Karma Rewards
Happy Holidays

The Most Wonderful Time
of the Year Begins Here

Your Home Away For The Holidays

We’ve placed you at the top of our Nice List from now through December. Come celebrate the season with a sparkling lineup of festivities even Scrooge wouldn’t dare miss. With fashion shows, a “Friends-Giving” Turkey Day Eve, Black + White Movie Nights, a Bootlegger’s Ball and so much more, this is sure to be the coziest, cocktailiest holiday ever.

Peruse the list below and start planning all the joy your holiday calendar can handle.

November 22nd – Cozy Up @ The Gray

Enjoy a cozy cocktail at Vol. 39 or Boleo as we debut our holiday décor. We will keep the toddies hot!

November 27th – Black + White Movie Night

Join us for a double feature of black and white holiday movies in the Robie Room (floor 2). Beverages for purchase at Vol. 39 and complimentary popcorn served. Evening begins at 6pm.

December 11th – Free 2-Hour Gift Wrapping & Writing Workshop

Join Emily Star Brown at The Gray Hotel with Raub Welsh (artist, interior design and gift wrapping extraordinaire), for free two-hour Holiday Gift Wrapping and Writing Workshop from 7pm to 9pm! You will learn the basics of brush tip calligraphy, gift wrapping and bow styling. All materials and champagne included. This workshop will be capped at 25 students. Reserve Your Spot Today!

December 12th – The Gray at Chriskindlmarket

Visit The Gray, Boleo and Vol. 39 as we host a pop-up booth at the Chriskindlmarket. Open from 11am-8pm selling favorites from the Gray!

December 19th – Black + White Movie Night

Join us for a double feature of black and white holiday movies in the Robie Room (floor 2). Beverages for purchase at Vol. 39 and complimentary popcorn served. Evening begins at 6pm.

More

December 5th – Bootlegger's Ball

Come Celebrate Repeal Day at Vol 39! Each ticket includes three specialty cocktails crafted just for the evening and appetizers. Party begins at 8pm and ends at 11pm.

Prepaid reservation for 1-10 guests, $45 per person. Purchase tickets here!

December 31st - New Year's Eve in Vol 39

Ring in the New Year with Vol 39 from 8pm - 1am. We will take you back to Paris in the beginning of the 20th century when jazz was in the air and champagne was plentiful.

Open Bar (Featuring Absolut Elyx, Havana Club Rum, Beefeater Gin, Jameson, Glenlivet, Martell Cognac and Perrier Jouet Grand Brut), and Passed Appetizers.

Live Music brought to you by Sam Trump and Burlesque performances featuring the one and only Michelle L'Amour.

Prepaid reservation for 1-6 guests, $125 per person. Purchase tickets here!

Holiday Things To Do Downtown

It’s the holidays. You’re in Chicago. And what to your wondering eyes should appear, but classic theater, ice skating, spiced wine and twinkle lights galore!

This town is brimming with magical moments that sink into your memory like a fruit cake in a snow drift. Below are just a few of the many ways to get your jolly on. Enjoy one or two or every single one of them, then come back to The Gray and share your favorites with us.

Top Theater Events

"Ken Ludwig's 'Twas the Night Before Christmas" playing at Broadway Playhouse

"Irving Berlin’s White Christmas" playing at Cadillac Palace Theatre


"A Christmas Carol" playing at Goodman Theatre


"Hamilton" not holiday related, but too great to miss, playing at CIBC Theatre

Top Free Events

ZooLights - musical light shows, spiced wine, sweet treats & more at Lincoln Park Zoo

City of Chicago Christmas Tree Lighting - the 104th annual event at Millennial Park 


Macy’s Holiday Window Exhibits - enchanting scenes at the State Street store


Magnificent Mile Tree Lighting Parade - one million lights adorning 250 trees, fireworks and more, on North Michigan Avenue

Top Family Events

Christkindlmarket - the city’s largest open-air Christmas market in downtown’s Daley Plaza. Visit The Gray, Boleo and Vol. 39 as we host a pop-up booth on December 12th!

Winter Wonderfest - indoor playground with ice skating, slides and more at Navy Pier

Christmas Around the World / Holiday of Light - four story Grand Tree plus 50 smaller trees showcasing traditions from around the world at the Museum of Science + Industry

Hotel Packages To Brighten Your Stay

Christkindl at The Gray

  • Best Flexible Rate
  • Two Christkindlmarket Mugs
  • Two Baderbrau Holiday Beers
  • Available November 17- December 24

Book Now

Stay & Valet

  • Valet Parking's Included
  • In & Out Privileges

Book Now

AAA Holiday Special

  • Receive 20% Off
  • Available November 16-26
And December 17-28

Book Now