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2026-11-09
2026-11-10
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Vacation Rentals in Chicago

The Bright Retreat In Andersonville

1343 West Winona Street 1W, Chicago, United States Show map

Located around 700 metres from Argyle Street, the 1-bedroom The Bright Retreat In Andersonville Chicago apartment is within a 7-km distance of a top family-friendly place like the 35 - acre Lincoln… More

From US$ 253 Book Now

Wrigleyville Art Deco Retreat Garage

1128 West Addison Street, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the spacious 3-bedroom The Addison Art Deco Executive Retreat Garage Apartment Chicago, which is within 10 minutes' drive of the 35-acre beautifully… More

From US$ 1326 Book Now

2Br Garden Suite In Lakeview Walk To Wrigley

902 W Newport Ave, Chicago, United States Show map

The spacious 79 m² 2Br Garden Suite In Lakeview Walk To Wrigley Chicago is a good choice for accommodating up to 5 guests, offering a prime setting just 0.9 km from the baseball stadium "Wrigley… More

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City Retreat

10601 South Edbrooke Avenue Unit 2, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the spacious 84 m² City Retreat Chicago apartment, which is within 20 minutes' walk of A. Philip Randolph Pullman Porter Museum and approximately 2 km from… More

From US$ 124 Book Now

North Chicago Spacious Home

5808 North Winthrop Avenue, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the 4-bedroom North Chicago Spacious Home apartment, which is merely 550 metres from Saint Andrew's Greek Orthodox Church and just 0.7 km from Emanuel… More

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East Lincoln Park Gem Spacious 4 Br

650 West Wrightwood Avenue G, Chicago, United States Show map

The 232 m² East Lincoln Park Gem Spacious 4 Br Chicago apartment boasts views of the garden and is located 25 minutes' walk from North Avenue Beach. The apartment features Wi-Fi, along with parking… More

From US$ 359 Book Now

Wabash 4Br - Pool Free In & Out Parking 1

626 South Wabash Avenue, Chicago, United States Show map

Located in the South Loop district, the spacious Wabash 4Br - Pool Free In & Out Parking 1 Apartment Chicago is only 10 minutes' walk from Buckingham Fountain and 2.7 km from the third-smallest… More

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Livn Millennium Park Downtown Chicago Prem Studio

19 South Wabash Avenue, Chicago, United States Show map

Located in the Theatre district of Chicago approximately 25 minutes' walk from the 1924 open-air stadium "Soldier Field", the 3-room Livn Millennium Park Downtown Chicago Prem Studio accommodates up… More

From US$ 487 Book Now

Closest Condo To The United Center 3 Bedrooms & Futon

2212 West Monroe Street, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the spacious 130 m² Closest Condo To The United Center 3 Bedrooms & Futon Chicago, which is 4.8 km from Chicago Cultural Center and around a 10-minute drive… More

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Walk To The Beach • Private Office • 5Br

1220 W Columbia Ave, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the spacious 158 m² Walk To The Beach • Private Office • 5Br Chicago apartment, which is within 25 minutes' walk of Touhy Park and just 1.6 km from Jarvis… More

From US$ 386 Book Now

Spacious Chicago Group Home! Walk To Train & Eats

4454 N Hermitage Ave, Chicago, United States Show map

Featuring a terrace and barbecue for a delightful experience, Spacious Chicago Group Home! Walk To Train & Eats offers a prime location 6 minutes' walk from Architectural Artifacts. Located steps… More

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Garden Apt Private Patio Fire Pit Pets Ok

851 North Fairfield Avenue, Chicago, United States Show map

Situated 6 minutes' walk from Komoda Gift Shop, Garden Apt Private Patio Fire Pit Pets Ok Chicago offers proximity to various nearby tourist attractions. The maximum occupancy at this spacious 74 m²… More

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Luxury 3Br Spacious Suite Sleeps 8 Guests With Patio, Skyline View, Optional Parking And Gym Access Near Mccormick Place And Lakefront

2036 South Michigan Avenue Unit 309, Chicago, United States Show map

Featuring a prime location just a 5-minute walk from Second Presbyterian Church of Chicago, the 88 m² Skyline View Patio Suite: McCormick Place 3BR Retreat Chicago accommodates up to 8 guests. More

