Chicago with Kids: A Perfect Family Day

Chicago with Kids: A Family Vacation


It is fitting that Chicago, Illinois, is known as the "windy city," because visiting this engaging Midwestern city is a breeze with tots in tow. There are enough things to do in Chicago to last you several days or even a week, but if one day is all you have, there are several must-see sites and must-do activities that will make your trip to Chicago the best family vacation ever. Here are my suggested family vacation ideas for the perfect day in Chicago with kids.


Get an early start to your day at Ina's (1235 W. Randolph Street, 312-226-8227), also known as the Breakfast Queen. Ina Pinkney, who "can't wait to feed you," has appeared in Quaker Oats commercials as herself and was a leader in the effort to ban trans fats. The pink and green walls, fresh flowers and ornamental chickens lining the window sill all make you feel like you're having breakfast in your favorite aunt's kitchen. Staff here care about the restaurant and the food. The kids' pancakes come with milk or juice at $5.79 and parents should try the vanilla bean waffles served with seasonal fruit, well worth the $8.79 price tag.

Traveling to Chicago on a family vacation without visiting Millennium Park (201 E Randolph Street, 312-742-1168) would be a shame. You can't miss Cloud Gate, known to locals as The Bean because it looks just like -- you guessed it -- a giant bean. The statue is a 110-ton stainless steel sculpture that reflects the breathtaking Chicago skyline. Stand underneath The Bean to get a distorted, amusement-park-mirror view of yourself. One of the other best things to do in Chicago with kids is to visit the Crown Fountains: two 50-foot glass towers that project faces of local Chicago personalities.

Insider tip: It's best to visit the fountains during the warmer months, when water spews from the mouths of the 50-foot faces and kids vie for the coveted spot directly underneath the waterfall mouth. Expect to get a little wet even if you stand on the sidelines.

Next on your Chicago family vacation itinerary is Lincoln Square, a picturesque German neighborhood with a store no child (or adult!) can resist: Timeless Toys (4749 N Lincoln Avenue, 773-334-4445). This is an old-fashioned toy store offering wooden animals, musical instruments, classic Radio Flyer toys, books, stuffed animals and costumes for dressing up. With your newly purchased toys, head to the fountain just south of the store where there are benches for the adults to relax and plenty of room for kids to run. A pastry from Café Selmarie (4729 N Lincoln Avenue, 773-989-5595) next door might be just the boost you need to keep your energy up.


You'll need a hearty lunch to continue your exploration of Chicago with kids, so when your brood gets hungry, try Drew's Eatery (2207 W Montrose, 773-463-7397). A wonderful place to broaden your choice of hot dog toppings, Drew's features organic, sustainably produced foods free of high fructose corn syrup and other nasties -- but that doesn't mean it skimps on taste. There are vegetarian and vegan options, but if beef is your thing Drew has that too. Try the Well's Park hot dog with white cheddar cheese -- the name is a shout out to the park across the street where kids from all over Chicago come to play summer sports. Drew's also has a Kidz Corner, where a miniature Oscar Mayer Weiner mobile is available for children to scoot back and forth while you wait for your food.

A few blocks down the street you'll find the famous Old Town School of Folk Music (4544 N Lincoln Avenue, 773-728-6000). The Wiggleworm class is for children from six months to three years old, and offers a chance for moms and dads to listen to music and dance with their young ones. For the older kids in your family, the school offers dance and movement classes which can help kids focus their energy and build self-esteem. Be sure to check schedules online and sign up before you go.


Dinner is next on your Chicago family vacation plan, and Wishbone (3300 N Lincoln Avenue, 773-549-2663) is your best bet for a hearty meal that will satisfy even the pickiest of eaters. The restaurant features "southern reconstruction cooking" in a family-friendly atmosphere. There are lots of options for kids: the mac 'n' cheese will melt in your mouth and the "goober jam" (peanut butter and jelly sandwich) is a great deal at $2.75. Dinner prices for adults are around $10 and the menu features salads, sandwiches and seafood as well as vegetarian and vegan options. The walls are brightly painted with cows, pigs, fruits and veggies, so there's always something to look at. The staff is very friendly and willing to accommodate large groups. Reservations aren't necessary; they can usually get you in pretty quickly since the restaurant is spacious.

After dinner, plan a sweet ending to your best family vacation ever by heading to Margie's Candies (1960 N Western Avenue, 773-384-1035). Margie's is an old-fashioned candy store and ice cream shop with carpet on the floor, dolls in the windows and cozy booths. Along with the old-school charm comes history -- the Beatles ate here when they were in town for a concert! You'll have time to look over the menu as you wait in line for a table. Try "grandpa's turtle" -- three big scoops of ice cream with a candy turtle in the middle, generously drizzled with creamy caramel and topped with whipped cream, finely chopped nuts and a cherry. It's all served in a big white dish shaped like a sea shell and accompanied by a side of fudge to drizzle yourself. It's a family vacation after all -- and the kids won't forget this place!

If the children aren't cranky and you have some leftover energy, check the show times at the Cadillac Palace Theatre for kid-friendly shows like "Shrek the Musical" or Disney's "The Lion King." Kids will laugh their way through the show and you'll feel merrier for the experience.

And there you have it: A recipe for the perfect family vacation day in Chicago with kids, that everyone will be talking about for years to come.

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