There’s a reason Chicago is known as the Windy City. When we visited Chicago at the beginning of September, still summer in the northern hemisphere, we expected to see the city on its sunny and warm days. Instead, it was cold and cloudy. Despite the luminous clouds drifting across the blue sky on the third day, the air was still chilly. My understanding is that having Lake Michigan bordering Chicago’s entire eastern side, the local temperature often drops and shifts even during the summer.
But don’t let Chicago’s climate scare you away. During the summer months, the city offers an array of attractions with indoor and outdoor activities for visitors of all ages. Whether we pursued beautiful parks, an architectural boat ride, Chicago’s renowned food, history, or something else, we found it to be a fantastic destination to visit with family.
After a three-day visit to Chicago, here is our ultimate family-friendly itinerary:
1. Explore the Millennium Park
Millennium Park is to Chicago what Central Park is to New York City. No matter what season, it is beautiful and attracts locals and visitors all year round. Covering 25 acres of green space, the Park holds stunning architecture, public art, concert venues, playgrounds, restaurants, gardens, walking paths, fountains, and much more. Everywhere we looked, there was something to do and see.
Here are the attractions you shouldn’t miss when visiting Millennium Park:
Inspired by liquid mercury, the British artist Anish Kapoor shaped a 66-foot long by 33-foot high structure using stainless steel plates welded together. Highly polished, all seams disappeared. A 12-foot-high archway allowed visitors to stroll under to the concave chamber beneath the sculpture. The artist named it Cloud Gate. Locals affectionately call it ‘The Bean’ because of its appearance. Whether reflecting Chicago’s skyline and clouds above or distorted selfies, ‘The Bean’ is one of the most iconic and stunning landmarks in the city.
Crown Fountain consists of giant LCD screens on two 50-foot towers placed on the edge of a black granite reflecting pool. The towers show videos of random Chicago citizens’ faces to represent the city’s diversity and emphasize that anyone can bring art to life. Repeatedly, the faces appear to spout water into the shallow pools below. During warm days, the fountain is a popular destination for kids and adults alike to cool off.
The Pritzker Pavilion is both an impressive outdoor venue and a stunning piece of architecture! During the summer, it packs a busy calendar with events such as movie nights, concerts, yoga, and workout classes. The lawn seats are free, and the speaker system over the top of the pavilion is known for making the audience feel as if they are sitting in the paid seats. It is a perfect place to bring a picnic basket, choose a spot on the well-manicured grass, and catch one of the park’s many actions. Meanwhile, enjoy the city’s skyscrapers which stand as a gorgeous backdrop for the pavilion.
We loved the serenity and beauty of Lurie Garden. Protected by 15-foot-high green hedges, it was like walking in a secret garden in the middle of Chicago’s concrete jungle. A lovely wooden footbridge over shallow water divided the area into two sections filled with plants from ten specific regions of the country.
To maximize your visit, check Lurie Garden and learn about the history, design, updated events, and free tours.
2. Walk along the BP Pedestrian Bridge and play at Maggie Daley Park
When we finished exploring the Millennium Park, we strolled to the lakefront Maggie Daley Park. The span itself was interesting as we walked along the winding BP Pedestrian Bridge that connects the two parks. This beautifully designed stainless-steel bridge is almost a thousand feet long and crosses over the busy Columbus Drive. At each curve we had different views including Chicago’s skyline.
Maggie Daley Park is more than a playground. Built atop 4,000 parking spaces, this engaging 20-acre recreational area features manicured lawns and uncommon park settings. You don’t have to be a kid to appreciate it.
If you have children under 12 years of age, start at the 3-acre Play Garden. Divided into several sections, each area will feed the young people’s imaginations as they play and explore at The Sea, Enchanted Forest, The Watering Hole, The Harbor, Wave Lawn, and Slide Crater. For older kids or adults alike, check out the 40-foot rock-climbing walls, play mini-golf, or rent a pair of roller blades or a scooter at Skating Ribbon.
Check Maggie Daley Park for more information.
3. Check out the Buckingham Fountain
The Buckingham Fountain is a source of joy! We visited it twice.
My first view of Buckingham Fountain took my breath away. Pictures don’t do justice to its size and beauty. The pool is 280 feet in diameter, but the three fountains’ basins downsize from bottom to top. The first two basins measure respectively 103 and 60 feet wide. The top of the upper basin, which measures 24 feet in diameter, stands 25 feet above the pool. Notably, the fountain’s acclaimed performance happens every hour, for 20 minutes, when a center jet shoots water into the air to the height of 150 feet. The fountain is constructed of Georgia pink marble and contains 1,500,000 U.S. gallons (5,700,000 l) of water. During a display, more than 14,000 U.S. gallons per minute (0.88 m3/s) are pushed through its 193 jets. It is STUNNING!
For more information about hours, history, and location, click here.
4. Go for an Architecture River Cruise
The 75-minute Architecture River Cruise was a fabulous way to get a different perspective of the city. While the boat traveled along the three branches of the Chicago River, we navigated under beautiful bridges, saw stunning skyscrapers, and journeyed near the Navy Pier. Meanwhile, our guide, an architect, taught us about Chicago’s interesting history and accomplishments.
As the guide pointed out numerous buildings along the beautiful waterfront, he also gave plenty of information about the distinct architectural styles and architects that left their mark in Chicago. We heard about the historic Great Chicago Fire in 1871 that burned for three days and killed about 300 people, destroyed thousands of buildings, and left more than 100,000 residents homeless. His lecture included how the new Chicago was rebuilt. Last but not least, we were thrilled to hear that in 1900 engineers achieved the remarkable feat of reversing the flow of the Chicago River. Originally flowing into Lake Michigan, it then started running inland. As a result, the goal was accomplished to divert sewage away from the Lake Michigan water supply. The tour was fabulous!