From US$ 452 Book Now

Majestic Modern Style Beach Front Rooftop Wfh Gym

1049 West Lawrence Avenue 812, Chicago, United States Show map

The stylish Majestic Modern Style Beach Front Rooftop Wfh Gym Chicago apartment is a 5-minute walk from Uptown Poetry Slam and includes a fitness centre. This apartment features Wi-Fi, along with… More

From US$ 188 Book Now

Wrigley Luxe Stay 3Br Free Parking

1045 West Dakin Street, Chicago, United States Show map

Located a mere 9 minutes' stroll from the baseball stadium "Wrigley Field", the spacious 149 m² Wrigley Luxe Stay 3Br Free Parking Chicago apartment accommodates up to 6 guests. Enjoying a prime… More

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Livn Millennium Park Downtown Chicago 1 Br

19 South Wabash Avenue, Chicago, United States Show map

Located in the Theatre district, the 37 m² Livn Millennium Park Downtown Chicago 1 Br Apartment is a mere 9 minutes' walk from The Art Institute of Chicago and 2.3 km from the American football… More

From US$ 656 Book Now

Chicago 2Br Skyline Views - 5 Min Walk To Grant Park

8 E 9Th St, Chicago, United States Show map

The 2-bedroom Chicago 2Br Skyline Views - 5 Min Walk To Grant Park Apartment, located in Downtown Chicago, which is an incredible destination for art, fashion, and adventure, approximately a 20… More

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Lyons' Suite

1831 West Belle Plaine Avenue, Chicago, United States Show map

Located nearly a 25-minute walk from Swedish American Museum, the spacious Lyons' Suite Chicago is approximately 6 km from a top family-friendly place like the 35 - acre Lincoln Park Zoo. Guests can… More

From US$ 314 Book Now

Central Chicago Suite2 Access To Patio

1220 West Augusta Boulevard #1, Chicago, United States Show map

Featuring a prime location, the 2-bedroom Central Chicago Suite2 Access To Patio apartment offers views of the city, nearly a 25-minute walk from Chicago-style pizza. This spacious apartment is… More

From US$ 388 Book Now

Luxury Stylish 3Br Home Minutes From Downtown

6417 North Magnolia Avenue Unit 2, Chicago, United States Show map

The 1550 m² Luxury Stylish 3Br Home Minutes From Downtown Chicago apartment is located 2.1 km from Touhy Park and merely a 7-minute walk from Mundelein College. Wi-Fi and a car park are also… More

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Spacious Modern Pilsen Retreat Sleeps 8 Near Downtown Chicago

1841 West 21St Street, Chicago, United States Show map

The 3-bedroom Spacious Modern Pilsen Retreat Sleeps 8 Near Downtown Chicago apartment is about a 5-minute stroll from National Museum of Mexican Art and can accommodate up to 8 guests. The apartment… More

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Casa De Alma

2505 S Christiana Ave Unit 1 Rear, Chicago, United States Show map

Set 4.8 km from the indoor United Center Arena, the 2-bedroom Casa De Alma Apartment Chicago comprises a seating area and a dining area overlooking the garden. At the spacious 93 m² apartment, Wi-Fi… More

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West Loop - City Views With In & Out Parking 4

315 South Peoria Street, Chicago, United States Show map

The spacious 4-bedroom West Loop - City Views With In & Out Parking 4 Chicago apartment provides swift access to various city landmarks, such as National Hellenic Museum, located nearly a 5-minute… More

From US$ 1502 Book Now

Near Downtown Nest

1912 South Sawyer Avenue, Chicago, United States Show map

Featuring a prime location a 5-minute walk from Douglas Park Baptist Church, the spacious Near Downtown Nest Apartment Chicago accommodates up to 6 guests. Wi-Fi and parking are also available at… More

From US$ 252 Book Now

Chicago Stay 3 King Beds Near Wicker Park

1360 W Evergreen Ave, Chicago Il 60642, Chicago, United States Show map

Chicago Stay 3 King Beds Near Wicker Park apartment is a great place to stay in West Town with a busy stretch of West Chicago Avenue, dotted with New American restaurants and cafes, 3.3 km from the… More

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Walkable 2Br Apartment In Chicago South Loop With Optional Parking And Gym Access Near Mccormick Place, Museum Campus & Lakefront

2036 South Michigan Avenue Unit 505, Chicago, United States Show map

Situated in South Loop, set including historic Printers Row, nearly 5 minutes' walk from Second Presbyterian Church of Chicago, the spacious 2-bedroom Walkable 2Br Apartment In Chicago South Loop… More

