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2026-11-09
2026-11-10
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Holiday Homes in Chicago

Windy City Getaway - 3Br 2Ba Chicago Townhouse Home

3721 North Milwaukee Avenue, Chicago, United States Show map

Located 7 km from the baseball stadium "Wrigley Field", Windy City Getaway - 3Br 2Ba Chicago Townhouse Home gives access to various tourist sites in the vicinity. The 3-bedroom holiday home hosts up… More

From US$ 511 Book Now

Game Room • Fire-Pit • Playground • Gym • Billiard

2146 N Kilpatrick Ave, Chicago, United States Show map

Game Room • Fire-Pit • Playground • Gym • Billiard Chicago villa is located in the vicinity of Grant Park and provides a games room to make your visit more entertaining. The 4-bedroom holiday home… More

From US$ 863 Book Now

Downtown Park11 - Mich Ave Ph Gym Plus Rooftop

820 South Michigan Avenue 1211, Chicago, United States Show map

The 1-bedroom Downtown Park11 - Mich Ave Ph Gym Plus Rooftop Chicago villa is situated nearly a 5-minute walk from the American Museum of Contemporary Photography, featuring such comforts as Wi-Fi… More

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Near Lake & Museum • Modern • Game Area

2714 E 76Th Pl, Chicago, Il 60649, Usa, Chicago, United States Show map

Suitable for 12 guests, Near Lake & Museum • Modern • Game Area Chicago villa offers a location within 400 metres of Windsor Park Lutheran Church and features an aqua park and a golf course. The 5… More

From US$ 277 Book Now

Envitae Hotel 4Br Luxury Modern Apartments

853 West Blackhawk Street, Chicago, United States Show map

Up to 10 guests can stay at the 6-room Envitae Hotel 4Br Luxury Modern Apartments Chicago and enjoy REI Camping Store, located approximately 5 minutes' walk away. The 4-bedroom and 3-bathroom villa… More

From US$ 417 Book Now

Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck

67 East Cedar Street, Chicago, United States Show map

Up to 26 guests can stay at the 6-bedroom Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck Chicago villa and enjoy Ruth Page Center for the Arts Dance School, located approximately a 5… More

From US$ 999 Book Now

Chicago Home Near Navy Pier & Shedd Aquarium!

544 E 92Nd Pl, Chicago, United States Show map

Chicago Home Near Navy Pier & Shedd Aquarium! is situated just a 5-minute walk from Burnside Baptist Church, featuring such comforts as Wi-Fi and a private parking lot. More

From US$ 159 Book Now

Mich Ave Downtown Penthouse - Rooftop Plus Gym 8

820 South Michigan Avenue 1208, Chicago, United States Show map

Located merely 6 minutes' walk from the American Museum of Contemporary Photography, the 1-bedroom Mich Ave Downtown Penthouse - Rooftop Plus Gym #8 Chicago villa offers quick access to various city… More

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Modern 3Br Apartment Near North Ave Shops

853 West Blackhawk Street, Chicago, United States Show map

Located in Near North Side, which is home to iconic skyscrapers like the 1920s Wrigley Building, as well as 360 Chicago, a 94th-floor observation deck, 300 metres from REI Camping Store, Modern 3Br… More

From US$ 849 Book Now

Large Condo With Outdoor Deck In Historic Chicago District Home

1729 N St Michaels, Chicago, United States Show map

Located a 10-minute drive from Millennium Public Park, Large Condo With Outdoor Deck In Historic Chicago District Home gives access to various tourist sites in the vicinity. More

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Sleeps 18 • 7Br • Gym • Game Room • Theater

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

The 7-bedroom Sleeps 18 • 7Br • Gym • Game Room • Theater Chicago villa, located a mere 5 minutes' walk from Bethlehem Unity M.B. Church, can host up to 18 guests. The holiday home features… More

From US$ 894 Book Now

1 Mi To Washington Park: Spacious 1St-Floor Condo!

6210 S Evans Ave Unit G, Chicago, United States Show map

The 2-bedroom 1 Mi To Washington Park: Spacious 1St-Floor Condo! Chicago villa offers proximity to nearby tourist spots, such as the Sprawling hands-on Museum of Science and Industry, situated… More

