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2026-11-08
2026-11-09
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Vacation Rentals in Chicago

Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts

3558 North Wilton Avenue, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the 3-room Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts Chicago apartment, which is 3.3 km from the 35-acre Lincoln… More

From US$ 82 Book Now

5430 Happy Home

5430 South Dearborn Street, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at 5430 Happy Home Chicago apartment, which is 3.7 km from the Sprawling hands-on Museum of Science and Industry and 10 minutes' drive from the Frederick C. More

From US$ 29 Book Now

Hollywood Rentals Llc

1656 West Hollywood Avenue, Chicago, United States Show map

Hollywood Rentals Llc Chicago apartment is located 2.4 km from Foster Beach and a 25-minute walk from the energetic urban Kathy Osterman Beach. Wi-Fi and a car park are among the essentials at… More

From US$ 9 Book Now

2F Chicago'S Little Italy Near West Loop & Downtown

1506 West Polk Street 3F, Chicago, United States Show map

The 4-bedroom 2F Chicago'S Little Italy Near West Loop & Downtown Apartment offers a convenient location only a 6-minute walk from Arrigo Park. This spacious apartment sleeps up to 8 guests and… More

From US$ 215 Book Now

Perfect Place To Enjoy The City Or Just Relax

1902 South Sawyer Avenue, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the 1-bedroom Perfect Place To Enjoy The City Or Just Relax Chicago apartment, which is around 15 minutes by car from the super - tall skyscraper "Willis… More

From US$ 107 Book Now

Lincoln Park 3 Bedroom Penthouse

2633 North Sheffield Avenue, Chicago, United States Show map

The spacious 165 m² Lincoln Park 3 Bedroom Penthouse Chicago apartment offers a convenient location approximately 300 metres from the midsize Apollo Theater Chicago. The 3-bedroom apartment is… More

From US$ 227 Book Now

Pulaski Point Properties

3936 North Pulaski Road, Chicago, United States Show map

The 6-room Pulaski Point Properties Chicago apartment offers a convenient location nearly 5 minutes' walk from Irving Park Lutheran Church. The apartment also provides guests with conveniences like… More

From US$ 53 Book Now

Adorable 2 Bedroom With Free Street Parking

1902 South Sawyer Avenue, Chicago, United States Show map

Featuring a convenient location nearly 5 minutes' walk from Douglas Park Baptist Church, the spacious 2-bedroom Adorable 2 Bedroom With Free Street Parking Chicago apartment accommodates up to 4… More

From US$ 175 Book Now

Forrestville Ave Large Suite

4510 South Forrestville Avenue, Chicago, United States Show map

Located in the Bronzeville district of Chicago, nearly a 5-minute walk from Ebenezer Missionary Baptist Church Building, the spacious 2-bedroom Forrestville Ave Large Suite Chicago accommodates up to… More

From US$ 145 Book Now

The Avondale Guesthouse

2973 North Elston Avenue, Chicago, United States Show map

The 3-bedroom The Avondale Guesthouse Chicago villa offers swift access to various city sites, such as Algonquin Park, situated nearly 5 minutes' walk away. This accommodation boasts a terrace and a… More

From US$ 313 Book Now

Experience Downtown Chicago At Millennium - Luxury Apartments In The Loop

29 South La Salle Street, Chicago, United States Show map

2-bedroom Experience Downtown Chicago At Millennium - Luxury Apartments In The Loop lies approximately 2 km from the premier natural-history Field Museum and merely 350 metres from Monroe tube… More

From US$ 259 Book Now

1F Cozy Home In Little Italy Near Downtown West Loop United Center

1506 West Polk Street, Chicago, United States Show map

The 3-bedroom 1F Cozy Home In Little Italy Near Downtown West Loop United Center Chicago apartment is located merely 1.9 km from Chicago Union train station and only a 6-minute walk from Arrigo Park.… More

From US$ 200 Book Now

Red Robin Rentals - Wicker Park

1446 North Artesian Avenue, Chicago, United States Show map

The 2-room Red Robin Rentals - Wicker Park Chicago apartment lies 2.6 km from Eckhart Park and merely a 10-minute stroll from Western tube station. The spacious apartment features Wi-Fi, along with a… More

