One of the first things you notice about Logan Square in Chicago is the beautifully manicured boulevards that traverse through the neighborhood. These boulevards hold incredible historic significance — they were part of a 26-mile planned greenway system that connected parks and encouraged real estate development along the outskirts of the city. The boulevards were meant to be “linear parks” where residents and visitors could ride horses and promenade on a Sunday afternoon. The boulevards are famous for their majestic graystones — homes build with gray Indiana limestone. Current-day Logan Square is a Mecca of accessible art, rich Latin culture and diverse culinary creations.
Logan Square is a northwestern neighborhood of Chicago, with Milwaukee Avenue cutting through it diagonally. The area is accessible by the Blue Line (Logan Square stop), the Healy station on Metra’s Milwaukee District North line, and CTA buses #56 and #76.
90 Miles Cuban Cafe is as close as you can get to taking a trip to the island itself. The Gonzalez family braved stormy seas on a shrimp boat in 1980, landing in Key West, eventually making their way to Chicago to bring their culture to our community. The restaurant itself is filled with bright colors, chatting patrons, upbeat music and a casual, festive atmosphere. Kids love the empanadas — savory pastries filled with meat and/or cheese, and can try a new tropical shake flavor like Guanabana or Passion fruit.
Where: 2542 N. Milwaukee, Chicago
Nestled near the Illinois Centennial Monument, Andros Taverna was named one of the Best New Restaurants in America in 2021. Don’t let this deter you from bringing the kids though; they have a menu for the littles! Make sure to order the octopus and expect your children’s eyes to widen at the sight of this visually stunning and stunningly delicious dish. Pro tip: order the honeyed crispy kataifi cheese pie for dessert. The husband-and-wife team behind Andros create an elegant yet comfortable atmosphere, with the absolute best pita bread you will eat. Ever. Brunch is an affair to remember, where sweet and savory live in perfect harmony.
Many of us remember elephant ears from our youth. Well, churros are the handheld version of that nostalgic fairground dessert. These crispy-on-the-outside, chewy-on-the inside treats are the product of testing hundreds of recipes to create this addictive sweet. They also offer churro shakes, flavored churro-topped hot chocolate and sundae funnel cakes. Best part about churros? They are the perfect grab-and-go dessert, ideal for eating while you stroll.
Keeping kids entertained is at the forefront of many parents’ minds, and Paulie Gee’s provides plenty of live entertainment for those who might be squirmy. The open kitchen concept allows your crew to view the tossing of the pizza pies and an impressive wood-burning pizza oven. They do not take reservations, but open at 4 p.m. for dinner on the weekends so you can beat the crowd. The menu changes seasonally, so they keep you coming back for more every quarter!
For more than a century, this theater has continued to serve the community as Logan Square developed around it. Thanks to rounds of renovations, the original plaster work, stained glass and marble walls allow patrons to fully experience the glamor of the early 1900s theater experience. Film festivals, open mic nights, private birthday parties and more are hosted here, as well as daily movies of all genres. Best of all, ticket prices have remained relatively low.
Where: 2200 N. Kedzie Ave., Chicago
At almost eight acres, this park is connected to Logan Square and Humboldt Park by the boulevard system. Runners will delight in the updated running track that borders the green space, so grab your jogging stroller and go to town. If you are a fan of the Velveteen Rabbit, Palmer Square Park has a custom-designed play space based upon this beloved children’s book. Rabbit sculptures adorn the hilly terrain, and a rabbit trail links elements in the book.
If you have kids that love to climb, swing, tumble and soar, Aloft is the place to go. They teach, train and host performances for aerial and circus arts. Classes are offered for kids from ages 2+ (2-3 years old with parents), and even offer youth performing troupes for those whose interests are piqued by classes. The space is breathtaking — they transformed a 112-year-old church into a Big Top dream.
Where: 2430 W Logan Blvd., Chicago
Located under the highway, this 1.29 acre skate park has plenty of room for little ones who want to bike, skate or scooter around. There are obstacles for the older kids and green areas that are perfect for cooling off.
Want to show your kids how to shop for local groceries in an easy way? Head to the Dill Pickle Food Co-Op! They prioritize produce grown within 300 miles as well as items that are socially responsible. In addition, the food co-op is owned by the community members who shop there, not a corporate chain. Everyone is welcome to shop, though, and you can find some incredible produce fresh from the farm.
Where: 3131 W. Logan Blvd., Chicago
Have a crafty kid that loves making jewelry? Or a budding photographer who might be the next Ansel Adams? Show them how makers market their wares at this incubator-style retail store. More than 300 local artists sell their creations here, plus it hosts a slew of workshops and events, including a make-your-own jewelry class and pinchpot workshops.
Bring your furry friends to this dog-friendly independent book store! They have a keen focus on children’s literature, so your child can peruse a carefully curated section with everything from YA, middle grade, early readers and picture books. Their event schedule is rich with local authors, poetry salons and numerous book clubs. Stephanie, the owner, is a former librarian and loves to connect readers of all ages to the perfect book.
Teenage Mutant Ninja Turtles. Voltron. Blanche The Golden Girls Action Figure. These are all vintage toys found at Toy de Jour. What more fun can you have than showing past playmates to your family? School your son on all things Jem and the Holograms. Describe to your daughter how a vintage Hot Wheels Car is almost as good as the real thing.
Where: 3109 W. Logan Blvd., Chicago
With more than 20 years in the toy industry, *play is serious about a concept that our world needs play now more than ever. This bright, cheery store welcomes kids of all ages and carries a wide variety of toys, games, instruments, books, blocks and even some sweets. Not sure what to get? Check out the *play’s picks list, a thoughtful selection of things like school readiness books and board games that teach cooperation.
At one point in the not-too-distant past, Logan Square had the least amount of green space per capita out of any neighborhood in Chicago. Many minds came together to develop the concept of the Bloomingdale Trail, which transformed the defunct Bloomindale Line into a park and trail system that connects four neighborhoods. It spans 2.7 miles through Logan Square, Humboldt Park, Bucktown and Wicker Park. This isn’t just a path, though. The 606 houses a stunning nature display, science lessons, and temporary and permanent art exhibits.
Logan Square has a plethora of unique murals dotted throughout the community. From portraits to collages, cartoons to gentrification controversy, there are so many stories behind these public works of art. One of the most famous is the “Greetings from Chicago” mural, located at 2226 N. Milwaukee Ave. This mural, completed in 2016, is the first in a planned series for every state in the U.S. Another must see is the Robin Williams mural, a stunning depiction of the late comedian surrounded by a laughing Genie, the character he famously voiced in Disney’s Aladdin.
Where: 2529 W. Logan Blvd., Chicago
Within Park 556 lies the Logan Square Dog Park, where you can take your furry friends for a playdate. True to Logan Square’s artistic nature, a colorful mural depicting playful pups and owners. The park includes an off-leash area with a separate section for smaller dogs as well as drinking areas.
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