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2026-06-29
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Chicago holiday rentals

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 provides easy access to various city attractions, such as The Noble Horse Theatre, situated about a 5… More

From US$ 1049 Book Now

Midway Paradise With Kids Room

5233 South Keating Avenue, Chicago, United States View map

Staying at the 2-bedroom Midway Paradise With Kids Room Chicago villa, guests can visit Freedom Park, which is approximately a 10-minute ride away. More

From US$ 217 Book Now

Old Town Pied-A-Terre With Private Terrace And Parking!

1515 North Wells, Chicago, United States View map

**Old Town Pied-A-Terre With Private Terrace And Parking!** Offers a delightful urban retreat nestled in the vibrant Near North Side of Chicago. Surrounded by iconic landmarks such as the historic… More

From US$ 337 Book Now

Luxe Sfh Bucktown Retreat With Garage Parking

1629 N Rockwell S, Chicago, United States View map

The 3-bedroom Luxe Sfh Bucktown Retreat With Garage Parking Villa Chicago offers easy access to such tourist spots as Church Of God John 3, located only a 5-minute walk away. More

From US$ 1275 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$ 325 Book Now

Modern Sfh Near Mccormick Place & Soldier Field

1614 S Desplaines St, Chicago, United States View map

Situated around a 25-minute walk from McCormick Place Convention Center, the 3-bedroom Modern Sfh Near Mccormick Place & Soldier Field Chicago villa provides access to numerous tourist attractions in… More

From US$ 1498 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

Roscoe Village Family Hideaway

1811 West Eddy Street, Chicago, United States View map

The 4-bedroom Roscoe Village Family Hideaway Chicago villa is situated only 5 minutes' walk from the Juniper Playlot Park, featuring such comforts as Wi-Fi and parking. Located in the vicinity of the… More

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Best Location Downtown - River North Near Mag Mile

870 North Orleans Street, Chicago, United States View map

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From US$ 867 Book Now

Tranquil Urban Retreat

10346 South King Drive, Chicago, United States View map

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From US$ 434 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

Envitae Hotel 4Br Luxury Modern Apartments

853 West Blackhawk Street, Chicago, United States View map

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

From US$ 417 Book Now

Lovely Updated Raised Ranch With Suburban Feel

12231 South Loomis Street, Chicago, United States View map

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

From US$ 334 Book Now

Luxurious 3Br 3Ba Duplex With King Bed, Gym And Big Yard

4237 North Mobile Avenue, Chicago, United States View map

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

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5Br 5Ba Architectural Estate-Theatre Gym Rooftop

1856 North Fairfield Avenue, Chicago, United States View map

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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Skyline X Treetop Roof Deck, Attached Garage

751 West 15Th Street, Chicago, United States View map

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From US$ 213 Book Now

Trendy Wicker Park Loft With Parking

1554 N Ashland Ave, Chicago, United States View map

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From US$ 232 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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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

Amazing Penthouse Skyline Views!

1549 North Milwaukee Avenue Unit 4S, Chicago, United States View map

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

From US$ 710 Book Now

Windy City Getaway - 3Br 2Ba Chicago Townhouse Home

3721 North Milwaukee Avenue, Chicago, United States View map

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

From US$ 304 Book Now

Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck

67 East Cedar Street, Chicago, United States View map

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

From US$ 999 Book Now

Spacious West Town Oasis With Parking!

1656 West Erie Street, Chicago, United States View map

**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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Modern Lincoln Park Hideaway 1 Bd And 1Bath

1410 W Diversey Pkwy, Chicago, United States View map

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From US$ 311 Book Now

Central Downtown Location-Modern 2Br Condo

210 North Wells Street Unit 1401, Chicago, United States View map

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420 Friendly 12 Pm Check Out 1 Bedroom Basement

8132 South Harvard Avenue, Chicago, United States View map

420 Friendly 12 Pm Check Out 1 Bedroom Basement Chicago villa is nestled within a 7-km distance of the Sprawling hands-on Museum of Science and Industry and provides a hot tub. Offering Wi-Fi, this… More

From US$ 131 Book Now

Spacious 4-Bedroom Home With Stunning Backyard Deck In Chicago

1850 N Neva Ave, Chicago, United States View map

**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

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Townhouse In Rogers Park

2337 W Chase Ave, Chicago, United States View map

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From US$ 198 Book Now

Beautifully Remodeled Flat Downtown #3N

858 North Orleans Street #3N, Chicago, United States View map

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

From US$ 239 Book Now

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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Goose Island Central Downtown Prime Location With Access To Patio Chi - 1

West Augusta Boulevard 1220, Chicago, United States View map

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

From US$ 179 Book Now

Tuscan Charm In Chicago'S Heart

3412 North Greenview Avenue, Chicago, United States View map

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

From US$ 293 Book Now

Large Condo With Outdoor Deck In Historic Chicago District Home

1729 N St Michaels, Chicago, United States View map

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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Cozy Bungalow Home In Chicago

6200 South Campbell Avenue, Chicago, United States View map

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Amazing Wicker Park Penthouse With Skyline Views

1549 North Milwaukee Avenue #4, Chicago, United States View map

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

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Sleeps 18 7Br Gym Game Room Theater

33 S Waller Ave, Chicago, Il 60644, Usa, Chicago, United States View map

Situated a 10-minute stroll from the Third Unitarian Church, Sleeps 18 7Br Gym Game Room Theater Chicago villa provides access to numerous tourist attractions in the area. More

From US$ 4680 Book Now

Tulsa Twilight Terrace Stfrancis

5829 East 64Th Street, Chicago, United States View map

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

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Gorgeous Wrigley Greystone

West Cuyler Avenue 968, Chicago, United States View map

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La Casa La Fortune St Francis

6417 South Kingston Avenue, Chicago, United States View map

**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

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Steel And Sky

1358 North Campbell Avenue, Chicago, United States View map

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

From US$ 1415 Book Now

Modern 4 Bedroom Greystone

South Calumet Avenue 3626, Chicago, United States View map

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

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Chicago Getaway With Pool Table & Modern Comfort Home

7538 South Prairie Avenue Greater Grand Crossing, Chicago, United States View map

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Rare, Remarkably Gorgeous, Executive Georgian Home

542 East 84Th Street, Chicago, United States View map

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

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Sleeps 18 • 8Br • Game Room • Gym • Theater

4038 N Central Ave, Chicago, Il 60634, Usa, Chicago, United States View map

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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Huge Bright Modern 2Br Home In Heart Of Bucktown

Unit 4W, 1748 W North Ave, Chicago, United States View map

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Luxury Studio King Bed Chicago Remodeled

5105 North East River Road, Chicago, United States View map

**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

From US$ 361 Book Now

Bluenile

7538 South Prairie Avenue, Chicago, United States View map

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Cheerful 3-Bedroom Residential Home

6555 W. Addison Street Unit D, Chicago, United States View map

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Best Location Downtown - River North Near Magmile

870 North Orleans Street, Chicago, United States View map

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Chicago Big House

4511 North Melvina Avenue, Chicago, United States View map

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

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