Holiday Events in Chicago for Every Age

Walking down Michigan Avenue in the evening while glittering snowflakes fall has to be one of the most joyful things to do in Chicago. The energy in the air is palpable and the decor- sophisticated yet whimsical. Simply put, the holiday season in Chicago is pure magic. There are so many holiday events in Chicago for every age, from the little ones with apprehensive smiles to the boomers whose nostalgia makes the season bitterweet. Here are some of my favorite ways to share time with those you love! Most are appropriate for every age, but these are just guidelines.

Holiday Events in Chicago for Every Age

Ages 2-6: Beatrix Potter Holiday Tea Party

Although I had heard rave reviews about this event, I had never actually attended until this year. SO happy I had the opportunity! This is a show that is perfect for newbie theatergoers (and parents who are nervous about taking their kids to a performance for the first time). The Tea Party occurs at the Chicago Children’s Theatre, which has a strict “no shushing” policy. This means if your kid loudly asks, “Why does that frog look so funny?” in the middle of a pivotal moment, you don’t have to sweat it.

Beatrix Potter Holiday Tea Party- holiday events in Chicago for every age

The show lasts just under and hour and is performed by three actors + props that they operate. There are four vignettes set on stage, and each tells a different tale of a character from the Beatrix Potter books. Live music plays a role as well- one actor plays a violin among other non-traditional instruments. This is the 5th year this show has run, which makes it one of the holiday events in Chicago that has stood the test of time and love of audience members.

After the highly animated performances, guests of all ages are invited to the stage to test out the props. The actors are on hand to show how to operate the various puppets so children get to see the magic behind the stage.

Chicago Childrens Theatre

Families then retire to the communal tables outside of the theater that are set up as a Victorian tea party. Everyone gets to enjoy hot cocoa and sinfully rich cookies with their group. This is a memorable outing that you will enjoy right alongside your kids. Mine were captivated from the moment the show started right up to the last sip of cocoa. This is the perfect way to act like a kid this holiday season and get carried away by make believe.

Holiday Tea Party

Show times are Saturday and Sunday at 11:30 a.m. and 2p.m. through December 30th with additional holiday performances added as well as those for special needs. For more information and to book your ticket, visit the Chicago Children’s Theatre website.

Ages 6+: Holiday Lights Tour

This is the third year I have taken my family on this tour, and each year I get THAT feeling. You know the one- the holiday warm glow that makes you joyful, nostalgic and grateful all in one. If you are having a tough time getting into the holiday spirit, the Chicago Trolley Holiday Lights Tour will jump start your heart.

Zoolights at Lincoln Park Zoo- holiday events in Chicago for every age

A classic red trolley decorated for the holidays picks you up outside of the John Hancock building. As you wait, check out the tree in front of the Cheesecake Factory- it is massive, stunning and never crowded.

First, you are given a bag of Garrett’s Popcorn in the Hot Cocoa CaramelCrisp Mix. They take their classic caramel popcorn and drizzle it in Belgian dark and milk chocolate. The perfect post-dinner sweet treat to get you in the mood and is only available during the holidays.

The trolley takes you to Christkindlmarket in Wrigleyville for a 45 minute stroll around the market. I discovered the most delicious snack (dinner for me because I ate the whole thing by myself)- a raclette sandwich on a crusty French baguette paired with cured meat, spring onions, Dijon mustard and baby gherkin pickles. As you walk up to the stall, there is a massive half round of gooey cheese being melted. They scrap the melty part off and plop it on crisp-on-the-outside-soft-on-the-inside bread. Get one, you won’t be disappointed. There are also foot long hot dogs, as my son had to have:

Food at Christkindlmarket in Wrigleyville

The trolley then transports you to the Lincoln Park Zoo for their Zoolights display– a 2.5 million light wonderland that is free to visit. There are lights set to music, light tunnels, animals created from lights, you get the idea. You pop in for 45 minutes, just enough time to do a few laps and snap some photos at your fave locations.

Zoolights at Lincoln Park Zoo

I adore this tour because it makes transportation AND parking so easy for multiple locations. You just hop on and hop off, and they ferry you around the the most spirited, special holiday spots in the city.

Ages 13-18+: Bub City Brunch

Brunch with your parents where you have to get dressed up in some lame outfit and be quiet for two whole hours? Yeah, that’s what your teenagers think when you force them to go to a fancy schmancy brunch where there is more than one fork. I discovered a brunch with the perfect blend of casual + spirited with some entertainment tossed in! This might not be one of the classic holiday events in Chicago, but I made it my own.

