• Marcy Farrey

indieland's 30 days of Christmas - Day 3 - Neighborhood Festivities

Updated: Nov 30, 2018

A look at how some of Chicago's neighborhoods are celebrating the holidays!

When it comes to holidays in Chicago, many would think first of the traditional events, such as ice skating or shopping on Michigan Ave. But many of Chicago's neighborhoods have their own traditions and are celebrating the holidays in their own festive ways. These more intimate neighborhood activities are among my favorites for the holiday season! I've called out events happening in a few areas, including late shopping nights and festivals. You might see some of these again in our Indie Weekend Guide, but consider this a roundup of what's happening through the whole holiday season!

Shop Late Lincoln Square Thursday, November 29 and Thursday, December 13

6-9 PM

You'll have not one but TWO opportunities to shop late this holiday season in Lincoln Square. Participating shops will stay open late and offer special deals for shoppers (check the list at the link above). If you spend $50 at the participating businesses during the shop late event, you'll get a free drink (draft beer or house mixed drink up to $7) at Carbon Arc Bar & Board. We suggest stopping to take a picture with their beautiful Christmas tree in Giddings Plaza!

Damen at Night

Thursday, December 6 and Thursday, December 20


Businesses on Damen and Montrose participate in this event that includes treats, specials, and deals. If you spend $50 at the participating businesses on one of those evenings, you'll receive a FREE drink at Fountainhead Chicago.

Andersonville Late Nights

Friday, December 7 and Friday, December 21

6-9 PM

Like Lincoln Square, you'll have two opportunities to shop late in Andersonville. There are more than 70 (yes, 70!) businesses participating. They'll be offering later shopping hours and special deals for customers. Check out the list at the link above. We recommend a visit to one of our favorite restaurants, Lady Gregory's.

Holidays on the Square - Logan Square

Saturday, December 1

Holidays on the Square (HOTS) is Logan Square's "annual multi-location kick-off to the winter holidays." Participating small businesses and not-for-profits in Logan Square will have special events, deals, treats, and a variety of activities. You can view a list of participating businesses at the link above, and also follow their Facebook page for features and updates. Local business owners and volunteers organize this event that encourages residents to shop local and engage with their community. We recommend visiting two great bookstores in the neighborhood: City Lit and Uncharted Books.

Roscoe Village Winterfest

Saturday, December 1 and Sunday, December 2

Shops in Roscoe Village will stay open late on Saturday night for late night shopping from 5 to 9 PM. The evening includes a tree lighting, hot chocolate, and holiday cider from Virtue Cider. And on Sunday afternoon from 1 to 5 PM, bring the whole family for children’s activities, caroling, a holiday trolley, and a visit with Santa Claus! We recommend stopping at Moondance, Winnie Cooper Boutique, and Roscoe Books. (And if you want to catch a good brunch on Sunday, check out Orange.)

Hyde Park Holly-Day Celebration

Saturday, December 1, 10 AM-5 PM

A full day of holiday fun is planned for Hyde Park on December 1! Events include holiday movies, cookie decorating, crafts, caroling, ice carving demonstrations, and even live reindeer! Check out the schedule. If you visit Hyde Park, we recommend stopping in 57th Street Books and 57th Street Wines.

Shop Jarvis Square Saturday, December 1, 10AM-5PM

Check out Jarvis Square in Rogers Park for their annual holiday shopping bazaar. The event features over 30 artist and artisan vendor booths, which are located inside multiple business venues that will also offer food, beverages, and gifts. It all takes place at the intersection of Jarvis and Greenview. Get the details at the link above. (And if you're looking to spend the whole day in the Rogers Park area, we recommend stopping by XO Marshmallow and Heartland Cafe.)

Yes, many of these events are happening on the same day! But if you're efficient, perhaps you can make it to a bit of each! Or simply wake up and see where you feel like heading that day. Every neighborhood has great shops and restaurants, so it is highly likely you'll find something you enjoy. And hopefully, you'll discover a new favorite place!

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