The spot: 31s Street Beach and playground (3100 S. Lake Shore Drive, 312-742-5121, cpdbeaches.com/beaches/31st-Street-Beach)
Why it's a gem: The trifecta of an awesome ADA-accessible playground, beautiful beach with southern views of the skyline, and the uncrowded picnic spot on the “green roof” above the parking garage, overlooking the harbor.
Gather provisions: The Medici (1327 E. 57th Street, 773-667-7394, medici57.com) is a short trip south on Lake Shore Drive to Hyde Park. You'll be rewarded with a bakery and deli stocked with fresh-baked breads and pastries as well as a full menu of specialty sandwiches (gluten-free options available) and build-your-own offerings (perfect for picky eaters).
The spot: North Park Village Nature Center (5801 N. Pulaski Road, 312-744-5472, chicagoparkdistrict.com)
Why it's a gem: You'll find trails through the 46-acre nature preserve with wetlands, woodlands, prairie and savanna where it's not uncommon to spot deer and other wildlife.
Gather provisions: Top Dog (6005 N. Sauganash Ave., 773-957-3607, topdogsauganash.com) In addition to Chicago dogs, fries and milkshakes, this fast-casual spot offers a variety of salads, sandwiches, vegetarian and Mexican-food options.
Why it's a gem: Sometimes you want to picnic on a rainy day. Do it surrounded by palm trees, flowers and fountains inside Navy Pier's atrium. The gardens are steps away from the Chicago Children's Museum and other pier attractions.
Gather provisions: Skip the same old food-court fare and place an order to go at the new pop-up restaurant City Porch Chicago, located within the pier's Smith Museum of Stained Glass, where grown-ups can get summery lobster rolls, fish tacos and po' boys, and the kids' menu includes chicken tenders and burgers.
The spot: Independence Grove (16400 W. Buckley Road, Libertyville, 847-968-3499, lcfpd.org)
Why it's a gem: With canoeing, kayaking, pedal boats, stand up paddleboards, fishing boats, bikes, swimming beach and playground, there are plenty of recreational activities to work up an appetite on this 115-acre lake. On Tuesdays throughout the summer, pack an evening picnic and catch a concert by the water.
Gather provisions: Sushi Thai (1742 N. Milwaukee Ave., Libertyville, 847-816-4557, sushithaionline.com/libertyville) has options—cooked, raw, vegetarian, deep fried, fruit-stuffed. Beyond the impressive selection of sushi, there are plenty of Asian entrees, curries, noodle and rice dishes. Kids can munch on fresh spring rolls, vegetable tempura or crispy wrapped shrimp.
The spot: Oz Park (2021 N. Burling St., 312-742-7898, chicagoparkdistrict.com)
Why it's a gem: Wizard of Oz fans of all ages will enjoy hunting for the statues of Dorothy, the Scarecrow, Tin Man and Cowardly Lion. Young climbers will be picnic-ready after scampering around the impressively large, and recently remodeled, wooden playground. A beautiful fenced garden is prime picnic-blanket real estate.
Gather provisions: Expand your brood's culinary horizons with a stop at Rickshaw Republic (2312 N. Lincoln Ave., 773-697-4750, rickshawrepublic.com), where the Asian street food offerings include kid-pleasing satays, lumpia (Filipino spring rolls) and bala bala (veggie fritters). Reward their willingness to try new things with warm, gooey baked goods from Insomnia Cookies (2260 N. Lincoln Ave., 877-632-6654, insomniacookies.com).