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Best Things to do in Chicago During December

I look forward to December in Chicago every year; not because I like the cold and snow but because of all of the activities packed into the month.  There’s so much to do in the month of December with many events being free or low cost so most can take advantage of them!  Here’s a list of can’t miss activities happening during December in the city!

Christkindle Market

Inspired by the Christkindle Market in Nuremberg, Germany, this free outdoor market takes place in Daley Plaza.    Explore German food, drinks, shopping, and entertainment thru December 24th.   You can also catch the market in Wrigleyville.  Entry into the Christkindle Market is FREE.

Dine at Time Out Market Chicago

This food and cultural market brings the best of the city under one roof with a curated mix of 18 kitchens and three bars. Further, the 50,000 square foot space includes a demonstration kitchen, event kitchen, entertainment platform with bleacher seating, and an all-season rooftop bar. Get all the details here.

One-of-a-Kind Show at The Mart

Browse hundreds of handmaid one-of-a-kind items from over 600 artists at The Mart December 5-8th!  Tickets start at $12 or choose from ticket packages starting at $18.  Pro Tip:  If you sign up for emails from some of the featured artists you can score free tickets. Shoppers will have the opportunity to meet and engage with over 600 participating artists to learn about them, their creative process, and their work while shopping art, fashion, jewelry, wood, photography, glass, furniture, home goods, pet products, bath & body, and so much more!  Everything you’re looking for in one place!

Maggie Daley Skating Ribbon

Take in the skyline as you skate the ribbon at Maggie Daley Park.  This family-friendly activity is always a highlight of winter in Chicago.

Visit the World’s Largest Starbucks Roastery Reserve

The Chicago Starbucks Reserve Roastery has five floors, including an outdoor rooftop, and spans 35,000 square feet. Guests of the roastery will enjoy specialty coffees and teas, on-premise roasters and massive coffee casks where freshly roasted beans are held. They also have bars with craft cocktails and fresh baking onsite.

Art on The Mart

This free display happens Wednesdays-Sundays at sunset.  Hang out on the Chicago River Walk as the Merchandise Mart turns into the largest digital art projector in the world.  Thirty-four projectors will showcase the works of four renowned contemporary artists during the 2-hour shows.  The Mart spans two city blocks and is over 25 stories high, don’t miss this spectacular display!

West Town Winter Fest’s Jolly Trolley

Hop on the Jolly Trolley to shop the Blocks of West Town during Winterfest on December 7th.  Over 20 retailers will feature special promotions, one-of-a-kind items, and trunk sales.  The guided tour lasts 3 hours, features all the shopping blocks and provides a “checked shopping bag” service, so you don’t have to worry about your gifts while you shop. Receive a $20 Gift Certificate when you purchase a $10 Jolly Trolley ticket.  Adult beverages are provided during the trolley ride.

ZooLights at Lincoln Park Zoo

The one-of-a-kind experience offers fun, free, family-oriented festivities, and hundreds of dynamic displays all under the glow of 2.5 million lights. The display begins on December 3rd. Zoolights is free entry.

Lincoln Park Zoo Lights
Photo courtesy of Lincoln Park Zoo

Ride the Polar Express

Hop on board AMTRAK’s Polar Express taking off from Chicago’s Famous Union Station! This is the only time it’s acceptable to wear your pajamas in public, since guests are encouraged to come dressed in their PJs, lol.    Each 3-hour memorable ride includes live entertainment, delicious hot chocolate, a cookie, and a keepsake. Click here for tickets.

Navy Pier’s Winter Wonderfest

Winter WonderFest at Navy Pier is an annual Chicago winter event, featuring 170,000 square feet of carnival rides, giant slides, holiday-themed activities, festive carousel, inflatable rides, an Indoor Ice Skating Rink, and more. Experience thrills without the chills beginning December 6th! Get your tickets here.

Illumination:  Tree Lights at Morton Aboretorum

Walk a mile long paved path amid a multitude of colors as interactive lighting effects highlight the beauty of trees in winter. Enjoy seasonal music, stare in amazement at the ever-changing, interactive lighting designs, and warm up by a crackling fire with a cozy drink or roast marshmallows for s’mores. Click here for the calendar and tickets.

Visit the Friends Popup Experience

Could this experience be any cooler? Celebrate 25 years of Friends at the AT&T popup on the Magnificent Mile. Reminisce on your favorite episodes and maybe test your Friends knowledge during one of their trivia events. The FREE popup is open through the end of December.

Navy Pier Fireworks

Take in the New Years Eve Fireworks Show over Lake Michigan on December 31st starting at 12 a.m.  This event is free!

