New York City may get most of the attention as America’s idyllic Christmas destination, but it’s Chicago that is truly the winter wonderland of your dreams. Among the bustling food scene, awe-inspiring productions, and world-famous museums, there is an abundance of restaurants and activities for anyone landing a spot on this year’s Nice (and even Naughty) List. But if time is of the essence and you’re not entirely sure where to begin, we’ve combed through all of the Windy City’s festive offerings to present a comprehensive guide to our favorite December hot spots. All you need is a coat, some cash, and the ability to put your everyday stresses aside. It’s time to surrender to the holy holiday spirit and let it take over your body. Praise be to Chitown.

Chicago Events and Productions

Joffrey Ballet’s “The Nutcracker”

Cheryl Mann/The Joffrey Ballet

Even the biggest of Scrooges will have something to smile about at Chicago’s most popular holiday production, now in its fourth season. With the city itself as the backdrop, show-goers will revel in the most adorable, whimsical, and nostalgic performance of the season, complete with world-class dancing, intricate costumes, dazzling lights, and the familiar Tchaikovsky numbers you’ll be humming for the entire rest of your trip. You’d be remiss to miss out! Click here for tickets.

Chicago Museums

You won’t find a shortage of museums in Chicago, with most presenting holiday exhibits that not only thrill, but educate during this busy time of year. The Museum of Chicago + Industry presents a “Christmas Around the World” that highlights cultural holiday traditions, while the Art Institute of Chicago channels their inner Nate Berkus with the tiniest of Holiday Thorne Rooms. Either way, consider these annual staples a necessary respite to Chicago’s notoriously bitter cold. You’re going to need it.

Macy’s (The Walnut Room) 


There’s no department store more famous on the Magnificent Mile than Macy’s, and Christmastime is where Santa’s headquarters truly shines. Beyond the ornate window displays is the Walnut Room, a wood-paneled restaurant boasting Russian and Austrian chandeliers among a cozy, decked-out dining space. Order Mrs. Hering’s Chicken Pot Pie, admire the giant Christmas tree, and allow yourself to be immersed in the contagious spirit. There may be no better place to capture the sights and sounds of the holidays that you so desperately crave during this time of year. Click here for more information.

Chicago Brunch Spots



Cue “Funky Town,” except replace the song’s lyrics with Funkenhausen. This is one of the most buzzed-about restaurants to hit Chicago’s dining scene, offering a unique mash-up of Southern and German cuisines (think schnitzel meets grits) in a beer-forward environment. It’s the perfect prerequisite to Chicago’s Christkindlmarkt, where you can enjoy even more German-inspired treats and libations. Fröhliche Weihnachten, everyone. Click here for more information.

Mott St

Let’s give ‘em something to Mott about. And that something is an award-winning burger served only from 6-7 p.m., or exclusively at their bar and during brunch service. Selected as Thrillist’s Best Burger in Chicago, this Asian-inspired delight features a drool-worthy miso butter atop jalapeño pickles, American cheese, double patties, Hoisin aioli, and fried sweet potato sticks. Needless to say, you’re going to need some sake to wash it all down. Click here for more information.

Chicago Dinner Spots

Odyssey Chicago River Dinner Cruise

Odyssey Chicago River Cruise

The weather outside may be frightful (it’s Chicago, after all), but that doesn’t mean you can’t enjoy the sights and sounds of the city from the comfort of a boat. Odyssey boat tours continues to run daily (no icy lakes or Titanic-esque icebergs to get in the way), including a glass ceiling dinner cruise with an open bar. It’s the perfect outing with friends and an excellent excuse to get out of sweatpants for an evening full of food and dranks. Just be sure to monitor your champagne intake. Not everyone wants to see those “dance moves” you’ve been saving for under the mistletoe. (Two cruise offerings are also available on Christmas Eve, in case you’re not entirely sure what to do with those pesky in-laws.) Click here for tickets.


The Feast of Seven Fishes may be an important Christmas custom for Italian families across the country, but for this Italian, it’s all about pasta, pasta, pasta. And nobody serves more innovative tagliolini, agnotti, and gnochetti than Monteverde. From spicy arrabbiata to cacio whey pepe, there’s a hand-made noodle and sauce combo for every type of personality. You may even find yourself asking which elf your tastebuds tipped to get on the culinary Nice List this year. Pro tip: Don’t leave without ordering the burrata appetizer, which is my favorite appetizer in Chicago. Click here for more information.


Galdones Photography

Even Santa has to pace his cookie consumption during the holidays. If you’re looking for a necessary break from gluttony to reboot and recover from rich food overload, look no further than what is arguably one of the best Japanese establishments in the city. Aside from fresh, innovative sushi, you’ll find dozens of small plates, both hot and cold, that will satisfy any craving. And we do mean literally any craving, from soy marinated quail eggs wrapped in bacon to sweet tomato tartare on Japanese milk bread. Click here for more information.


Casual fine dining has never felt more chic. In an ever-changing list of dishes based on ingredient seasonality and chef collaborations, this Lakeview gem offers an approachable menu with inspiring takes on familiar favorites. Plus, it’s only a short drive from Lincoln Park’s Zoo Lights, making it an ideal first stop for a night full of LED-enhanced magic. Click here for more information.


This Pilsen hidden gem has become a permanent staple on the locals’ “must-try” list…and deservedly so. Offering innovative, beautiful, and tasty dishes in a chic and industrial atmosphere, Chef Stephen Gillanders wows with a seasonal menu that doesn’t lend itself well to the indecisive. To help, start with the signature Cornbread Madeleines and Black Truffle Croquettes before diving into Asian-inspired entrees like the Foie Gras Bibimbap or Organic Fried Chicken with fermented hot sauce. And definitely save room for dessert. Pastry chef Tatum Sinclair is a master with sugar…and a blow torch! Just check out her fiery Black Truffle Pavlova hereClick here for more information.

Chicago Hotel

W Chicago – City Center


It’s important to feel like you’re in the middle of all the lights, bells, and garland that define the holiday season and there is, perhaps, nowhere more central than the appropriately-named W Chicago – City Center. This modern and trendy property boasts spacious rooms with eclectic furniture, branded and adorned with the W’s iconically inspirational (and sometimes hilarious) daily affirmations like “settle in and mix it up” above the minibar. The hotel also offers a dramatic MSC Bar within its lobby and Midland Social Club for food, so you’re never far from a delicious meal or an even-more-delicious libation (or seven…depending on how the family has been treating you this trip). Click here for reservations.

Header image courtesy of Cheryl Mann.

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