Book Luxury Airbnb Alternatives in Chicago

We selected the 41 homes worth renting in this location

Home spotlights in Chicago

The Jeweler's Gem

The Jeweler's Gem

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Snug yet stylish, this studio apartment is perfect for a lone traveller or couple wanting a cosy stay in Chicago. We love the sleek design and jewel tones – fitting, seeing as this flat is situated along the famous Jewelers Row.

South Soul

South Soul

  • 2 guests

  • 1 bedrooms

South Loop, Chicago

Looking for a stylish bolthole in a buzzy pocket of Chicago? Then this smart studio apartment, located in the residential district of South Loop, might tick your boxes.

Skyscraper

Skyscraper

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Arriving at this home in downtown Chicago, you’re sure to be charmed by the typically Chicagoan high rise. Gaze down on the city above, and delight in the central location in the North River district – it's famous for its abundance of galleries and arty culture.

Diamonds Are Forever

Diamonds Are Forever

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

In an iconically Chicago building designed by Adler & Sullivan, this apartment sits amidst jewellery shops that have been trading since the 19th century and is just a couple of blocks from the sculpture-strewn Millennium Park. As well as old-world jewellery shops, contemporary galleries and trendy eateries fill the streets surrounding this apartment.


We selected the top 3% holiday homes in Chicago Airbnb Alternatives

Explore the 41 most perfect homes in our collection

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Most popular homes in Chicago

On Cloud Nine

On Cloud Nine

  • 2 guests

  • 1 bedrooms

Near North, Chicago

The Jeweller

The Jeweller

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Flaming Saganaki

Flaming Saganaki

  • 4 guests

  • 1 bedrooms

Greektown, Chicago

New Millennium

New Millennium

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

Loop In

Loop In

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Hey Mr DJ

Hey Mr DJ

  • 6 guests

  • 2 bedrooms

South Loop, Chicago

Drive Me Loopy

Drive Me Loopy

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Southern Loop

Southern Loop

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

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Frequently asked questions

Explore our collection of the most remarkable Airbnb Alternatives that Chicago, Cook County, Illinois, United States has to offer. Every home you'll find on Plum Guide comes fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Before being accepted into our collection, each home much pass a meticulous vetting process, culminating in a personal home visit from an independent Home Critic. Rent one of Plum Guide's luxury Chicago Airbnb Alternatives, and enjoy a long or short stay to remember. Should you need any assistance with your booking, our friendly team of experts will be on hand to guide you through the process.

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