Chicago is home to deep dish pizza, the Cubs, and Ferris Bueller. Yes, when I think of Chicago identifiers, Ferris comes to mind. (What can I say, I’m a child of the eighties!) Finding fun activities with teens and tweens can be tricky while traveling, but not here. Chicago with kids is more fun than Ferris Bueller’s Day Off! I’m breaking it down into a Two Day Plan on how to tour Chicago with your tweens and teens that will have them declaring. “This place is cool!”
Two Days in Chicago with Teens and Tweens
Frank Sinatra had it right when he sang these lyrics about Chicago:
“This is my kind of town, Chicago is
My kind of town, Chicago is
My kind of people too
People who smile at you.”
You’ll be singing this tune too once you discover all the cool things to do in Chicago with kids in this vibrant, thriving city. We crammed as much as we possibly could in our two days. Since we were staying in the suburbs, our activities were all daytime in the city, so we didn’t have any nighttime experiences. Guess I have to go back then!
From flying high in a ferris wheel to hanging out in Willis Tower FERRIS style, and Cloud Gate to Cloud Lemonade at Dylan’s Candy Bar, here are the highlights of our two day blitz.
Things to Do in Chicago with Teens and Tweens
DAY ONE IN CHICAGO:
- Skydeck at Willis Tower
- Navy Pier
- Magnificent Mille Shopping/Sightseeing
DAY TWO IN CHICAGO:
- Millenium Park
- Art Institute
- Dylan’s Candy Bar
Ferris Bueller Moment
The Van Halen song “Jump” comes to mind when visiting the Skydeck at Willis Tower. At 103 stories and once the tallest building in the world, the Ledge at Skydeck boasts an unparalleled vantage point of the city: straight down from 1,353 feet in the air! This is not for those afraid of heights.
You might wonder: Where did they get such a crazy idea? The inspiration for “The Ledge” came from hundreds of forehead prints visitors left behind on Skydeck windows every week. From the memorable scene in Ferris Bueller’s Day Off to curious children going right up to the window, visitors are constantly trying to catch a glimpse below. No more craning of heads or forehead prints-just unobstructed, one of a kind views.
- Willis Tower is 1,450 feet (443 meters) high – 1,730 feet (520 meters) including twin antenna towers.
- Willis Tower is the eighth-tallest building in the world; it is the second tallest building in the North America and the Western Hemisphere, standing 1,450 feet and 110 stories tall.
- The Skydeck is the highest observation deck in the United States.
- Approximately 1.5 million tourists visit the Skydeck each year.
- The Ledge’s glass boxes extend out 4.3 feet from the skyscraper’s Skydeck on the 103rd floor. Each box weights 7,500 lbs.
- The Ledge is built to withstand four tons of pressure and can hold 10,000 lbs!
Cost: $ 25 for adults and $ 17 for youth ages 3-11. Save money buying tickets through 365TicketsUSA ($20.77 for adult admission and $16.50 for youth).
OR Get a City Pass that includes day/night admission for Skydeck (see below for CityPass info).
Tip: There are two ledges where you can make your own photos, but be prepared for a wait and possibly other people overflowing into your photos. The third ledge has a dedicated photo opportunity, but it will cost a premium for their photos. (We purchased 2 8×10 photos for $36.)
Since its reopening in 1995, more than 180 million visitors have come to enjoy Navy Pier and its attractions and events. Other spots of interest on Navy Pier’s sprawling 50 acres include the Chicago Children’s Museum, Chicago Shakespeare Theater, an Imax theater, and a multitude of shops and restaurants. Navy Pier is also a hotspot for sightseeing cruises, dining cruises, and charters.
The Centennial Wheel is a 200-foot wheel, and can accommodate up to 180 more passengers per ride. Featuring temperature controlled gondolas, the Centennial Wheel can now be operational 365 days year and provide the latest in amusement technology. Nightly, guests will experience the magic of the Ferris wheel as it lights up Chicago’s skyline.
Pricing: Centennial ticket prices range from $18 for an adult single ride, $15 for military personnel and children 3-11, and free for children under 3. Tip: Order tickets online and save $ 2 per ticket!