From US$ 210 Book Now

Amazing Wicker Park Penthouse With Skyline Views

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

Up to 14 guests can stay at Amazing Wicker Park Penthouse With Skyline Views Villa Chicago and enjoy Buzz Killer Espresso, located 5 minutes' walk away. The 3-bedroom holiday home features… More

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Immaculate Brand New Penthouse Chicago

1630 West Warren Boulevard, Chicago, United States Show map

Staying at Immaculate Brand New Penthouse Chicago Villa, guests can visit Randolph Street Market, which is an 8-minute stroll away. More

From US$ 799 Book Now

Luxury Gold Coast Penthouse With Deck & Views

22 East Elm Street, Chicago, United States Show map

Offering a patio and a golf course for guests' leisure, Luxury Gold Coast Penthouse With Deck & Views Villa Chicago is situated about a 25-minute walk from the 35-acre beautifully landscaped Lincoln… More

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5-Bedroom House In Pilsen Near Medical District

2031 W Coulter St, Chicago, United States Show map

Situated only a 5-minute stroll from Lincoln United Methodist Church, the 5-bedroom 5-Bedroom House In Pilsen Near Medical District Chicago villa offers quick access to numerous city landmarks nearby. More

From US$ 707 Book Now

Charming Andersonville Coach House 3Br 2,5Ba Townhouse

1736 W Summerdale Ch, Chicago, United States Show map

Charming Andersonville Coach House 3Br 2,5Ba Townhouse Chicago villa is nestled a 9-minute walk from Swedish American Museum and can accommodate up to 5 guests. Providing guests with Wi-Fi and a car… More

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Portage Park, Jacuzzi, Movie Theater, Games & Arcade

5635 W Waveland Ave, Chicago, United States Show map

With the capacity to host 16 guests, the 5-bedroom Portage Park, Jacuzzi, Movie Theater, Games & Arcade Villa Chicago is located around 15 minutes by car from such significant cultural landmarks as… More

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Downtown Mich Ave, Grant Park, Museums 2Bd-2Ba #20

1212 South Michigan Avenue 2001, Chicago, United States Show map

Located in South Loop, set including historic Printers Row, merely a 6-minute walk from Statue of Christopher Columbus, the 2-bedroom Downtown Mich Ave, Grant Park, Museums 2Bd-2Ba #20 Villa Chicago… More

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Wrigley 4Br Home, Sleeps 10

3623 N Ashland Ave, Chicago, United States Show map

Offering access to entertainment venues such as the restored theater "Music Box Theatre", situated only 0.8 km away, the 4-bedroom Wrigley 4Br Home, Sleeps 10 Chicago can host up to 10 guests. More

From US$ 1934 Book Now

1 Mi To Wrigley! Quintessential Chi-Town Greystone

3622 N Hermitage Ave Unit 2, Chicago, United States Show map

Hosting up to 6 guests, the 3-bedroom 1 Mi To Wrigley! Quintessential Chi-Town Greystone Villa Chicago offers a prime location only 1.6 km from sports attractions such as the baseball stadium… More

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

1220 N Paulina, Chicago, United States Show map

Up to 12 guests can stay at Wicker Park 6Bd 4Ba, Steps From Cta, Parking Incl Home Chicago and enjoy Foxtrot Market, located a 5-minute walk away. Offering a car park as well as Wi-Fi, the 6-bedroom… More

From US$ 894 Book Now

Luxe 4Br With Hot Tub & Game Room

1654 West Ohio Street, Chicago, United States Show map

Luxe 4Br With Hot Tub & Game Room Chicago villa is located within 4 km of Millennium Public Park, giving access to various tourist spots nearby. More

From US$ 967 Book Now

Dearborn Duplex L Sleeps 10 L Free Parking

642 North Dearborn Street, Chicago, United States Show map

Situated approximately 5 minutes' walk from the restored gilded age mansion "Richard H. Driehaus Museum", the 1-bedroom Dearborn Duplex L Sleeps 10 L Free Parking Villa Chicago offers easy access to… More

