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). 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 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.
As you walk, you’ll 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.
In the heart of the park, you’ll find your destination: Rock climbing on two walls, at points 40 feet tall, overlooking skyscrapers on one side and the lake on the other. 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.
Equipment can be rented in the adjacent fieldhouse, which also offers locker rentals. Partake in Open Climb, and if you want some training, you can sign up for lessons.
For those who don’t want to leave solid ground, Maggie Daley Pak has you covered. 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.
After all that activity, you’ll be hungry. Fortunately, there are several 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, 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 Avenue and venture into Millenium Park. You’ll 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.
You’ll end the evening by taking in some of the park’s unique attractions — you may as well while you’re there. Follow your eyes to The Crown Fountain, a shallow reflecting pool that projects images of Chicago residents on two giant glass towers.
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. It’s easy to delight in watching images reflected on the infinity surface. Sure, it’s touristy, but it’s hard to deny the appeal of the architectural artwork.