From US$ 451 Book Now

Chicago 1Br Free Parking, Near Transit And Dining

1727 West North Shore Avenue, Chicago, United States Show map

The 84 m² Chicago 1Br Free Parking, Near Transit And Dining Apartment is located 2.2 km from the 13-acre urban Indian Boundary Park and only a 7-minute walk from Living Water Community Church. At… More

From US$ 201 Book Now

Business Ready 2Br Apartment In South Loop With Skyline View, Optional Parking & Gym Access Close To Mccormick, Downtown & Cta

2036 South Michigan Avenue Unit 512, Chicago, United States Show map

The spacious Business Ready 2Br Apartment In South Loop With Skyline View, Optional Parking & Gym Access Close To Mccormick, Downtown & Cta Chicago offers views of the city and a location 7 minutes'… More

From US$ 423 Book Now

River North Private Deck With In And Out Parking

153 West Ohio Street, Chicago, United States Show map

Located a 17-minute walk from the public Cloud Gate Sculpture, River North Private Deck With In And Out Parking Chicago apartment overlooks the city. The maximum occupancy at the spacious apartment… More

From US$ 564 Book Now

Luxurious 3Bd Penthouse L Private Patio L Gym L Stunning Rooftop

1122 West Chicago Avenue, Chicago, United States Show map

The spacious 3-bedroom Luxurious 3Bd Penthouse L Private Patio L Gym L Stunning Rooftop Chicago apartment is located 2.9 km from Chicago Union train station and just 6 minutes' walk from Eckhart Park… More

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Studio Near Wrigley • Sleeps 4 • Games • Fireplace

3114 West Waveland Avenue, Chicago, United States Show map

Studio Near Wrigley • Sleeps 4 • Games + Fireplace Chicago is located about a 25-minute walk from Riverview Plaza Shopping Center and about 7 km from the 35 - acre Lincoln Park Zoo. This apartment… More

From US$ 220 Book Now

Spacious 2Br Apartment Steps From Uic Rush Stroger Hospital And Restaurant Row

1440 West Fillmore Street, Chicago, United States Show map

Spacious 2Br Apartment Steps From Uic Rush Stroger Hospital And Restaurant Row Chicago is located just 1.9 km from Chicago Union train station and within 5 minutes' walk of Saint Basil Greek Orthodox… More

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Amazing 3Br 3 Ba Property In Chicago

2154 West Ohio Street, Chicago, United States Show map

Situated approximately a 15-minute ride from the half-mile-long Navy Pier, the spacious 223 m² Amazing 3Br 3 Ba Property In Chicago apartment also boasts easy access to Chicago Union train station… More

From US$ 413 Book Now

River North Private Balcony With In And Out Parking

153 West Ohio Street, Chicago, United States Show map

Located merely 6 minutes' stroll from the scenic Chicago Riverwalk Walkway, the spacious 82 m² River North Private Balcony With In And Out Parking Chicago apartment accommodates up to 5 guests. The 2… More

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2Br W/ Workspace - Coffee Bar - Near Transit

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

2Br W/ Workspace - Coffee Bar - Near Transit Chicago apartment is located 4.1 km from Lindberg Park Nature Preserve and about a 25-minute walk from Amundsen Park. The maximum occupancy at the… More

From US$ 308 Book Now

Luxury Fulton Market Condo - Prime Location

660 West Wayman Street Apt 307, Chicago, United States Show map

The spacious 84 m² Luxury Fulton Market Condo - Prime Location Chicago is located nearly 25 minutes' walk from the 20 - acre Maggie Daley Public Park and offers Wi-Fi for either business or leisure. More

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21St Floor Skyline 2Br Near Grant Park & Field Museum

8 E 9Th St, Chicago, Il 60605, Chicago, United States Show map

The 2-bedroom 21St Floor Skyline 2Br Near Grant Park & Field Museum Apartment Chicago enjoys a prime location only a 9-minute walk from the central Harold Washington Library Center. The spacious 112… More

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Cozy Woodlawn Garden Apt

6115 South Rhodes Avenue Garden Apartment, Chicago, United States Show map

Featuring a convenient location a 5-minute walk from Saint Philips Lutheran Church, the spacious Cozy Woodlawn Garden Apt Chicago accommodates up to 2 guests. Wi-Fi and a car park are also available… More