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Lakeview Lux 20Min To Wrigley Free Parking

4125 North Ashland Avenue, Chicago, United States Show map

Lakeview Lux 20Min To Wrigley Free Parking Chicago villa offers proximity to such city sites as Cuyler Covenant Church, located only a 10-minute walk away. More

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Steps To Lake & Beach! Multi-Level Oakland Haven

3975 S Ellis Ave, Chicago, United States Show map

The 4-bedroom Steps To Lake & Beach! Multi-Level Oakland Haven Chicago villa is located within 5 minutes' walk of Mandrake Park, giving access to various tourist spots nearby. With a maximum capacity… More

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Stay Awhile In Chicago Comfortable Furnished Home

10143 South Racine Avenue, Chicago, United States Show map

Situated 3.7 km from 50-Acre Park, Stay Awhile In Chicago Comfortable Furnished Home provides access to numerous tourist attractions in the area. More

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Commuter-Friendly Bungalow In Chicago'S South Side

8817 S Merrill Ave, Chicago, United States Show map

Located approximately 15 minutes' drive from the Sprawling hands-on Museum of Science and Industry, the 3-bedroom Commuter-Friendly Bungalow In Chicago'S South Side provides access to various tourist… More

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Cozy Downtown Mich Ave Gym And Rooftop #7

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

The 2-bedroom Cozy Downtown Mich Ave Gym And Rooftop #7 Chicago villa offers swift access to various city sites, such as General John Logan Memorial, situated merely a 5-minute walk away. Providing… More

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2 Rooftops 2 Car Garage 4 Stories

North Hudson Avenue 1501, Chicago, United States Show map

2 Rooftops 2 Car Garage 4 Stories Chicago villa, located merely a 5-minute walk from The Noble Horse Theatre, can host up to 14 guests. Located about 6 km from the premier natural-history Field… More

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Sleeps 26 • Modern Multi-Unit • Gym • Workspaces

3114 West Waveland Avenue, Chicago, United States Show map

The 7-bedroom Sleeps 26 • Modern Multi-Unit • Gym • Workspaces Chicago villa offers easy access to such tourist spots as Prop Thtr, located only 6 minutes' walk away. More

From US$ 1235 Book Now

Spacious 3Br Urban Getaway W Gym

2550 South Wabash Avenue, Chicago, United States Show map

Spacious 3Br Urban Getaway W Gym Chicago villa, located a mere 6 minutes' walk from Trinity Episcopal Church, can host up to 8 guests. The property features opportunities for kayaking and cycling in… More

From US$ 554 Book Now

Arcade • Theater • Gym • Office • Sleeps 15

6137 West Giddings Street, Chicago, United States Show map

Situated merely a 7-minute walk from Saint Constance Catholic Church, the 7-bedroom Arcade • Theater • Gym • Office • Sleeps 15 Villa Chicago is ideal for up to 15 guests. Providing guests with Wi-Fi… More

From US$ 948 Book Now

Your Chicago Retreat

7132 North Ashland Boulevard, Chicago, United States Show map

The 3-bedroom Your Chicago Retreat villa, located nearly a 5-minute walk from Rogers Park Presbyterian Church, can host up to 6 guests. Providing guests with Wi-Fi and parking, the property is 2.2 km… More

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Cozy Wicker Park Home With Movie Room

1523 North Artesian Avenue, Chicago, United States Show map

The 4-bedroom Cozy Wicker Park Home With Movie Room Chicago offers proximity to nearby tourist spots, such as the half - mile - long Navy Pier, situated about 7 km away. More

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West Town Estate 6Br, Game Room, Decks, 5Gbps

851 N Fairfield Ave, Chicago, United States Show map

Located merely 6 minutes' walk from Komoda Gift Shop, the 6-bedroom West Town Estate 6Br, Game Room, Decks, 5Gbps Chicago villa gives easy access to various tourist attractions in the area. The… More

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

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

The 8-bedroom Sleeps 18 • 8Br • Game Room • Gym • Theater Chicago villa is located approximately 5 minutes' walk from Romanian Eastern Orthodox Church of Saint Mary and allows guests to enjoy ping… More

