Museum hopping? Hanging by the beach? Playing tourist for the day? Exploring one of Chicago’s many ethnic neighborhoods? Or sticking close to home? How would you spend a “Perfect Chicago Day” with your family? The possibilities are endless. To inspire your hometown adventures, we spoke to six Chicago area families to learn how they would spend their perfect family day.
Family members: Debi Lilly, Mike Springer, Lilly, 12, and Parker, 9
The plan: We would wake up to sleepy, bedhead kids crawling into our bed for a delicious family morning curled up cozy together. For breakfast, Lilly would whip up her famous scrambled eggs and cinnamon toast for the whole family. We’d walk to the gym for a family racquetball tourney and wear each other out bouncing all around the courts. Next, we’re off for a long walk down sunny Southport to Julius Meinl for lunch. Favorites include quinoa citrus salad and infused green tea.
Next, we’d enjoy an afternoon strolling in Millennium Park and then grab tickets to a show or musical the whole family can enjoy downtown, stopping for a pre-theater dinner at Atwood Cafe at the corner window table on State Street.
The kids will beg for a pit stop at Margie’s Candies for late night ice cream—and I will cave as always and say of course!
Family members: Angela, Matt, Tess, 20, Alec, 16, and Maya, 13
The plan: First, we’d hit Chinatown for dim sum (we like MingHin) and check out tchotchkes in the gift emporiums. Next, we’d visit the museum campus where it’s so hard to choose between the Atwood Sphere at the Adler, shark feeding at Shedd or the gem collection at Field. Then on to the Salvation Army on Devon Avenue and wandering the shops further west to buy henna, bangles and sweets. We’d end our day with dinner at Swati or Punjab Dhabi buffet.
Family members: Steve Vihon, Ana Belaval, Amelia, 6, and Alexander, 1
Neighborhood/suburb: South Loop
The plan: We love to take a walk around Museum Campus first thing in the morning. Our kids are early risers so we can head out before the crowds, right after sunrise. After our son takes a morning nap, we can hop on the #3 Bus that takes us to the Art Institute, which our daughter has just begun to discover. After that, we cross the street to Millennium Park for some splashing in the fountains. If our daughter has her way, we would end up at Navy Pier to see the Chicago Shakespeare Theatre Children’s summer production, which is always great. Back to the South Loop for dinner with the family at Cafe Bionda or Kroll’s.
Family members: Sandeep, Anupy, Neha, 11, and Aria, 8
Neighborhood/suburb: Lincoln Park
The plan: I would start our day with a relaxed morning where everyone would sleep in until about 9 a.m. and roll out of bed for a quick Indian breakfast of stuffed/savory bread with a dollop of butter on the side. Next, we’d take the bus down to Michigan Avenue from our Lincoln Park home because my girls love public transportation. We’d end up doing some window shopping along with a rather long stop at the Lego store. Then, we’d enjoy lunch at Le Colonial because my kids love Asian cuisine.
Next, we would head over to the Art Institute where we would check out all the latest and greatest exhibits (along with the kid-friendly play rooms in the back), and then head back to our neighborhood for dinner at Taco Joint, our fave Mexican place. Of course I would call ahead to make sure we can get my daughter’s favorite vegetarian taco and my husband and I would celebrate with grapefruit or blood orange margaritas.
Family members: Johanna, Marvin, Elijah, 12, Sofia, 7, and Samantha, 4
The plan: A perfect Chicago day would take place sometime in late spring, summer or early fall. Those are my favorite times of the year! Since we live in the suburbs, we love spending overnights in the city to really soak in the city life. We love Hyatt Regency on Wacker and the Intercontinental Hotel. The morning would be spent checking out a local bakery or breakfast joint. Even though we love staying in hotels on Mag Mile, we love to venture out to our old neighborhood of Lincoln Square. Before we expanded our family and moved to the ‘burbs, we lived here when it was “up and coming.” We’d buy pastries and cappuccinos at Cafe Selmarie, sit by the fountain to listen to musicians and watch the kids run around and play. We like to visit local shops and walk the streets looking at the beautiful homes. No real agenda.
After a day of chilling in Lincoln Square, we like to go back to the hotel to swim, a definite must-do if you are staying at Intercontinental. They have the most beautiful pool! And Purple Pig is a really fun place to eat that is just steps away. But because my son is completely obsessed with basketball, Michael Jordan’s Steakhouse usually wins if we’re staying in the hotel. Spending the night in the hotel watching movies and catching up on sleep ends our perfect Chicago day!
Family members: Matthew, Marcie, Liam, 3, Ryan, 1, and baby #3 due in September
Neighborhood/suburb: Ukrainian Village
The plan: Our perfect Chicago day would start with some delicious doughnuts from Glazed and Infused (Crunchy PB&J is a favorite). On the walk home, we would stroll through the Wicker Park Farmers Market and let out some energy on the Wicker Park Playground before heading over to the Pulaski Park kids’ pool. For lunch we would stop at Smoke Daddy on Division Street. The food is amazing, reasonably priced and always kid-friendly.
If we were heading outside our neighborhood, we would include a stop at the Lincoln Park Zoo. Our kids love the trains and carousel there. Then off for some play time at Little Beans Cafe, my son’s favorite indoor play space. Dinner might include pizza and salad from Roots where they give kids their own personal dough balls to play with while waiting for the pizza to cook. To cap it off we would walk down to Black Dog Gelato for some unique gelato flavors.
Caitlin Murray Giles is a full-time mother of three and part-time freelance writer living in Wicker Park.
See more of Caitlin's stories here.
Let us plan your weekend with the best family events and activities in Chicagoland.
Start the week right with deals, prizes, parent life hacks and more delivered straight to your inbox.
Need last-minute ideas for a weekend of family fun? No worries. We've got you.
Get the inside scoop on the people, places and things we are loving right now.
Resources, tips, inspiration and more for parents of children with special needs.
Score exclusive offers from our fabulous advertisers.