The Best Christmas & Holiday Pop-Up Markets, Bars, & Events in Chicago

Tis the season of joy and creativity. Speaking of the holidays, how can you miss out on the best Christmas and holiday pop-up events and bars in Chicago? Whether it’s Thanksgiving or you want to start Christmas early, one of these pop-ups will bring you a unique experience. Food, themed nights, art markets, and more… We guarantee you’ll find something to do from the list below!

Recess

838 W Kinzie St, Chicago, IL 60642

Chicago’s largest outdoor patio at Recess is now partially enclosed and filled with space heaters all throughout the deck, which is ideal for the forthcoming Christmas and holiday pop-up bar that will be taking over the patio.

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Launching December 8, Recess will transform into an elaborate holiday pop-up in the West Loop, featuring your favorite holiday movies, with six Christmas and Holiday films playing throughout the shipping containers with decor to match. Special hot cocktails and menu items will coincide with the pop-up, guaranteed to help keep you in the holiday spirit. More information is coming soon and can be found by visiting www.chicagoinrecess.com.

The Press Room

1134 W Washington Blvd, Chicago, IL 60607

This holiday season, The Press Room is bringing diners the ultimate speakeasy experience and re-launching their weekly live music performances. Join the Press Room with live music from some of Chicago’s best — Jon Allegretto, Toronzo Cannon, and Nick Moss, while enjoying food from their menu, cocktail, and wine list selected specifically for the live music events.

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Each live show will be 90 minutes. The Press Room will open their doors at 6:15pm with the live performance starting at 7:00 p.m.

Showtimes:

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  • December 5: Jon Allegretto at 7:00pm

  • December 12: Toronzo Cannon at 7:00pm

  • December 19: Nick Moss at 7:00pm

the rambler food
Image Credit: Papergirl PR

The Rambler

4128 N Lincoln Ave. Chicago, IL 60618

Tribute to the 1964 beloved classic Rudolph The Red-Nosed Reindeer television special and the Island of Misfit Toys, The Rambler Kitchen + Tap in North Center will host a “Misfit Christmas” pop-up beginning the day after Thanksgiving, Friday, November 26 through Sunday, January 2.

A themed food menu will feature sweets like warm baked Snickerdoodle Pretzels topped with cinnamon sugar and served with icing, Reindeer Food with rice cereal, chocolate, peanut butter, powdered sugar, and red and green M&M’s, and Sam the Snowman shaped powdered sugar donuts and more. Savory dishes will include a Toy Taker Turkey Sandwich with roasted turkey breast, stuffing, mashed potatoes, gravy, and a side of cranberry sauce, and an Open Faced Chicken Pot Pie on two buttermilk biscuits. Complete menus available upon request.

8 crazy night holiday pop ups in chicago
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The Graystone Tavern

3441 N Sheffield Ave, Chicago, IL 60657

Back by popular demand for its third year, The Graystone Tavern in Wrigleyville will open “8 Crazy Nights,” Chicago’s first and only Hanukkah-themed popup bar, through Sunday, January 2.

Throughout the pop-up, a special food menu, ranging in price from $5 to $16, will feature traditional and spins on Jewish favorites like Matzo Ball Soup and three flavors of Latkes including classic with sour cream and applesauce, cilantro jalapeno with chipotle sour cream and herb cheddar with chive sour cream.

Festive cocktails with traditional Hanukkah flavors will be available for $12 each like the Festival of Lights Martini, Gelt Martini, Mazel Tov, The Chosen MF and a Mensch Mule.

Sleigh Bells

Medinah Temple, 600 N Wabash Ave, Chicago, IL 60611

Check out Sleigh Bells—a trippy and immersive holiday pop-up full of color, sound, lighting, murals, technology, art and Christmas spirit! Taking over 45,000 square feet of the bottom and first floors of the property from December 2nd, 2021- January 3, 2022, Sleigh Bells invites guests to make their way through large-scale, interactive art installations that will transport them to vibrant and visually stimulating spaces like an infinity mirror ice cave, Santa’s workshop, Santa’s armory, and a dazzling oversized ornament light show display.

