Tasting Chicago: The Holiday Edition
Tasting Chicago: The Holiday Edition
In this festive edition of Tasting Chicago, Sylvia Perez explores four of the city’s most over-the-top holiday-themed bars and rooftops, where the décor is dazzling, the cocktails are creative, and the holiday spirit is turned all the way up.
CHICAGO - Each winter, some of Chicago’s bars and restaurants transform into a collection of full-on festive destinations. Think themed cocktails, over-the-top décor, and holiday magic in every corner.
Join Fox 32’s Sylvia Perez as she visits four standout spots that don’t just celebrate the season, they become it.
The Gwen (River North)
Address: 521 North Rush Street
Discover a cozy winter hideaway atop The Gwen, where fire-pit lounges, curling lanes, and a lineup of festive cocktails and warm holiday sippers set the mood. The twinkle-lit rooftop offers an elevated retreat with stunning Chicago views that are perfect for embracing the magic of winter in the heart of the city. Before you head outside to the rooftop, don’t miss a one-of-a-kind surprise in the lobby: Chicago’s only Champagne Vending Machine. Yes—Champagne at the push of a button!
The Dandy Crown (River West)
Address: 694 North Milwaukee Avenue
Each December, The Dandy Crown transforms into "A Very Dandy Holiday." It’s a festive hideaway glowing with warm lights, cozy fire pits, and a lineup of seasonal cocktails served in delightfully cheerful glassware. Sip on a Merry & Bright Margarita, warm up with a Fireside Old Fashioned, or indulge in their famous Peppermint Bark Espresso Martini as you settle into heated indoor and outdoor spaces overflowing with holiday charm in the heart of River West. The holiday menu keeps the spirit going with shareable favorites.
Hubbard Inn (River North)
Address: 110 West Hubbard Street
The Hubbard Inn becomes "The Christmas Inn," a multi-level holiday pop-up with themed floors ranging from classic Christmas nostalgia to cheeky, over-the-top décor. Guests can wander through the immersive displays while enjoying creative seasonal drinks. The menu is over the top for both dinner and brunch with a mile high chicken pot pie and brunch offerings that include chicken and waffles and egg and caviar toast.
Graystone Tavern (Wrigleyville)
Address: 3441 North Sheffield Avenue
Every December, Wrigleyville turns into what’s called "Wrigleyville Wonderland. It’s become Chicago’s biggest holiday pop-up district with more than 25 themed bars. One of the standout stops is 8 Crazy Nights, the city’s only Hanukkah pop-up at The Graystone Tavern. The space glows with blue-and-white lights, dreidels, menorahs, and spirited décor, all paired with festive bites and Hanukkah-inspired cocktails. And as the owners like to say: you don’t have to be Jewish to join the fun!
What you can do:
Want to be featured on a future episode? Send us a 30-to 60-second video telling us why we should check out your favorite restaurant, bar or hidden gem. Email your submission to TastingChicago@fox.com — and we just might show up with a camera crew!
About the show:
Tasting Chicago takes you on a delicious half hour tour of the city’s food scene. Join Fox 32’s Sylvia Perez as she drops into Chicago’s hottest restaurants, neighborhood classics, and buzzy cocktail spots.