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2026-11-16
2026-11-17
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Chicago holiday rentals

The Avondale Guesthouse

2973 North Elston Avenue, Chicago, United States Show map

Located nearly a 5-minute walk from Algonquin Park, the 3-bedroom The Avondale Guesthouse Chicago villa offers quick access to various city attractions in the vicinity. The property is located 3.4 km… More

From US$ 313 Book Now

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

2713 West Balmoral Avenue, Chicago, United States Show map

The 4-bedroom Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find Villa Chicago is located about a 25-minute walk from Andersonville and welcomes its guests to enjoy badminton and darts. This 2… More

From US$ 270 Book Now

Suite 2 On Southport 4 Queen Beds

2501 North Southport Avenue, Chicago, United States Show map

Suite 2 On Southport 4 Queen Beds Chicago villa offers quick access to such tourist spots as Saint Josaphat Catholic Church, situated just 500 metres away. More

From US$ 614 Book Now

The Black And White Suite

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

Accommodating up to 8 guests, the 4-bedroom The Black And White Suite Chicago villa is situated 3.1 km from renowned cultural sites such as Smart Museum of Art. More

From US$ 313 Book Now

Designer Themed 4 Bedroom In Best Location With Patio And Fireplace

329 West Schiller Street Back, Chicago, United States Show map

The 4-bedroom Designer Themed 4 Bedroom In Best Location With Patio And Fireplace Chicago villa offers easy access to such tourist spots as Plum Market Old Town, located just 6 minutes' walk away. More

From US$ 529 Book Now

Spacious Row Home Next Transit Near Downtown W Parking

3133 West Fulton Street, Chicago, United States Show map

The 4-bedroom Spacious Row Home Next Transit Near Downtown W Parking Chicago offers proximity to such city sites as Central Memorial M.B. Church, located approximately a 5-minute walk away. With a… More

From US$ 452 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 is situated nearly 5 minutes' walk from Moksha Yoga Center and offers guests to relax with a sauna. Offering a car park on site… More

From US$ 301 Book Now

Spacious 5-Br House Near Transit W Parking

1868 South Millard Avenue, Chicago, United States Show map

The 5-bedroom Spacious 5-Br House Near Transit W Parking Chicago villa can host up to 16 guests, boasting a convenient location about 10 minutes by car from iconic cultural attractions such as… More

From US$ 262 Book Now

Historic Luxury Townhouse In Downtown Chicago

71 East Bellevue Place The Townhouse, Chicago, United States Show map

The 5-bedroom Historic Luxury Townhouse In Downtown Chicago Villa offers quick access to such city attractions as Fourth Presbyterian Church, located only 6 minutes' walk away. This Chicago holiday… More

From US$ 1165 Book Now

Romantic 3 Bed Home In The Heart Of The Park

5923 South Indiana Avenue, Chicago, United States Show map

Situated about a 25-minute walk from the private research University of Chicago, Romantic 3 Bed Home In The Heart Of The Park Chicago entices guests to explore various tourist attractions in the area. More

From US$ 393 Book Now

Chicago Condo W/ Balcony: Walk To Cta Stations!

813 S Bell Ave #3, Chicago, United States Show map

The 2-bedroom Chicago Condo W/ Balcony: Walk To Cta Stations! villa can host up to 3 guests, boasting a prime location approximately a 15-minute drive from iconic cultural attractions such as the… More

From US$ 138 Book Now

Chic Green L Near Downtown & Il Medical District

602 South Western Avenue, Chicago, United States Show map

Offering a location around 6 km from The Art Institute of Chicago, Chic Green L Near Downtown & Il Medical District Chicago villa gives access to various tourist spots in the area. More

From US$ 118 Book Now

Beautifully Renovated House 10 Mins From Downtown

4244 South Prairie Avenue, Chicago, United States Show map

Situated a 25-minute stroll from Lakefront Trail, Beautifully Renovated House 10 Mins From Downtown Villa Chicago offers guests to enjoy a sundeck, water slides, and a picnic area. Located 7 km from… More

From US$ 779 Book Now

Breathtaking Downtown Penthouse A - Sleeps 11

811 N Sedgwick St, Chicago, United States Show map

Breathtaking Downtown Penthouse A - Sleeps 11 Villa Chicago provides easy access to various city attractions, such as the long-standing Carl Hammer Gallery, situated just a 6-minute walk away. More

From US$ 329 Book Now

The Upscale Getaway Near Downtown

2331 West Harrison Street Unit 3, Chicago, United States Show map

Along with Wi-Fi and a private parking lot, the 2-bedroom The Upscale Getaway Near Downtown Villa Chicago offers proximity to the super - tall skyscraper "Willis Tower", located 4 km away. Offering a… More

From US$ 479 Book Now

Stunning 5Br Home In Heart Of Chicago With 2 Rooftops

1307 North Bell Avenue, Chicago, United States Show map

The 5-bedroom Stunning 5Br Home In Heart Of Chicago With 2 Rooftops accommodates up to 16 guests and offers a convenient location merely a 7-minute stroll from such places of worship as Holy Trinity… More

From US$ 1501 Book Now

Spacious Luxury Retreat 8 Bed Oasis With 6 Baths

2630 South Throop Street, Chicago, United States Show map

The 7-bedroom Spacious Luxury Retreat 8 Bed Oasis With 6 Baths Chicago villa is located around 25 minutes' walk from Guaranteed Rate Field, giving access to various tourist spots nearby. The… More

From US$ 1322 Book Now

Chicago Home Near Navy Pier & Shedd Aquarium!

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

The 3-bedroom Chicago Home Near Navy Pier & Shedd Aquarium! provides easy access to various city attractions, such as Burnside Baptist Church, situated around 5 minutes' walk away. This property… More

From US$ 159 Book Now

Chicago Treasure 4 Bed Getaway

712 North Willard Court, Chicago, United States Show map

Chicago Treasure 4 Bed Getaway Villa provides easy access to various city attractions, such as Lush Wine & Spirits, situated 6 minutes' walk away. More

From US$ 231 Book Now

5 Bedroom Huge House In Best Location Parking Fireplace Back Yard

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

Located approximately a 20-minute walk from the 35-acre Lincoln Park Zoo, the 5-bedroom 5 Bedroom Huge House In Best Location Parking Fireplace Back Yard Chicago villa gives access to various tourist… More

From US$ 754 Book Now