Holiday Homes in Chicago

The 6-room The Avondale Guesthouse Chicago villa offers swift access to various city sites, such as the Algonquin Park, situated nearly 5 minutes' walk away. This 3-bedroom holiday home hosts up to 6… More

Located in Lincoln Park with plenty of places within the neighborhood to help stretch your legs, only a few steps from Rotofugi Gallery, the 1-bedroom Lincoln Park Living - 3 Queen Beds - Sleeps 6… More

Located in Lincoln Park with plenty of places within the neighborhood to help stretch your legs, a mere 6 minutes' walk from Holy Covenant United Methodist Church, the 2-bedroom Lincoln Park Living -… More

Located 25 minutes' walk from the Welles Park, Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find Villa Chicago offers a games room for guests' leisure. Located within easy reach of Korean… More

Located in Daan District, which is home to educational institutions including National Taiwan University, plus Gongguan and Linjiang night markets, both filled with food stalls, just 6 minutes' walk… More

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

Situated around 500 metres from Saint Josaphat Catholic Church, Suite 2 On Southport 4 Queen Beds Chicago villa offers easy access to numerous tourist spots in the area. More

The 2-bedroom Lincoln Park Living - Suite 2 Chicago villa can host up to 10 guests, boasting a convenient location within a 7-km distance of iconic cultural attractions such as the Art Institute of… More

The 4-bedroom Designer Themed 4 Bedroom In Best Location With Patio And Fireplace Chicago villa provides easy access to various city attractions, such as The Noble Horse Theatre, situated about a 5… More

Hosting up to 10 guests, Stunning Duplex Condo #1 - Downtown River North Chicago villa offers a convenient location within a 6-km distance of sports attractions such as the baseball stadium "Wrigley… More

Accommodating up to 16 guests, the 5-bedroom Spacious 5-Br House Near Transit W Parking Chicago villa is situated 3.6 km from renowned cultural sites such as the National Museum of Mexican Art. More

Situated just 5 minutes' walk from 345 Art Gallery, the 4-bedroom Spacious Row Home Next Transit Near Downtown W Parking Chicago entices guests with views of the garden. Located about 7 km from the… More

Located in Logan Square with plenty of bars and restaurants at an affordable price, around 5 minutes' walk from the live music venue "Congress Theater", the 4-bedroom Magnificent New Home W/8 Beds &… More

Romantic 3 Bed Home In The Heart Of The Park Chicago provides easy access to various city attractions, such as Greater Metropolitan MB Church, situated 6 minutes' walk away. More

The 5-bedroom Historic Luxury Townhouse In Downtown Chicago Villa is nestled a mere 6 minutes' walk from the skyscraper 360 Chicago Observation Deck and can accommodate up to 10 guests. More

Located 6 km from the premier natural-history Field Museum, Chic Green L Near Downtown & Il Medical District Chicago villa gives access to various tourist sites in the vicinity. More

Located a 10-minute drive from the Guaranteed Rate Field, Beautifully Renovated House 10 Mins From Downtown Villa Chicago offers karaoke for guests' leisure. Located 6 km from the premier natural… More

Situated approximately 25 minutes' walk from the super - tall skyscraper "Willis Tower", Breathtaking Downtown Penthouse B - Sleeps 11 Villa Chicago invites guests to relax at a patio. Offering a… More

Breathtaking Downtown Penthouse A - Sleeps 11 Villa Chicago offers quick access to such city attractions as the long-standing Carl Hammer Gallery, located merely a 6-minute walk away. More

Located about a 25-minute walk from the National Veterans Art Museum, the 3-bedroom Historic Home With Outdoor Hot Tub Near Downtown In Public Transportation Hub Chicago entices guests to relax in a… More

The Village Inn By Dakota Gal Digs Chicago villa can host up to 8 guests, boasting a prime location a 25-minute walk from iconic cultural attractions such as the Chicago History Museum. More

Situated only 5 minutes' walk from the Chicago History Museum, Beautiful Remodeled Penthouse Unit In Old Town Villa Chicago is ideal for up to 14 guests. More

Stunning 5Br Home In Heart Of Chicago With 2 Rooftops is nestled within a 6-km distance of the skyscraper 360 Chicago Observation Deck and provides a sauna. Offering Wi-Fi, the Chicago holiday home… More

Spacious Luxury Retreat 8 Bed Oasis With 6 Baths Chicago villa is located 2.6 km from the private research university "Illinois Institute of Technology" and invites guests to enjoy a patio. Located… More

Situated only a 9-minute walk from the St. Malachy and Precious Blood Church, Chicago Mid-Century Gem By United Center Villa provides access to numerous tourist attractions in the area. More

