Skydeck and Ledge at Willis Tower

By Eileen Ogintz

You could have your name on Chicago’s tallest building. It’s only $20,000 a month for the naming rights. Willis Tower, once the tallest building in the world and formerly known as the Sears Tower, still provides the best view of the Windy City.

On a clear day, you can see four states—Illinois, Indiana, Wisconsin, and Michigan–from the famous Skydeck and the Ledge. It features five glass floor balconies that extend 4.3 feet from Willis Tower and stand 1,353 feet above N. Wacker Drive. You’re safe! It’s made of three layers of half inch glass. 

No wonder Skydeck welcomes three million visitors a year from 155 countries. No wonder there are over 1000 proposals here a year—and over 100 weddings on The Ledge.

“I tell everyone if they are coming to Chicago for the first time, they should come here first,” said our guide, Laurie Peterson. “This is a great place to get oriented to the city,” and to take selfies.

A good place to base yourselves with kids, if you can afford a bit of luxury, is The Four Seasons Chicago, celebrating its 35th birthday. This year, the hotel welcomed a mascot for kids, Sammy the Skyscraper (Chicago is recognized not only for its skyline but for some of the tallest buildings in the country, partly as a result that destroyed much of central Chicago in 1871 with the new building ushering in the steel-frame skyscraper era, we learned at the interactive museum at the Willis Center.) It’s a great location, steps from Oak Street Beach and the Magnificent Mile which includes the Lego Store, American Girl Doll and more. 

Photo courtesy Four Seasons Chicago
Photo courtesy Four Seasons Chicago

For junior Four Seasons visitors, Sammy the Skyscraper acts as a tour guide. The plush character is shaped like a skyscraper, a nod to Chicago’s skyline and the iconic skyscraper in which the Four Seasons is located.

When they check in, besides Sammy, kids get a special gift from a Treasure Chest and a custom Passport to Adventure, Sammy’s guide to fun. (Check in on a Friday and there will be special seasonal crafts from 2 pm-4 pm.)

Photo courtesy Four Seasons Chicago
Photo courtesy Four Seasons Chicago

I love that instead of just room service, there is an on-call Ice Cream cart for sundaes in your room. You can also find the In-Room Gamer Menu including VR glasses, consoles, and Nintendo Switches. 

There is a special Kid’s’ Room on the 32nd floor where families can play arcade and video games, have a snack, and join a weekly movie night on Friday and Saturday night. Parents can get a break at the hotel spa or with a bespoke cocktail from the new cocktail menu.

Families also will love the indoor heated pool complete with a dome skylight while Bubbles Academy is located on the sixth floor. The hotel concierges are ready to curate a kid-friendly itinerary, including of course the Willis Tower and SKYDECK. 

(Adult and Youth admission ranges from $24-$32, with expedited admission starting at $55.)

But don’t rush up to the 103d floor, suggests our guide, Laurie Peterson. Fun Fact: The Ledge was inspired by the movie “Ferris Bueller’s Day Off” where he and his pals visited, their faces pressed to the glass. There is plenty of space to inspire photos and guests can upload their Ledge social media photos (#skydeck #upshow)

Replica of Second City improv stage at Willis Tower Skydeck and Ledge
Replica of Second City improv stage at Willis Tower Skydeck and Ledge

Take time at the lower level for the museum that is a combination history museum, children’s museum, a riverboat museum, architecture museum and a great place to take selfies (Perhaps sitting in the giant CHICAGO sign or in front of “Wrigley Field.” Perhaps the iconic Cloud Gate sculpture in Millennium Park called The Bean because of its shape like a kidney bean.)

Pose with famous Chicagoans including the Obamas, Oprah Winfrey, and Michael Jordan.

There is a section on unique Chicago eats—from deep dish pizza to Greek flaming Saganaki, Italian beef sandwiches having a renaissance from the hit TV show The Bear. And, of course, Chicago hot dogs with all the trimmings (mustard, onions tomato, sweet pickle relish, pickle, and celery salt!) 

Kids love laying down on the cushy Deep Dish pizza piece where they become the toppings as they look in the mirror above. For the uninitiated, deep dish pizza is made in a pan like a cake with a tall rust and upside down toppings with the tomato sauce on top.

I love that there is a big map suggesting where visitors go for different iconic foods (Logan Square for craft beers; Pilsen for Tacos, Bronzeville for Soul Food.

Chicago is also famous for its arts and music scene. Improv got its start at Second City, as did many of today’s stars including Stephen Colbert, Steve Carell, Tina Fey, and Amy Poehler. (Take a selfie on the stage!)

Chicago is famous for its jazz and blues scene and there is another map suggesting where visitors might go.

Take a ride on Chicago’s “El” the elevated trains that first began in 1892 and has 700,000 riders daily. You go through nine different neighborhoods including the Museum Campus, Hyde Park, Pilsen, North Halsted among them, with scenes of those neighborhoods whizzing by. “Just don’t think you can take one train to all those places,” Peterson laughed.