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Chicago holiday rentals

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

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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2Br Travelers Favorite Modern

5425 W Drummond Pl, Chicago, Il 60639, Usa, Chicago, United States View map

Situated in the heart of Chicago, the 2Br Travelers Favorite Modern Villa seamlessly blends contemporary elegance with a welcoming ambiance, making it an ideal retreat for both leisure and business… More

From US$ 261 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

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

Luxury Gold Coast Penthouse With Deck & Views

22 East Elm Street, Chicago, United States View map

Located a 25-minute walk from the half - mile - long Navy Pier, Luxury Gold Coast Penthouse With Deck & Views Villa Chicago offers a casino for guests' leisure. This villa features opportunities for… More

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Hello Again, Chicago!

1856 West Huron Street, Chicago, United States View map

Staying at Hello Again, Chicago! Villa, guests can visit the Mariano's, which is only 450 metres away. More

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Charming & Bright Multilevel Townhome With Parking

Chicago, United States View map

Charming & Bright Multilevel Townhome With Parking Chicago villa provides easy access to various city attractions, such as Saint Michael Roman Catholic Church, situated nearly 5 minutes' walk away. More

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3 Bedroom Spacious Home In Ideal Location W Free Parking Back Yard Pets Welcome

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

3 Bedroom Spacious Home In Ideal Location W Free Parking Back Yard Pets Welcome Chicago offers easy access to such tourist spots as Zanies, located just 7 minutes' walk away. More

From US$ 949 Book Now

Pet-Friendly With Pool Table Walk To Wrigley Field

1045 W Dakin St Unit 1, Chicago, United States View map

Offering a location 4 km from the free Lincoln Park Zoo, Pet-Friendly With Pool Table Walk To Wrigley Field Villa Chicago gives access to various tourist spots in the area. More

From US$ 1249 Book Now

New Construction Building In River North

811 N Sedgwick St, Chicago, United States View map

The 669 m^2 New Construction Building In River North Apartment Chicago is located 4.2 km from Shedd Aquarium and about a 25-minute walk from Chicago Cultural Center. Situated a few moments from St. More

From US$ 1119 Book Now

Wrigley 4Br Home, Sleeps 10

3623 N Ashland Ave, Chicago, United States View map

Situated nearly 5 minutes' walk from Juniper Park, the 2-bedroom Wrigley 4Br Home, Sleeps 10 Chicago offers easy access to numerous tourist spots in the area. More

From US$ 2047 Book Now

1 Mi To Wrigley! Quintessential Chi-Town Greystone

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

To enjoy your vacation in Chicago, stay at 1 Mi To Wrigley! Quintessential Chi-Town Greystone Apartment Chicago, which is merely 1.6 km from the Graceland Cemetery and nearly 20 minutes' walk from… More

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3Br Gym Workspace Chicago Condo

3656 North Osage Avenue Unit 2, Chicago, United States View map

Welcome to the luxurious 3Br Gym Workspace Chicago Condo, a magnificent urban retreat nestled in the heart of the city. Located just 21 kilometers from the bustling Ogilvie Transportation Center and… More

From US$ 440 Book Now

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

1220 N Paulina, Chicago, United States View map

Positioned in the vibrant Wicker Park neighborhood, Wicker Park 6Bd 4Ba, Steps From CTA, Parking Incl Home invites guests to experience the essence of urban living intertwined with modern comfort. More

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Top 1 Rated 4Br Lincoln Park House - King Bed

210 W St Paul Ave, Chicago, Il 60614, Usa, Chicago, United States View map

### Discover the Charm of the Top 1 Rated 4Br Lincoln Park House - King Bed The Top 1 Rated 4Br Lincoln Park House - King Bed stands out not only for its prime location but also for the seamless… More

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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

Romantic 3 Bed Home In The Heart Of The Park

5923 South Indiana Avenue, Chicago, United States View map

Nestled in the vibrant hearts of urban landscapes, the Romantic 3 Bed Home In The Heart Of The Park offers an exquisite retreat, blending luxury and comfort for an unforgettable stay. This charming… More

