Chicago’s November & December Scene: Things to Do, Places to Celebrate, and Neighborhood Magic
The crisp air is here, and Chicago is getting cozy! This is the season for neighborhood strolls, festive lights, and discovering local gems. Whether you’re thinking about moving, love exploring, or just want to enjoy the city, here are some experiences that make fall-into-winter in Chicago extra special.
Not-to-Miss Events
City of Chicago Christmas Tree Lighting Ceremony
When: November 21
Where: Millennium Park
Kick off the holiday season with the official tree lighting. Feel the city-wide cheer and connect with Chicago’s downtown energy.
Christkindlmarket
When: November 20–December 24
Where: Daley Plaza & Wrigleyville
A European-style holiday market. Browse handcrafted ornaments, sip warm spiced wine, enjoy festive food, and soak in seasonal music and lights.
Randolph Street Holiday Market
When: Third weekends in November & December
Where: West Loop, Plumbers Hall (1340 W. Washington Blvd)
Stroll, shop for unique gifts, and explore one of Chicago’s most vibrant neighborhoods.
Neighborhood Adventures & Cozy Spots
Take a slow walk through Chicago’s neighborhoods and discover hidden gems, cozy cafés, holiday markets, and festive spots.
Warm drinks at cafés:
Oromo Cafe (Lincoln Square)
Sawada Coffee (West Loop)
Heritage Bicycles Coffee & Espresso Bar (Logan Square)
Goddess & Grocer (Lakeview)
Holiday markets and pop-up shops:
West Loop & Fulton Market
Randolph Street Holiday Market – November 15–16 & December 13–14, Plumbers Hall, 1340 W. Washington Blvd
West Loop Holiday Pop-Up – Various weekends in December, local artisan goods and festive treats
Lincoln Square & Ravenswood
Shop Late Lincoln Square – Thursdays, December 4, 11 & 18, 5:00 PM – 8:00 PM. Local shops stay open late with special deals, holiday refreshments, and pop-up vendors
Holiday Market at Gateway To Learning – Ongoing in December, 4925 N. Lincoln Ave. Community-driven market with local vendors, festive apparel, and Santa visits
The Irish American Heritage Center Holiday Market – Early December, 4626 N Knox Ave. Handcrafted gifts, local art, and live music
Lincoln Park
Holiday Market: A Nowhere Collective Collaboration – December 2, Lincoln Park Zoo. Eco-friendly market featuring upcycled and handcrafted goods amidst ZooLights
Chicago Fair Trade Pop-Up Shop – November 1 – December 23, 2717 N. Clark St. Fair trade gifts, home goods, and accessories from around the world
Lincoln Park Conservatory Holiday Show – December, 2391 N. Stockton Dr. Seasonal plants, flowers, and festive décor
Lakeview & Wrigleyville
Belmont Harbor Ice Rink – Seasonal, perfect for evening skating with holiday lights
Wrigleyville Holiday Walk – Stroll along Clark Street to enjoy shop windows, festive street lights, and local cafés
Evening strolls under twinkle lights:
Check out Logan Square, Wicker Park, the Loop, and Old Town for beautifully lit streets, holiday displays, and festive city charm.
New Restaurants Opening This Fall
Dēliz (Bucktown)
Opens: December
Address: 1840 W. North Avenue
Italian steakhouse featuring in-house pastas, Australian wagyu steaks, and dramatic presentations like a fog-topped seafood tower. Two levels: cozy downstairs and lively upstairs.
Hooligan (Fulton Market)
Opens: November
Location: Second floor of Time Out Market
A 50-seat seafood and wine bar from Michelin-recognized chef Christian Hunter. Menu highlights include dressed oysters with XO sauce, squash aguachile crudo, and playful gumbo fusion.
Cultural Highlights
2025 Chicago Architecture Biennial (Through Feb 28, 2026)
Venues: Chicago Cultural Center & 840 N. Michigan Ave
Theme: “SHIFT: Architecture in Times of Radical Change”
Explore global projects addressing housing challenges and reimagining urban spaces.
Why This Matters
For Buyers:
Experience neighborhoods at their liveliest. It’s about more than houses — it’s community, walkability, lights, cafés, and seasonal markets.
For Sellers:
Knowing your neighborhood vibe helps you prepare your home and share stories that help buyers imagine living there.
For Everyone:
These months let you connect with the city and people in a unique way. It’s not just finding a house — it’s finding a home where memories happen.
Enjoy exploring Chicago this season and discovering all the cozy corners that make it feel like home!
Warmly,
Kate
