4 hip Chicago ‘hoods to hit this fall

One of the coolest things about Chicago is the fact that we have so many different neighborhoods — and each area has its own distinct character, from serene and beachy to hipster cool. Get out of your own neighborhood and spend a day exploring each of these spots with the family.

South Loop

If you’re heading this way to go to the aquarium, the Field Museum or the planetarium, it would be such a shame to go straight back home when you’re done. Instead, skip the café in the museum and head over to Chicago Waffles, where you can get a waffle flight which has red velvet, chocolate, Liege and Belgium mini waffles. Walk off your meal via a stroll on the lake, or run around at the South Loop’s new playground, located in the middle of The Shops at Roosevelt Collection. The playground is fantastic for kids — and it’s smack dab in the center of some parent-favorite stores: Lululemon, The Container Store, H&M (they have a kids’ section at this one) and White House Black Market, plus others. There’s even a movie theater here with stadium seating.

Logan Square

It’s getting a reputation — in a good, fun way — for becoming a hipster paradise. And this up-and-coming neighborhood loves its kids. Start by filling up your bellies at Bang Bang Pie Shop. It’s only been in the neighborhood for about three years, but it’s already a hot spot — for good reason. They’ve got savory food served on warm biscuits, which is perfect for breakfast, lunch or a breakfast-y dinner (you must have the Candied Bacon Biscuit plus the grits). And you can’t leave without one of their seasonal pies. Next, take a walk down the brand new 606, an elevated 21 ½-block trail. When the kids need a break, they can play at the Palmer Square Park, a grassy area that was inspired by The Velveteen Rabbit. While it doesn’t have a lot of park equipment, it does have two adorable rabbit statues, a lot of grass, a slide and enough room to run your sillies out.

Check out our video tour of Logan Square!

Little Italy& University Village

Tucked away near the University of Illinois, Chicago, is a neighborhood that’s really starting to hit its stride. We can’t mention this area without drooling over our favorite place in all of Chicago: Mario’s Italian Lemonade. These handmade Italian ices come in just about every flavor, from chocolate to watermelon, and they’re just $1.75 for a small. They are worth every.single.penny. There’s a line on weekends and evenings, but if you go during the day, you can usually grab one without a wait, before you camp out on a stoop to eat it. For lunch (yes, dessert came first), head over to County Barbeque, which is a Bib Gourmand recipient. Their corn pudding is essentially a cobbler stuffed with corn kernels, and the ribs have a rich crust and a chewy, deep flavor. Then, walk or drive (parking is a cinch) over to Sheridan Park, which is a spacious park outside a park district building.


This quieter community on the north side of Chicago, seven miles from the Loop, contains a whole lot of family fun. Since Edgewater runs along the lake, it’s got a fabulous beach: The Kathy Osterman Beach. The water is calm, street parking is a usually a breeze, there are clean bathrooms and there’s even free Wi-Fi. And unlike the North Avenue Beach, where you’re packed like sardines every time the sun considers shining, this one always seems to be peacefully tranquil. Broadway Cellars is a family-friendly brunch spot with bottomless mimosas and bottomless Bloody Marys for the parents. Next, let the munchkins play at Berger Park, where there’s a playground, a café and plenty of benches for adults to chill and take in the gorgeous water views.

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