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2026-02-23
2026-02-24
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Private Villas in Chicago

Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find

2713 West Balmoral Avenue, Chicago, United States View map

**Welcome to Northside Famlynest Lincoln Sq, a Cozy Family Gem in Chicago** Exploring the vibrant neighborhood is a breeze, with the Lincoln Park Zoo just 9 km away, allowing you to immerse yourself… More

From US$ 270 Book Now

The Black And White Suite

611 East 41St Street, Chicago, United States View map

Immerse yourself in the timeless elegance of The Black, where sophistication meets comfort in an ideal urban setting. This luxurious retreat caters to both leisure and business travelers… More

From US$ 313 Book Now

Spacious 5-Br House Near Transit W Parking

1868 South Millard Avenue, Chicago, United States View map

Nestled in the heart of Chicago, the Spacious 5-Br House Near Transit W Parking offers a unique blend of comfort and convenience, ideal for both families and groups traveling together. Just 10… More

From US$ 357 Book Now

Beautifully Renovated House 10 Mins From Downtown

4244 South Prairie Avenue, Chicago, United States View map

Experience the charm and elegance of the Beautifully Renovated House 10 Mins From Downtown, an exquisite retreat just moments away from the vibrant heart of the city. This thoughtfully designed haven… More

From US$ 654 Book Now

Magnificent New Home W/8 Beds & Free Parking

2019 North Bingham Street, Chicago, United States View map

Welcome to the Magnificent New Home W/8 Beds & Free Parking, an exquisite haven nestled in the vibrant Logan Square neighborhood of Chicago. This elegantly designed residence is a part of the… More

From US$ 301 Book Now

Historic Home With Outdoor Hot Tub Near Downtown In Public Transportation Hub

3742 N. Keeler Avenue, Chicago,, Chicago, United States View map

Set in a vibrant neighborhood, the Historic Home With Outdoor Hot Tub Near Downtown In Public Transportation Hub offers a unique blend of charm and accessibility. This thoughtfully restored residence… More

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Historic Luxury Townhouse In Downtown Chicago

71 East Bellevue Place The Townhouse, Chicago, United States View map

Boasting the location within 5 minutes' stroll of Oak Street Beach, the 5-bedroom Historic Luxury Townhouse In Downtown Chicago Villa is also 1.1 km from Shops at Northbridge. Located in the Downtown… More

From US$ 1472 Book Now

Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests

111 West Elm Street, Chicago, United States View map

The 4-bedroom Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests Chicago offers quick access to such city attractions as Moody Bible Institute, located only a 6-minute walk away. More

From US$ 764 Book Now

The Village Inn By Dakota Gal Digs

2111 North Kenmore Avenue Unit 1, Chicago, United States View map

Situated in the vibrant Lincoln Park area of Chicago, The Village Inn By Dakota Gal Digs serves as an oasis amidst the bustling cityscape. This charming establishment is surrounded by an array of… More

From US$ 592 Book Now

Hamaline Luxury Guest House

76 East 37Th Street, Chicago, United States View map

Located approximately 5 minutes' walk from Indiana Avenue Pentecostal Church of God, the 1-bedroom Hamaline Luxury Guest House Chicago villa gives easy access to various tourist attractions in the… More

From US$ 336 Book Now

A Home Away From Home!

8858 South Constance Avenue, Chicago, United States View map

Offering a location 4.9 km from Meyering Park, the 3-bedroom A Home Away From Home! Chicago gives access to various tourist spots in the area. More

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Chicago Home Near Navy Pier And Shedd Aquarium!

Chicago, United States View map

**Experience Chicago's Charm at Chicago Home Near Navy Pier and Shedd Aquarium** Nestled in the vibrant heart of the Windy City, Chicago Home Near Navy Pier and Shedd Aquarium offers a perfect blend… More

From US$ 159 Book Now

The Logandale: Huge Mid-Century Home, Sleeps 15

2920 North Gresham Avenue, Chicago, United States View map

The 3-bedroom The Logandale: Huge Mid-Century Home, Sleeps 15 Chicago provides easy access to various city attractions, such as Saint Wenceslaus Roman Catholic Church, situated approximately 5… More

From US$ 698 Book Now

Modern Wrigley Oasis With Parking!

