Exploring Chicago Neighborhoods,  random adventures

celebrate the holidays chicago style

Update for 2020: This post is originally from December 2019. Most links will bring you to online options for this year. Hopefully things will resume next year. 

Is it just me or does it seem like we are going to skip Thanksgiving this year and go straight to celebrating the holidays? I saw my first Christmas commercial the day after Halloween (thanks, Target). *sigh* If you can’t beat ’em … I’m heading out of town next week to celebrate Thanksgiving and wanted to get this posted because some items are happening this weekend. Here are some ideas to help you ease into celebrating the holidays Chicago style. No rush, when you are ready. First, have a great Thanksgiving.

get crafty & go shopping

There are many wonderful holiday craft shows that are great for getting your holiday shopping done. You get unique gifts while supporting artists & their small businesses. A win-win.

A couple of my favorites are Show of Hands (free in Ravenswood) and Randolph St Market (here’s my post about RSM & to get discounted Groupon tickets click here) both this weekend November 23-24.

Millennium Park Art Market Unique items for sale from student artists from the School of the Art Institute of Chicago & Columbia College Chicago. In a heated tent in the North end of Millenium Park. Free. November 23-24 While you are at Millennium Park go see The City of Chicago Christmas Tree on display until January 6.

One of a Kind Show at the Merchandise Mart. (Get discounted Groupon tickets here.) December 5-8

Here is a comprehensive list of other holiday markets throughout the city.

embrace the darkness

ComEd is offering customer discounts to attend festive holiday light shows all around Chicagoland. Click here for discounts and to see which events are free.

Aurora Festival of Lights at Phillips Park
Holiday Magic at Brookfield Zoo
Home for the Holidays at Rialto Square Theatre, Joliet
Illumination at Morton Arboretum, Lisle
Lightscape at Chicago Botanic Garden
Stroll on State in Rockford
ZooLights at Lincoln Park Zoo

LOL, This is either a suggestion or a warning. Bring the kiddos to see the Magnificent Mile Festival of Lights. A tree-lighting parade with Mickey & Minnie as the Grand Marshalls that ends with fireworks (Oak St to Wacker/the Chicago River) on Saturday, November 23.

Christmas Caroling at Cloudgate (aka the Bean) in Millennium Park on Friday Nights. November 29

enjoy a holiday classic

When was the last time you saw a holiday classic like The Nutcracker or A Christmas Carol? I saw the Joffery Ballet’s Nutcracker last year at the beautiful Auditorium Theatre (celebrating its 130th anniversary next month) with an updated storyline that takes place during the 1893 World’s Columbian Exposition. It’s a beautiful interpretation. Click here for a few versions of the Nutcracker around Chicagoland.

Another way to celebrate the holidays Chicago style is to go check out the wreathing of the Lions at the Art Institute. Gather on the steps and enjoy complimentary hot chocolate & a performance by the Chicago Gay Men’s Chorus. Friday, November 29

Calling all sugar plum fairies and mouse kings! Come join the Dance-Along Nutcracker at the Cultural Center. Sunday, December 8

All you closet (er, uh shower) singers, now’s your chance! Participate in a Do-It-Yourself-Messiah. Here are a few that I found:

Do-It-Yourself-Messiah at St. James Cathedral in the Gold Coast

Do-It-Yourself-Messiah at Harris Theatre for Music and Dance in Millennium Park

Do-It-Yourself-Messiah at Waukegan First United Methodist Church

Be on the lookout for the CTA Holiday Train that begins Friday, November 29. Here’s the schedule. You can also catch the Holiday Bus. Find routes on the CTA’s website and keep tabs on its location using the Holiday Bus Tracker.

Have you ever been to the Music Box for their Annual Christmas Sing-A-Long and Holiday Double Feature? Consider joining in the celebration of their 36th annual this year under the lovely clouds in this charming theatre. Thursday, December 12- Tuesday, December 24

stay local & go shopping

Here are some of my go-to places to shop locally. Lincoln Square: enjoy & Merz apothecary. Ravenswood: Alapash, Ravensgoods at 4703 N Damen Ave & Hazel. Andersonville: The Galleria. North Center: Union Handmade. Pilsen: Winter Market & Holiday Market. Where are your favorite places to shop locally? Please leave a comment & share. Don’t forget that Small Business Saturday is Saturday, November 30.

Love this! Northwest Holiday Trolley. (No trolley in 2020 but hopefully next year it will resume. The link is for a Northwest Holiday gift guide so you can still support these neighborhoods). A great way to explore & support the neighborhoods of Jefferson Park, Portage Park, 6 Corners, Irving-Austin, Montrose-Milwaukee, Austin-Lawrence & Austin-Irving – Small Business Saturday, November 30

drink & be merry

Having trouble getting into the holiday mood? Try one of these pop-up bars. They are over-the-top decked out and offer some tasty concoctions that will surely get you in the mood.

be grateful & give back

When I’m craving a nice piece of pie my go-to place is First Slice Pie Cafe. But it is so much more than a cafe. Besides the delicious food and pie, they offer a subscriber program that is a unique meal sharing program. It gets your family three high-quality meals every weekend and helps them provide over 750 meals a week to those in our community who struggle with hunger & homelessness. Another win-win. Read all about chef Mary Ellen Diaz & her subscriber program here. Oh, and while you are at it you can order your holiday pie as well.

Do you remember the last time you donated blood? Supplies are critically low in the winter. Please consider giving blood and earn the title of life-giver. Click here for more info.

I hope this gives you some ideas to help you celebrate the holidays Chicago style. First I’m celebrating Thanksgiving with family in Texas then I’ll be ready.


  • mimi

    Thanks for reading & your support Susie!

  • mimi

    Thanks for reading & your comment! You can sign up for my email list & you’ll receive my latest blog posts.

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