West Town
Settled by Eastern European immigrants, the side-by-side neighborhoods of Bucktown and Wicker Park, as well as Ukrainian Village to the south, have long played host to creative types. Many of the old local dives have ceded street space to galleries and cafés, but the area's blend of authentic grittiness and newly arrived charm (not to mention its culinary wonders and green space) make it one of the city's most desirable destinations for parents with tattoos and 401(k)s. Start at the busy intersection of Damen, Milwaukee, and North avenues: The streets fan out into a walkable, stroller-friendly enclave of funky storefronts and eateries. Browse the shops, then hit the newly renovated playground, Holstein Park.
Eat
Milk & Honey Café
Granola made from scratch, and a popular brunch on weekends.
1920 W. Division St., (773) 395-9434
Try its delicious thin-crust pizza—worth the break from Chicago's signature deep-dish.
1927 W. North Ave., (773) 772-4422
Shop
The T-shirt Deli Co.
A classic deli counter serves up custom-made onesies and tiny tees with bags of chips.
1739 N. Damen Ave., (773) 276-6266
Limited-edition robots and designer collectible figurines.
1953 W. Chicago Ave., (312) 491-9501
Leather goods like booties and calfskin stuffed animals.
1723 N. Damen Ave., (773) 782-1570
Do
Holstein Park
Swings and climbing structures with a futuristic design.
2200 N. Oakley Ave., (312) 742-7554
Kids' activities include flower planting and scavenger hunts.
300 N. Central Park Ave., (312) 746-5100
