Gwen for The Holidays

Experience the epitome of holiday sophistication at The Gwen. Enjoy rooftop curling under Chicago’s cityscape, sip on signature festive cocktails, indulge in exquisite seasonal menus, and create memories in a setting of unmatched luxury.

Special Offers & Packages

The Gwen Hotel

Mistletoe on Michigan Avenue

Celebrate under the mistletoe at The Gwen! Enjoy a romantic luxurious stay in the heart of downtown Chicago.
The Gwen Hotel

Sip, Savor & Sleigh

Sleigh your holiday plans at The Gwen! Escape with your besties to the heart of Chicago for a glamorous, joy-filled getaway.
Curling & Cocktails

Gwen's Winter Curl & Chill

Celebrate the holiday season at Upstairs at The Gwen’s rooftop terrace with Gwen’s Winter Curl & Chill. Enjoy a lively game of curling, then unwind with a curated menu of festive delights. Indulge in boozy hot chocolate, mulled wine, and holiday-inspired cocktails paired with seasonal treats—all crafted to keep you cozy and warm.

Tipsy Tea

Martha May's Merry Tipsy Tea

Celebrate the season in whimsical Whoville style at The Gwen’s Grinch-themed Tipsy Tea Party this December. Sip on festive tea-infused cocktails while enjoying festive tunes from a live DJ. Indulge in a seasonal tea tower brimming with delights such as Who-Spanakopita, Mount Crumpit Pfeffernüsse, and Sweet Cindy Lou’s Panna Cotta. Embrace your inner Martha May and celebrate the holidays with playful elegance!

gift wrapping workshop at The Gwen

Gift Wrapping Workshop

Transform your gift-wrapping skills with a festive workshop on Friday, December 20, from 6pm to 8pm, hosted by Gift Wrap Boss. Learn professional seamless techniques, bow-making, and creative ways to wrap unique shapes. To elevate your gift-wrapping experience, bring your own items to wrap and enjoy wine, cocktails, and bites from Upstairs at The Gwen.

New Year's Eve at Upstairs at The Gwen

New Year's Eve

Celebrate New Year’s Eve at The Gwen with an unforgettable evening of indulgence and style. Savor a special menu including roasted Wellfleet oysters and a 32 oz prime tomahawk ribeye, perfectly paired with an exclusive bottle menu and Grey Goose-crafted cocktails. Enjoy live DJ tunes from 9pm to 1am and toast to 2025 with complimentary bubbly at midnight. For a truly chic start to the new year, reservations are encouraged for Upstairs at The Gwen, whether inside the lounge or by a cozy firepit on our rooftop terrace.