From US$ 153 Book Now

2 Bed Apt W/ Office, Free Parking, Near Wrigley

3623 North Ashland Avenue, Chicago, United States Show map

The spacious 2-bedroom 2 Bed Apt W/ Office, Free Parking, Near Wrigley Chicago is located approximately 9 km from Chicago Union train station and nearly a 5-minute walk from Merryman Playlot Park. More

From US$ 507 Book Now

The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile

747 North Wabash Avenue, Chicago, United States Show map

Set in Streeterville with a growing number of high-end leisure activities, The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile Chicago is an 18-minute walk from Museum of Broadcast… More

From US$ 585 Book Now

Linea Luxury Living With Indoor Pool And Rooftop Views In The Loop

215 West Lake Street, Chicago, United States Show map

Situated about 25 minutes on foot from the tall skyscraper "Willis Tower", the 9-room Linea Luxury Living With Indoor Pool And Rooftop Views In The Loop Chicago apartment also boasts easy access to… More

From US$ 418 Book Now

Luxury Chicago Suite

2910 West Farragut Avenue, Chicago, United States Show map

The spacious 1-bedroom Luxury Chicago Suite is a good choice for accommodating up to 3 guests, offering a convenient setting around 25 minutes' walk from Horner Park. The apartment offers modern… More

From US$ 173 Book Now

Chicago Charm

2139 West Granville Avenue, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the spacious 125 m² Chicago Charm Apartment, which is 3.3 km from Foster Beach and approximately a 10-minute ride from the community Pottawattomie Park. Wi… More

From US$ 269 Book Now

Aurelien Spacious Apartments In The Heart Of Gold Coast

833 North Clark Street, Chicago, United States Show map

Located in Downtown Chicago, which is an incredible destination to experience, the 5-room Aurelien Spacious Apartments In The Heart Of Gold Coast Chicago is only 8 minutes' walk from the skyscraper… More

From US$ 266 Book Now

Bucktown Private Condo

1913 West Armitage Avenue Apt 2Rw, Chicago, United States Show map

The spacious Bucktown Private Condo Chicago is nestled in the Bucktown district, a 5-minute walk from the restaurant AMK. Guests can make use of high-speed Internet access for both business and… More

From US$ 363 Book Now

Kenwood Apartments, Downtown Hyde Park

6156 South Kenwood Avenue, Chicago, United States Show map

Kenwood Apartments, Downtown Hyde Park Chicago is located 12 km from Chicago Union train station and only a 6-minute walk from Woodlawn Baptist Church. Guests can make use of Wi-Fi for both business… More

From US$ 84 Book Now

Chic Retreat

612 East 95Th Street, Chicago, United States Show map

The spacious Chic Retreat Apartment Chicago is 25 minutes' walk from Bronzeville Children's Museum. At the apartment, Wi-Fi and private car parking are also provided. More

From US$ 304 Book Now

Fulbrix Bright Designer Apartments With West Loop Views

160 North Elizabeth Street, Chicago, United States Show map

Fulbrix Bright Designer Apartments With West Loop Views Chicago is located about 3 km from Millennium Public Park and a mere 5 minutes' walk from City Winery. Private parking is available for USD 50… More

From US$ 123 Book Now

Boho Bliss - 1Br, 1Bath W/Patio!

1813 North Kedzie Avenue 3, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the 1-bedroom Boho Bliss - 1Br, 1Bath W/Patio! Apartment Chicago, which is approximately a 10-minute drive from the 184 - acre Garfield Park Conservatory… More

From US$ 197 Book Now

Classic Chicago Upstairs Apt Private Balcony

4036 North Saint Louis Avenue, Chicago, United States Show map

The spacious 2-bedroom Classic Chicago Upstairs Apt Private Balcony lies merely 550 metres from Grace Evangelical Covenant Church and a mere 0.9 km from Addison tube station. The apartment capacity… More

From US$ 124 Book Now

Wrigley Oasis! Steps From The Field! - 3Bd 1Ba

1207 West Eddy Street, Chicago, United States Show map

Located in Lakeview, which is one of the 77 community areas of Chicago, Illinois, the 3-bedroom Wrigley Oasis! Steps From The Field! - 3Bd 1Ba Apartment Chicago is only a 6-minute walk from the beer… More

