Self-Catering Chicago, Illinois

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The West Wind Charm

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms Welcome to a dazzling retreat in the heart of West Loop. A vibrant ambience invites you to immerse yourself, enveloped by the rhythm of the city's live music and savory aromas from nearby culinary gem...   View Rental

The Urban Villa

Illinois, Chicago 6 guests 2 bedrooms 2 bathrooms A striking interplay between tradition and trend elevates this property nestled within the vibrant Streeterville neighbourhood. Combining nostalgic tales of Chicago's history with an undercurrent of w...   View Rental

Italian Villa Immersion

Illinois, Chicago 8 guests 3 bedrooms 2 bathrooms Immerse yourself in the experience that is The Zeus, centrally positioned in the exciting Streeterville neighborhood. Here, a unique blend of classic allure fuses with an internationally inspired desi... From €1,181 Nightly View Rental

The West-Loop Wavelength

Illinois, Chicago 17 guests 8 bedrooms 8 bathrooms Welcome to a unique urban retreat, igniting the senses, and beckoning guests to indulge in the transformative charm of West Loop. Once an industrial essence, it has blossomed into a locus of gastronom...   View Rental

Chicago Chic

Illinois, Chicago 4 guests 2 bedrooms 2 bathrooms This pet-friendly apartment in Downtown Chicago puts the best of the city at your feet. Millennium Park, The Art Institute, theatres, restaurants, and shops are all just a short stroll away. When you’...   View Rental

Westside Retreat

Illinois, Chicago 7 guests 3 bedrooms 3 bathrooms Welcome to our charming haven, nestled in the vibrant neighborhood of River West, Chicago. This urban oasis offers a serene escape from the bustling city, allowing you to experience the best of both w...   View Rental

Chicago's Gemstone

Illinois, Chicago 7 guests 3 bedrooms 2 bathrooms All resting eyes behold a unique sanctuary blending urban spirit with an enchanting skyline whisper. The escape, nestled in the heart of Chicago's cherished West Loop, extends far beyond the eye, unfo...   View Rental

Chicago Charisma

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms Immerse yourself in the heart of downtown at this retreat tucked away in Chicago's vibrant Financial District. Each experience here invites a journey into iconic city attractions, folds back layers of... From €641 Nightly View Rental

Urban Vistas

Illinois, Chicago 4 guests 2 bedrooms 2 bathrooms This Illinois apartment won us over the moment we clapped eyes on the sweeping views of Chicago’s skyline and that private balcony. But the perks don’t end there. Part of a high-end serviced apartment...   View Rental

The High Way

Illinois, Chicago 4 guests 2 bedrooms 2 bathrooms This smart city sanctuary boasts incredible views across the Chicago skyline. The rooms have been thoughtfully designed to inspire ease and relaxation. Nespresso coffee is on hand to help get your day... From €437 Nightly View Rental
Self-Catering Chicago
Listing 21-30 of 36 Top Holiday Rentals
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