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Spacious 3Br 420-Friendly | Mccormick & Uic Campus

2001 South State Street, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the 3-bedroom Spacious 3Br 420-Friendly | Mccormick & Uic Campus Chicago apartment, which is merely 0.8 km from Chicago Chinatown and around 300 metres from… More

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New 3Bed 2Bath Condo With Parking By United Center

2110 West Washington Boulevard, Chicago, United States Show map

Situated a 6-minute walk from West Side Community Church, the spacious New 3Bed 2Bath Condo With Parking By United Center Chicago looks out onto the city. This apartment capacity is based on up to 6… More

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Wrigleyville Getaway

950 West Addison Street, Chicago, United States Show map

Located just 6 minutes' stroll from the baseball stadium "Wrigley Field", the spacious 158 m² Wrigleyville Getaway Chicago apartment accommodates up to 12 guests. The 4-bedroom apartment enjoys a… More

From US$ 421 Book Now

Mccormick Place Studio With Optional Parking And Sleeps Up To 4

2036 South Michigan Avenue, Chicago, United States Show map

Situated merely 5 minutes' stroll from Second Presbyterian Church of Chicago, the 1-bedroom Mccormick Place Studio With Optional Parking And Sleeps Up To 4 Chicago features a lift and a vending… More

From US$ 783 Book Now

Livn West Loop Chicago King Studio

555 West Jackson Boulevard, Chicago, United States Show map

Located in Downtown Chicago, which is an incredible destination to experience 25 minutes' walk from the public sculpture "Crown Fountain", Livn West Loop Chicago King Studio accommodates up to 2… More

From US$ 375 Book Now

Mccormick Place 2Br Suite With Patio, Skyline View And Optional Parking Sleeps 6 Near Soldier Field And Grant Park

2036 South Michigan Avenue Apartment 311, Chicago, United States Show map

The spacious 88 m² Mccormick Place 2Br Suite With Patio, Skyline View And Optional Parking Sleeps 6 Near Soldier Field And Grant Park Chicago features a prime location within a 3-km distance of the… More

From US$ 405 Book Now

Streeterville Studio W Gym Pool Nr Navy Pier Chi-450

445 E Ohio St, Chicago, Il 60611, Usa, Chicago, United States Show map

Located in Magnificent Mile with luxury shopping, dining and entertainment, the 55 m² Streeterville Studio W Gym Pool Nr Navy Pier Chi-450 Chicago is a mere 9 minutes' walk from the long-standing… More

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Logan Square Urban Oasis: 2 Mi To Local Hotspots!

4642 W Montana St, Chicago, United States Show map

The spacious 84 m² Logan Square Urban Oasis: 2 Mi To Local Hotspots! Apartment Chicago is a good choice for accommodating up to 4 guests, offering a convenient setting about a 15-minute drive from… More

From US$ 275 Book Now

City Villa Sleeps 10-20 Free Tv & Parking

3152 North Pine Grove Avenue, Chicago, United States Show map

Located about 7 km from Chicago Union railway station, the 232 m² City Villa Sleeps 10-20 Free Tv & Parking Chicago is just a 7-minute walk from Belmont Harbor. Wi-Fi and a car park are also… More

From US$ 234 Book Now

Central 2Br South Loop Location With Optional Parking & Gym Access Near Mccormick Place, Shedd Aquarium & Navy Pier

2036 South Michigan Avenue Unit 606, Chicago, United States Show map

Featuring a prime location 350 metres from the indoor Wintrust Arena, the spacious Central 2Br South Loop Location With Optional Parking & Gym Access Near Mccormick Place, Shedd Aquarium & Navy Pier… More

From US$ 514 Book Now

Prime Chicago 2Br Skyline - 5 Min To Museum Campus

8 E 9Th St, Chicago, United States Show map

The 2-bedroom Prime Chicago 2Br Skyline - 5 Min To Museum Campus Apartment is situated in South Loop, set including historic Printers Row, nearly a 20-minute walk from Millennium Public Park, and… More

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Downtown Chicago Stay With Free In & Out Parking 4

59 East Van Buren Street, Chicago, United States Show map

The 3-bedroom Downtown Chicago Stay With Free In & Out Parking 4 apartment is situated in the Theatre district of Chicago, merely 14 minutes' walk from the super-tall skyscraper "Willis Tower", and… More

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