Book Luxury Summer Rentals in Chicago

We selected the 40 homes worth renting in this location

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Home spotlights in Chicago

Charming River Retreat

Charming River Retreat

  • 14 guests

  • 6 bedrooms

River West, Chicago

Welcome to a true haven in the heart of Chicago's vibrant River West neighborhood. Surrounded by trendy restaurants, bars, and shops, this elegant and modern retreat offers a tranquil escape from the hustle and bustle of the city.

Chicago Vista

Chicago Vista

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Step inside The Leto, where classic charm mingles with vibrant culture in the bustling Streeterville neighborhood of Chicago. This locale promises an immersive experience into not only traditional Chicago history but also the nuances of Italian villa architecture and other globally inspired design details.

The Treasury

The Treasury

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Welcome to your urban oasis at The Kroc, a hidden gem located in Chicago's vibrant Financial District. This luxurious cityscape haven offers breathtaking panoramic views of the iconic Chicago skyline, creating an unforgettable experience for discerning guests.

The West-Loop Wavelength

The West-Loop Wavelength

  • 17 guests

  • 8 bedrooms

West Loop, Chicago

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 gastronomy, nightlife, and style, dazzling visitors with its fusion of historic mortar and modern vibrance.


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

Explore the 40 most perfect homes in our collection

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Most popular homes in Chicago

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Classic Chic Retreat

Classic Chic Retreat

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Charming Chicago Charm

Charming Chicago Charm

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Charming Chic Retreat

Charming Chic Retreat

  • 7 guests

  • 3 bedrooms

River West, Chicago

Metropolis Respite

Metropolis Respite

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

Serenity by the Riverside

Serenity by the Riverside

  • 16 guests

  • 9 bedrooms

River West, Chicago

Wicked Windy Retreat

Wicked Windy Retreat

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

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Check upcoming rates & availability for Chicago Vacation Rentals for Summer


Frequently asked questions

Explore our remarkable range of luxury Summer Rentals in Chicago, Cook County, Illinois, United States. There's no time for average stays, so treat yourself to a stay in one of the most impressive rentals around. Each and every home in our selection is put through numerous rounds of thorough testing, with everything from shower pressure to a home's design being closely checked for quality. Only the finest 3% of homes are awarded the prestigious Plum Award, so you can book with total confidence. Rentals in our range come fully furnished, with a well-equipped kitchen, essential bathroom toiletries, and all linen included to make you feel right at home. Book a memorable trip to an unforgettable Vacation Rental for Summer in Chicago today, and make the most of the year's warmest season. If you require any assistance, call on the help of our experts - they're on-hand to help you discover the perfect home.

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