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Friday, September 18, 2026 | 5:00pm to 10:00pm
Saturday, September 19, 2026 | 12:00pm to 10:00pm
Sunday, September 20, 2026 | 12:00pm to 8:00pm
Retro on Roscoe (Sept 18-20, 2026) – A Blast from the Past in the Heart of Chicago!
Get ready to time-travel at Retro on Roscoe, one of Chicago’s most beloved street festivals, happening September 18-20 in the charming Roscoe Village! This throwback extravaganza is packed with live music, classic car shows, vintage shopping, and old-school fun for all ages.
Stroll down Roscoe Street and soak in the nostalgic vibes, from decades-spanning hits on multiple stages to rows of rare and restored classic cars gleaming in the sun. Indulge in delicious eats from top local vendors, sip on craft beer, and let the kids enjoy the family-friendly games and activities in the dedicated children’s area.
Whether you’re a rock ‘n’ roll fanatic, a vintage lover, or just here for the good times, Retro on Roscoe is your ticket to a fun-filled weekend of music, memories, and retro magic!
Sat, September 19, 2026| 11am to 10pm
Sun, September 20, 2026 | 11am to 8pm
World Dumpling Fest celebrates diverse cultures throughout Chicago and the world with music, dance, and of course, dumplings! The Chicago Cultural Alliance is excited to host their sixth annual World Dumpling Fest in it’s new Lincoln Park home.
This all-ages event features food, music, and local small businesses sharing their cultural identities through their respective crafts. World Dumpling Fest features diverse cultural “dumplings” from +10 neighborhood-based restaurants in and around Chicago.
World Dumpling Fest is a fundraiser held to support the work of the Chicago Cultural Alliance with the mission of supporting, promoting, and advocating for over 40 centers of cultural heritage from around the Chicagoland area.
Bring on autumn and pull out the lederhosen! One of Chicago’s most popular celebrations of fall and all things Bavarian — Oktoberfest Chicago at St. Alphonsus — returns for its 24th year of seasonal revelry. Oktoberfest at St. Alphonsus has grown tremendously since its inception, expanding from a parking lot in West Lakeview into Southport and neighboring streets for 3 days of beer, brats, bands, and all things Bavarian. Two stages host some of Chicago’s favorite festival bands including 16 Candles, Polkaholics, and School of Rock. It takes more than 500 volunteers to make our ‘Fest a success. Volunteering for Oktoberfest is a great way to help out the community, make new friends, and have a lot of fun! Volunteers are involved in serving food and beer, selling tickets, and more. All volunteers will be emailed their fact sheet/training guide upon signing up. All volunteers who are 21 a...
Clark Street Live is a brand-new music festival bringing two days of live entertainment, food, drinks and nonstop energy to the heart of Wrigleyville. Taking place September 26 and 27 in the shadow of Wrigley Field, the festival will feature a mix of country and rock music, neighborhood favorites, local businesses and everything that makes Clark Street one of Chicago’s most exciting entertainment destinations.Guests can dance to live bands, enjoy delicious food and refreshing drinks, explore the neighborhood and experience Wrigleyville’s unmistakable festival atmosphere. Whether you come for the music, the local flavor or a full weekend out with friends, Clark Street Live is ready to turn up the volume on one of Chicago’s most iconic streets
Get ready to raise a glass 🍷 — the Lincoln Park Wine Fest is proudly celebrating its 10th anniversary 🎉 this year in the heart of Chicago’s Jonquil Park neighborhood. With ten years of bringing together wine lovers, local food vendors 🍽️, and the crisp beauty of autumn 🍁 in the city, this milestone marks a decade of memorable tastings, lively ambiance, and community connection. Located at 1001 W Wrightwood Ave, the festival transforms the park into a vibrant open-air celebration where guests can sip, savor, and socialize in true Chicago style. ✨
Throughout the weekend, guests will enjoy ticketed tasting sessions where an impressive selection of varietals will be on display — from classic whites and reds 🍇 to specialty pours sampled by VIP ticket-holders. 🥂
The event keeps it inclusive and festive: general admission offers standard tastings and a commemorative wine glass 🍾, while VIP guests enjoy extra pours, private seating, and priority access. Proceeds benefit the local community through the Wrightwood Neighbors Association, helping maintain and enhance the park that serves as the setting for this beloved annual tradition. 🌳💛
Whether you’re a seasoned sommelier 👨🍷 or just looking for a fun fall outing with friends, the 10th edition of the Lincoln Park Wine Fest promises to be a memorable mix of wine, food, great company, and Chicago neighborhood charm.
Sat, October 10th, 2026| 10am to 2pm | If brunch is your jam (pun fully intended), then Lincoln Brunch Fest is the place to be this fall! Back for its 3rd annual celebration, this can’t-miss event—presented by the West Lakeview SSA 27—takes over Lincoln Avenue from Diversey to Wellington this October, serving up a morning-to-afternoon feast of flavor and fun.
From 10am to 2pm, top local restaurants will dish out their signature brunch bites (and your new favorites), while live entertainment and kid-friendly activities turn the street into a brunch lover’s paradise. It’s the ultimate way to kick off your weekend—and start planning your next one.
Curated maker market featuring independent artisans and handmade goods.
Vendor applications (checked 2026-09-15): unknown. Official maker application landing page lists this 2026 market. Portal requires an account; live portal request returned an empty account-page response, so current category availability is unconfirmed. No public closing date confirmed.
Curated maker market featuring independent artisans and handmade goods.
Vendor applications (checked 2026-09-15): unknown. Official maker application landing page lists this 2026 market. Portal requires an account; live portal request returned an empty account-page response, so current category availability is unconfirmed. No public closing date confirmed.