Navy Pier Fireworks
Photo courtesy Navy Pier

Themed Pop-Up Bars

There are a slew of festive winter-themed pop-up bars happening around the city. Here’s a list:

Apres Ski After Dark-Swiss Hotel

Woman holding a cocktail in front of festive decor at Swiss Hotel Chicago
Apres Ski Pop-Up at Swiss Hotel Chicago

Visit the Swiss Hotel’s apres’s ski pop-up bar on Fridays in December. The Presidential suite will be filled with photo-worthy festive cocktails and shot skis, a chair lift photo opp, and a live DJ! The space is stunning, a must see!

Reindeer’s at the Chit Chat Lounge

Reindeer’s will take over the basement formally home to Chit Chat Lounge (416 N Desplaines in River West) and include a brand new menu of themed holiday libations and snacks; holiday dive inspired décor, seasonal entertainment, and more. There’s a cozy upper lounge reminiscent of your grandma’s living room to chill in, but I think the incredible music blaring through the speakers may lure you to the downstairs dance floor! Open to the public Wednesday – Fridays 5 pm – 2 am, Saturdays 12 pm – 3 am, and Sundays 12 pm – 2 am through the end of the year.

Wrigleyville Pop-Ups

8 Crazy Nights

The Graystone Tavern: 3441 N. Sheffield Dec. 1 – 31 Mondays – Fridays: 4 p.m. – 2 a.m. Saturdays – 11 a.m. – 3 a.m. Sundays 11a.m.– 2 a.m.

This no-cover Hanukkah pop-up includes fun decor, food, drinks, and Schmaltz beers on tap! Classic Eastern European Jewish dishes will be served, such as matzo ball soup, latkes, and brisket.

Bad Santa Photo Shoot Pop Up

Sheffield’s: 3258 N. Sheffield , ONE DAY ONLY – Saturday, Dec. 7 – 6 p.m. – 10 p.m.

Christmas Club

Country Club: 3462 N. Clark – Nov. 20 – Jan. 1 Mondays – Thursdays: 4 p.m. – 2 a.m. Fridays – Sundays: 11 a.m. – 2 a.m.

This no-cover pop up includes two floors and appearances by Santa, as well as other various characters. Three different rooms in three different bars, and guest DJs every week.

Elf’d Up

Stretch: 3485 N. Clark Nov. 20 – Jan. 21 Tuesdays – Fridays: 5 p.m. – 2 a.m. Saturdays: 12 p.m. – 3 a.m. Sundays: 12 p.m. – 2 a.m.

This Elf movie-themed pop up will offer specialty cocktails, rotating season drafts, a themed food menu, including Buddy’s Breakfast Pasta! There will even be weekly appearances of Buddy the Elf Thursday through Saturday (anytime between 9 p.m. and 12 a.m.). Elf trivia will be on Dec. 4, 11, and 18 at 7 p.m. Buddy’s Brunch will happen every Saturday and Sunday 11 a.m. to 2 p.m. (The pop up will be closed Dec. 2)

Griswold’s Christmas Vacation Pop Up Bar

Houndstooth Saloon: 3369 N. Clark Nov. 17 – Feb. 9 11 a.m. – 2 a.m.

There will be Griswold and 80’s themed food, drinks, and specials, and the bar will feature Uncle Eddy’s decked out 1977 RV, and three themed rooms, The Griswold living room, the tiki Bar, and Clark’s attic. Cousin Eddie will stop by in the RV to hand out hot chocolate and cocktails on opening day, and there will be a champagne toast at midnight each night! The $5 cover goes into effect after 5pm, or you may donate a toy to Toys for Tots in lieu of the cover fee.

Jingle Junkie

Roadhouse 66: 3478 N. Clark Nov. 27 – Jan. 6 Mondays – Fridays: 10 a.m. – 2 a.m. Saturdays: 10 a.m. – 3 a.m. Sundays: 10 a.m. – 2 a.m.

This pop up will consist of a heated ski lodge-inspired patio with seasonal beers and cocktails, and festive food.

John Vincent Holiday Pop-Up Shows

Rizzo’s Bar & Inn/365-viii: 3658 N. Clark Thursday, Dec. 5th 7:30 p.m. – 9 p.m. Friday, Dec. 6th: 8 p.m. – 10:30 p.m. Thursday, Dec. 12th: 7:30 p.m. – 9 p.m. Sunday, Dec. 15th: 4 p.m. – 6:30 p.m. Thursday, Dec. 19th: 7:30 p.m. – 9 p.m. Friday, Dec. 20th: 8 p.m. – 10:30 p.m. Saturday, Dec. 21st: 8 p.m. – 10:30 p.m. Sunday, Dec. 22nd: 4 p.m. – 6:30 p.m.

