25 Things to do in Chicago this Holiday Season

The winter holidays are a time of celebration.. Of joining your community, your culture, your city in our collective traditions. With that in mind, we present twenty-five options for you and your loved ones to do to enjoy this beautiful city of ours.

1. Ice skating in Millennium Park

The beautiful McCormick Tribune Ice Rink in Millennium park (free, $12 dollar skate rentals) is a classic tradition. Spend a lolling Saturday with loved ones, or possible-soon-to-be loved ones, and enjoy the timeless fun of the skate.


2. Michigan Avenue

The storefronts of Michigan Ave have taken holiday cheer to an art form. Window shop in the bustling crowds, stroll hand-in-hand and feel urban Chicago as it is meant to be. Alive and with the quaint charm of the flaneur's heart. Bedecked in lights, the avenue is transformed by lights into a romantic walk for couples and families.


3. Lincoln Park ZooLights Festival

Every year, the Lincoln Park zoo transforms into a living, breathing animal of a fashion designed with a stunning luminescence display... A family-oriented retreat; stay for the 3d art installations, the educational lectures, musical light shows, and for the adults, enjoy the toasty warm spiced wine and perfectly poured lagers. (Brewsnight, Adults-only is available on Dec. 7th)


4. The Field Museum

Spend a day coming face-to-face with a T. Rex, exploring an indigenous village, learning about culture through tattoo and oceanic travel. The Field museum, one of the premiere museums in the world, hosts and caters to a wide variety of topics appropriate for all ages.


5. Hanukkah Concert at the Gardens 

Enjoy a day at the gardens and take in the soon-to-be classic (with a twist) Hanukkah Concert at the Chicago Botanic Gardens. Enjoy the Wonderland Express exhibit and holiday-rock out to the Maxwell Street Klezmer Band for a special two performances, one day only! Thursday, December 29th, 11 am- 1pm in the Alsdorf Auditorium.


6. Macy's on State street

World famous for their window displays. Every year, thousands of people descend on Macy's to see the evocative stories told within a single glance. A must-see for those with an interest in narrative-within-art and interior design. Parsing the story of the moment, like good photography, will push on the creative muscles of the viewer and evoke a warmth unexpected.


7. John Hancock Observatory Ice Skating

Ice Skating can be fraught with the intimate but have no fear, for John Hancock Ice skating rink allows the fun-driven to Ice skate with a panoramic view high above the city. Nervous first timers fear naught, this is an ice rink that demands you look down a bit.


8. Carriage Ride

There's no greater romance than a carriage ride through the city. Snuggle close with the one who matters most in these Winter holidays. 



9. Take a winter stroll along the lake Chicago lakefront path

The lakefront path is 18 miles of gorgeous trails, breathtaking views. Various difficulties for the most experienced hiker to the casual stroller in all of us. Get away from the city with these beautiful jaunts.


10. Go to a Latkes celebrity chef competition

There's something to be said about the potato-pancake that is the latke. Namely, that they are delicious. A latke competition? With Mindy Segal of Hot Chocolate and Mary Rubenstein the Latke maker extraordinaire? Yes, please. Spend a night with friends, lovers and family at Anshe Emet Synagogue. Play dreidel games. Enjoy a dinner. Listen to music. Play a social action project! Enjoy your moments with the people of our great city. December 15th at Anshe Emet Synagogue at 6:30-7pm. Tickets will go fast so order online from ansheemet.org


11. Visit The Hershey’s Chicago candy store

The Hershey's Chicago candy store really isn't a candy store. It's a Hershey branded homage to Charlie and the Chocolate factory. Savor rich chocolates, from milk to offensively high cacao dark chocolate. Gawk at the large kiss. Remember what chocolate's about. Kiss.


12. The DuSable Museum's Kwanzaa Concert

The DuSable Museum of African American History and The Bolozi Wazee/Shule Ya Watoto present a Kwanzaa celebration. Bring the little ones to learn about another culture at the noon drum circle by the talented Thunder Sky Drummers. Tour the museum after performances by Maggie Brown or the Najwa Dance Corps. Holidays are about togetherness. So why not learn something new? Tuesday, December 27th, noon-2:30pm! 


13. Adler Planetarium

Overcast skies can linger in our hearts and minds. In our holidays, it's often a good idea to hold perspective of where we are. To take account of the good and the bad. To see the galaxy at the Adler Planetarium is a treat. Take a walk through time and space and learn a bit about the meaning of things and ultimately yourself.


