates up to four guests, and features a dedicated dog run, on-site pet care, and a "Fur Friendly" policy making it ideal for travellers with pets.

Located in the prime downtown Chicago district, this luxury apartment is just 500 meters from major dining, shopping, and attractions, with excellent public transport links.
This pet-friendly 4-bedroom apartment accommodates up to 10 guests, boasting a fully-equipped kitchen, spectacular city views, and in-unit laundry for a comfortable stay.