Mark your calendars! The West Town Chicago Chamber of Commerce  produces a number of special events throughout the year to promote the chamber, the West Town commercial districts, to foster economic development, and provide area wide marketing. Funds raised at these events supplement the chamber’s operating budget and benefit specific commercial corridors, local schools, parks, and other local non-profits. 

Festival photo credit: 

West Town Winterfest

December 9, 2017

Saturday 11am-7pm

HEADQUARTERS: The Rookery 2109 W. Chicago Ave. - Grab Maps & Shopping Guides and Get on the Trolley at headquarters. Trolleys depart at NOON and at 3pm.

Join us THIS Saturday, December 9th from NOON-6:00pm for West Town Winterfest.

We invite you to "Shop the Blocks" of West Town as over 20 stores show off their spirit this holiday shopping season as you follow the Winterfest shopping guide through the neighborhood. Participating retailers will feature one of a kind items, special promotions, trunk sales, and other holiday wares.

Collect Winterfest bucks as you shop, the more you spend, the more you earn - for every $40 spent at a participating retailer you earn $20 in Winterfest Gift Certificates to be used to ring in the 2018 New Year.

Hop on the West Town Winterfest guided Jolly Trolley tour and enjoy Winterfest without the walking. The guided tour lasts 3 hours, features all of the shopping blocks and provides a "checked shopping bag" service so you don't have to worry about your gifts while you shop. Receive a $20 Gift Certificate when you purchase a $10 Jolly Trolley ticket. Limit 1 per store, 5 per person.

Reserve your seat on the Jolly Trolley guided shopping tour today!

Collect holiday stickers as you shop West Town and enter to win raffle prizes from participating locations in the neighborhood.

West Town Winterfest Holiday Shopping Guides can be picked up at any of the participating locations, there is no wrong way to Shop West Town this holiday season!

Participating Businesses:


Ad Hoc 1948 W. Chicago

Dovetail 1452 W. Chicago

Dynamic Salon 1501 W. Chicago

Penelope's 1913 W. Division

Seek Vintage 1432 W. Chicago

Squasht Boutique 2556 W. Chicago

Study Hall 2016 W. Chicago

Tarnish 2024 W. Chicago


Paperish Mess 1955 W. Chicago

Steve Quick Jeweler 1909 W. Division

West Town Jewelry & Loan 2059 W. Chicago


Epic Spices 1725 W. Chicago

Wixter 2110 W. Division


Apt 528 2136 W. Chicago

Beehive Chicago 2501 W Chicago

Inside Home 1942 W. Chicago

Marguerite Gardens 2444 W. Chicago Ave.

Sprout Home 745 N. Damen

Sprout Home Kitchen & Table 744 N. Damen

Urban Source 1429 W. Chicago

Velvet Goldmine 2001 W. Division


Holy Trinity Orthodox Cathedral 1121 N Leavit (open for tours)

The Rookery 2109 W. Chicago - Winterest Headquarters & After Party

Spoke Apartments 728 N Morgan

Non Jolly Trolley riders can pick up the Shopping Guides at any participating location and are encouraged to visit each store as they "shop the blocks." As participants explore West Town and visit each location they may pick up 1 sticker from each location they visit, visiting 50% of the locations and collecting stickers will enter them into a raffle for a chance to win gifts from a participating business. Drop off the stickered maps at the WTCC office (1819 W. Chicago Ave. 60622) in the mailbox, OR mail their maps in.

Want to get a picture with Santa? Join us at Winterfest Headquarters at The Rookery 2109 W. Chicago from 3pm-6pm for professional photos with Santa!

On the Naughty List? Don't miss the official Winterfest After Party at The Rookery 2109 W. Chicago Ave. 6pm-10pm.

Do Division Street Fest & Sidewalk Sale

June 1st, 2nd & 3rd 2018

5-10pm Friday

12-10pm Saturday & Sunday

on Division Street at Damen

Visit for more information and vendor applications.

Chicago’s quintessential summer street festival is also one of the first of the season. Now in its 12th year, Do Division Street Fest & Sidewalk Sale 2018 kicks off June 1 – 3, promising the return of over 10 blocks of local food, shopping, art and live tunes. This year’s blacktop bash includes two fests-within-a-fest; Family Fun Fest and Do Fashion Fest, in addition to a multi-block sidewalk sale, crafts, artisans and plenty of ice cold beer. The highlight of the three-day mêlée is the live music programmed by iconic Chicago venues, Subterranean and Empty Bottle Presents. Music critics and fans alike usually rate the lineup among the best of fest season – and at only $5 it’s one of the least expensive too. Do Division Street Fest gives attendees each year a taste of what makes West Division Street one of the coolest destination corridors in the city! A percentage of proceeds benefit the West Town Chamber of Commerce and local schools including Friends of Pritzker and LaSalle II PTO.

