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 the Vibrant Heart of Chicago** Beyond the comforts of your accommodations, the holiday home offers exceptional services designed to enhance your stay. More

**Discover the Charm of Lincoln Park Living - Suite 1** Positioned conveniently within reach of public transportation, this suite serves as a perfect hub for exploring all that Chicago has to offer. 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

**Welcome to Stunning Condo #2 - Downtown River North**, a remarkable residence nestled in the vibrant Near North Side of Chicago. This spacious retreat, featuring three elegantly appointed bedrooms,… 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

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

Located in Lincoln Park with plenty of places within the neighborhood to help stretch your legs, approximately 5 minutes' walk from the petite South Lakeview Playground Park, the 2-bedroom Lincoln… 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

Stunning Duplex Condo #1 - Downtown River North Chicago villa offers proximity to such city sites as the long-standing Carl Hammer Gallery, located just a 6-minute walk away. This Chicago holiday… 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

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

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

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

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

Nestled within the vibrant Near North Side of Chicago, the Breathtaking Downtown Penthouse B - Sleeps 11 offers an exceptional urban escape infused with modern elegance. This airy and spacious… 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

Situated in the vibrant Lincoln Park area of Chicago, The Village Inn By Dakota Gal Digs serves as an oasis amidst the bustling cityscape. This charming establishment is surrounded by an array of… 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

**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

Welcome to the Cozy 4Bd House Fireplace And Pond, a charming retreat that seamlessly blends comfort and tranquility. Situated just 20 km from both Ogilvie Transportation Center and Midway… More

Welcome to the Logan Square Oasis, an enchanting haven nestled in one of Chicago's most vibrant neighborhoods. This remarkable oasis stands at the crossroads of art and culture, showcasing the… 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

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

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

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

Breathtaking Chi Unit In River North With Rooftop Deck - Penthouse A - Sleeps 11 Chicago villa provides easy access to various city attractions, such as the long-standing Carl Hammer Gallery… 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 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

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 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

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

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

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

Located in Lincoln Park with plenty of places within the neighborhood to help stretch your legs, merely 5 minutes' walk from Rosa's Lounge, the 5-bedroom Entire Building-Walk To Lincoln Park Or The… 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

2 Newly Built Luxury Condos With Private Roofdeck Chicago villa offers quick access to such city attractions as the long-standing Carl Hammer Gallery, located merely a 6-minute walk away. Offering a… 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

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