I always see my friends’ brunch photos posted on social media over the holidays. The girls were either a velvet or tartan dress, and boys are stuffed into a collared shirt adorned with an occasional bow tie. Sometimes they look happy to be at the table, and others…you can tell the parents told them to “STOP banging on the table for once and smile for the damn camera!”

Bub City Chicago decorated for the holidays
Bub City Chicago image via Instagram

I decided I wasn’t going to play that game. This year, I took my family to Bub City for brunch. Mimosas, Bloody Marys and some rock n’ roll. Check out their live music schedule here, and see if you can book a table for brunch (or lunch or dinner!) when someone is on the mic. The venue is decorated to the nines with strings of lights, window paintings and wreaths made out of beer cans- hilarious.

Brunch at Bub City Chicago

We had a blast- my son ate peanut butter + banana + bacon pancakes, and my mom (!) had a Bloody Mary with a beer back (she didn’t know what to do with it, so I snagged it). The band played music from the 70s on through today, and everyone at the table was focused on the atmosphere instead of which fork to use.

Ages 21+: Santa Baby Bar

This is at the top of my holiday experience list this year…I just need to find a babysitter and a fabulous holiday-inspired ensemble. The Santa Baby Bar is Wrigleyville’s over-the-top holiday pop up experience.

Santa Baby Bar- Wrigleyville; holiday events in Chicago for every age
Photos via Santa Baby Bar website

Tickets vary in price for entry- I saw a range of $10-$20 depending upon time of day and day of the week. Go during the weekdays- it is free! From what I gather, there are dozens of IG-worthy scenes to snap a photo, and fun drinks in line with the theme of CHRISTMAS EVERYWHERE (hello Clausmopolitan!).

Holiday Cocktails at Santa Baby Bar
Photos via Santa Baby Bar website

According to reviews, you go for the atmosphere. The food is basic bar food, the cocktails are meh, but soak in that holiday spirit! Yes, kids are allowed in until 8pm and they do have a kids menu, but you have to pay to get in and there are cocktails galore….so….I say leave them at home and head out by yourself with friends at night. I am planning to take my kids during the day during the week when admission is free and feed them before. This is one of the trendy holiday events in Chicago that can be fun for any age!

Ages 30+ (Ideal for parents/grandparents!): An Unforgettable Nat King Cole Christmas: Starring Evan Tyrone Martin at Mercury Theater

You might not be able to list the songs that Nat King Cole sang off the top of your head, but once that sweet melody starts you will recognize most. The Mercury Theater has a cozy Venus Cabaret right next door, a perfect lounge for soulful, moving music. This holiday season, they are featuring Evan Tyrone Martin as he sings songs by Nat King Cole, with a little history and personal stories mixed in.

Mercury Theater Chicago- Nat King Cole Music

Nat King Cole’s most famous song is probably “Unforgettable,” which Evan Tyrone Martin sang and dedicated to his father who passed away. Both the sentiment and the song were so beautiful that I had tears streaming down my face a minute into the melody. His voice is expressive, velvety and almost hypnotic, and he shared tidbits of Nat King Cole’s life and how he was inspired by the iconic star. This is definitely a show for all ages, but anyone who was alive during Nat King Cole’s life and career (he passed in 1965) would especially enjoy.


In addition to the plush atmosphere and incredible vocals, the cocktails were festive and fantastic. The Kir Royale was so divine I had to order another, and was wrapped in a warm fuzzy feeling through the evening while I swayed to the sounds of the season. This show runs through December 15th, with a new show opening on December 20th featuring Heidi Kettenring singing Karen Carpenter, another of the memorable holiday events in Chicago that you will cherish.

Karen Carpenter

For tickets, hop on the Mercury Theater website!

Cheers to celebrating the holidays in Chicago at every age. Spending time together is the best gift you can give.

Disclosure: I received tickets to Mercury Theater and Beatrix Potter Holiday Tea parts for review purposes. All opinions are honest and my own.



  1. December 16, 2019 / 9:50 am

    What a great list of ideas. I love your research :):

    • alldressedupwithnothingtodrink
      December 17, 2019 / 8:55 am

      Thank you!!! I just love planning outings that get me in the holiday spirit. Much love to you and the family!