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2026-07-02
2026-07-03
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Chicago holiday rentals

Convenient 1Br/1Bath Apt In River North By Domio!

Chicago, United States Show map

Convenient 1Br/1Bath Apt In River North By Domio! Holiday home entices guests with 1 bedroom with views of Millennium Park. More

From US$ 166 Book Now

Historic Wicker Park Bungalow

1510 North Wood, Chicago, United States Show map

The 3-bedroom Historic Wicker Park Bungalow Villa offers quick access to such tourist spots as Belmont Army Wicker Park, situated merely 7 minutes' walk away. More

From US$ 1975 Book Now

Swank Victorian Near United Center W/ Backdeck

2740 West Adams Street, Chicago, United States Show map

Swank Victorian Near United Center W/ Backdeck Holiday home offers an 8-room accommodation 1.7 km from The Painted Door. This property also includes a sunny patio. More

From US$ 283 Book Now

Safe And Spacious Gold Coast Chicago Mansion

1214 North Lasalle Drive, Chicago, United States Show map

Safe Spacious Mansion In❤️️Downtown is a contemporary venue in vicinity of LaSalle Street Church. The villa is located in Near North Side district of Chicago, 25 minutes' drive from Midway airport. More

From US$ 1173 Book Now

Historic Chicago Bungalow About 12 Mi To Downtown

Chicago, United States Show map

Situated approximately 10 minutes by car from Ridgeland Common Ice Arena Recreation Center, the 2-bedroom Historic Chicago Bungalow About 12 Mi To Downtown entices guests to explore various tourist… More

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Tulsa Twilight Terrace Stfrancis

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

Located a mere 5 minutes' walk from Apostolic Church of God, Tulsa Twilight Terrace Stfrancis Villa Chicago hotel gives quick access to various city sites. More

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3Br Modern Condo Near Wrigley Depaul +Free Parking

2742 North Ashland Avenue, Chicago, United States Show map

Staying at 3Br Modern Condo Near Wrigley Depaul +Free Parking Chicago villa, guests can easily reach the huge outdoor Cloud Gate Sculpture, located around 7 km away. More

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Downtown Mich Ave - 6 Penthouses, Sleep 25

820 South Michigan Avenue 1207, Chicago, United States Show map

Offering a patio overlooking the lake, Downtown Mich Ave - 6 Penthouses, Sleep 25 Chicago villa is located a few steps from the General John Logan Memorial. More

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H&H 1896 - Spacious, Fully Stocked, & Free Parking

1820 N Keeler Ave, Chicago, United States Show map

Providing guests with baggage storage, H&H 1896 - Spacious, Fully Stocked, & Free Parking Chicago villa is conveniently positioned 10 minutes' drive from from revered religious sites like Our Lady of… More

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Modern 4 Bedroom Greystone

South Calumet Avenue 3626, Chicago, United States Show map

Located approximately a 25-minute walk from the Lakefront Trail, Modern 4 Bedroom Greystone Chicago villa offers a casino for guests' entertainment. Boasting access to a patio, this accommodation… More

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Secret ❤️Gallery On The Park

Chicago, United States Show map

Secret ❤️Gallery On The Park Holiday home is a contemporary property, located in Near North Side district, right next to Maya Polsky Gallery. The accommodation consists of 2 bedrooms and 1 bathrooms. More

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The Winchester - Custom Home W Amazing Outdoors

Chicago, United States Show map

3 Level Bucktown Home apartment gives direct access to Wicker Park and features views of the garden. This 2-bedroom accommodation sleeps up to 12 guests. This property includes complimentary parking… More

From US$ 473 Book Now

Ultra Modern Luxury - New Construction 4 Bedrooms

5039 North Winthrop Avenue, Chicago, United States Show map

Ultra Modern Luxury - New Construction 4 Bedrooms Chicago villa offers quick access to such tourist spots as Vietnam, situated nearly a 5-minute stroll away. More

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Great Home

720 West Evergreen, Chicago, United States Show map

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Amazing House At Larrabee St

Chicago, United States Show map

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From US$ 431 Book Now

Beautiful 7 Bed, 3.5 Bathroom

1523 North Artesian Avenue 101, Chicago, United States Show map

Located a 7-minute stroll from Greater Exodus Baptist Church, the spacious 153 m² Beautiful 7 Bed, 3.5 Bathroom features a car park for those who travel by car. At a distance of 750 metres from… More

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4 Bedroom West Town Luxury Penthouse

1504 West Huron Street, Chicago, United States Show map

4 Bedroom West Town Luxury Penthouse comprises 4 bedrooms and a sunny patio, set in West Town district of Chicago. It includes a full kitchen and 3 bathrooms. The entire property comfortably… More

From US$ 167 Book Now

Stunning Luxury Home In Heart Of Bucktown!

2064 North Oakley Avenue, Chicago, United States Show map

Stunning Luxury Home In Heart Of Bucktown! is a 3-bedroom venue, which can accommodate up to 6 guests in Bucktown district of Chicago. It includes a full kitchen and 3 bathrooms. The villa offers… More

From US$ 280 Book Now

Home With Fenced Backyard In Chicago!

12827 S Morgan St, Chicago, United States Show map

Offering a location nearly 25 minutes on foot from Riverdale Park Recreation Center, the 2-bedroom Chicago Vacation Rental, 19 Mi To Downtown Area! gives access to various tourist spots in the area. More

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Bucktown Beauty - Luxurious & Quiet 4 Bdr Home

1623 North Bell Avenue, Chicago, United States Show map

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From US$ 463 Book Now

Huge Lakeview Retreat Sleeping 20 With Parking!

