Chicago holiday rentals

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Discover the allure of the Immaculate Brand New Penthouse Chicago, an exquisite oasis nestled in the vibrant West Loop. This luxurious retreat seamlessly combines modern sophistication with the… More

Envitae Hotel 4Br Luxury Modern Apartments Chicago villa is located just 1.9 km from Oz Public Park and welcomes its guests to enjoy horseback riding, cycling, and fishing. More

Nearly a 10-minute walk from the 4-bedroom Lovely Updated Raised Ranch With Suburban Feel Villa takes guests to Hopewell Baptist Church, while A. Philip Randolph Pullman Porter Museum is about 6 km… More

The 3-bedroom Luxurious 3Br 3Ba Duplex With King Bed, Gym And Big Yard Villa is a luxurious property at a 6 km distance from Wonder Works Children's Museum. This Chicago villa also has a fully… More

Located a 5-minute walk from Katherine Anne Confections, 5Br 5Ba Architectural Estate-Theatre Gym Rooftop Chicago villa offers a patio with a view over the city. Pampering guests with a sauna, this… More

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Set in the vibrant West Town neighborhood, the Luxe 4Br With Hot Tub & Game Room is the quintessential urban retreat, perfectly combining modern amenities with a lively culinary scene. Just moments… More

The 3-bedroom Old Town 3Bd 3Ba Coach House, Garage Parking Incl Villa Chicago provides easy access to various city attractions, such as Eva's Cafe, situated approximately 5 minutes' walk away. More

Welcome to Zen Escape-Chicago's Urban Oasis, your serene retreat nestled in the vibrant West Town neighborhood. This gem is ideally situated along the bustling stretch of West Chicago Avenue… More

White Sox Best House Chicago villa offers proximity to such city sites as South Park Baptist Church, located approximately a 5-minute walk away. More

**Experience Luxury at the Breathtaking Downtown Penthouse A - Sleeps 11 Villa** Nestled in the vibrant Near North Side of Chicago, the Breathtaking Downtown Penthouse A - Sleeps 11 Villa offers a… More

Staying at the 3-bedroom Amazing Penthouse Skyline Views! Villa Chicago, guests can visit Eckhart Park, which is nearly a 25-minute walk away. The Chicago villa includes a free private car park and a… More

Nestled a 5-minute drive from the Bread & Wine, Windy City Getaway - 3Br 2Ba Chicago Townhouse Home entices guests to explore various tourist destinations nearby. The 3-bedroom holiday home hosts up… More

The 6-bedroom Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck Chicago villa, located just 5 minutes' walk from the Ruth Page Center for the Arts, can host up to 26 guests. More

**Welcome to the Spacious West Town Oasis With Parking!** Nestled in the vibrant West Town neighborhood of Chicago, this delightful retreat is surrounded by a dynamic stretch of West Chicago Avenue… More

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**Welcome to the Spacious 4-Bedroom Home With Stunning Backyard Deck in Chicago**, a delightful sanctuary that encapsulates comfort and elegance. This exquisite property is perfectly situated just 16… More

The 1-bedroom Stylish Chicago Duplex Close To Parks And Dtwn villa offers proximity to such city sites as Carbide and Carbon Building, located about a 5-minute walk away. More

**Discover the Spacious Ukrainian Village Retreat** Nestled in the vibrant heart of West Town, the Spacious Ukrainian Village Retreat offers an exceptional experience that blends comfort with the… More

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Welcome to the Beautifully Remodeled Flat Downtown #3N, a chic urban retreat nestled in the vibrant Near North Side of Chicago. This incredible location grants guests immediate access to iconic… More

Located 2.6 km from Lincoln Park Conservatory, the 1-bedroom Cozy Condo Sleeps 4 Chicago villa provides access to various tourist attractions in the vicinity. More

Welcome to Goose Island Central Downtown, where urban vibrancy meets comfortable elegance. Nestled within West Town, this exquisite retreat offers easy access to the lively stretch of West Chicago… More

Located nearly 5 minutes' walk from St. Lukes Lutheran Church, Tuscan Charm In Chicago'S Heart villa offers quick access to various city attractions in the vicinity. More

Large Condo With Outdoor Deck In Historic Chicago District Home offers quick access to such tourist spots as Eva's Cafe, situated only a 5-minute walk away. More

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Amazing Wicker Park Penthouse With Skyline Views Villa Chicago boasts a location around a 5-minute stroll from the Buffalo Exchange and offers guests to enjoy a casino. Featuring a patio, the Chicago… More

Positioned in the heart of Tulsa, the Tulsa Twilight Terrace Stfrancis offers a captivating blend of modern sophistication and local charm. Just 15 kilometers from the bustling Ogilvie Transportation… More

**Welcome to La Casa La Fortune St Francis Chicago**, where luxury and comfort seamlessly blend to create an unforgettable experience. Nestled just 18 km from the bustling Ogilvie Transportation… More

Offering a location just an 8-minute walk from Bryn Mawr Community Church, 2 Mi To South Shore Beach: Urban Retreat W/ Yard Chicago villa gives access to various tourist spots in the area. More

Located within 5 minutes' walk of Richard's Fabulous Finds, the 3-bedroom Steel And Sky Villa Chicago gives easy access to various tourist attractions in the area. More

Modern 4 Bedroom Greystone Chicago villa offers swift access to various city sites, such as the 1930s Supreme Life Building, situated 6 minutes' walk away. Nestled in the Bronzeville district, the… More

While staying at the 3-bedroom Rare, Remarkably Gorgeous, Executive Georgian Home, you'll be nearly a 15-minute ride from the Sprawling hands-on Museum of Science and Industry and within 2.5 km of… More

Sleeps 18 • 8Br • Game Room • Gym • Theater Chicago villa is located nearly a 25-minute walk from the Saint Constance Catholic Church and welcomes its guests to enjoy table tennis and pool. More

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**Welcome to the Exceptional Luxury Studio King Bed Chicago Remodeled** Ideally located, the Luxury Studio King Bed Chicago Remodeled puts guests in close proximity to major attractions, shopping… More

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Welcome to the Chicago Big House, a tranquil haven located just 30 minutes by car from the hustle and bustle of Ogilvie Transportation Center. This elegant villa is perfect for those seeking a blend… More

**Welcome to the Chic Chicago Abode Steps From Magnificent Mile!** Nestled in the heart of Chicago, this splendid retreat is positioned conveniently, just 15 km from both Ogilvie Transportation… More

2 Rooftops 2 Car Garage 4 Stories Chicago villa provides easy access to various city attractions, such as Eva's Cafe, situated a 5-minute walk away. More

**Welcome to Cherry Street Getaway, a captivating urban retreat nestled in the heart of Chicago. This charming destination offers an ideal blend of modern comfort and classic elegance, making it a… More

Staying at Game Room, Firepit, Playground, Gym, Billiard Chicago villa, guests can easily reach the 184-acre Garfield Park Conservatory, located approximately a 10-minute drive away. More

Set in the vibrant heart of Chicago, Main House At Cherry Street 4Bdr offers a luxurious retreat for both leisure and business travelers. This sophisticated residence combines modern comfort with… More

The 1-room Chicago Vacation Rental Apt - 6 Mi To Downtown! apartment is nestled in the Bronzeville district of Chicago, about 10 minutes' drive from Museum of Science and Industry. More

Envitae Hotel 4Br Modern Sleek Apartment Chicago villa is located just 300 metres from REI and allows guests to enjoy horse riding, cycling, and fishing. Along with a casino, the Chicago holiday home… More

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