The Logandale: Huge Mid-Century Home, Sleeps 15 Chicago offers quick access to such city attractions as the Saint Hyacinth Roman Catholic Church, located about a 5-minute walk away. More

Located 7 km from the Sprawling hands-on Museum of Science and Industry, Cozy 4Bd House Fireplace And Pond Chicago villa gives access to various tourist sites in the vicinity. More

Staying at Logan Square Oasis Villa Chicago, guests can easily reach Half Italian, located just 0.6 km away. More

Up to 5 guests can stay at the 3-bedroom Victorian Mansion In Garfield Park Villa Chicago and enjoy Chicago Community Mennonite Church, located 500 metres away. More

The 5-bedroom Gorgeous 5 Bedroom Gem With Games Chicago villa offers proximity to such city sites as Saint Sabina Roman Catholic Church, located a mere 6 minutes' walk away. Suitable for up to 16… More

The 4-bedroom Stylish Chicago Retreat: Walk To Loyola University villa offers easy access to such tourist spots as Mundelein College, located nearly a 5-minute walk away. Providing guests with Wi-Fi… More

Situated just a 5-minute walk from Katherine Anne Confections, 5Br 5Ba Architectural Estate-Theatre Gym Rooftop Chicago villa entices guests with views of the city. Featuring a hot tub and a sauna… More

The 4-bedroom Roscoe Village Family Hideaway Chicago villa offers proximity to such city sites as the Juniper Playlot Park, located nearly a 5-minute walk away. More

Up to 12 guests can stay at the 5-bedroom Boutique Garden House Chicago 3-Story Sleeps 12 Villa and enjoy First Progressive Church of Christ, located approximately 5 minutes' walk away. Located 4.3… More

Offering access to entertainment venues such as the Chicago Theatre, situated nearly a 25-minute walk away, 2 Newly Built Luxury Condos With Private Roofdeck Chicago villa can host up to 16 guests. More

Situated 2.9 km from the large Norridge Park District, Charming Home In Portage Park Chicago provides access to numerous tourist attractions in the area. More

Located around 5 minutes on foot from the Holy Name Cathedral, River North Hideaway With Amazing Views And Parking Villa Chicago offers quick access to various city attractions in the vicinity. More

Nestled a 9-minute walk from the Buffalo Exchange, Chicago New 2Br Home W 3 Beds And Highspeed Internet entices guests to explore various tourist destinations nearby. More

Situated around 25 minutes' walk from the lit 1926 theater "Cadillac Palace Theatre", Breathtaking Chi Unit In River North With Rooftop Deck - Penthouse A - Sleeps 11 Chicago villa provides access to… More

Situated approximately 5 minutes' walk from the Komoda building, Chic 4-Bedroom Haven: Designer'S Dream Home Chicago offers easy access to numerous tourist spots in the area. More

4Br Modern Urban Escape Walk To Zoo Lakefront & Red Line Chicago villa is located about 4 km from the half-mile-long Navy Pier and invites guests to join cycling. More

Overlooking the garden, Hello Again, Chicago! Villa enjoys a prime setting 5 minutes' walk from the Paperish Mess. Located a few steps from the Mariano's, this holiday home provides Wi-Fi and private… More

Modern 3Br Near Mccormick & South Loop Villa Chicago is located around a 25-minute walk from the premier natural-history Field Museum and provides cycling for active guests. More

Perfect Location Across From Park & Train Station Villa Chicago, located 6 minutes' walk from Midwest Athletic Club, can host up to 13 guests. Providing guests with Wi-Fi and a private parking lot… More

Located 6 km from the Art Institute of Chicago, Newly Updated Vintage 6 Bedroom Single Family Home Home Chicago gives access to various tourist sites in the vicinity. The 6-bedroom holiday home hosts… More

Along with Wi-Fi and private car parking, 5 Bedroom Huge House In Best Location Parking Fireplace Back Yard Chicago villa offers proximity to the neo - Gothic skyscraper "Tribune Tower", located 2.3… More

Spacious Chicago Group Home! Walk To Train & Eats offers swift access to various city sites, such as the Architectural Artifacts, situated 6 minutes' walk away. More

The 5-bedroom Entire Building-Walk To Lincoln Park Or The Beach Chicago villa offers swift access to various city sites, such as the petite South Lakeview Playground Park, situated approximately a 5… More

Downtown Lake Views, Mich Ave, Museums 2Bd- 2Ba #10 Chicago villa offers quick access to such tourist spots as the General John Logan Memorial, situated only a 6-minute walk away. More

The 3-bedroom Woodlawn Oasis Villa Chicago provides easy access to various city attractions, such as Woodlawn Baptist Church, situated about 5 minutes' walk away. More