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Staywell Hospitality

Staywell Properties Are In Chicago's Best Neighborhoods

A curated collection of homes in the Loop, River North, Fulton Market, and Streeterville.
Industrial loft with exposed brick walls, wooden beam ceiling, large windows, dining table with modern chairs, and blue sofa in living area.

Locally Owned. Thoughtfully Curated.

Founded and operated by lifelong Chicagoans, Staywell brings an intimate knowledge of the city and a personal approach to hospitality. Rather than managing hundreds of properties, we focus on a carefully selected collection of residences in neighborhoods we know and love. Each home is chosen for its character, comfort, and thoughtful details, with an emphasis on creating an exceptional experience for every guest.

What Your Stay Comes With

  • Prime Downtown Location

    Every home sits in the Loop, Fulton Market, Streeterville, or River North, Chicago.

  • City & Lake Views

    Corner units and penthouses with skyline and Lake Michigan views on most floors.

  • Rooftop & Deck Access

    Most homes include a private roof deck or shared rooftop high above the city streets.

  • Dedicated Workspaces

    Every home has a proper desk setup so that work trips don't feel like a compromise.

  • Full Kitchen & Appliances

    Cook-ready kitchens with full-size appliances, solid cookware, and a dishwasher.

  • High-Speed WiFi

    Fast, reliable internet in every home, strong enough for video calls and streaming.

The Details We Handle

Modern living room with teal sofa, wood desk, and large windows overlooking historic city buildings and skyline

Guest Support

Real people answer when you need something during your stay.

  • 24/7 Direct contact available

  • Local knowledge shared

  • Issues resolved quickly

Aerial view of the Chicago Loop skyline with skyscrapers and morning sunlight

Honest Pricing

What you see is what you pay, with no surprise fees.

  • Clear rate breakdown

  • No hidden charges

  • Fair cancellation terms

Industrial loft living space with exposed brick walls, wooden beam ceiling, large windows, and mid-century modern furniture

Local Knowledge and Recommendations

Insider knowledge to help you make the most of your stay.

  • Discover neighborhood favorites and standout restaurants.

  • Explore local attractions, cultural highlights, and hidden gems.

  • Practical tips for navigating Chicago with ease.