There’s a little something for everyone at the One of a Kind Show. Now in its 25th year, this is Chicago’s premier holiday shopping destination for unique, handmade gifts for everyone on your list. The One of a Kind Holiday Show brings together over 600 exceptional artists, designers and makers with thousands of shoppers that love art and quality work. Now in its 25th year, this is Chicago’s premier holiday shopping destination for unique, handmade gifts for everyone on your list. The One of a Kind show takes place at the historic Merchandise Mart. “If you love to support artisans and small businesses, you should come. There were some really great finds and I was able to tick off several gifts from my Christmas list.” “It's a huge, fun, unique show that I enjoy attending with friends.”
Here to see, to serve, to love anyone in need. Catholic Charities Chicago received a generous contribution of $100,000 to help households affected by the August 11 storms within southern Cook County. Please know that Catholic Charities has already received close to 10,000 inquiries about this funding. You do not need to be Catholic to receive services from Catholic Charities. We welcome anyone in need, regardless of faith, gender, race, or ethnicity, serving 270,000+ people annually across Cook and Lake counties. As the charitable arm of the Catholic Church in Chicago, our mission calls us to feed the hungry, welcome the stranger, and provide resources and community for those in need as we partner to witness mercy and hope. Our front-line teams lead us in bringing to life our values — solidarity, courageous compassion, faith-filled hope and joy, and meaningful, measurable impact — thr...
Maifest Chicago returns to Lincoln Square at Lincoln Avenue and Western Avenue May 29 through 31, 2026, with live German music and entertainment each day. Highlights include the Maifest Queen crowning and keg tapping on Friday evening, plus bands such as Paloma, the Phenix Band and funkaducci performing across the weekend.
Shop your favorite artists and discover over 250 new ones at Renegade Chicago! We're back with a curated springtime Fair featuring the most inspiring creatives from the city and beyond. Save the date & see you there!
Ribfest Chicago takes place every summer in the Northcenter neighborhood! Celebrating 26 years of BBQ, Ribfest Chicago continues to be Chicago’s most anticipated food festival. Come enjoy the sweet smells of BBQ filling the streets of Lincoln, Damen and Irving Park Rd. Lincoln Ave. between Irving Park Rd. and Hutchinson We request a $10 suggested donation at the gate. Proceeds from the gate donations are invested right back into the Northcenter community and help support local schools and nonprofit organizations, economic development and greening efforts. To date, the fest has provided nearly $400,000 in direct funding to these worthy causes. Street festivals are non profit fundraisers, not city funded events. Learn More
The Lincoln Park Greek Fest brings all the aromas, sounds, tastes and traditions of Greece to your doorstep. St. George Greek Orthodox Church in the Lincoln Park area of Chicago’s north side and was established in 1923 by Greek immigrants. St. George remains an important center for worship and fellowship for its parishioners and friends from throughout the Chicagoland area. Through the gifts of the holy spirit in faith and determination these new Americans were able to purchase the Lutheran Church at 2701 N. Sheffield Avenue and adapt it for Orthodox worship in time for services to be held in April 1923. Being Greek means relishing the world around you and enjoying life to its fullest. Come experience the Ancient Greek concept of “filoxenia” and the famous hospitality of the Greek culture. The Lincoln Park Greek Fest gives us the opportunity to open our arms, our hearts and our kitche...
The 57th Street Art Fair is a free, juried outdoor art fair in Chicago's Hyde Park neighborhood, running along 57th Street between Woodlawn and Kenwood Avenues and on Kimbark Avenue. Held on the first full weekend of June each year, the 2026 fair marks its 80th annual edition and draws more than 20,000 visitors, with live blues music at the Buddy Guy's Legends stage. Artists exhibit their work in booths throughout the weekend and apply through Zapplication with a non-refundable jury fee.
Community Day Thursday, Freestlye Friday, Saturday Noche Tropical, Sunday Dia de la Salsa - See Schedule: 47th Annual Puerto Rican People's Day Parade -Saturday, June 14, 2025, 2pm, Division St, corner of Campbell Ave... More Info: The carnival is coming to Town! A Fun Family weekend.Free Entry for kids 12 & Under - Buy your armbands here: Let's Play! Fun games area where you can watch & play Dominoes, Giant Jenga, Chest, Bags, Ping Ball and More! Enjoy a burst of flavors as the festival concession stands offer a variety of Puerto Rico's traditional beverages. Experience Puerto Rico’s flavors featured at the Authentic Food Stands, Food Trucks, Artisans and Tropical beverages.
Old Town Art Fair takes place on Saturday, June 13 and Sunday, June 14, 2026 in the heart of the charming Old Town Triangle Historic District in Chicago.
Thanks for a great 2026 Wells Street Art Festival! The 2026 Wells Street Art Festival had 127 talented artists, delicious festival food, and great live music. We are so grateful to our sponsors, our involved and enthusiastic community, and everyone who attended June 13th and 14th, 2026. Stay informed on all things Old Town for fun events and activities throughout the year. Check out the new 2026-27 Neighborhood Guide featuring the culinary style and neighborhood spirit of Old Town! Street Festivals are ubiquitous to a Chicago Summer. Most of our Street Festivals, including the Wells Street Art Festival, are NOT CITY FUNDED . Local non-profit organization s – i.e. Old Town Merchants & Residents Association – pay for and produce street festivals and depend on your donation at the gate to make these festivals possible. Old Town Merchants & Residents Association is part of the Save our...
City guides with the venues that host festivals, who issues the permits, what the weather does to an outdoor season, and the local vendors worth calling.