858 West Fletcher, Chicago, United States Show map

Huge Lakeview Retreat Sleeping 20 With Parking! is situated only 6 minutes' stroll from Our Lady of Mount Carmel Church, featuring such comforts as Wi-Fi and a car park. More

From US$ 500 Book Now

Cozy + Home In Chicago W/ Sauna VIII

1328 North Leavitt Street, Chicago, United States Show map

The 4-bedroom Cozy + Home In Chicago W/ Sauna VIII provides easy access to various city attractions, such as Debonair Social Club, situated 5 minutes' walk away. Located 2.7 km from Treasure Island… More

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Handsome Designer Mccormick 2/2 Loft

Chicago, United States Show map

Featuring a patio with a shower, Handsome Designer Mccormick 2/2 Loft Holiday home is located in Chicago, next to Chicago Chinatown. Guests can also relax in a nice balcony. More

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Four-Bedroom On S Oakley Boulevard

Chicago, United States Show map

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Old Town Upscale Five Bedroom Home

1645 North Sedgwick Street, Chicago, United States Show map

Situated near Chicago History Museum, Old Town Upscale Five Bedroom Home features a patio. The venue is fitted with 5 bedrooms, a kitchen and a detached bathroom. More

From US$ 733 Book Now

Single Family Home With 3 Bedrooms Plus Attic With 2 Beds

3036 North Gresham Avenue, Chicago, United States Show map

Nestled within 25 minutes' walk of Tony's Fresh Market, Chicago 2 Beds Family Retreat With Attic Space villa entices guests to explore various tourist destinations nearby. More

From US$ 264 Book Now

Wrigley 4Br Home, Sleeps 10

3623 N Ashland Ave, Chicago, United States Show map

Nestled a 7-minute walk from Saint Andrew Roman Catholic Church, Wrigley 4Br Home, Sleeps 10 Chicago entices guests to explore various tourist destinations nearby. More

From US$ 4540 Book Now

Cheerful 3-Bedroom Residential Home

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

Situated 3.4 km from Saint Constance Catholic Church, Cheerful 3-Bedroom Residential Home provides access to numerous tourist attractions in the area. More

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Cloud Cover

175 North Harbor Drive #3704, Chicago, United States Show map

Situated in Near East Side district of Chicago, Cloud Cover apartment is 20 km from Midway airport. Cloud Gate is 10 minutes stroll away. More

From US$ 417 Book Now

Best Location Downtown - River North Near Magmile

870 North Orleans Street, Chicago, United States Show map

Situated just a 5-minute walk from Saint Matthew United Methodist Church, the 2-bedroom Best Location Downtown - River North Near Magmile offers easy access to numerous tourist spots in the area. More

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Vintage Bucktown 3Bd

Chicago, United States Show map

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From US$ 141 Book Now

Gold Coast - Downtown Hideaway

67 West Chestnut, Chicago, United States Show map

Along with Wi-Fi and parking, Gold Coast - Downtown Hideaway Villa offers proximity to Willis Tower, located nearly 25 minutes' walk away. More

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Chic Chicago Abode Steps From Magnificent Mile!

6510 S Ellis Ave, Chicago, United States Show map

Located merely 5 minutes' walk from Woodlawn Baptist Church, the 2-bedroom Chic Chicago Abode Steps From Magnificent Mile! Villa offers quick access to various city attractions in the vicinity. More

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Charming 5 Bedrooms 2 Bathrooms

8027 South Kimbark Avenue, Chicago, United States Show map

Offering a location around a 25-minute walk from Nat King Cole Park, Charming 5 Bedrooms 2 Bathrooms Chicago villa gives access to various tourist spots in the area. More

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Charming 3Bd Bungalow In Vibrant Andersonville Home

1619 W Bryn Mawr, Chicago, United States Show map

Situated just 6 minutes on foot from The Brown Elephant, the 3-bedroom Charming 3Bd Bungalow In Vibrant Andersonville Home Chicago offers easy access to numerous tourist spots in the area. More

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Game Room, Firepit, Playground, Gym, Billiard

2146 N Kilpatrick Ave, Chicago, United States Show map

Situated 10 minutes by car from the 184-acre Garfield Park Conservatory, Game Room, Firepit, Playground, Gym, Billiard Chicago villa provides access to numerous tourist attractions in the area. More

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2 Mi To Calumet Park And Beach Windy City Escape!

9830 S Yates Blvd, Chicago, United States Show map

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Luxury Studio King Bed Chicago Remodeled

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

Situated about a 25-minute walk from Schiller Woods South, the 1-bedroom Luxury Studio King Bed Chicago Remodeled villa entices guests to explore various tourist attractions in the area. More

From US$ 361 Book Now

Rare, Remarkably Gorgeous, Executive Georgian Home

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

Rare, Remarkably Gorgeous, Executive Georgian Home Chicago offers proximity to such city sites as Saint Mark United Methodist Church, located just 250 metres away. More

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4 Mi To Dtwn Chicago Modern Home With Outdoor Space

Chicago, United States Show map

The 4-bedroom Modern Home about 4 Mi to Downtown Chicago! offers quick access to such city attractions as The New Landmark Missionary Baptist Church, located a mere 6 minutes' stroll away. More

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Wicker Park 6Bd 4Ba, Steps From Cta, Parking Incl Home

1220 N Paulina, Chicago, United States Show map

Staying at Wicker Park 6Bd 4Ba, Steps From Cta, Parking Incl Home Chicago, guests can easily reach the public Cloud Gate Sculpture, located 4.6 km away. More

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