Chicago Loop Homes for a Watersports Holiday

We selected the 56 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Chicago Loop

The Lofted Escape

The Lofted Escape

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

Welcome to The Fitz Gerald! To ensure safety, all guests must pass our screening process and provide proper ID.

Chicago's Gemstone

Chicago's Gemstone

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

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, unfolding boundless options for dining, shopping, and entertainment.

Westside Retreat

Westside Retreat

  • 7 guests

  • 3 bedrooms

River West, Chicago

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 worlds.

Chicagoan Idyll

Chicagoan Idyll

  • 6 guests

  • 3 bedrooms

River West, Chicago

This modern penthouse is stylish, well-located, and boasts sensational skyline views – how can you go wrong? You'll find it near the West Loop, known for its top-notch restaurants and vibrant nightlife.

We selected the top 3% holiday homes in Chicago Loop Homes for a Watersports Holiday

Explore the 56 most perfect homes in our collection

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Most popular homes in Chicago Loop

Chicago Chateau

Chicago Chateau

  • 12 guests

  • 6 bedrooms

River West, Chicago

Artists' Rendezvous

Artists' Rendezvous

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Loop Haven

Loop Haven

  • 12 guests

  • 6 bedrooms

Chicago Loop, Chicago

Elevated Luxe

Elevated Luxe

  • 5 guests

  • 2 bedrooms

Fulton River District, Chicago

The High Way

The High Way

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

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Check upcoming rates & availability for Chicago Loop Homes for a Watersports Holiday

Frequently asked questions

Find the best homes for a watersports holiday in Chicago Loop. Every one of our properties has been meticulously vetted by our Plum Guide experts, so you don't have to worry about anything, from the WiFi speed to water pressure. All of our homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Arrange your getaway today, and stay in one of the best homes for a watersports holiday in Chicago Loop.

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