From US$ 393 Book Now

Commuter-Friendly Bungalow In Chicago'S South Side

8817 S Merrill Ave, Chicago, United States View map

Offering a location around 7 km from the Sprawling hands-on Museum of Science and Industry, Commuter-Friendly Bungalow In Chicagos South Side gives access to various tourist spots in the area. More

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2 Rooftops 2 Car Garage 4 Stories

North Hudson Avenue 1501, Chicago, United States View map

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

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Sleeps 22 • Modern Multi-Unit • Gym • Workspaces

3114 West Waveland Avenue, Chicago, United States View map

Sleeps 22 • Modern Multi-Unit • Gym • Workspaces Chicago villa offers swift access to various city sites, such as Prop Thtr, situated merely 6 minutes' walk away. More

From US$ 1377 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

Spacious 3Br Urban Getaway W Gym

2550 South Wabash Avenue, Chicago, United States View map

Spacious 3Br Urban Getaway W Gym Chicago villa is located just 600 metres from Quinn Chapel African Methodist Episcopal Church and invites guests to enjoy a patio. Guests can enjoy cycling at this… More

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Breathtaking Chi Unit In River North With Rooftop Deck - Penthouse A - Sleeps 11

North Sedgwick Street 811, Chicago, United States View map

Located merely 1.1 km from Chicago-style pizza, the 3-room Breathtaking Chi Unit In River North With Rooftop Deck - Penthouse A - Sleeps 11 Apartment Chicago is about 25 minutes' walk from a top… More

From US$ 1205 Book Now

Cozy Wicker Park Home With Movie Room

1523 North Artesian Avenue, Chicago, United States View map

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8Br Kids Room, Game Room, Gym Andtheater

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

Welcome to the exquisite 8Br Kids Room, Game Room, Gym Andtheater Chicago, where luxury and leisure blend seamlessly. Nestled just 30 minutes by car from the bustling Ogilvie Transportation Center… More

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6 Mi To Dtwn: Dog-Friendly Condo W/ Hot Tub!

4839 S Vincennes Ave Unit 2, Chicago, United States View map

6 Mi To Dtwn Dog-Friendly Condo With Hot Tub! Chicago villa offers easy access to such tourist spots as Harold Washington Cultural Center, located merely a 6-minute walk away. More

From US$ 362 Book Now

Downtown Living: Walkable, Modern Chicago Condo

235 W Van Buren St Unit 2220, Chicago, United States View map

Nestled a 25-minute walk from the avant - garde Harris Theater, Downtown Living: Walkable, Modern Chicago Condo villa entices guests to explore various tourist destinations nearby. More

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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

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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Bronzeville 42 Art & Hospitality

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

Nestled 7 km from the Art Institute of Chicago, Bronzeville 42 Art & Hospitality Chicago villa entices guests to explore various tourist destinations nearby. More

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Breathtaking Downtown Penthouse A - Sleeps 11

811 N Sedgwick St, Chicago, United States View map

**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

From US$ 329 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

Chic 4-Bedroom Haven: Designer'S Dream Home

2655 West Huron Street, Chicago, United States View map

**Chic 4-Bedroom Haven: Designer's Dream Home** is a splendid escape nestled in the vibrant West Town neighborhood of Chicago. This stylish sanctuary is situated along a lively stretch of West… More

From US$ 1155 Book Now

Extended Stay: Walk To Uic Campus & Train!

