Standout Dining in a World-Class Culinary City

There’s service; then there’s hospitality — a long-held value at the heart of everything we do. Experience a genuinely warm welcome at Upstairs at The Gwen, our Art Deco-inspired rooftop retreat, offering seemingly endless skyline vistas, sunrise to sundown dining, and masterful mixology in a laid-back, twinkle-lit atmosphere. 

The only thing to rival The Gwen’s dining options? The gorgeous spaces that house them.


Check out our Special Promotions

Upstairs at The Gwen Rooftop Terrace

Upstairs at The Gwen

Lounge fireside with small plates, big views, and a perfected craft cocktail.

Private Dining in Private Affairs Space at The Gwen

Private Affairs

Grab a choice table at an afternoon Tipsy Tea, an evening ‘Salon’ literary event or a Sunday concert.

Tipsy Tea at The Gwen

Tipsy Tea Party

Put your pinky down grandma, this is Gwen Tipsy Tea! Complete with a live DJ and even livelier libations, experience our high energy, boozy twist on traditional high tea.

Chef Matt Jergens at The Gwen Hotel

Matt Jergens

Executive Chef

Modern. Classic. Lively. Executive Chef of The Gwen, Matt Jergens’ culinary philosophy is shaped by his Italian upbringing and early life in Iowa and Boston. After graduating from the Cambridge Culinary Arts School, Jergens spent five years at The Liberty Hotel before joining us at The Gwen.

Special Offers & Packages

  • An Everlasting Wedding Package The Gwen Hotel

    Make it Forever

    Cherish your milestone at The Gwen, where history meets style. Tie the knot in 2024 for perks, including a Gwen Lux Suite stay.
  • Rewarding Connections The Gwen Hotel

    Rewarding Connections

    With a unique rooftop terrace and over 15,000 square feet of polished event space, you can host any social gathering that embodies the classic luxury style of The Windy City.
  • Tipsy Tea Bridal Shower The Gwen Hotel

    Tipsy Tea Bridal Shower

    Treat your bride-to-be to a tea party with a twist featuring inventive bites.