The shimmering towers of Chicago glimmer in the sunlight, like a diamond-studded strand adorning her skyline. Each building is a work of art, mirroring blue skies and tourmaline waters. It’s a city more beautiful than New York and still bursting with things to do from every corner– from art museums and boating along the Chicago River, to blues shows and craft cocktail bars. Regardless of how many times you visit, you can find some new attraction along its wind-swept streets.
Prior to 2023, my last visit to Chicago was in 2018 when I interviewed with EY. I had neither time nor a desire to sightsee. I was five months pregnant, but confident I wasn’t yet showing under my lucky suit. However, there was a moment during my interview, foggy with preggo-brain, I simply stopped speaking mid-sentence, unable to resume my train of thought. I was pretty sure I had botched the entire thing, and spent the rest of the afternoon lamenting to a mentor about how badly I had embarrassed myself. When I returned home, I was ready to email the recruiter to request a second chance to present myself.
Before I could do so, I was extended an offer.
That’s one of the reasons that Chicago holds significant memories for me, and I’m always willing to return.
Thus, when it came time to plan a Memorial Day weekend trip with the kids, I was eager to visit Chicago again, this time at a more leisurely pace and to sightsee like a tourist. Affordable fares, plenty to do, brilliant skies, and perfect weather at this time of year made it ideal.
Plus, there’s no dearth of activities to keep the kiddos engaged. Mine were literally jumping out of the stroller to dance along the boardwalks of the Chicago River and Lake Michigan. Exploring the city through their eyes was a real treat.
What to Do in Chicago with Kids in Spring
Teeter at the edge of the world at the Willis Tower Skydeck
Ears will pop as you swiftly rise through and descend from one the tallest building in the world, the Willis Tower, which remains an engineering marvel. Its distinctive black exterior and iconic Skydeck, featuring glass-bottomed ledge, provide unobstructed views of the city. The building was designed by Bruce Graham and Fazlur Rahman Khan, and it’s a symbol of Chicago’s architectural innovation as it addressed unprecedented structural challenges.
The highlight of the Skydeck is “The Ledge,” a glass box extending outward from the building’s 103rd floor. Kids can step onto the glass floor to feel the sensation of floating above the city. The sheer thrill of standing high above the ground and looking down through the transparent floor is both exhilarating and memorable.
Float through the city’s architectural gems
Deconstruct the city’s skyscrapers with an informative and engaging boat tour of its architecture.
While I had to use every ounce of strength to hold my toddler still so he wouldn’t try to jump off the side of the boat, my 4-year-old daughter was thrilled to see the reflective buildings glinting off of each other. Each building in Chicago has character, and learning about how each was designed with intention and beauty in mind made this tour totally worth it.
Many skyscrapers have a nickname, typically coined in reference to what it most closely resembles. Among our favorite buildings were the concrete Corncob towers, the gravity-defying Guillotine, the Art-Deco Champagne Bottle and the commanding Tribune Tower, designed in the neo-Gothic style.
The Corncob towers, also known as Marina City, are a unique residential complex designed by architect Bertrand Goldberg. These circular towers, with their innovative use of reinforced concrete, were a groundbreaking experiment in urban living at the time and have become an iconic part of the Chicago River’s skyline. I’m pretty sure I visited a friend in this building when I was in Chicago in 2014 for a bachelorette party.
The Guillotine is one of the most fascinating buildings in Chicago’s skyline. It reverses traditional design such that the building balances precariously as if on the tip of a pencil-point-shaped base. Among the many structural stabilizers it uses, at the center of the tower’s top levels are tanks filled with 160,000 gallons of water to keep it from swaying in Chicago’s winds.
The “Champagne Bottle,” or Carbide & Carbon Building, is a striking example of Art Deco architecture, a style popular during the 1920s and 1930s. It reminded me of something straight from an F. Scott Fitzgerald novel. It features a sleek and ornate design characterized by geometric patterns, intricate detailing, and a sense of verticality. The dark green color of the building (up close it looks black), combined with gold leaf detailing is what makes it look like a bottle of bubbly.
Stomp through history at the Field Museum
Little ones will love exploring the exhibits of The Field Museum. From towering dinosaur skeletons to captivating exhibits on ancient Egypt and China, this museum promises an educational and engaging experience. The kids will love exploring Sue, the largest and most complete T. rex fossil ever discovered. Kids get hands-on with science through the interactive play lab, DNA Discovery Center and immersive underground adventure, which demonstrates what its like to experience life as an insect.