14. Self-Tour of Famous Chicago Sights

There's a surreal moment for the native Chicagoan. We catch sight of our fair city often in films, but we never walk in those shoes. But why not? Take a self-guided tour of the city, movie style, while visiting streets and haunts made famous on the silver screen. http://www.itsfilmedthere.com/p/list-of-chicago-movies.html


15. Daley Center Tree Lighting Ceremony

No traditional Chicago Christmas can be official without a view of the famous Daley Center Tree Lighting Ceremony. The painstaking chore of finding the perfect tree, the gilded filigree, the sentimental hopes and dreams of the city, for both the holiday and years' end, is perfectly capsuled in this ceremony. A heart warming moment and tradition that binds the city together. Be a part of it.


16. Christkindlmarket at the Daley Center

Also at the Daley Center (as well as a satellite in Naperville), the Christkindlmarket is an open air market/festival for the whole family or for the astute, playful adult. A German tradition, eat various -wursts, pretzels, lagers, and ales. Be regaled by brass bands and carolers. Go on scavenger hunts. Meet Christkind. A city unto a city. Make of it what you'd like. There's something for everyone.


17. Classic Tea Time at the Palmer Hotel

The Palmer House, that staple of the gold coast, opens up its doors for a sophisticated afternoon tea during the holidays. Sip premium Harney & Sons teas brewed to perfect and enjoy a scone, tart, or sandwich.


18. Illumination: Tree Lights at The Morton Arboretum

The Morton Arboretum goes all out and this year is no exception. Walk through the winter woods, hug trees (that light up and sing!), feel a bit nutty watching light installations dance to the Nut Cracker. Enjoy the fairytale of it all in this mile stretch of wonder.


19. A Charlie Brown Christmas

Can't get tickets to Hamilton? You're in luck… The classic charmer, A Charlie Brown Christmas, is playing at the Broadway Playhouse at Water Tower Place for the holidays. A great way to introduce your children to the theatre or dip ones toe in nostalgia. The production captures hearts and reminds one of what matters.


20. A Cozy day at the bookstore

Chicagoans love to read and we're spoiled with some of the best bookstores in the country. The classic Powell's bookstore to explore over an afternoon. The new up-and-comer on the used bookstore scene, Uncharted Books, has a lively atmosphere that grants intimacy and favors mingling. Anderson's Books has author events regularly from Bernie Sanders to Zadie Smith. For the more discerning fan, the specialty store Centuries and Sleuths, a bookstore dedicated to Mysteries and Historical novels.


21. Hot Chocolate

Hot chocolate can be found at every Starbucks, most delis, some restaurants. But it's never right. It's never the way we had it in our youths, the way it was made at home.. Where are the little marshmallows? Why does it taste like water instead of milk? The restaurant Hot Chocolate has answered this desperate desire for real hot chocolate with aplomb. Enjoy a meal, some piping hot cocoa, and take your mind off the pressing things that lay ahead.



22. Double Feature Sing-a-long at the Music Box Theatre

The most well-known art house theatre in Chicago continues for its 33rd year the double feature sing-a-long of White Christmas and It's a Wonderful life. Croon with Bing Crosby… and a lot of other people. Bask in nostalgia and good cheer. Laugh. Sing. Drink. Be merry! If those movies aren't your speed, they do have an alternative & limited double feature of Gremlins and Die Hard.


23. The Museum of Science and Industry together with Lego's

MSI and Lego's have joined forces on an exhibit: Christmas around the world. Be stunned by lights. Learn about craftsmanship, building, the mad, wonderful world of science. Meet Santa and be tricked by Elfish pranksters. Watch custom toys being made by robots. The Museum of Science and Industry has 4 floors of dedicated holiday cheer with a science bend that will educate and entertain.


24. Art Institute of Chicago Museum

Beware the lion statue. This museum has a bite. An intensely well-curated museum (free to Illinois state residents on Thursday nights) the contemporary exhibits are a treat. The works speak for themselves. A romantic day in Chicago just isn't what it could be without a stroll through the vast collection of works this Museum provides to the public. Enjoy. Explore.


25. Have a drink at Richard's Bar

You've done a lot on this list. Your legs are tired. Your hearts all warm. You want to unwind. You want to go to Richard's Bar. No fuss. Not over done. Nothing fancy. Just have a good drink and think about how good you've got it. This is the bar for that moment. 


It's hard to know what's best for you and for your family. Winters are long, memories fickle, hearts hopefully warm. We hope you found some good ideas here, went out into new neighborhoods, saw bright lights against overcast sky, cuddled close with your family, and fell in love with the holidays and being together all over again. 




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