3406 N Seminary Ave, Chicago, United States View map

Welcome to the Modern Wrigley Oasis With Parking!, A captivating retreat nestled in the vibrant Lakeview neighborhood of Chicago. Conveniently situated near West Diversey Parkway and the shores of… More

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Cozy 4Bd House Fireplace And Pond

8813 South Euclid Avenue, Chicago, United States View map

Welcome to the Cozy 4Bd House Fireplace And Pond, a charming retreat that seamlessly blends comfort and tranquility. Situated just 20 km from both Ogilvie Transportation Center and Midway… More

From US$ 535 Book Now

Luxurious Classic Gold Coast Villa For 12 Guests

109 West Elm Street, Chicago, United States View map

Luxurious Classic Gold Coast Villa For 12 Guests lies in proximity of Clark/Division underground station and approximately a 15-minute walk from Museum Of Contemporary Art Chicago. The 4-bedroom… More

From US$ 565 Book Now

Stunning 5Br Home In Heart Of Chicago With 2 Rooftops

1307 North Bell Avenue, Chicago, United States View map

The 4-bedroom Stunning 5Br Home In Heart Of Chicago With 2 Rooftops is situated merely 6 minutes' walk from Buzz Killer Espresso, featuring such comforts as Wi-Fi and parking. Located 4.4 km from… More

From US$ 1501 Book Now

5 Bedroom Huge House In Best Location Parking Fireplace Back Yard

1426 North North Park Avenue, Chicago, United States View map

During the stay at 5 Bedroom Huge House In Best Location Parking Fireplace Back Yard Chicago villa, guests can indulge in tennis or visit the Navy Pier, located a 10-minute ride away. More

From US$ 1924 Book Now

Boutique Garden House Chicago 3-Story Sleeps 12

7131 South Michigan Avenue, Chicago, United States View map

Boutique Garden House Chicago 3-Story Sleeps 12 Villa offers proximity to nearby tourist spots, such as Museum of Science and Industry, situated 4.6 km away. More

From US$ 629 Book Now

Charming Home In Portage Park

4109 North Narragansett Avenue, Chicago, United States View map

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From US$ 107 Book Now

River North Hideaway With Amazing Views And Parking

1 E Huron St, Chicago, United States View map

**Welcome to the River North Hideaway, your exquisite sanctuary nestled in the heart of the Magnificent Mile.** This chic retreat allows guests to fully immerse themselves in Chicago's vibrant… More

From US$ 264 Book Now

Chicago New 2Br Home W 3 Beds And Highspeed Internet

West Potomac Avenue 1731, Chicago, United States View map

**Experience Urban Elegance at Chicago New 2Br Home W 3 Beds and Highspeed Internet** Conveniently located just 17 kilometers from Midway International Airport and 4 kilometers from Ogilvie… More

From US$ 139 Book Now

Chicago Treasure 4 Bed Getaway

712 North Willard Court, Chicago, United States View map

Located merely 6 minutes on foot from Santa Maria Addolorata Parish, the 3-bedroom Chicago Treasure 4 Bed Getaway Villa gives easy access to various tourist attractions in the area. More

From US$ 231 Book Now

Logan Square Oasis

2508 N Spaulding Ave, Chicago, United States View map

Welcome to the Logan Square Oasis, an enchanting haven nestled in one of Chicago's most vibrant neighborhoods. This remarkable oasis stands at the crossroads of art and culture, showcasing the… More

From US$ 142 Book Now

New Modern 3Br, Gym, Workspace, Quiet Location

3656 N Osage Ave Unit 3, Chicago, Il 60634, Usa, Chicago, United States View map

Welcome to the New Modern 3Br, Gym, Workspace, Quiet Location, a sophisticated retreat designed for comfort and productivity in the heart of Chicago. Just 15 km from the bustling Chicago O'Hare… More

From US$ 147 Book Now

Old Town 3Bd 3Ba Coach House, Garage Parking Incl

1435 N Mohawk Ch, Chicago, United States View map

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

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2 Mi To South Shore Beach Urban Retreat With Yard

1653 E 70Th St, Chicago, United States View map

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Modern 3Br Near Mccormick & South Loop

2550 South Wabash Avenue, Chicago, United States View map

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Victorian Mansion In Garfield Park

3461 W Adams St, Chicago, United States View map

Situated 950 metres from the Catholic church "Our Lady of Sorrows Basilica", Victorian Mansion In Garfield Park Villa Chicago invites guests to relax at a patio. More

From US$ 162 Book Now

Perfect Location Across From Park & Train Station

244 North Hamlin Avenue, Chicago, United States View map

Nestled in an enviable position, the Perfect Location Across From Park & Train Station Villa offers a luxurious retreat in the heart of the city, just 400 meters from the scenic Conservatory-Central… More

From US$ 358 Book Now

Gorgeous 5 Bedroom Gem With Games

7928 South Ada Street, Chicago, United States View map

**Welcome to Gorgeous 5 Bedroom Gem With Games, where modern luxury meets a vibrant Chicago ambiance. Nestled about 15 kilometers from Midway International Airport and just 17 kilometers from Ogilvie… More