1070 W 15Th St Unit 147, Chicago, United States View map

The spacious 116 m² Extended Stay Walk To Uic Campus And Train! Chicago apartment is only 8 minutes' walk from Prospectus Art Gallery. Offering a patio, the apartment also features a swimming pool… More

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Charming 5 Bedrooms 2 Bathrooms

8027 South Kimbark Avenue, Chicago, United States View map

Nestled a 10-minute ride from Museum of Science and Industry, Charming 5 Bedrooms 2 Bathrooms Chicago villa entices guests to explore various tourist destinations nearby. More

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River West Modern 4-Bd Home With Patio & Balcony

657 North Carpenter Street, Chicago, United States View map

During the stay at River West Modern 4-Bd Home With Patio & Balcony Chicago, guests can indulge in cycling or visit Macy's on State Street, located around 25 minutes' walk away. More

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King Bed L Cta L United Center L Near Kasama L Patio

924 North Wolcott Avenue G, Chicago, United States View map

Offering a location 4.7 km from Millennium Public Park, King Bed L Cta L United Center L Near Kasama L Patio Villa Chicago gives access to various tourist spots in the area. More

From US$ 374 Book Now

Chicago Chic, Cozy 1Br With Stylish Workspace

3114 W Waveland Ave, Unit 2A, Chicago, Il 60618, Usa, Chicago, United States View map

Welcome to the Chic, Cozy 1Br With Stylish Workspace, a serene retreat nestled in the heart of vibrant Chicago. This stylish haven offers guests a perfect blend of modern comfort and urban… More

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Cute And Cozy Chicago Modern Condo

1625 W Superior St 3F, Chicago, Il 60622, Usa, Chicago, United States View map

Located 20 minutes' walk from an indoor arena, Cute And Cozy Chicago Modern Condo villa gives access to various tourist sites in the vicinity. More

From US$ 526 Book Now

Ultra Modern Luxury - New Construction 4 Bedrooms

5039 North Winthrop Avenue, Chicago, United States View map

Staying at Ultra Modern Luxury - New Construction 4 Bedrooms Chicago villa, guests can visit Lane Sandy Beach, which is about a 25-minute walk away. More

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Wicker Park 4Bd 3Ba, Steps From Cta, Parking Incl Home

1220 N Paulina, Chicago, United States View map

Nestled in the vibrant heart of Wicker Park, the stylish Wicker Park 4Bd 3Ba, Steps From CTA, Parking Incl Home captures the essence of this trendy neighborhood. Known for its eclectic mix of… More

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Chic Green L Near Downtown & Il Medical District

602 South Western Avenue, Chicago, United States View map

Located 6 km from Buckingham Fountain, Chic Green L Near Downtown & Il Medical District Chicago villa gives access to various tourist sites in the vicinity. More

From US$ 118 Book Now

2 Mi To Red Line: Chicago Home Near Sherman Park

5205 S May St, Chicago, United States View map

Offering a location just 550 m from the Sherman Park, 2 Mi To Red Line Chicago Home Near Sherman Park gives access to various tourist spots in the area. More

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White Sox Best House

3801 South Calumet Avenue, Chicago, United States View map

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

From US$ 162 Book Now

Quiet Chicago Townhome: Walk To Subway Stations

220 N Laporte Ave 1, Chicago, United States View map

Situated approximately 5 minutes' walk from One Lord One Faith Missionary Baptist Church, the 1-bedroom Quiet Chicago Townhome Walk To Subway Stations villa offers easy access to numerous tourist… More

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Spacious 3-Bed West Loop Townhouse, 1 Car Garage

920 W Van Buren St, Chicago, United States View map

Nestled a 17-minute walk from the Skydeck Chicago, Spacious 3-Bed West Loop Townhouse, 1 Car Garage Chicago villa entices guests to explore various tourist destinations nearby. More

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Envitae Hotel 4Br Modern Sleek Apartment

853 West Blackhawk Street, Chicago, United States View map

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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Game Room, Firepit, Playground, Gym, Billiard

2146 N Kilpatrick Ave, Chicago, United States View map

Staying at the 2-bedroom Game Room, Firepit, Playground, Gym, Billiard Chicago villa, guests can easily reach Maplewood Brewery & Distillery, located approximately a 10-minute drive away. More

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2 Newly Built Luxury Condos With Private Roofdeck

811 N Sedgwick St, Chicago, United States View map

The spacious 167 m^2 2 Newly Built Luxury Condos With Private Roofdeck Chicago includes a patio and is situated around a 5-minute stroll from Saint Matthew United Methodist Church. The baseball… More

From US$ 2399 Book Now