From US$ 268 Book Now

Superior

1467 W. Superior, Chicago, United States Show map

The spacious 139 m² Superior Apartment Chicago lies only 300 metres from Dovetail and merely 10 minutes on foot from Chicago tube station. The maximum occupancy at the 3-bedroom apartment is 9 guests. More

From US$ 2260 Book Now

Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find

2713 West Balmoral Avenue, Chicago, United States Show map

Overlooking the garden, Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find Villa Chicago enjoys a convenient setting a 6-minute walk from North Shore 7th Day Adventist Church. Located just around… More

From US$ 270 Book Now

Beautifully Remodeled Second Floor Flat In River North With Private Rooftop - 2S

North Orleans Street 858, Chicago, United States Show map

Featuring a convenient location, the 2-bedroom Beautifully Remodeled Second Floor Flat In River North With Private Rooftop - 2S Chicago offers views of the city, nearly a 20-minute walk from the… More

From US$ 662 Book Now

The Lyons' Lair

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

Situated nearly a 10-minute ride from the baseball stadium "Wrigley Field", the 2-bedroom The Lyons' Lair Apartment Chicago also boasts easy access to Chicago Union train station which is… More

From US$ 180 Book Now

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

West Augusta Boulevard, Chicago, United States Show map

Located in West Town with a busy stretch of West Chicago Avenue, dotted with New American restaurants and cafes, a 5-minute walk from Polish Museum of America, the spacious Goose Island Central… More

From US$ 491 Book Now

La Villita - Gateway To Chicago

2419 South Troy Street, Chicago, United States Show map

Featuring a prime location 5 minutes' walk from Jacques Marquette Monument, the 70 m² La Villita - Gateway To Chicago Apartment accommodates up to 6 guests. Offering a sunbathing terrace and a picnic… More

From US$ 215 Book Now

The Penthouse, Lux Stay Near Downtown, Uofc & Lake

4419 South Greenwood Avenue, Chicago, United States Show map

The spacious 135 m² The Penthouse, Lux Stay Near Downtown, Uofc & Lake Chicago apartment provides easy access to various city attractions, such as Muddy Waters' House, situated only a 5-minute walk… More

From US$ 240 Book Now

Chicago 2Br Suite Perfect For Convention And Business Trips Near Mccormick Place, Arena, Soldier Field And Grant Park

2036 South Michigan Avenue Apt 403, Chicago, United States Show map

Situated only 0.9 km from McCormick Place Convention Center, the spacious 88 m² Chicago 2Br Suite Perfect For Convention And Business Trips Near Mccormick Place, Arena, Soldier Field And Grant Park… More

From US$ 303 Book Now

Spacious 5-Br Apt Next To Transit Free Parking

1847 South Millard Avenue, Chicago, United States Show map

Spacious 5-Br Apt Next To Transit Free Parking Chicago is located 2.6 km from the Catholic church "Our Lady of Sorrows Basilica" and 10 minutes' drive from the indoor United Center Arena. This… More

From US$ 376 Book Now

Historic And Unique Brownstone In Gold Coast - Downtown - 3

East Cedar Street 57, Chicago, United States Show map

The spacious 1-bedroom Historic And Unique Brownstone In Gold Coast - Downtown - 3 Apartment Chicago is located in Streeterville with a growing number of high-end leisure activities, nearly a 5… More

From US$ 91 Book Now

Lincoln Park Apartment With Backyard!

722 West Wrightwood Avenue, Chicago, United States Show map

The spacious 2-bedroom Lincoln Park Apartment With Backyard! Chicago is situated in Lincoln Park with plenty of places within the neighborhood to help stretch your legs, about 25 minutes' walk from… More

From US$ 204 Book Now

Modern 3 Bedroom Close To Downtown Chicago

4034 S Prairie Ave Basement North, Chicago, Il 60653, Chicago, United States Show map

The 3-bedroom Modern 3 Bedroom Close To Downtown Chicago apartment offers proximity to such tourist attractions as Metropolitan Apostolic Community Church, situated nearly 5 minutes' walk away. This… More

