Rent Luxury Accommodation for Groups in Chicago Loop

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

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.

Artists' Rendezvous

Artists' Rendezvous

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Make a date with The Blues, a delightful haven nestled in the West Loop. This home away from home exudes an unmistakable charm, harmonising old-world coziness with a dash of modernity.

Charming Chicago Charm

Charming Chicago Charm

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Welcome to a gem nestled in the heart of Chicago's Financial District, offering guests a unique blend of historical architecture, city excitement and stunning views over the Chicago Riverwalk. The location is unmatched, mere steps away from Millennium Park and State Street, both alive with incredible cuisine and eclectic shopping experiences.

Loop Haven

Loop Haven

  • 12 guests

  • 6 bedrooms

Chicago Loop, Chicago

Welcome to The Jordan! Nestled in Chicago's iconic Chicago Loop, this urban oasis provides a tranquil retreat amidst the bustling cityscape.


We selected the top 3% holiday homes in Chicago Loop Accommodation for Groups

Explore the 56 most perfect homes in our collection

View on map

Most popular homes in Chicago Loop

Culture Haven

Culture Haven

  • 12 guests

  • 4 bedrooms

Rush & Division, Chicago

WindyCity Wonders

WindyCity Wonders

  • 5 guests

  • 2 bedrooms

West Loop Gate, Chicago

Italian Villa Immersion

Italian Villa Immersion

  • 8 guests

  • 3 bedrooms

Rush & Division, Chicago

Metropolis Respite

Metropolis Respite

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

The Heart of the Loop

The Heart of the Loop

  • 16 guests

  • 8 bedrooms

Chicago Loop, Chicago

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

The Windy City Retreat

The Windy City Retreat

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Metropolis Retreat

Metropolis Retreat

  • 18 guests

  • 9 bedrooms

Fulton River District, Chicago

View all

Check upcoming rates & availability for Chicago Loop Accommodation for Groups


Frequently asked questions

Reserve a stay in one of the impeccable homes in our collection of luxury Group Holiday Accommodation in Chicago Loop. You won't find such consistent quality anywhere else, as every single Plum Guide home comes fully furnished with all linens, a brilliantly-equipped kitchen, and essential bathroom toiletries included. Our experts really do obsess over the smallest details, with shower pressure and a bedroom's decibel levels being tested to ensure absolute quality in your hunt for the perfect home. Rent Chicago Loop Accommodation for Groups today, and learn the true meaning of luxury. Call on our team of experts too, who can help you through the booking process and guarantee that you end up with the ultimate home for you.

Search Our Collection