Windy Kiddie: Kids Outing to Chicago

School is only days away—still plenty of time for a family vacay in Chicago.
Blue Man Group at Briar Street Theatre

The school-year grind is bearing down, the kids are whining about the end of the break, and you’re wondering where the summer went. What the brood needs is a last blast of fun. Chicago landed on U.S. News & World Report’s list of best summer vacation spots, and Parents magazine called the city “one of the best to visit with your family.” Are we there yet?!

The Ferris wheel made its international debut at the 1893 World’s Fair in Chicago, and Navy Pier’s beloved model, upgraded this summer, now stands 50 feet taller, with climate-controlled gondola cars. Maggie Daley Park, opened in 2014, has the mother of all playgrounds, with get-wet features and fantastical landscapes like an Enchanted Forest and a Wave Lawn (even cooler than they sound). The 20-acre lakefront rec area also includes a 40-foot climbing wall and mini golf.

With wacky skits, audience participation, and gross-out humor, the Blue Man Group at Briar Street Theatre appeals to all ages. So does Kings Lincoln Park in the Newcity entertainment complex, which cranks up ordinary bowling to a “cosmic” level with psychedelic black-lit lanes and a dance-party soundtrack. The young’uns will want a Wicked Awesome Milkshake—which naughty parents can order with booze—while waiting for the four-person air hockey table.

Kings Lincoln Park
Retro Kings Lincoln Park

Families get VIP treatment at Loews Chicago Hotel, whose packages include “dive-in movies” in the pool, photo-op scavenger hunts, and kids’ backpacks containing compasses and sunglasses. Shopping on Michigan Avenue can be fab for the little ones, too, thanks to the bespoke British Galt Toys + Galt Baby store and its wooden toys, trains, dollhouses, puzzles, and books. Hop On Hop Off tours by Chicago Trolley highlight sites along the way—meaning the kids might accidentally learn something before school starts.



Locals eschew touristy deep-dish for the secret-recipe dough and signature sausage at Lou Malnati’s Pizzeria.


On the way, Merrillville’s Albanese Candy Factory Outlet has gummies in every color of the rainbow.


Shedd Aquarium’s Stingray Touch is an exotic twist on the petting zoo.