Best Cookies in Chicago

"A staple of Chicago’s Humboldt Park for over 100 years, this Roeser’s Bakery celebrates true vintage fashion by selling incredible baked goods for cheap. This bakery in Chicago features custom cakes, tortes, and cookies and more, making Roeser’s Bakery everyone’s go-to place for amazing quality sweets."

"Roeser’s Bakery is the ancient family-owned bakery still in the same location in Chicago. They are now in their fourth generation, with John C. Roeser IV leading the way. They are truly passionate about what they do, you can see it in the wide variety of products they offer."

"One of Chicago's oldest food purveyors, venerable Roeser's Bakery has been in business in Humboldt Park for more than 100 years. Beautiful custom cakes and tortes are a specialty, but don't miss the cookies and holiday items at this long-running local institution."

"A post shared by Insomnia Cookies (@insomniacookies) on Jul 17, 2019 at 12:04pm PDT. If even picking up cookies is low on your to-do list, Insomnia Cookies comes to the rescue. This chain specializes in late-night cookie delivery (yes, you read that right), including sugar cookies, double chocolate mint cookies and drool-worthy smores cookies."

"Insomnia cookies are next on this list of the best desserts in Chicago. Cookies are the perfect addition to any day, so why not stop by Insomnia Cookies for an ice cream sandwich fix?. Unlike some other joints that offer ice cream sandwiches, Insomnia Cookies lets you customize your treat every step of the way!"

"6 locations in and near the city; Online: insomniacookies.com. View this post on Instagram. A post shared by Defloured Bakery (@deflouredbakery) on Aug 4, 2019 at 8:26am PDT"

"Sweet Shot Cookies specializes in infused cookies and cookie cakes. Their homemade gooey infused cookies can be filled with anything from marshmallow fluff to dark chocolate ganache—you name it, they infuse it. They can be ordered pre-filled or if you're a DIY'er, they can be delivered with a syringe of flavor so you can inject it yourself with as much filling as you'd like."

"If you judge an ice cream shop solely on how close it looks to a Willy Wonka-type Wonderland, then Windy City Sweets is your golden ticket. This classic Lakeview haunt is chock full of so much Americana sweets and ice cream that you practically get a cavity just by entering the front door. The candy (and fudge!) supply is great, but the ice cream is truly special."

"You can probably already tell that we love our cupcakes here in Chicago. More Cupcakes is known for their upscale environment and minimalist display. Stop by for delicious cupcakes with unique toppings."

"The Annoyance Theatre is (proudly) edgier than the other comedy bars in the Windy City — think buckets of fake blood, actors stripping down to their underwear, and wacky premises for improv shows. The theater’s first big hit was its original musical, “Coed Prison Sluts,” which ran for 11 straight years, and then came back to the stage in the late 2000s. Although the musical isn’t currently being performed, you don’t need to fret — the theater has replaced it with plenty of other bawdy shows."

"The Annoyance Theatre & Bar is in the process of moving their venue, but it is well worth following their updates to see when they reopen. They focus strictly on improv shows, from all out themed shows to witty comedians doing their best one-offs. They usually enter the night with the mentality of ‘there are no rules’, but the rule of ‘no comedian can refuse a drink’ comes into play on occasion to transform an already hilarious comedian into a hot-mess that entertains like no other."

"Probably the best-known of Chicago’s comedy clubs, the Second City has a long history of tickling its audience’s funny bones. The original club opened in December 1959, and its members have redefined improv and sketch comedy over the past six decades. Just about everyone knows the names of its most famous alumni: Tina Fey, Amy Poehler, Steve Carell, Stephen Colbert, and Bill Murray, among other."

"Chicago is the place where comedians Steve Carell, Tina Fey and John Belushi all launched their careers. So, as you can imagine, there’s a thriving comedy scene here. If you love improv and sketch comedy, then one of the best places to visit is The Second City."

"Spoon presents a dazzling menu packed with delicious bites and full-blown meals in addition to seasonal specialties. And their B.Y.O.B option, a neat feature among some of the best restaurants in Chicago, allows you to choose your own beverage."