You’ll start the adventure at Maggie Daley Park, on the northeastern part of Grant Park. This 20-acre majesty opened in 2014 and is named for the city’s former first lady (1989–2011) who was deeply committed to improving the lives of children. In addition to seemingly endless green spaces, the park offers picnic areas, a cafe, rock-climbing walls and so much more — unparalleled views of the city, too.
There’s no wrong way to explore Maggie Daley Park. You’ll want at least an hour there but could easily spend a half — or full — day here. There are several entrances, each close to parking and public transportation. Once inside, stroll along the paved walking path. You’ll pass picnickers lounging on the lawn, kids cavorting around and friends taking selfies.
Gage Wolt, who handles events and marketing for Maggie Daley Park, explains its appeal for families.
Make your way to The Play Garden, which comprises half a dozen themed play areas. Kids five and under will delight in The Harbor, a nautical space. The Slide Crater offers a variety of slides for kids ages 5-12, and The Enchanted Forest and Wave Lawn are enticing for all ages. You may have to wait for a turn on a swing or other equipment, but the turnover is quick as kids are eager to try a little of everything.
Gawk at (or join!) climbers on the two climbing walls in the heart of the park. This seasonal attraction is perhaps the best way to get an aerial view of the park — if you’re bold enough to take your eyes off your next move. Kids aged four and up can sign up for lessons or partake in Open Climb, and equipment can be rented in the adjacent fieldhouse, which also offers locker rentals.
Be sure to stop by the Skating Ribbon, a quarter-mile path designed for walking, roller skating, rollerblading and scooters in the warmer months. In the winter, it freezes over and serves as a fun and festive ice skating rink. Depending on the time of year you visit, you can rent rollerblades, scooters or ice skates from the fieldhouse, and you can always bring your own equipment.
As you walk through the park, you’ll see many of Chicago’s iconic buildings in the background. Even if they haven’t seen “Adventures in Babysitting,” the kids will undoubtedly recognize the diamond-shaped Crain Communications Building and will be awed by the messages on the windows of the Blue Cross Blue Shield building.
With all that activity, the whole gang will get hungry. Fortunately, there are a number of nearby spots to grab a nosh for an urban picnic. Hot Woks Cool Sushi stands out as a family-friendly crowd-pleaser, on a strip of Michigan Avenue that otherwise has a plethora of fast food places and fancier bars. The sushi spot’s creative and eclectic menu of Asian favorites includes maki, stir-frys, bento boxes and even sushi donuts.
Place your order over the phone or on the website as you leave the park, and it should be ready for pickup by the time you walk the half-mile west to the restaurant. Start with a house-made yuzu soda, a refreshing alternative to other lemon-lime drinks. The veggie spring rolls are perfectly crispy and come free with any order over $20. Edamame is an easy snack that kids will love to dissect, and the cucumber salad is tart and tasty.
The Philly maki offers familiar flavors of salmon and cream cheese and is an easy foray into sushi. For vegetarians, the Mega Vega maki is an outstanding choice packed with broccoli, beets, tempura sweet potatoes and topped with avocado. Adventurous eaters can choose from sashimi such as Tako (octopus), Ikura (salmon roe) or Tamago (cooked egg).
Once you’ve picked up your food, cross Michigan Ave and venture into Millenium Park. The whole gang will have to go through a simple security check, as is standard now with major attractions in busy cities. Find a spot on the lawn to sprawl out and marvel at the stunning architecture around you while you eat.
After everyone is satiated, you’ll end the evening by taking in some of the park’s unique attractions. Follow your eyes to The Crown Fountain, a shallow reflecting pool that projects images of Chicago residents on two giant glass towers. If the weather is warm enough, let the kids kick off their shoes and wade in the ankle-deep water.
If you can pull them away, make an obligatory final stop at The Bean, also known as “Cloud Gate.” This iconic landmark reopened in July 2024 after a year of renovations and is shinier and more spectacular than ever. The kids will delight in watching mirror images of themselves reflected on the infinity surface. Sure, it’s touristy, but have a passerby snap a picture of your group with the skyline and the sunset in the background — you’ll savor the family photo for years to come.
