Packed with unique shops, delicious food, skilled artists and friendly people, Montrose Avenue in Ravenswood is a delightful place to explore this holiday season for those seeking thoughtful, out of the ordinary gifts.

Come out on Saturday, December 5th (12-5pm) for the Ravenswood Holiday Walk, a day of special deals, treats and entertainment that helps support our small business community while offering a chance to connect with friends and neighbors. Take the CTA’s Holiday Train into the Montrose Brown Line Station and enjoy visits from Santa Claus, discounted shopping, special products and activities and entertainment from some amazing participating businesses.
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Holiday Train | Santa’s Route | Choir Performances | Cashback Rewards | Deals & Activities

Holiday Train Schedule

Catch a ride on the CTA Holiday Train! Santa and his elves will ride the train passing out candy canes and season’s greetings.

This spectacular train is an amazing sight! Thousands of twinkling lights outline the shape of the train and windows, with even more lights running across the tops of the cars. Interiors of the cars are decked out with thousands of multi-colored lights, red bows, garland, and red and green overhead lighting. The hand poles are wrapped to look like candy canes.

As the train pulls into each station, Santa waves to the boarding passengers from his sleigh on an open-air flatcar carrying his reindeer and decorated holiday trees.

Ravenswood Brown Line Stops

Towards downtown
Damen 1:00, 6:48
Montrose 1:02, 6:50
Irving Park 1:04, 6:52

Towards Kimball
Damen 5:59
Montrose 5:57
Irving Park 5:59

Santa’s Route

10854175_962905247072396_4906907173668641571_oCourtesy of SSA #31, St. Nick himself will be making stops at several Montrose businesses during the Holiday Walk, posing for pictures and meeting with Ravenswood children.

12:00  Neighborly – 2003 W Montrose 
1:15      Sweet Sensations Pastry – 1918 W Montrose
2:15     Starbucks – 1900 W Montrose
3:15     Spoken Cafe – 1812 W Montrose
4:15     Urban Pooch – 4501 N Ravenswood 

Amundsen High School Choir Performances


Join Amundsen High School’s choir as they walk Montrose Avenue performing a variety of holiday selections. See the Holiday Train at the Brown Line Station, try the Christmas rum cakes at Sweet Sensations, catch Santa at Starbucks and take in the final performance outside Margie’s Candies while picking up some tasty stocking-stuffers.

12:45   Montrose Brown Line – 1812 W Montrose
1:25     Sweet Sensations Pastry – 1918 W Montrose
2:00    Starbucks – 1900 W Montrose
2:25    Margie’s Candies – 1813 W Montrose

Shop Ravenswood Cashback Program

As a part of Shop Ravenswood, we’re offering $20 cash back to shoppers who collect at least $100 worth of receipts from Ravenswood businesses on Saturday, December 5th. Receipts from businesses between Clark, Leavitt, Foster and Irving Park are eligible (excluded: grocery stores, automotive repairs). One $20 reward per household, must be picked up from the Greater Ravenswood Chamber of Commerce (1802 W. Berteau, Suite 102) during regular business hours by Thursday, December 17th. 

Montrose Businesses

The GRCC local businesses in conducting a Winter Hat & Glove Drive to benefit our friends at Ravenswood Community Services. Businesses with collection boxes will be marked with a .

ServYoSelf – 2024 W Montrose
Extraordinary froyo isn’t just a summer treat! Enjoy some delicious soft-serve in a totally kid-friendly space featuring artwork from neighborhood children.

Giordano’s Pizza – 2010 W Montrose 
Our local Giordano’s is offering $25 gift certificates to Holiday Walk shoppers that purchase $100 in Giordano’s gift cards! Get your office mates some holiday pizza while covering dinner for yourself at the same time!

Ravenswood Used Books – 2005 W Montrose
Ravenswood’s favorite used book store will be hosting free musical performances between 2-5pm, including sets from:

Neighborly – 2003 W Montrose
Neighborly will be offering complimentary refreshments for Holiday Walk visitors, and they’ll also be the first stop on Santa’s Ravenswood tour! Find a gift with extra meaning from Neighborly’s collection of gifts that give back! Many support local Chicagoans in need including Neighborly’s custom-designed “Mugs for Meals” coffee mug, all profits from sales of the mugs are donated to the Greater Chicago Food Depository.

Fountainhead  – 1970 W Montrose
One of Ravenswood’s most celebrated comfort food destinations, Fountainhead is the perfect place to grab a delicious lunch and a cold craft beer before continuing with your holiday shopping.

