Best Cookies in Chicago

"It doesn’t get any more old school than Chicago’s oldest family-owned bakery, which has been servicing Humboldt Park sweet tooths since 1911. As a specialty, Roeser’s offers low-glycemic options for birthday boys and girls who could benefit from reduced sugar, carbs and calories. Follow the bakery’s iconic neon sign to find cakes baked using recipes perfected over 4 generations with culinary skills to decorate to any theme you could possibly imagine, including a wide variety of licensed character cakes."

"Restaurants Bakeries Humboldt Park. One of Chicago’s oldest family-run businesses has operated out of the same storefront, distinguished today by its vertical neon sign and quaint painted lady facade, since its establishment in 1911. Today it’s a good all-arounder, with doughnuts and danish for breakfast, and a wide selection of cake slices and cookies (many in Chicago sports team motifs) for dessert."

"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."

"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."

"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."

"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."

"Chicago’s Lakefront Trail I promised we’d do a lot of walking today, so next, head back towards Lake Michigan and enjoy the lakefront trail, a nearly 20-mile stretch of paved walkway that meanders down the city’s coastline. The views are spectacular and it’s a great way to see the city’s skyline from a distance. If you’d prefer to bike the trail (highly recommended!), check out the city’s bike-sharing system, Divvy, where you can grab a bike for a 24-hour rental period from one of the city’s many stations"

"BridgeportWhen you think of Bridgeport, the first thing that comes to mind usually isn’t nature. And this park (nicknamed “Mount Bridgeport” and formerly known as Stone Quarry) fits right in with a 27-acre site that has transformed itself from quarry to landfill to park. Cruise the crushed stone running path and peep the fishing pond and wetlands as you stroll the grass amidst preserved quarry walls at this neighborhood hidden gem."

"Opened on the site of an old limestone quarry, Palmisano Park unfurls an urban prairie landscape with great views of the Chicago skyline. Locals come here to fish for bluegill in the lagoon in summer and sled the hills in winter. The winding walkways, made of recycled construction debris, are great for a stroll anytime."

"27 acres of wetlands and urban fishing make Palmisano Park a fun place to visit. The park also offers a phenomenal view of Chicago. In winter, it’s a great place to go sledding."

"The Lincoln Park Conservatory, with its glass walls and exotic plant species, feels like a sanctuary in the middle of the bustling city. The Victorian-era building is divided into four spaces: the Fern Room, Orchid House, Palm House, and the Show House. Each houses thousands of plant and flower varieties that thrive in the conservatory’s balmy conditions all year round."

"The Lincoln Park Conservatory is a conservatory and botanical garden in Chicago's Lincoln Park neighborhood. The conservatory is best known for its horticultural collections, community work, and educational programming. It is also housed in a glass house from the Victorian Era that is stunning to view on its own."

"Lincoln Park Conservatory has been a beautiful getaway since the 1890s. Inside, you’ll find tropical palms, ancient ferns, and plenty of other exotic plants."