Chicago Homes for Two People

We selected the 5 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

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.

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Here awaits The Cooke, where guest security and solace are paramount. Ensconced in the heart of Chicago's distinguished Financial District, this property is a gateway to an array of unforgettable Windy City attractions.

The Lion

The Lion

  • 5 guests

  • 2 bedrooms

Rush & Division, Chicago

This home is the perfect place to relax and enjoy your stay in Chicago. The home is located in the Gold Coast neighborhood, which is known for its luxury shops, fine dining, and lake Michigan charm.

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.


We selected the top 3% holiday homes in Chicago Homes for Two People

Explore the 5 most perfect homes in our collection

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Most popular homes

All Things Glow

All Things Glow

  • 3 guests

  • 2 bedrooms

Hyde Park, Chicago

Chicago Charisma

Chicago Charisma

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

All Things Glow

All Things Glow

  • 3 guests

  • 2 bedrooms

Hyde Park, Chicago

The Lion

The Lion

  • 5 guests

  • 2 bedrooms

Rush & Division, Chicago

Chicago Vista

Chicago Vista

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

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Check upcoming rates & availability for Chicago Homes for Two People


Frequently asked questions

Explore our collection of homes for 2 people in Chicago. Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short or extended stay in the best 2 person homes that Chicago has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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