From US$ 87 Book Now

Hyde Park Modern Private Room - Near Univ Of Chicago

4808 South Drexel Boulevard Unit #E, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at Hyde Park Modern Private Room - Near Univ Of Chicago, which is within a 7-km distance of the premier natural-history Field Museum and around 25 minutes on… More

From US$ 104 Book Now

Avenir West Loop Penthouses With Iconic City Views

730 North Milwaukee Avenue, Chicago, United States Show map

Situated nearly a 10-minute drive from the downtown Museum Of Contemporary Art Chicago, the 6-room Avenir West Loop Penthouses With Iconic City Views Chicago apartment also boasts easy access to… More

From US$ 354 Book Now

Flexhome Ukrainian Village • 2Br • Walkable + Private Balcony - Sleeps 6

908 N Damen Ave, Chicago, Il 60622, Usa, Chicago, United States Show map

Featuring a prime location merely a 5-minute walk from Holy Trinity Orthodox Cathedral, the 55 m² Flexhome Ukrainian Village • 2Br • Walkable + Private Balcony - Sleeps 6 Chicago apartment… More

From US$ 233 Book Now

Modern 2Br Loft With Amazing City Skyline View And Optional Parking For 8 Guests Near Mccormick Place And Soldier Field

2036 South Michigan Avenue 712, Chicago, United States Show map

The 2-bedroom Modern 2Br Loft With Amazing City Skyline View And Optional Parking For 8 Guests Near Mccormick Place And Soldier Field Chicago apartment is situated in South Loop, set including… More

From US$ 329 Book Now

Wrigley Garden Unit

820 W. Newport Ave, Chicago, United States Show map

The spacious 50 m² Wrigley Garden Unit Apartment Chicago boasts a prime location merely 300 metres from Boystown. The 3-bedroom apartment is situated within 7 km of Chicago Union train station and… More

From US$ 303 Book Now

Modern 2Br In South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail

61 East 21St Street Unit 612, Chicago, United States Show map

The spacious Modern 2Br In South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail Chicago apartment is located 3.2 km from the 20-acre public Maggie Daley Park and 13 minutes' walk… More

From US$ 308 Book Now

Magnificent New Home W/8 Beds & Free Parking

2019 North Bingham Street, Chicago, United States Show map

The 4-bedroom Magnificent New Home W/8 Beds & Free Parking Chicago offers quick access to such tourist spots as the live music venue "Congress Theater", situated merely 5 minutes' walk away. Offering… More

From US$ 301 Book Now

Chic Euro City Getaway- Close To Downtown

4927 S Prairie Ave, Chicago, Il 60615, Usa, Chicago, United States Show map

The spacious 111 m² Chic Euro City Getaway- Close To Downtown Chicago apartment offers a convenient location around 5 minutes on foot from First Unity Baptist Church. The 3-bedroom apartment is… More

From US$ 163 Book Now

City-View Chicago 3-Br Rooftop

1619 North Clybourn Avenue C, Chicago, United States Show map

The 189 m² City-View Chicago 3-Br Rooftop apartment is located in Lincoln Park with cafés and boutique shops, only a 6-minute walk from Newcity Mall. This 3-bedroom apartment can hold up to 6 guests. More

From US$ 231 Book Now

The Black And White Suite

611 East 41St Street, Chicago, United States Show map

The Black And White Suite Chicago villa offers proximity to nearby tourist spots, such as Lakefront Trail, situated 2.6 km away. More

From US$ 313 Book Now

Beautiful Big 3 Bedroom Quiet Apt Near Downtown

7825 South Cregier Avenue, Chicago, United States Show map

The spacious 5-room Beautiful Big 3 Bedroom Quiet Apt Near Downtown Chicago is located just 0.6 km from Temple of Brotherly Love Community Church and only a 6-minute walk from Avalon Regal Theater. More

From US$ 335 Book Now

K2 Sky High Apartments With Stunning Chicago Views In West Loop

365 North Halsted Street 3305, Chicago, United States Show map

Located 19 minutes' walk from Chicago-style pizza, the 6-room K2 Sky High Apartments With Stunning Chicago Views In West Loop is 3.8 km from a top family-friendly place like the 35-acre Lincoln Park… More

From US$ 283 Book Now