Get ready to shop ’til you drop on the Magnificent Mile. The Magnificent Mile is the 13-block stretch of North Michigan Avenue that runs from the Chicago River to the south all the way to Oak Street to the north. At last total, more than 460 stores, 275 restaurants, 60 hotels and unique entertainments and attractions abound in this one square mile area. Fun fact: Michigan Avenue was originally planned after the Champs-Elysees in Paris.
My teen especially wanted to find the Lush Store for bath bombs and beauty essentials. My tween was keen on locating the Lego Store. Meanwhile, I was distracted by the sweet smells wafting from Molly’s Cupcakes. Something for everyone!
Chicago with Teens and Tweens: Day Two
I’m loving Millennium Park, which boasts 25 acres of green space, architectural wonders, a huge amphitheater for concerts, and fun fountains for splashing around.
Let’s start with Cloud Gate (aka “the Bean”). Made of approximately 200 stainless steel plates and weighing 100 tons, this iconic Chicago landmark took some serious tweaking before it was unveiled in 2005. Judging by all the photos being taken at the Bean, you could say it’s a hot spot!
Another cool attraction is the Crown Fountain-literally because it’s a reflective pool that beckons kids to splash to their heart’s content. Two 50 foot media displays flank the pool, showing facial images of Chicago citizens as they cascade water to the delight of squealing kids below.
Finally, take a stroll through Lurie Garden as you make your way to the Art Institute. This green space helps Chicago maintain the nickname “City in a Garden.” The area features a combination of perennials, bulbs, shrubs and trees. It’s an oasis in the middle of the city. You may have a moment where you forget you are in a huge metropolitan city because it’s so serene. So much so that my teen and her friend decided to do yoga poses!
Tip: As you walk through the Lurie Garden, you will end up at the side entrance to the Art Institute, which is less crowded than the main entrance.
You might wonder if teens and tweens would like to experience the Art Institute. While it may depend on your kids, I think the Art Institute is a must when visiting Chicago. But if you’re kids aren’t art buffs, here’s how you approach it.
We did a one hour-ish blitz tour of the museum (thanks in part to my pal Shannan who is a local and knows her way around!) Our focus was on art that we all knew like Monet’s Water Lilies, American Gothic, and Nighthawks.
It was also a bit like a Ferris Bueller tour, stopping to pose in front of A Sunday Afternoon on the Island of La Grande Jatte and stare at the little girl like Cameron did. We marveled at the Chagall America Windows where Ferris and Sloane stopped to kiss. The teens even went into dancer mode to strike poses alongside sculptures.
For us, it was the perfect amount of time. My tween couldn’t stay for much longer, so we saved our ace in the hole for our next stop…
You will be considered a rock star parent if you take your kids to Dylan’s Candy Bar. Imagine a two story Willy Wonka wonderland with rows and rows of candy bins, nostalgic candy, chocolates, personalization station, and cafe. The kids went into overdrive selecting candy and having fun looking at all the varieties there.
Since we were celebrating my daughter’s birthday, we just HAD to stop in the cafe for a treat. Recommendation: the Pink Cloud Lemonade, made of hibiscus syrup, lemon, pink lemonade Nerds, soda, pink sugar rim & pink cotton candy. Pure sugar heaven!
Chicago with Teens and Tweens: Get a CityPass
Once again, I must plug the CityPass for Chicago. I’m a huge fan of seeing lots of tourist friendly destinations and saving money, so the CityPass is the absolute combination of both! Here are the attractions included in this pass:
- Shedd Aquarium – PRIORITY ENTRY
- Skydeck Chicago – DAY/NIGHT ADMISSION
- Field Museum – ALL-ACCESS PASS
- Museum of Science and Industry – ENTRY + 1 TICKETED EXPERIENCE OR 360 CHICAGO Observation Deck – EXPRESS ENTRY
- Adler Planetarium – PREMIUM PASS OR Art Institute of Chicago – FAST PASS
CityPass is currently priced at $ 108 for adults and $89 for kids 3-11.
What’s on YOUR list for Chicago? Share with me your favorite attractions and adventures.
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