Book Luxury Airbnb Alternatives in Chicago

We selected the 39 homes worth renting in this location

Home spotlights in Chicago

On Cloud Nine

On Cloud Nine

Near North, Chicago

  • 2 guests

  • 1 bedrooms

£485 night

Chicago isn't just known for its lively music scene and deep-dish pizza, but also for its larger-than-life architecture – after all, those skyscrapers speak for themselves. The best way to make the most of the magnificent metropolis?

Indigo Wabash

Indigo Wabash

Chicago Loop, Chicago

  • 4 guests

  • 2 bedrooms

£319 night

A hidden gem among the towering skyscrapers and bustling streets, the building was designed by Adler & Sullivan and is surrounded by jewellers, some dating as far back as 1872. It's fair to say you've unearthed a diamond.

Diamonds Are Forever

Diamonds Are Forever

Chicago Loop, Chicago

  • 2 guests

  • 1 bedrooms

£385 night

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 39 most perfect homes in our collection

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Most popular homes in Chicago

Skyscraper

Skyscraper

Near North, Chicago

  • 3 guests

  • 1 bedrooms

£736 night

Running Loops

Running Loops

South Loop, Chicago

  • 6 guests

  • 3 bedrooms

£978 night

The Jeweler's Gem

The Jeweler's Gem

Chicago Loop, Chicago

  • 2 guests

  • 1 bedrooms

£391 night

Flaming Saganaki

Flaming Saganaki

Greektown, Chicago

  • 4 guests

  • 1 bedrooms

£507 night

Southern Loop

Southern Loop

South Loop, Chicago

  • 4 guests

  • 1 bedrooms

£416 night

Chicago Morning

Chicago Morning

Printer's Row, Chicago

  • 8 guests

  • 4 bedrooms

£1,143 night

Hey Mr DJ

Hey Mr DJ

South Loop, Chicago

  • 6 guests

  • 2 bedrooms

£651 night

Savings Account

Savings Account

Near North, Chicago

  • 3 guests

  • 1 bedrooms

£488 night

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Frequently asked questions

Airbnb is a shot in the dark. We meticulously vet all our homes in Chicago to ensure you won’t waste your precious holiday. 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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