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Hancock Lookout|Steps To Beach&Transit, Chi Views

1701, 1220 North State Parkway, Chicago, United States Show map

Situated merely 11 minutes' walk from the skyscraper 360 Chicago Observation Deck, the 2-bedroom Hancock Lookout|Steps To Beach&Transit, Chi Views Chicago villa provides access to numerous tourist… More

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Historic 1930S Retreat! Walk To Wicker Park

2021 W Dickens Ave, Chicago, United States Show map

Offering access to entertainment venues such as the live music venue "Congress Theater", situated only 1.3 km away, the 2-bedroom Historic 1930S Retreat! Walk To Wicker Park Villa Chicago can host up… More

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Bridgeport Bungalow Sleeps 4

447 West 27Th Street, Chicago, United States Show map

Located approximately a 5-minute stroll from All Saints St Anthony Church, Bridgeport Bungalow Sleeps 4 Chicago offers a terrace and a dining table for guests' enjoyment. Offering Wi-Fi, the Chicago… More

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Modern Chicago 2Br Retreat Parking + Patio

Apt. 3, 553 West 31St Street, Chicago, United States Show map

Located nearly 10 minutes' walk from Central Assembly of God Church, Modern Chicago 2Br Retreat Parking + Patio Villa offers quick access to various city attractions in the vicinity. Located in… More

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Designer 3Br Near Beach & Obama Center

6110 South Dorchester Avenue, Chicago, United States Show map

Designer 3Br Near Beach & Obama Center Chicago villa is located a mere 1.6 km from the Sprawling hands-on Museum of Science and Industry, giving access to various tourist spots nearby. More

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Mich Ave 5 Downtown Grant Park, Museums 2Bd-2Ba

1212 South Michigan Avenue 501, Chicago, United States Show map

The 2-bedroom Mich Ave 5 Downtown Grant Park, Museums 2Bd-2Ba Chicago villa offers easy access to such tourist spots as General John Logan Memorial, located only a 6-minute walk away. The Chicago… More

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Bronzeville 42 Art & Hospitality

615 East 42Nd Street, Chicago, United States Show map

Featuring private car parking, the 1-bedroom Bronzeville 42 Art & Hospitality Chicago villa is located in the Bronzeville district and 7 km from such cultural tourist attractions as Buckingham… More

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Private Yard Near Beach & Obama Center

6110 South Dorchester Avenue, Chicago, United States Show map

Offering a location nearly a 20-minute walk from the Sprawling hands-on Museum of Science and Industry, Private Yard Near Beach & Obama Center Chicago villa gives access to various tourist spots in… More

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Beautiful 6-Bedroom, Private Mansion With Hot Tub

7157 South Perry Avenue, Chicago, United States Show map

Staying at Beautiful 6-Bedroom, Private Mansion With Hot Tub Chicago villa, guests can visit First Progressive Church of Christ, which is just 1 km away. More

From US$ 619 Book Now

Modern Wrigley Oasis With Parking!

3406 N Seminary Ave, Chicago, United States Show map

Located merely an 11-minute walk from the baseball stadium "Wrigley Field", Modern Wrigley Oasis With Parking! Villa Chicago provides access to various tourist attractions in the vicinity. More

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Beautiful Condo In The Middle Of Andersonville

5441 N Ashland Ave Unit 3, Chicago, United States Show map

Situated just a 5-minute walk from Andersonville, Beautiful Condo In The Middle Of Andersonville Chicago villa is ideal for up to 4 guests. More

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Charming 5 Bedrooms 2 Bathrooms

8027 South Kimbark Avenue, Chicago, United States Show map

Situated 4.6 km from the Frederick C. Frank Lloyd Wright's Robie House, Charming 5 Bedrooms 2 Bathrooms Chicago villa entices guests to explore various tourist attractions in the area. More

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Near Parks & Eats! Elegant Southwest Chicago Home

2805 W 83Rd Pl Unit Main Level, Chicago, United States Show map

Nestled a 10-minute drive from the petite Scottsdale Playground Park, Near Parks & Eats! Elegant Southwest Chicago Home entices guests to explore various tourist destinations nearby. With a maximum… More

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