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

Suite 2 On Southport 4 Queen Beds Chicago villa offers easy access to such tourist spots as Supera Park, located only 6 minutes' walk away. 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 2-bedroom Lincoln Park Living - Suite 2 Chicago villa, located around 5 minutes' walk from the petite South Lakeview Playground Park, can host up to 10 guests. 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

Situated nearly 25 minutes' walk from Millennium Public Park, Stunning Duplex Condo #1 - Downtown River North Chicago villa features a patio with views of the city. Offering Wi-Fi, the property is… 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

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

Situated just 500 m from the skyscraper 360 Chicago Observation Deck, the 5-bedroom Historic Luxury Townhouse In Downtown Chicago Villa is ideal for up to 10 guests. 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

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 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

Set in the vibrant West Town neighborhood, the Luxe 4Br With Hot Tub & Game Room is the quintessential urban retreat, perfectly combining modern amenities with a lively culinary scene. Just moments… 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

Beautiful 6-Bedroom, Private Mansion With Hot Tub Chicago villa is located only 9 minutes' walk from Mount Nebo Church Baptist, giving access to various tourist spots nearby. 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

Beautiful Remodeled Penthouse Unit In Old Town Villa Chicago accommodates up to 14 guests and offers proximity to the Chicago History Museum, located around 5 minutes' walk away. 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

**Welcome to the No. 1 Rated Lincoln Park House - Golf Simulator Villa, a refined retreat nestled in the vibrant and fashionable Lincoln Park neighborhood of Chicago.** This lively area is renowned… 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

**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

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

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

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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

Along with Wi-Fi and a car park, the 5-bedroom Spacious Luxury Retreat 8 Bed Oasis With 6 Baths Chicago villa offers proximity to Willis Tower, located 4.7 km away. More

The 1-bedroom Chic Chicago Retreat Home offers swift access to various city sites, such as Our Lady of Tepeyac Parish, situated approximately 5 minutes' walk away. More

Spacious Bucktown Sanctuary Chicago villa offers proximity to such city sites as Moth, located a mere 5 minutes' walk away. More

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

Offering city views, Chicago Mid-Century Gem By United Center Villa is situated just an 8-minute walk from United Center. Located 4.4 km from The Chicago Theatre, the 4-bedroom holiday home provides… More

Stunning 5Br Home In Heart Of Chicago With 2 Rooftops hosts up to 16 guests and is nestled 4.7 km from natural sites such as the scenic Chicago Riverwalk Walkway. Located about a 15-minute drive from… More

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Situated 3.3 km from Historic Pullman Foundation Exhibit Hall, Historic Chicago -Style Bungalow Villa provides access to numerous tourist attractions in the area. 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 A Terrific House For A Large Group, a perfect oasis for those seeking both comfort and convenience. Nestled just 15 kilometers from Chicago O'Hare International Airport, this charming… More

Boutique Garden House Chicago 3-Story Sleeps 12 Villa, located just a 5-minute walk from First Progressive Church of Christ, can host up to 12 guests. More

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The 4-bedroom Amazing 4Br 4Ba Oasis W Rooftop & Stunning Design Chicago villa is situated 350 m from Yoga For All Beings, featuring such comforts as Wi-Fi and parking. Located 4.8 km from Cloud Gate,… 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

Staying at Duplex Chic River North Retreat Chicago villa, guests can easily reach Chicago Children's Museum, located nearly 25 minutes' walk away. More