The project is being produced by Dom Brown and John Schroeder of Superfrüit. The local duo has curated experiential installs and pop-ups for some of Chicago’s most notorious brands such as Lollapalooza, Spring Awakening Music Festival, North Coast Music Festival, Morgan Manufacturing, and Red Bull. Superfruit has also brought on Keegan Moon (Dine|Amic Hospitality, Evening Entertainment Group) of Thyme Management to head up food and drinks. Seasonally themed offerings will be served by way of a hot chocolate and ice concession stand housed within a massive 44-foot dome with a 360° mirror cave.

Tickets are to be reserved in advance online at Sleighbellspopup.com or https://feverup.com/chicago.

Classic Holiday Decor at The Blackstone

Lobby Entrance On, 636 South Michigan Avenue, E Balbo Dr, Chicago, IL 60605

It might be cold outside, but inside The Blackstone it’s warm and cozy. Stop by this wintery season and enjoy a classic holiday display featuring dazzling toy trains. Hear hissing steam, squeaking metal and whistles blowing in the lobby of the storied architectural icon rooted in Chicago’s legendary past.

Witness a joyful scene featuring five toy trains placed around the decorated Christmas tree, within the window display and other locations throughout the hotel. Inspired by Timothy Blackstone, president of Union Stock Yards and the Chicago & Alton Railroad, who built the mansion now known as The Blackstone, the model trains are a must-see for locals and visitors alike. Don’t leave without watching Chicago’s classic L Train swiftly move around a model replica of the hotel and snap a photo or two.

holiday pop ups in chicago long grove vintage market
Image Credit: Vintage Holidays

Vintage Holidays in Historic Downtown Long Grove

Historic Downtown Long Grove invites holiday shoppers to rediscover the magic of the holiday season.

The annual Long Grove Vintage Holidays campaign is a tribute to the classic small town holiday market experience – quaint shops, old-world charms, and family memories. On November 19th, Long Grove officially transitions into holiday mode when its famous single lane covered bridge and village merchants flip on the holiday lights.

Christkindlmarket Chicago

50 W Washington St, Chicago, IL 60602

We’ve been waiting forever since the unveiling of their 25th anniversary designs! The smell of roasted nuts, fresh pretzels, bratwurst and hot spiced wine, the sound of festive music, and the glimmer of sparkling Christmas ornaments, all in a cozy atmosphere – a visit to the market takes all your senses on a journey! The best part? It’s admission-free. The even better part? We can help you find the most inexpensive parking in the Loop when heading there!

 

The Christkindlmarket will run from now until December 24th this year. The market is open Monday thru Thursdays from 11:00 am to 8:00 pm, and Fridays & Saturdays from 11:00 am to 10:00 pm.

The One of a Kind Holiday Show

222 W Merchandise Mart Plaza, Chicago, IL 60654

The Mart brings art back to us once again! Looking for that perfect holiday piece that will speak your amazing personality? Come check out the One of a Kind Holiday Show! This year, the show and pop-up bar in Chicago will bring together 400 talented artists, artisans, and makers from across North America to offer the best in everything from fine art to handmade goods, gourmet cafes, bar areas, and live entertainment and activities for all to enjoy. Tickets are for $10 a day at oneofakindshowchicago.com.

World’s Tiniest Tree Lot

2952 W Armitage Ave, Chicago, IL 60647

Big on holiday spirit, tiny on trees – join Half Past and Parson’s Chicken & Fish for the World’s Tiniest Tree Lot on Saturday, December 11 in support of Love Fridge, a Chicago mutual aid group grounded in food justice. Stop by for an expansive array of complimentary mini Christmas trees, Santa Claus photo ops and mini ornament decorating, as well as plenty of Chicago’s favorite fried chicken and Half Past.

This is a free event with mini Christmas trees and activities. However, menu offerings are a la carte

Featured Image Credit: Paper Girl PR