We all know Chicago is a hoilday town. Yes, we live for the season: the lights, music, and… how could you not talk about the brilliant holiday pop ups in Chicago every year that bring the north pole to our Windy City? Here are nine of the best pop ups we’ve gathered in and near the city for those of you looking for a cool date idea, a family outing, or to show a visiting friend around. By the way, don’t forget to check out our list of Chicago holiday lights and light fests too!

Image Credit: Mordecai

‘Mistletoe’ at Mordecai

3632 N Clark St, Chicago, IL 60613

Upon entering Mistletoe, visitors will feel as if they are entering a holiday storybook (take a look yourself!). Delivering more than just festive decorations, the experts at Mordecai have curated an exclusive holiday cocktail list that features both contemporary & vintage creations, with their “Keep The Change, Ya Filthy Animal!” winter-inspired old-fashioned being a must-try. Mordecai’s full dinner menu & standard cocktail list will also be available. 

With Mistletoe being a part of Winterland at Gallagher Way, those visiting can also take advantage of nearby festive activities, such as Christkindlmarket Wrigleyville and Gallagher Ice Rink, among others! 


Chicagoans can experience Mordecai’s ‘Mistletoe’ throughout the holiday season, beginning on Friday, November 18th. Due to the demanding popularity Mistletoe brings each year, reservations are required, and groups of 1-6 can reserve two-hour blocks on Tock, Thursday through Saturday.

Image Credit: 4 Star Restaurant Grou

Lumberjack’s Lodge at Smoke Daddy Wrigleyville

3636 N Clark St, Chicago, IL 60613


‘Tis the season for festive cocktails, cozy bonfires, and ugly sweaters! Smoke Daddy is kicking off the holidays with LumberJack Lodge as it takes over the Wrigleyville location! So, grab that sweater Aunt Betty was so proud to give you back in 2016, and head on over for great food and delicious drinks among friends. The lumberjack-themed pop-up is bringing the winter cabin to the city!

From dramatic ceiling canopies full of garland and ornaments to woodland backdrops with a 7-foot brown bear, the only thing missing is a bone-chilling snowstorm…but living in Chicago, anything is possible. So come hide at Lumberjack’s Lodge before the storm hit, quench your thirst with sensational holiday cocktails, and satisfy your appetite with comforting, stick-to-your-ribs bites!


Christmas Inn at Hubbard Inn

110 W Hubbard St, Chicago, IL 60654


Hubbard Inn, Chicago’s premier three-story dining and nightlife destination in the heart of River North is transforming into “Christmas Inn,” to celebrate the holiday season. Starting December 1 through December 25, Christmas Inn will feature over-the-top festive décor, daily activiti4es and happy hours, seasonally themed parties and more for all to participate in. Featuring a special winter happy hour offering $1 oysters, $7 select martinis $7 hot Christmas cocktails, $30 charcuterie boards, guests can also enjoy different holiday programming such as Holiday Trivia Tuesdays, Tini-time Thursdays, Christmas Inn Ladies Night, and more.

The Lodge Tavern

21 W Division St, Chicago, IL 60610

Division Street’s favorite bar is getting a holiday makeover! The Lodge Tavern—already known for its cozy winter cabin feel— is transforming into a holiday wonderland complete with twinkling lights, wreaths, garland, and more. From the holiday menu, guests can choose from festive rifs on classic cocktails like the Skrew-Dolph, Mule-Tide Greetings, Mai Tai-Dings, Ebenezer’s Old Fashioned, and more. And for those looking to warm their bellies, The Lodge Tavern will offer a hot cocktail menu featuring the Ho Ho Hot Toddy, Irish You A Merry Christmas, St. Nick Cider, and more.

Jojo’s Winter Wonderland

23 W Hubbard St, Chicago, IL 60654

Hot chocolate, Christmas trees, giant gift boxes, and holiday decors. Jojo’s never fails to impress when the holiday season comes.  JoJo’s Winter Wonderland is its latest immersive dining experience, inviting you to rock around the 17ft. Christmas tree to your favorite holiday tunes, or cozy up with a Hot Chocolate and friends in one of JoJo’s private igloos. The festive (and heated) patio setting is the perfect place to escape the cold and enjoy JoJo’s decadent milkshakes, holiday cocktails, and delicious diner.

Christmas Tree Lot at Big Star

551 N Ogden Ave, Chicago, IL 60642

This Holiday season, Chicago’s honky-tonk hangout, Big Star, is giving their iconic outdoor patios new life! The OG Wicker Park and brand-new West Town Mariscos locations will be slinging tacos, margs, and now trees with Christmas tree lot pop-ups on two weekends only: Dec. 3-4, and Dec. 10-11. Reservations for pre-order open soon with more details forthcoming on the Big Star websites and social, however guests are welcome to pop over for a warming, stiff bourbon, a smattering of tacos, and a peruse for the perfect pine to purchase day-of.

Winterland at Gallagher Way

3635 N Clark St, Chicago, IL 60613

Bumper cars on ice, light display, a Christkindlmarket… if these hit the spot, you need to get your tickets for Winterland right now! Moving the ice rink into the famous Wrigley Field, this year’s Winterland is on a completely different level compared to the previous years. If you’ore coming here, better plan a whole day to explore the rides, artisan goods, and installations. Then, after a long day diving in and out of the Christkindlmarket, hop over to a restaurant nearby to wrap up your day with some delicious food and tasty drinks!

Ski Village at Buffalo Creek Brewing

360 Historical Ln, Long Grove, IL 60047

Beer, bonfire, log cabin.. now we’re just waiting for that snow storm to hit! Okay, maybe not really. But BCB is turning their Biergarten into an Alpine ski village this year, and that “almost” makes us look forward to the snowing days. Featuring fresh winter brews and their all time favorites, alongide small bites and shared plates, Ski Village is the perfect place to catch up with fams and friends over winter festivities.

Featured Image: Mordecai

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