Fountainhead Market – 1966 W Montrose
Speaking of holiday shopping, Fountainhead’s new market is a great place to pick up a gift for that hard to find connesiour in your life, whether it’s fresh, organic food, high-end whiskey or gourmet chocolates.

Marmalade – 1969 W Montrose
Marmalade is breakfast with a twist, lunch with imagination, and brunch with a satisfying flair. The result is an exceptional meal in a comfortable setting, merging the zest of city dining with a neighborhood feel. Whether dining with a group of friends, enjoying a casual family brunch, or stopping in for coffee before hitting the next store, Marmalade will make your day a memorable one.

Celtica Gifts – 1940 W Montrose
During the Holiday Walk, Celtica will be showcasing their impressive selection of Irish gifts, including jewelry, Aran sweaters, Galway crystal, traditional Irish food and more.

Hazel Apparel – 1926 W Montrose
Since 2011, Hazel Apparel has been committed to bringing a well curated selection of men’s and women’s apparel and accessories to the Ravenswood neighborhood. Stop by during the Walk and find the perfect outfit to wear to all your holiday events! Hazel Apparel will also be offering complimentary gift wrapping on all purchases.

Sweet Sensations Pastry – 1918 W Montrose
Stop by Ravenswood’s favorite bakery for a variety of delicious seasonal treats; including cakeballs, cupcakes, holiday cakes and delectable pies. Sweet Sensations will also be hosting a visit from Santa during the Walk!

Hazel – 1902 W Montrose
Stop by Hazel’s gift store during the Holiday Walk for a large assortment of fun stocking-stuffers for all ages, Christmas ornaments from around the world, beautiful handcrafted jewelry and gifts made by artists local and worldwide! Don’t forget to check out the Apparel store at 1926 W Montrose for great gifts and the perfect outfit for your holiday events! And as always, enjoy their complimentary gift wrapping service on all of your purchases!

Starbucks – 1900 W Montrose
Our neighborhood Starbucks location will be one of Santa’s stops through the ‘hood!

Bar Rista Cafe – 1834 W Montrose
Haven’t checked out the new-to-Montrose Bar Rista Cafe yet? This is a perfect time to do it! Stop in and enjoy one of their scrumtious sandwhiches for lunch, and feel free to bring the little ones, as the cafe has a great Kids Menu.

Spoken Cafe – 1812 W Montrose
Stop by this coffee house with a cajun twist for visits from Santa, free kids hot chocolate, homemade hand pies, live music, a visit from Santa and a chance to pick up an Indie Coffee Passport that’ll let you sample delicious, independent brews from around the city.

Lillstreet Art Center – 4401 N Ravenswood
Ravenswood’s premier art school is also home to an incredible gallery store, featuring a variety of unique and exciting potential gifts. Also, consider giving a Lillstreet gift certificate for adult classes in all skill levels working in mediums such as: Ceramics, Digital Arts & Photography, Drawing & Painting, Metalsmithing & Glass, Printmaking & Book Arts, and Textiles.

Urban Pooch Canine Life Center – 4501 N Ravenswood
Not only is Urban Pooch the last stop on Santa’s route, but they’re again hosting their ultra popular dog caricature artist Marlene! Bring the pup for photos with St. Nick, snag a one of a kind caricature of the fuzzball, and take advantage of Urban Pooch’s awesome “pick-a-discount” promotion.

Eats and Sweets Cafe – 1636 W Montrose
This charming Ravenswood cafe and bakery invites you out for a seasonal brunch from 8 AM – 1 PM on 12/5. They’ll also be offering gift certificates and goods by local artists and artisans, including housewares, greeting cards and more!

Green Machine Cycles – 1634 W Montrose
GMC is hooking it up for local bikers this winter. They’re offering Holiday Walk shoppers a tune up, cleaning, and safe storage of their bike for the winter (until March) for only $100! While you’re there, asking about Green Machine’s series of engaging workshops and seminars on topics like cycling with families, bicycle touring, security, and bicycle care, throughout the winter. Need a gift for the hardcore cyclist in your life? They’ve got a nice selection of cold-weather cycling gear that they’ll teach you how to use during the Holiday Walk.

Cloud & Bunny  – 1604 W Montrose
Shopping for the little ones in your life? Visit Cloud & Bunny, a unique, fresh and affordable children’s boutique owned and operated by a local mother. Cloud & Bunny offers adorable and trendy clothes, toys and books at a fraction of what you’ll pay elsewhere.