From US$ 370 Book Now

Newly Updated Vintage 6 Bedroom Single Family Home Home

825 S Claremont, Chicago, United States View map

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Stylish Chicago Retreat Walk To Loyola University

6242 N Kenmore Ave Unit D, Chicago, United States View map

Situated 2.5 km from Touhy Park, the 4-bedroom Stylish Chicago Retreat, Walk To Loyola University villa provides access to numerous tourist attractions in the area. More

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Designer Themed 4 Bedroom In Best Location With Patio And Fireplace

329 West Schiller Street Back, Chicago, United States View map

The 3-bedroom Designer Themed 4 Bedroom In Best Location With Patio And Fireplace Chicago villa offers swift access to various city sites, such as The Noble Horse Theatre, situated around 5 minutes'… More

From US$ 479 Book Now

Spacious Row Home Next Transit Near Downtown W Parking

3133 West Fulton Street, Chicago, United States View map

**Experience Comfort and Convenience at the Spacious Row Home Next Transit Near Downtown W Parking** More

From US$ 452 Book Now

Roscoe Village Family Hideaway

1811 West Eddy Street, Chicago, United States View map

Staying at the 3-bedroom Roscoe Village Family Hideaway Chicago villa, guests can visit Merryman Playlot Park, which is about a 5-minute walk away. More

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420 Friendly 12 Pm Check Out 1 Bedroom Basement

8132 South Harvard Avenue, Chicago, United States View map

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From US$ 131 Book Now

Personal Gym Luxury Balcony Condo

5105 N East River Rd Unit 3F, Chicago, Il 60656, Usa, Chicago, United States View map

Welcome to the Personal Gym Luxury Balcony Condo, a remarkable retreat situated in the heart of O'Hare. This stylish accommodation offers an exquisite blend of modern elegance and unparalleled… More

From US$ 233 Book Now

Woodlawn Oasis

6433 South Minerva Avenue, Chicago, United States View map

**Discover Woodlawn Oasis Villa, a serene escape ideally situated just 15 kilometers from both Midway International Airport and the bustling Ogilvie Transportation Center. Nestled amid the charm of… More

From US$ 364 Book Now

The Avondale Guesthouse

2973 North Elston Avenue, Chicago, United States View map

**Welcome to The Avondale Guesthouse Chicago**, a charming retreat that seamlessly blends comfort with modern amenities in an inviting garden setting. This delightful haven, located only 20 km from… More

From US$ 165 Book Now

Art Downtown Fulton Market Entire 3 Bedroom Home Sleep10 Private Garage Roof Ev Tesla

467 North Armour Street, Chicago, United States View map

Boasting a location 4.3 km from Maggie Daley Park, the 3-bedroom Art Downtown Fulton Market Entire 3 Bedroom Home Sleep10 Private Garage Roof Ev Tesla Chicago provides a terrace with garden views. More

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2 Bedroom With Soaking Tub And Onsite Parking

841 North Mozart Street, Chicago, United States View map

Staying at 2 Bedroom With Soaking Tub And Onsite Parking Chicago villa, guests can easily reach the Cloud Gate, located approximately 7 km away. More

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3-Story Townhome Free Parking Private Patio Washer-Dryer

344 West Dickens Avenue, Chicago, United States View map

Situated a 5-minute walk from Park West, 3-Story Townhome Free Parking Private Patio Washer-Dryer Chicago villa entices guests with views of the lake. More

From US$ 237 Book Now

Stylish 3Br Gem In Prime Location

2550 South Wabash Avenue, Chicago, United States View map

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Windy City Getaway - 3Br 2Ba Chicago Townhouse Home

3721 North Milwaukee Avenue, Chicago, United States View map

Nestled a 10-minute drive from North Park Village Nature Center, Windy City Getaway - 3Br 2Ba Chicago Townhouse Home entices guests to explore various tourist destinations nearby. More

From US$ 304 Book Now

4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome

329 West Schiller Street, Chicago, United States View map

The 4-bedroom 4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome Chicago is situated about a 5-minute walk from Saint Michael, featuring such comforts as Wi-Fi and complimentary… More

From US$ 841 Book Now

Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck

67 East Cedar Street, Chicago, United States View map

The 5-bedroom Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck Chicago villa offers proximity to nearby tourist spots, such as DuSable Bridge, situated around 20 minutes' walk away. More

From US$ 999 Book Now

Immaculate Brand New Penthouse Chicago

1630 West Warren Boulevard, Chicago, United States View map

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

From US$ 799 Book Now

Luxe 4Br With Hot Tub & Game Room

1654 West Ohio Street, Chicago, United States View map

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

From US$ 967 Book Now

Zen Escape-Chicago'S Urban Oasis

841 North Mozart Street, Chicago, United States View map

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

From US$ 79 Book Now