Book Luxury Vacation Rentals in Chicago Loop

Award-winning homes from £98

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Home spotlights in Chicago Loop

The Skyline's Vision

The Skyline's Vision

  • 14 guests

  • 6 bedrooms

Fulton River District, Chicago

When you bring everyone to Chicago, you want a space that matches the occasion, and these skyline retreats near Fulton Market do exactly that. By day, the city is yours to explore: coffee and street art in the West Loop, vintage hunting at Randolph Street Market, picnics in Union Park, or a culinary crawl through some of the best restaurants in the Midwest.

The Chicago River Rhapsody

The Chicago River Rhapsody

  • 14 guests

  • 6 bedrooms

River West, Chicago

Picture yourself unwinding amidst the spirited charm of River West in The Kane. The vivacious neighborhood edges the restful waves of the Chicago River, its boulevard bustling with inviting eateries, captivating bars, and eclectic boutiques.

All Things Glow

All Things Glow

  • 3 guests

  • 2 bedrooms

Hyde Park, Chicago

This apartment in Chicago's Hyde Park is positively flush with luxury touches. We love the trendy, timeless design, which merges mid-century pieces with a modern flair.

WindyCity Wonders

WindyCity Wonders

  • 5 guests

  • 2 bedrooms

West Loop Gate, Chicago

Immerse in the life of West Loop Gate, Chicago at this lovely rental! As a former industrial area turned dining and nightlife hub, the scene offers a unique juxtaposition.


We selected the top 3% holiday homes in Chicago Loop Vacation Rentals

Explore the 56 most perfect homes in our collection

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Most popular homes in Chicago Loop

Windy City Haven

Windy City Haven

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Chicago Chateau

Chicago Chateau

  • 12 guests

  • 6 bedrooms

River West, Chicago

The West Wind Charm

The West Wind Charm

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Chicago's Gemstone

Chicago's Gemstone

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

The Windy City Retreat

The Windy City Retreat

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

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Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in Chicago Loop. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect Chicago Loop Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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