John Vincent is a local legendary performer, entertaining crowds of all types and varieties with his covers of Frank Sinatra, Louis B. Armstrong, Johnny Cash and more. He is also the current resident National Anthem singer for the Chicago Cubs. The December 12 pop up show will be a special Sinatra birthday performance! For guests aged 21 and older, ticket costs vary from $10 – $160. $10 offers standing room admission, or you may get a table for two for $40, a table for four for $80, or a cabana for eight for $160.


Hush Money/Mordecai: 3632 N. Clark Nov. 22 – Jan. 1 Tuesdays – Wednesdays: 5 p.m. – 11 p.m. Thursdays – Fridays: 5 p.m. – 12 a.m. Saturdays: 11 a.m. – 12 a.m. Sundays: 11 a.m. – 4 p.m.

The second floor of Mordecai (Hush Money) will be decked out in holiday decor, and there will be a special holiday cocktail menu!

Rock N Roll Christmas

HVAC Pub: 3530 N. Clark Dec. 21 – Jan. 31, 2020 Thursdays – Saturdays: 5 p.m. – 2 a.m.

Rotating holiday themed specials will be offered, and admission fees are dependent on planned shows/events/concerts. You may substitute the cover fee with a toy donation. There will be an ugly Christmas sweater contest with a $100 prize.

Rudolph’s Christmas Bar

Casey Moran’s: 3660 N. Clark Nov. 22 – Jan. 6 Mondays – Thursdays: 4 p.m. – 11 p.m. Fridays: 4 p.m. – 2 a.m. Saturdays: 11 a.m. – 3 a.m. Sundays: 9 a.m. – 11 p.m.

Multiple bars within Rudolph’s Christmas Bar will include: Grinch’s Piano Bar, Frosty’s Rooftop, Rudolph’s Lounge, and more. They will be partnering with Toys for Tots and will have on-site bins for donations with daily collection. Purchase tickets in advance; door ticket price subject to change.

Santa Baby Christmas Bar

Deuce’s Major League Bar: 3505 N. Clark Nov. 20 – Jan. 6 Mondays – Thursdays: 1 p.m. – 11 p.m. Fridays: 1 p.m. – 2 a.m. Saturdays: 11 a.m. – 3 a.m. Sundays: 9 a.m. – 11 p.m. 21+ after 8 p.m.

This pop up includes multiple bars, a Gingerbread Village, Alpine Ski Lounge, Santa’s Workshop, Winter Wonderland, and more. They will be partnering with Toys for Tots and will have on-site bins for donations with daily collection. Purchase tickets in advance; door ticket price subject to change.

Santa’s Workshop

Old Crow Smokehouse: 3506 N. Clark Mondays – Fridays: 4 p.m. – 2 a.m. Saturdays – Sunday: 10 a.m. – 2 a.m.

Country-style Christmas, the all-ages, no-cover popup will feature special menus, massive holiday décor, and three floors of festivities for a season-long celebration. There will be several giant Christmas trees and Santas, as well as two enormous rocking chairs, perfect for a photo op. See Santa take off in his reindeer run sleigh and roast marshmallows while Christmas movies play on the screens.


Gallagher Way: 3635 N. Clark Nov. 22 – Feb. 16

Winterland includes the return of the famous Christkindlmarket Wrigleyville, ice skating on an 8,000-square-foot ice rink, curling and skating lessons, Santa’s Workshop, wreath making classes, oversized decorative winter characters, holiday movies and much more. This year’s transformation will include a 30-foot holiday tree underneath the Wrigley Field Marquee, a tree lot at Big Star Wrigleyville, holiday programming at Hotel Zachary, Hush Money, Lucky Dorr, Smoke Daddy Wrigleyville and other restaurants around Gallagher Way, plus even more decorative lights around Gallagher Way

Click here for another fun Chicago experience!


  1. We spent some time in Chicago last year in December and LOVED our time in the city. Pinning this for reference as we must visit Chicago in December again. Thanks for sharing.

    • Flo says

      You’re so welcome! Happy to hear you enjoyed your time in the city!

    • Flo says

      Yes indeed! So enjoyable this time of year

  2. happymomhacks says

    Love Christkindlemarket! It’s a must do in Chicago ever year. I didn’t know about the Griswold pop up truck. We’ve got to check that out this year.

  3. travelwithaplan says

    Wow! This is truly the best round of up things to do in Chicago during the winter that I have ever read! Your photos are amazing! I have added some ideas to my list of things to do when we go there in January! Thanks!

    • Flo says

      Thank you! I’m so happy you enjoyed it and gained a few ideas!

  4. I’ve only been to the Christmas Market! I think I need to check some more things out! Some of those drinks look amazing!

    • Flo says

      Yes definitely, there’s something for everyone!

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