West Fest

July 6th, 7th & 8th 2018

Friday 5pm-10pm

Saturday & Sunday 12-10pm

on Chicago Avenue at Damen

Visit for more information.

When it debuted 14 years ago, West Town's little fest that could was a reflection of the vibrant up-and-coming neighborhood for the few thousand who turned out.  Today, massive crowds turn out to celebrate all of the best of the local hood in addition to some of the most highly-anticipated live music of the summer season.  Hailed as one of the top festivals in the city and suburbs by the Chicago Tribune, West Fest 2018 returns to one of today's “hottest neighborhoods” in the country (per).  As always, West Fest will feature critically-acclaimed live music on two stages (plus a third family-friendly stage) programmed by West Town's nationally-renowned live music venue, Empty Bottle Presents.  The annual street fest also features a popular Chicago House DJ stage, West Town's most popular boutiques and restaurants, Pet Fest with dog activities for charity, and Kid Fest – the family fun area.  A percentage of proceeds benefit local non-profits including the West Town Chamber of Commerce and Talcott Fine Arts and Museum Academy. 

Dancing In The Streets

August 4th & 5th

NEW Event on Hubbard Street at On Tour Brewing!

Saturday & Sunday, 12pm-10pm

on Hubbard St. between Wood and Paulina / 1725 W. Hubbard

Live music, jam bands, dancing, local food and retail vendors; plus craft beer by On Tour Brewing.

Website  & More Details TBA

Renegade Craft Fair

September 8th & 9th 2018

Saturday & Sunday, 11am-7pm

on Division Street between Damen and Paulina 

Visit for more information

Renegade Craft Fair is the world's largest curated showcase of independent craft and design. Renegade is a celebration of creative spirit and for each Fair gathers emergent and seasoned independent makers alike. 2018 will mark Renegade's 16th year in their hometown of Chicago! This Fair will be held outdoors rain or shine, and is free to attend.

West Town Art Walk

October 5th & 6th, 2018

Friday 5pm-8pm (After Parties from 8pm-10pm)

Saturday 12pm-6pm

on Chicago Avenue between Milwaukee & Hoyne 

Visit  for more information.

Located along the booming Chicago Avenue destination corridor, West Town Art Walk and West Town Food Truck Social will provide strollers with a curated selection of original art through every door as well as some of Chicago’s most popular mobile eats. 

The 8th annual West Town Art Walk celebrates art in all forms – visual, musical, performance, culinary, fashion – along Chicago Avenue (between Milwaukee Ave and Western Ave) while the West Town Food Truck Social (on Noble St between Chicago and Chestnut) is a celebration of Chicago’s diverse mobile food kitchens.  During this free Friday and Saturday event, attendees can enjoy whatever art forms they like most from over 35 West Town shops, businesses, restaurants, and galleries while experiencing street cuisine from over 12 food trucks.

West Town Food Truck Social

October 5th & 6th, 2017

Friday 4pm - 10pm

Saturday 11am - 10pm

on Noble St between Chicago Ave & Chestnut St. (800-900 N Noble)

Visit for more information.

The popular Food Truck Social brand is marrying up with the West Town Art Walk for the third year to create a one-of-a-kind neighborhood wide food and art festival, October 5th & 6th 2018. Located in the heart of West Town along the bustling Chicago Avenue corridor, West Town Food Truck Social & West Town Art Walk is presented by the West Town Chamber of Commerce – the driving force behind hallmark festivals like West Fest and Do Division Street Fest. The dual event gives guests a taste of some of Chicago’s best mobile eats with a side of Chicago’s most tantalizing original art.

Organizers are encouraging participants to “snack-n-stroll” through West Town.
West Town Food Truck Social will feature over 12 Food Trucks shelling out all of their specialties – from lobster rolls to jerk chicken to empanadas, donuts and pierogi. Maps for the West Town Art Walk will be available at the Food Truck Social Info Tent at the corner of Chicago Avenue and Noble Street and patrons can "snack-n-stroll" to discover great local artists, neighborhood retailers, restaurants, a public art installation walking tour, live art making and more.

Patrons may choose to purchase the $20 Sampler Ticket in advance or at the event (quantities limited) which will be comprised of six individual tickets that can be used to purchase a sample size tasting portion from the participating food trucks onsite. Food trucks will offer tasting size samples of their regular menu favorites. The food trucks will also feature their full regular sized food and beverage menu items available for individual cash purchase.

Superior Design Harvest

October 13th & 14th 2018

NEW! On Superior Street and at the Superior Street Center for the Arts 2744 W. Superior St.

Saturday & Sunday, 12pm-10pm

Local West Town retail designers and vintage showcase with live music and food trucks.

Website / More Details TBA

West Town, Wicker Park & Bucktown Trick or Treat

October 31st 2018

on Halloween 3pm-6pm

Trick or Treat at Over 35 businesses!

This community event is held to provide a fun (and safe) way for families to explore West Town businesses while trick or treating with their children. 

More Information & Links Coming Soon.