Best Cookies in Wicker Park

"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."

"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."

"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."

"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."

"The Burnham Wildlife Corridor is a 100-acre area of urban wilderness running through Burnham Park. There is a bird sanctuary, a bioretention basin, nature paths, and a centennial prairie. Native prairie grasses, savanna, and woodland ecosystems create the largest natural area along the lakefront, according to the park district."

"A photo posted by Infatuation Chicago (@infatuation_chi) on Mar 26, 2016 at 3:32pm PDT. This pizza joint is known for their PB&J special: a slice of pizza, can of PBR, and a shot of Jameson, all for $8.50. And no, this isn't one of those weekly specials — you can get this deal all day, every day."

"The heated, covered patio at this Logan Square restaurant is decorated with string lights and leafy plants for an enchanting effect. When it gets cold, a gas-powered fireplace will keep things toasty."

"A throwback family-owned Chinese spot of the highest order, Shanghai Inn is the type of place that is so simple, and yet so good, it makes you angry there aren’t places like this all over Chicago. Family-owned for multiple generations, it has a homey feel, and everything you could ever want from your local Chinese restaurant. Sweet and sour chicken?"

"The views of the Chicago River from the outdoor decks of both Pizzeria Portofino and its upstairs neighbor (and fellow Lettuce Entertain You hotspot) RPM Seafood allow you to heckle the kayakers below as they drift by, but you won’t even be tempted as you soak up the sun — or admire the night time twinkling of office tower lights in the water. Whether you’re feasting on RPM’s Red Snapper Seviche and Tuna au Poivre or Portofino’s fennel sausage- and rapini-laden Pugliese Pizza and twirling strands of Cacio e Quattro Pepe bucatini on your fork, you’ll be living your best Chicago life. Pizzeria Portofino: Open daily at noon."

"Restaurants River North. It might not be the Cinque Terre, but Pizzeria Portofino's airy patio, decked out with white wicker couches and plenty of sunlight, does its best to bring the Italian coast to the riverfront. Order one of the restaurant's hand-stretched pizzas and an Aperol-spiked cocktail to complete the effect."

"Patrons enjoy lunch at Pizzeria Portofino on the Chicago River on Aug. 13, 2019. (Abel Uribe / Chicago Tribune). The Riverwalk is a fun place for curious Epicureans, but along the way, many riverside restaurants have patios with delicious bites to boot."

"For theatre lovers, check out a performance at The Chicago Theatre. If you feel like doing an activity, head to 10pin Bowling Lounge under the Marina Towers north of the Chicago River. They offer a selection of beers and upscale snacks."