Best Cookies in Kathy Osterman Beach House

"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."

"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."

"Located at the north end of Lincoln Park Zoo, the Lincoln Park Conservatory features four serene greenhouses (Orchid House, Fern Room, Palm House and Show House) all displaying fantastic arrays of flora. During summer, venture outdoors to find a lush, French garden filled with a large variety of plants and flowers, and a beautiful fountain. Many Chicago residents utilize this space to sit and read, toss a football around, let their kids run freely or just take in the beauty of nature."

"For a big city, Chicago has a surprising number of places dedicated to all things green. For example, the Lincoln Park Conservatory, on the shores of Lake Michigan, has a botanical garden teeming with ferns, tropical flowers, and palms."

"The founders, former tech co-workers turned brewers, rehabbed much of the 19th-century industrial building themselves. The result is a soaring but cozy space that features brick walls, a 40-foot-long oak bar, a patio, and picnic tables that encourage mingling. They also encourage you to bring your everything, including food, games, darts, kids, and dogs — but they’re got the beer covered."

"Lo Rez has spent the last year posting snapshots of their great events so we're so excited that they have reopened their space (with precautions!). They are also offering cheap home delivery throughout the Chicago area."

"The Alarmist Brewing taproom, near Albany Park and West Ridge, is different for a reason. The family-owned spot wanted to create a community space where people could come together (which is why you won’t see any TVs in the taproom). It’s also super family-friendly, welcoming kids with snacks and juice boxes."

"Swing buy and shop for some brews, or order online for curbside pickup. Either way you get a top-notch drink!"

"Of the numerous buildings that Frank Lloyd Wright designed around Chicago, none is more famous or influential than Robie House. Because its horizontal lines resembled the flat landscape of the Midwestern prairie, the style became known as the Prairie style. Inside are 174 stained-glass windows and doors, which you'll see on the hour-long tours (frequency varies by season, but there's usually at least one tour per hour). Advance tickets are highly recommended."

"Named one of the 10 most significant buildings of the 20th century by the American Institute of Architects, the 9,000-square-foot Robie…"

"A National Historic Landmark, this South Loop church suffered a devastating fire in 1900, so the congregation hired architects Howard Van Doren Shaw and Frederic Clay Bartlett to rebuild the building in the then-popular Arts and Crafts style. Over the years, the church welcomed many famous Chicago families including the Pullmans, Blackstones, and Armours. Open Saturday, October, 19, from 10 a.m."

"Pablo Picasso produced this monumental piece of public art for Chicago in the mid-1960s. Standing in Daley Plaza, the Chicago Picasso weighs almost 147 metric tons and stands over 15 metres tall. Since it was unveiled in 1967, the work, rumoured to depict French model Lydia Corbett who sat for a series of drawings for Picasso in the 1950s, is a landmark for the city and something for kids to clamber on."

"This massive cubist sculpture by Pablo Picasso was the first major piece of public artwork of its kind in downtown Chicago, and today, this Daley Plaza piece is a major landmark. Choose your selfie position — “The Picasso” looks quite different depending on where you stand."