Located below The Den, a 1920s greystone-turned-hotel in Lakeview, the Blind Wolf Speakeasy is an intimate, approachable bar, event venue and home to a free weekly comedy show. Blind Wolf Comedy hosts a rotating roster of local and touring comics every Wednesday at 8pm. There's no cost to attend, but you can reserve a seat through their Instagram page. It’s often hard to step out of the house without shelling out a small fortune, so this free show feels like uncovering a true hidden gem. It’s safe to say this is one of the best free things to do in Chicago.

Looking for a great way to start your weekend? Lululemon ambassadors and local run leaders host a free weekly run club every Saturday morning. Runs start at the brand's Rush Street store in the Gold Coast, before heading down the Lakefront Trail and back to the store for post-run snacks. The run route is 3 miles, but multiple distances and durations are offered as well. Dogs, strollers and runners of all experience levels are welcome—just be sure to sign up in advance.

Yes, the comedians will be naked. This 21+ stand-up show at The Crib Comedy Playspace features six comics who will take the stage—sans clothes—for what will probably be the most revealing sets of their lives. After launching in New York, the show returns to Chicago for a night of unfiltered and undressed fun.

It’s not the holidays until you’ve heard "All I Want for Christmas Is You" a thousand times, so it only makes sense that a Mariah Carey-themed pop-up bar is returning to Chicago this winter season. The Queen of Christmas' cocktail pop-up at Experience 868 in River North is decked out with festive decor, photo-ops and a lineup of holiday-inspired drinks made with her Black Irish cream liqueur.