5. Stroll at the Navy Pier and ride the Centennial Ferris Wheel
Located right on Lake Michigan, this 50-acre landmark not only provided stunning lakefront and Chicago skyline views, but also a wide range of entertainment that delighted the three of us. Check out the indoor Crystal Gardens, stroll along the boardwalk, and savor a slice of Chicago’s famous pizza. Riding on the Centennial Ferris Wheel was the highlight for our daughter. It was a good angle to see the city as we sat inside one of the climate-controlled cabins.
Navy Pier is home to many other attractions, including an IMAX Theatre, the Chicago Shakespeare Theater, the Chicago Children’s Museum, an 18-hole mini-golf course, musical carousel, restaurants, shops, and more.
6. Pose for a picture on the Skydeck at Willis Tower if you dare
The Willis Tower, also known as Sears Tower, attracts over one million visitors every year. Wondering why? It is not only the second tallest building in the country but also home to the highest observation deck in the United States, called Skydeck. It consists of glass boxes that extend four feet out from the 103rd floor.
When we dared to step out onto one of these glass balconies, it became the most thrilling moment of our trip. While we stood or sat there for no longer than a few minutes, I could only look down for a moment. As scary as it was to walk out on it, I highly encourage you to do it for the jaw-dropping, birds-eye view of the city. It was a breathtaking experience.
Note: On a clear day it is possible to identify four states (Illinois, Indiana, Wisconsin, and Michigan) and view nearly 50 miles.
7. Visit the Money Museum
Located within the Federal Reserve Bank of Chicago building, this fascinating small museum is devoted to the monetary and banking history of the United States. At the Evolution of Money exhibit, we saw how civilization moved from the exchange of goods and services to electronic money used nowadays. There was also a U.S. Money Timeline, a large cube containing a million one-dollar bills, and an exhibition that explains the process of making money. We learned that U.S. currency is made primarily of cotton, like our blue jeans, instead of paper as usually thought. Then at Why Shred Money? kids can learn the importance of doing such things.
A series of hands-on exhibits were equally engaging. There were exhibits about Understanding Inflation, What is $1,000,000 Worth, and Create Your Own Currency just to name a few. Let’s not forget about the picture kiosks. One of them provided the opportunity to have your own face on a two-dollar bill. Last, but not least, there is a Scavenger Hunt that gives kids the opportunity to be involved when finding answers to a quiz.
It took less than 1 hour to see it all. Entrance was free, but security was close to what we have at airports:
- Show your photo ID.
- Walk through a metal detector.
- Have bags x-rayed before entering the museum
8. Get lost at the Museum of Science & Industry
Prepare for a full day of exploring and learning because this place is fantastic! People of all ages and interests will find something intriguing at the Museum of Science and Industry. We spent almost all day there and still didn’t have time to see everything.
Some of our favorite exhibits were the model-sized train system between Chicago and Seattle, the Science Storms which includes tornado, avalanche and tsunami simulators, and a phenomenal collection of antique cars. But there is so much more to see and do. We enjoyed the genetics exhibition where chicks hatched in front of our eyes, the Boeing 727 hanging from the ceiling, an actual World War II German submarine, the Art of Bicycles, and The Science Behind Pixar. The interactive exhibits about the human body and robotic manufacturing were fascinating too.
Check Museum of Science & Industry for more information.
9. Take a food tour
On our last day in town, we booked an outing with Chicago Secret Food Tour. First of all, it was more than just a food tour! It was a mix of flavors, history, culture, and architecture. It was fun and kept our daughter interested during the whole time.
We went to six stops, at five of which we tasted mouth-watering dishes. In between, we visited interesting sights that complemented the tour.
Meeting up at Gino’s East, we started with the deep-dish pizza. The thick, crunchy cornmeal crust was deep enough to hold a massive and delicious layer of cheese and tomato sauce. Thinking about it, I can still savor the flavors. A quick visit to the Chicago Public Library allowed us to see the Above and Beyond Vietnam War Memorial with 58,308 dog tags of all Vietnam veterans who died in the war. We also checked out the Winter Room on the top floor.
Pierogies, chocolates, and Italian Beef Sandwich
The second eatery was at Berghoff Restaurant where we had pierogies (potato dumplings) topped with a white sauce and served with a side of quinoa and arugula salad. Next, we sampled chocolates, including the world’s famous pixies at Fannie May. At the Italian Village Restaurant, we sat at the private Teatro Room and savored an Italian Beef Sandwich. Our guide led us to take a peek at another private room where Al Capone used to dine. Pretty cool.
Dessert at Terzo Piano Restaurant
After other quick stops, including the lavish foyer of Palmer House Hotel, we headed to our final taste at Terzo Piano Restaurant. Located on the upper level of the Art Institute, we not only had a fabulous view of downtown, but also a delightful dessert. My husband and I toasted our incredible trip to Chicago with one of their fabulous cocktails.
We were glad there was some walking involved because there was a lot of food to burn off. However, there was no better way to explore Chicago than sampling the renowned dishes while learning relevant facts about the city.
Note: The last stop was the Bean and the Crown Fountain in Millennium Park. Because we had already visited both sights and a flight to catch, we split off from the group.
Where to stay in Chicago
Chicago is easy to navigate, and many of the main attractions are concentrated downtown. To maximize your time, I would recommend finding a hotel in the downtown area. We stayed at the Hyatt Place, which had a terrific location. It was walking distance from Millennium Park, Willis Tower, Money Museum, Buckingham Fountain, and Maggie Daley Park.
Do you have other recommendations for visiting Chicago with kids? Please add any suggestion below.