Chicago holiday rentals

**Welcome to The Avondale Guesthouse Chicago**, a charming retreat that seamlessly blends comfort with modern amenities in an inviting garden setting. This delightful haven, located only 20 km from… More

**Welcome to Northside Famlynest Lincoln Sq, a Cozy Family Gem in Chicago** Exploring the vibrant neighborhood is a breeze, with the Lincoln Park Zoo just 9 km away, allowing you to immerse yourself… More

Located just 6 minutes' walk from Supera Park, Suite 2 On Southport 4 Queen Beds Chicago villa offers quick access to various city attractions in the vicinity. More

Immerse yourself in the timeless elegance of The Black, where sophistication meets comfort in an ideal urban setting. This luxurious retreat caters to both leisure and business travelers… More

The 3-bedroom Designer Themed 4 Bedroom In Best Location With Patio And Fireplace Chicago villa offers swift access to various city sites, such as The Noble Horse Theatre, situated around 5 minutes'… More

**Experience Comfort and Convenience at the Spacious Row Home Next Transit Near Downtown W Parking** More

Nestled in the heart of Chicago, the Spacious 5-Br House Near Transit W Parking offers a unique blend of comfort and convenience, ideal for both families and groups traveling together. Just 10… More

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

Located in Downtown Chicago, which is an incredible destination for art, fashion and adventure, just a 6-minute walk from the Fourth Presbyterian Church, the 5-bedroom Historic Luxury Townhouse In… More

Welcome to the Magnificent New Home W/8 Beds & Free Parking, an exquisite haven nestled in the vibrant Logan Square neighborhood of Chicago. This elegantly designed residence is a part of the… More

Providing access to an ice rink, Chicago Condo With Balcony Walk To Cta Stations! villa is located approximately 25 minutes' walk from such sports venues as the multi - purpose Credit Union 1 Arena. More

Located 6 km from the skyscraper 360 Chicago Observation Deck, Chic Green L Near Downtown & Il Medical District Chicago villa gives access to various tourist sites in the vicinity. More

Experience the charm and elegance of the Beautifully Renovated House 10 Mins From Downtown, an exquisite retreat just moments away from the vibrant heart of the city. This thoughtfully designed haven… More

Welcome to the enchanting retreat of Chicago Home, a serene escape conveniently located just 22 km from the bustling Ogilvie Transportation Center and 25 km from Midway International Airport. This… More

**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

Set in a vibrant neighborhood, the Historic Home With Outdoor Hot Tub Near Downtown In Public Transportation Hub offers a unique blend of charm and accessibility. This thoughtfully restored residence… More

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

Welcome to the Modern Wrigley Oasis With Parking!, A captivating retreat nestled in the vibrant Lakeview neighborhood of Chicago. Conveniently situated near West Diversey Parkway and the shores of… More

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

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

Offering a sauna for a relaxing experience, Spacious Luxury Retreat 8 Bed Oasis With 6 Baths Chicago villa is located 3.8 km from the 1924 open - air stadium "Soldier Field". Nestled in Bridgeport… More

Chicago Mid-Century Gem By United Center Villa with a prime location merely an 8-minute walk from the indoor United Center Arena entices guests with a sauna. More

Located in Wicker Park which makes for a thriving nightlife scene and within 6 km of the skyscraper 360 Chicago Observation Deck, Stunning 5Br Home In Heart Of Chicago With 2 Rooftops provides guests… More

**Experience Chicago's Charm at Chicago Home Near Navy Pier and Shedd Aquarium** Nestled in the vibrant heart of the Windy City, Chicago Home Near Navy Pier and Shedd Aquarium offers a perfect blend… More

The Logandale: Huge Mid-Century Home, Sleeps 15 Chicago provides easy access to various city attractions, such as Elastic Arts, situated around 5 minutes' walk away. More

Located merely 6 minutes on foot from Santa Maria Addolorata Parish, the 3-bedroom Chicago Treasure 4 Bed Getaway Villa gives easy access to various tourist attractions in the area. More

