Book Luxury Airbnb Alternatives in Chicago Loop

We selected the 21 homes worth renting in this location

Home spotlights in Chicago Loop

Running Loops

Running Loops

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

This stylish home-from-home is in Chicago’s artistic and culinary zeitgeist – South Loop. A cool and creative neighbourhood, known for its lively music scene, bold architecture and history, you’re within walking distance from the Museum Campus and Art Institute – perfect for city-breakers and culture vultures alike.

Indigo Wabash

Indigo Wabash

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

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.

Chicago Charisma

Chicago Charisma

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Immerse yourself in the heart of downtown at this retreat tucked away in Chicago's vibrant Financial District. Each experience here invites a journey into iconic city attractions, folds back layers of historic architectural treasures, and strolls along river cruises or the fabled Riverwalk.

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 Loop Airbnb Alternatives

Explore the 21 most perfect homes in our collection

View on map


Most popular homes in Chicago Loop

The Jeweller

The Jeweller

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Loop Luxe

Loop Luxe

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

The Treasury

The Treasury

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

New Millennium

New Millennium

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Swing Swing

Swing Swing

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Windy City Retreat

Windy City Retreat

  • 20 guests

  • 10 bedrooms

Chicago Loop, Chicago

Loop Haven

Loop Haven

  • 12 guests

  • 6 bedrooms

Chicago Loop, Chicago

View all


Check upcoming rates & availability for Chicago Loop Airbnb Alternatives


Frequently asked questions

Explore our collection of the most remarkable Airbnb Alternatives that Chicago Loop, 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 Loop 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.

Search our collection