Thanksgiving Weekend Kicks Off in Chicago—Enjoy Free Live Music, Ice Skating, and the Iconic Parade

We can’t believe Thanksgiving is already tomorrow, which means it’s officially the weekend! One of our favorite holidays, there are many ways to celebrate and give thanks, whether it’s watching the iconic parade, devouring delicious pies, or shopping small! If you’re looking for activities to do for Thanksgiving weekend in Chicago , we’ve got you covered! Black Wednesday bar nights and drink deals in Chicago ----------------------------------------------------------------------------------------------------------------------- Kick off the holiday weekend on Black Wednesday with a full night of bar-hopping, drink specials, and DJ parties across Chicago’s neighborhoods. From free live music and half-price happy hours at aliveOne to creative “Weird Wednesday” art nights at Remedy and laid-back cocktail deals at The Getaway, there’s a spot to match every friend reunion. 📍 Location: Multiple bars and lounges across Chicago, including Lincoln Park, Wicker Park, Lincoln Square, Lakeview, Logan Square, and more 🗓️ Dates: Black Wednesday, the night before Thanksgiving (Wednesday, November 26) Chicago Thanksgiving Parade 2025 guide -------------------------------------------------------------------------------------------------------- The Chicago Thanksgiving Parade fills State Street with giant balloons, marching bands, dancers, and festive floats for a lively holiday morning celebration. Join the crowds on State Street between Ida B. Wells Drive and Randolph Street and enjoy the procession from 8 a.m. to 11 a.m., or upgrade your experience with reserved bleacher seating in the TV Zone near Washington and Randolph. For the best views and shorter waits between floats, arrive early and choose a spot closer to the start of the route, as spaces along the parade path fill up quickly . Families, visitors, and locals alike can soak in the atmosphere while taking in all the entertainment of this classic holiday tradition, and plan their perfect Thanksgiving morning in downtown Chicago. 📍 Location: State Street from Ida B. Wells Drive to Randolph Street, Chicago 🗓️ Dates: Thursday, November 27, 2025, from 8 a.m. to 11 a.m. Best bakeries for Thanksgiving pies in Chicago -------------------------------------------------------------------------------------------------------------------------- Skip the grocery store this year and treat your Thanksgiving guests to artisan pies from some of Chicago’s most beloved bakeries. From roasted pumpkin and chocolate pecan at Bang Bang Pie & Biscuits to Turkish Coffee Chocolate Cream Pie at Café Yaya, this guide highlights local spots offering standout seasonal flavors and extra treats like biscuits, rolls, and savory pot pies. 📍 Location: Various bakeries across Chicago, including Logan Square, Lincoln Park, Wicker Park, the West Loop, and more Small Business Saturday trolley in Ravenswood --------------------------------------------------------------------------------------------------------------------------- Celebrate Small Business Saturday in Ravenswood with a free neighborhood trolley that makes it easy to shop local, eat, and explore without worrying about parking. The Greater Ravenswood Chamber of Commerce is hosting a festive route that links unique boutiques, breweries, artisan studios, pet shops, markets, and a beloved candy store! Three trolleys will run a continuous loop, and early birds who stop by the welcome station at Hazel Gift Store can snag “Shop Small” tote bags filled with perks and local offers. Use this Ravenswood Small Business Saturday trolley guide to plan a full day of browsing gifts, grabbing a drink, and discovering neighborhood gems. 📍 Location: Ravenswood, Chicago, with trolley stops at Hazel Gift Store, Dovetail Brewery, Chicago Glass Collective, Chicago Artisan Market, Urban Pooch, Is/Was Brewing, Salsa’s Family Market, and Amy’s Candy Bar 🗓️ Dates: Saturday, November 29, from 11 a.m. to 5 p.m. Festive holiday markets to shop in Chicago ----------------------------------------------------------------------------------------------------------------- Get into the gifting spirit at Chicago’s most iconic holiday markets, from German-inspired Christmas villages to sprawling indoor artisan fairs. With twinkling lights, European eats, hot drinks, and unique vendors, these Chicago holiday markets are perfect for finding one-of-a-kind gifts while soaking up cozy winter vibes. 📍 Location: Multiple venues across Chicago, including Daley Plaza and Gallagher Way Go ice skating -------------- The ice skating rinks are officially back! Maggie Daley Park’s quarter-mile skating ribbon is one of the City of Chicago’s most famous ice rinks, offering the chance to glide and glimmer on a 40-foot climbing wall in the heart of Chicago. The rink curves up and down around pine trees, with the city’s stunning skyline providing a stunning backdrop. 📍 Location: Maggie Daley Park Source: https://secretchicago.com/things-to-do-thanksgiving-in-chicago-2025/