During the stay at 5 Bedroom Huge House In Best Location Parking Fireplace Back Yard Chicago villa, guests can indulge in tennis or visit the Navy Pier, located a 10-minute ride away. More

The 4-bedroom Stylish Chicago Retreat: Walk To Loyola University villa offers swift access to various city sites, such as Mundelein College, situated nearly 5 minutes' walk away. Providing guests… More

Boutique Garden House Chicago 3-Story Sleeps 12 Villa, located merely a 5-minute walk from First Progressive Church of Christ, can host up to 12 guests. Located 4.3 km from the Sprawling hands-on… More

Situated 950 metres from the Catholic church "Our Lady of Sorrows Basilica", Victorian Mansion In Garfield Park Villa Chicago invites guests to relax at a patio. More

**Welcome to Gorgeous 5 Bedroom Gem With Games, where modern luxury meets a vibrant Chicago ambiance. Nestled about 15 kilometers from Midway International Airport and just 17 kilometers from Ogilvie… More

The 4-bedroom Roscoe Village Family Hideaway Chicago villa offers quick access to such city attractions as the Juniper Playlot Park, located nearly 5 minutes' walk away. Offering a convenient… More

Overlooking the city, 5Br 5Ba Architectural Estate-Theatre Gym Rooftop Chicago villa enjoys a convenient setting a 5-minute walk from Katherine Anne Confections. Situated 4.9 km from the baseball… More

Located 3.3 km from Bambi Park, Charming Home In Portage Park Chicago gives access to various tourist sites in the vicinity. More

**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

**Welcome to the River North Hideaway, your exquisite sanctuary nestled in the heart of the Magnificent Mile.** This chic retreat allows guests to fully immerse themselves in Chicago's vibrant… More

**Experience Urban Elegance at Chicago New 2Br Home W 3 Beds and Highspeed Internet** Conveniently located just 17 kilometers from Midway International Airport and 4 kilometers from Ogilvie… More

Situated nearly 5 minutes' walk from the General John Logan Memorial, Downtown Penthouse - Mich Ave 2Bd Gym And Views #12 Villa Chicago offers easy access to numerous tourist spots in the area. More

The 5-bedroom Near Lake & Museum • Modern • Game Area Chicago villa offers easy access to such tourist spots as New Spiritual Light M.B. Church, located only a 6-minute walk away. The Chicago holiday… More

Providing active guests with access to an ice rink, the 6-bedroom Newly Updated Vintage 6 Bedroom Single Family Home Home Chicago is around 25 minutes on foot from such sports attractions as the… More

The 4-bedroom Game Room • Fire-Pit • Playground • Gym • Billiard Chicago villa hosts up to 16 guests and is nestled within a 3-km distance of natural sites such as the Amundsen Park. More

Modern 3Br Near Mccormick & South Loop Villa Chicago is located a 19-minute walk from the Chicago Chinatown and provides cycling for active guests. More

### 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

**Discover Woodlawn Oasis Villa, a serene escape ideally situated just 15 kilometers from both Midway International Airport and the bustling Ogilvie Transportation Center. Nestled amid the charm of… More

Stylish 3Br Gem In Prime Location Villa Chicago is located nearly a 25-minute walk from the premier natural-history Field Museum and provides cycling for active guests. The holiday home can host 8… More

Offering a terrace overlooking the garden, the 3-bedroom Art Downtown Fulton Market Entire 3 Bedroom Home Sleep10 Private Garage Roof Ev Tesla Chicago is located 500 metres from Santa Maria… More

Situated a 5-minute walk from the South Pond, 3-Story Townhome Free Parking Private Patio Washer-Dryer Chicago villa entices guests with views of the lake. This holiday home features opportunities… More

4Br Modern Urban Escape Walk To Zoo Lakefront & Red Line Chicago villa provides easy access to various city attractions, such as Apple Store, situated a 6-minute walk away. This 8-room holiday home… More

The 4-bedroom 4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome Chicago provides easy access to various city attractions, such as The Noble Horse Theatre, situated about a 5… More

Spacious Chicago Group Home! Walk To Train & Eats is located a 25-minute walk from the Andersonville neighborhood and invites guests to enjoy a terrace. More