Romp at the Maggie Daley Children’s Park
We spent mid-mornings strolling the outdoor parks around Chicago to let the kids expend some energy. One of the most fun for the kids was the Maggie Daley Children’s Park, which has a variety of playgrounds for kids of different age groups (regardless, my kids preferred the largest playground with the tallest slides). Named after the former First Lady of Chicago, Maggie Daley Children’s Park is a paradise for kids. This sprawling play space features whimsical structures, including climbing walls, slides, and interactive sculptures. The enchanted garden and Storybook Castle are perfect for imaginative play.
Gaze at the dreamy sculptures at Millennium Park
The warped structures at Millennium Park serve as the focal point for downtown Chicago, balancing nature and urban sophistication. Let the kids splash around in the Crown Fountain, where interactive water features and digital art create a unique play space. The trippy Cloud Gate sculpture, affectionately known as “The Bean,” is a must-see. Pack a picnic and relax in the beautiful green spaces while the children explore the interactive art installations.
Pet stingrays and other sea critters at Shedd Aquarium
From land marvels, head towards the water for a marine adventure, at the nearby Shedd Aquarium. This world-class attraction invites families to explore a diverse range of aquatic life. Watch as dolphins perform acrobatics, behold the vibrant colors of the coral reefs, and get up close and personal with sharks. With engaging exhibits and interactive displays, Shedd Aquarium promises a full day of activities.
Note: Compared to some other aquariums we have visited, this one seemed older, more cramped, and more dimly lit. For instance, even stroller/accessibility seemed to be a bit of an afterthought as elevators or ramps weren’t conveniently located– unexpected for an attraction that would be frequented by multi-generational families. However, there is an impressive variety of exhibits, so it’s still worth visiting. We also caught the 4D movie on sharks and the live dolphin show.
Where to Eat
When we are with the kids, we typically stay away from high-end, ritzy restos and opt for fuss-free eateries. You’ll also notice that the establishments below have very airy spaces with ample light, offering city views while you stop for a bite.
Breakfast at Goddess and the Baker
Baked goods steal the show at the Goddess and The Baker. This cafe was a walkable distance from our hotel, and I just loved the bright, energetic and retro vibe it flaunted. It set just the right tone to get us revved for the day.
Brunch at Venteux Brasserie
Bite into a burst of flavors with this dressed up avocado toast and fresh yogurt bowl. The French bistro of Venteux is an elegant place to grab a coffee or light bite. The sunroom felt like the best place to take the kids. You can save the plush lounge and bar for a more romantic evening experience with your better half.
Brunch at Wildberry Cafe
Wildberry Pancakes is hands-down one of the best places for a daytime meal. I remember in a pre-COVID era this place was packed for a weekend brunch with a line out the door. However, when we visited this time around 1 p.m., it was right about the time they were going to close, so the crowd had dissipated. I don’t even remember what I ordered this time, I just remember loving it.
Lunch at Mercat a la Planxa
No visit to Chicago is complete for me without meeting with my friend, Prof. Bill Handy, whom I first met in 2012 when attending an investigative reporting workshop in the windy city. His restaurant recommendations are always on point. Tapas lunch at Mercat a la Planxa was no exception and the swanky setting of the Blackstone Hotel, in which it is located, did not disappoint. We enjoyed the patatas bravas, gem lettuce salad (minus the anchovy vinaigrette), and pan con tomate.
This historic hotel dubbed as “The Hotel of Presidents” is now part of Marriott’s Autograph Collection. Having accommodated more than a dozen U.S., the hotel has also become an icon for its role in Chicago’s role in presidential nominating conventions. The private discussions that took place at this hotel during the 1920 nominating convention are what led to the popular phrase “smoke-filled room” to describe a political process that goes on unwitnessed behind closed doors among power players.
Midday or late-night snack at Garrett’s
Garrett’s is the go-to for late night munchies for some people, but with all the sweet, salty, crunchy flavors that it packs, we picked up the classic combo to-go as a snack to hold us over for dinner.
Dinner at Noninna
Italian restaurants abound in Chicago, and many flaunt similar menus. During the Memorial Day weekend, we had trouble either finding a seat at some restaurants without reservations, or finding ones that were open. Nonnina, several blocks from the hotel where we staying, had good ratings and seemed family friendly.
Their rigatoni vodka was everything I needed that crisp evening. I asked the staff to add some veggies to the dish, and they delivered. Creamy, hearty, and a subtle sweetness made this dish exceptionally satisfying.
Outside of that, for the remaining evenings we were pretty spent from exploring and my little one wanted to be set free from the stroller, so we typically ordered Indian dinners in from Tandoor Char House and the let the kids run around in the hotel room.
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