The season of elegance has arrived and there’s no better place to celebrate than The Gwen. From golden autumn afternoons to sparkling winter nights, delight in festive dining, rooftop curling, and timeless holiday traditions. Every moment is an invitation to gather, indulge, and create memories that shine.
A Gilded Holiday at The Gwen: A Return to the Elegance of Festive Yesteryears
Gwen's Winter Curl & Chill
Celebrate the chill in style at Upstairs at The Gwen’s rooftop terrace. Challenge your friends to a game of curling, then cozy up with indulgent boozy hot chocolate, spiced mulled wine, and handcrafted signature cocktails. Pair these with a curated menu of seasonal delights for the ultimate cold‑weather retreat.
Mistletoe on Michigan Avenue: Holiday Room Package
Celebrate the season under the mistletoe at The Gwen. Enjoy a luxurious downtown escape with a bottle of prosecco, holiday sweet treats, a Gwen Magic Mistletoe keepsake, and a 4pm late checkout. Available for stays November 16, 2025 – January 3, 2026.
A Merry Gwen Christmas: Holiday Room Package
Embrace the spirit of the holidays at The Gwen with loved ones by your side and a cozy night in wrapped in luxury. Celebrate with a decorated in-room holiday tree, festive board games, and warm cookies and milk delivered to your door. Available for stays December 1, 2025 – January 3, 2026.
Lux Curl Escape: Holiday Room Package
Retreat to The Gwen’s 16th-floor multi-bedroom suite, complete with a private curling experience and elevated touches such as a welcome amenity, a s’mores fondue turndown, VIP guest services, and round-trip airport transportation for an unforgettable winter escape.
Midnight on Rush: New Year's Eve Room Package
Welcome the new year with a luxury retreat at The Gwen, where chic accommodations, celebratory midnight bubbles, and city lights set the perfect tone. Enjoy a bottle of Piper-Heidsieck Champagne, chocolate-covered strawberries, breakfast for two at Upstairs at The Gwen, and 3pm late checkout.
Bold & Gold: A Luxe Tipsy Tea
Bold & Gold infuses The Gwen’s iconic Tipsy Tea with golden sophistication, offered October through December. Delight in a curated selection of fragrant teas, radiant tea-infused cocktails, and seasonal bites that shimmer with refined indulgence—embracing the richness of fall, the sparkle of winter, and The Gwen’s signature touch of timeless elegance.
Golden Renewal - A Pilates & Sound Bath Experience
Join HIGH SOCIETY at The Gwen on Saturday, December 6 from 10am to 12pm for a 45-minute Pilates class led by Amplified Pilates, followed by a restorative sound bath experience provided by Ruby Room. Each participant will receive a special crystal gift provided by Ruby Room. We kindly ask that you please your mat. This event will be held on the 8th floor in Renaissance.
Post class, head to Upstairs at The Gwen, located on the 5th floor of the hotel, for light bites and crafted cocktails.
A Spirited Affair: Winter Floral Workshop & Wine Pairing with Prisoner Wine
On Wednesday, December 10 from 6 to 8pm, celebrate the holiday season in style at The Gwen with a winter floral centerpiece workshop led by local floral artist LeeLee. No experience needed and all materials provided. Discover the bold and unique flavors of The Prisoner Wine Company’s acclaimed wines, guided by sommelier Kimberly Tschantz, while enjoying expertly curated bites by The Gwen’s Executive Chef Matt Jergens, crafted to perfectly complement each pour.
Christmas Cheers at The Gwen
Cheers to a sparkling Christmas! Start December 25 at Upstairs at The Gwen with our festive-flavored mimosa lineup and an extended brunch until 2pm. When the mood strikes again, head back Upstairs for extended Happy Hour from 4–7pm. Because Christmas deserves multiple toasts.
Gwen's Gilded New Year's Eve
Celebrate New Year’s Eve at Upstairs at The Gwen with an unforgettable evening of indulgence and style. Savor a special menu crafted by Executive Chef Matt Jergens, perfectly paired with Moët & Chandon from our Moët champagne bar, craft cocktails, or wines from our curated list. Dance the night away to the music of DJ Stack and toast to 2026 with complimentary bubbly at midnight.
For a truly chic start to the new year, reservations are required to secure your spot in our indoor lounge.
