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Get cozy with a cocktail at Mama Delia’s. Photo courtesy of Mama Delia’s

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Resy’s 2022 Holiday Bucket List for Chicago

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To-do lists abound during the holiday season, especially when it comes to holiday gift shopping and grocery shopping but fret not — this list is all about savoring the special things that only happen during this time of year. It’s all about celebrating the season and making the very most of it, something you should definitely do here in Chicago.

From seasonal cocktails and fancy lunches to the best desserts and taking time out to be a tourist in your own town, here are a few of our favorite suggestions for how to best celebrate the season.

1. Get a seasonally minded cocktail.

Whether it’s a boozy hot number or simply a celebratory martini, drink specials abound this time of year, and you’d be wise to take advantage. Some of favorite cocktail spots for the winter weeks include:

  • Mama Delia’s pomegranate sangria is a house cocktail with major holiday vibes. Grab some conservas and sherry from the attached ultramarino (gourmet market) while you’re there. 
  • Eggnog aficionados know finding the really good stuff can be a holiday struggle. But Cafe Selmarie is a reliable source for a cold glass of creamy eggnog with just the right balance of sweet and boozy. Partake in their dining room or grab a bottle to-go.

2. Find the most festive holiday décor.

Some restaurants go all-out when it comes to the decorations:

  • Amanda Harth and Felton Kizer’s pop-up coffee shop, Monday Coffee, will keep you buzzing with coffee, tea, and espresso drinks like the popular Honey Cinnamon Latte. Their ongoing residency at the Garfield Park Conservatory, which is now exhibiting the Winter Flower Show, means the cafe’s backdrop is an actual wonderland brimming with breathtaking florals, like a 12-foot tree made of 200 white poinsettias. 

3. Be a tourist in your own town.

While a dinner out is entertainment in itself, there are lots of festive happenings that pair beautifully with your Resy. Spring for dinner and a holiday show:

4. Have a fancy Friday lunch.

Because one of life’s great luxuries is a special lunch on a wintry Friday. Whether it’s dim sum shared with friends or a classic destination with a long-lost friend, now is the perfect time to plan a long lunch.

  • Monteverde offers lunch service on Fridays and Saturdays. Go for pasta and a Negroni  that’s been barrel-aged for nearly two months, then wrap up your holiday shopping list with a copy of chef Sarah Grueneberg’s new cookbook.

5. Take advantage of all those holiday specials.

Whether it’s seasonal menu specials (latkes! tamales! crabs!) or a special holiday pop-up, now is the time to seize the day.

  • At Andros Taverna beverage director and sommelier Alexandria Brashears has curated an in-house wine “advent calendar” that features specially-selected Greek wines for you to enjoy each night starting December 13th.

6. Slow down.

The holiday season is always a whirlwind. Whether solo or with a loved one, take time to slow down, and have a quiet dinner in a cozy, candlelit restaurant. Maybe even without cell phones.

  • A cozy seat by the fireplace at Scofflaw is almost a nightcap by itself, but do grab something to eat (perhaps a hoisin-roasted pork sandwich) and drink (like a hot buttered rum with spices and brown sugar).
  • For a quick escape from Mag Mile chaos, dash toward Rush Street and swoop into Pierrot Gourmet, the bistro at The Peninsula Chicago. It recently reopened after a two-year hiatus and remodel, and is a welcoming nook for breakfast or lunch. For more razzle dazzle, however, consider afternoon tea inside the Peninsula’s lobby where proceeds this holiday season will support the work of the Chicago Public Library Foundation.

7. And whatever you do, don’t skip dessert.

Actually, maybe go out of your way to get some holiday desserts.

  • At Brown Sugar Bakery, Stephanie Hart’s classic Southern baked goods (especially the caramel cake) are simply legendary. Early orders are encouraged!