5 Tips for Visiting Chicago with Kids


As parents, we want the best for our children, the best schools, nutrition, doctors, etc. with the ultimate goal of raising self-sufficient adults who lead compassionate and fulfilling lives. In an effort to help prepare them for adulthood and add to their childhood memory bank, it is important to expose them to different cultures, educate them, and help them learn to appreciate diversity. And what better way to help them alleviate any biases or prejudices they may contain than by immersing them in different cultures through travel? 

I get it, who has the time or money for travel these days?! But here’s the thing, if we wait until we have the money and time it will never happen. So start today to put aside a bit of money, forgo that morning latte, eat in, or whatever you need to do to start your travel fund. When it comes to time allowance work with what you have, everyone has a weekend, take a weekend off from work, inform the coach you’ll be out of town, and make a family getaway a priority! The kids aren’t getting any younger, and who knows what the future might hold, no one saw 2020 coming! 

So we’ve established the significance of making travel a priority, and addressed the time constraint issue and financial component, now, let’s make the most of your trip! Here are my tips for making the most of your time and money in order to provide a culturally immersive experience that is educational and fun. I’ll be sharing our recent trip to Chicago! We managed to see, do, eat, and be exposed to a plethora of experiences in 48 hours! 

Tips for making the most of your time and money in order to provide a culturally immersive experience that is educational and fun in Chicago.

This is the world’s tallest building designed by a female architect and is the third tallest building in Chicago, St. Regis designed by Jeanne Gang.

Visit the Must-Sees that Are FREE in Chicago

After checking in at the hotel and finally figuring out how and where to park the car we ventured out into the city. Our first stop, was Navy Pier, the 3,300-foot-long pier on the shoreline of Lake Michigan, located in the Streeterville neighborhood.  I will warn you that when in Chicago one might underestimate the distance of their travel especially when on foot, so make certain children have comfortable shoes, socks, and pack water bottles. Navy Pier is one of Chicago’s top attractions with rides, games, shops, restaurants, and cruises but doesn’t fall for the trap!

You could easily drop all your money in one visit if you are not careful. Instead of participating in activities that you have at home, for example, festival and carnival games and rides, instead look at the Navy Pier calendar for free events, performances, etc, going on. And don’t forget the priceless and invaluable moments that lie in capturing candids with the Chicago skyline, now that’s definitely something you don’t get at home! Our next stop is Millennium Park! 

Millennium Park is home to the famous Cloud Gate Statue (“the bean”), the Pritzker Music Pavilion (designed by the architect Frank Gehry, who should sound familiar to Toledoans since Toldo has one of his buildings, the Center for the Visual Arts on the Toledo Museum of Art’s campus), there’s rock climbing, interactive fountains, artwork, playgrounds, and more! Again, prior to your visit check the Millennium Park’s calendar for free events. We had the pleasure of listening to the Grant Park Symphony Orchestra, the nation’s only remaining free outdoor classical music series. 

Additional FREE attractions to see while in Chicago include Buckingham Fountain, Garden Park Conservatory, Chicago Botanical Gardens, and Lincoln Park Conservatory. 

Eat at Establishments that are Iconic in Chicago 

You can’t say Chicago without deep-dish pizza coming to mind! The most iconic food renowned for the city has to be Chicago deep-dish pizza. And after walking around the city all day and enjoying the many free establishments, performances, and architecture the city has to offer you will be famished. And what better way to end the perfect day in Chicago than with a deep-dish pizza enjoyed back in the comforts of your own hotel room. Your dogs will be barking after walking around the city and chances are the kiddos’ patience will not withstand a restaurant so roughly 45 minutes to an hour before you plan on being back at your hotel to order your pizza. Remember these are deep dishes and they feed a lot. One large fed four kids and two adults. 

If you happen to be on Navy Pier during lunch Billy Goat Tavern is a great spot to stop off at, perfect for a reasonably priced family-friendly lunch or dinner and it is the home of the famed “Cheezborger” immortalized by John Belushi on Saturday Night Live. Check out the other Billy Goat Tavern locations located in and around the city. 

Additional world-famous food you don’t want to miss out on when in Chicago, Chicago hotdog, Carmel and cheese mix popcorn, and jibarito.

Educational and Fun Hot Spots in and Surrounding Chicago 

The Field Museum of Natural History, The Museum of Science and Industry, The Chicago Children’s Museum, Medieval Times, Shedd Aquarium, Skydeck at Willis Tower, Adler Planetarium, Frank Lloyd Wright Trust, etc. There is no disputing the fact that there is a significant amount of awesome educational and fun museums, tourist destinations, and experiences to be had in Chicago. The dilemma becomes deciding which ones to visit. When deciding it is important to take time and admission cost into consideration. Determine the proximity of your destination in relation to where you are staying, how long will it take you to walk or drive, and if driving what is the cost to park? Always factor in an additional 20 minutes to stop and give kids a break if walking and/or find a parking spot if driving. Secondly, determine the admission price for the family, and inquire about any discounts with reciprocity memberships, AAA, military, teacher, etc. Lastly, make reservations, most museums require reservations in advance. Since we only had 48 hours in the windy city we decided on one educational location for this trip, Shedd Aquarium!  

We used our Zoo membership to receive discounted tickets on admission. We arrived around 11am and our first stop was lunch. Yes, I said lunch, lol! They have a food court stocked full of options, kids’ meals, pizza, burgers and fries, salad, etc. There is something for every picky eater. So we grabbed lunch before the crowd and then explored. 

When visiting be sure to splurge on the 4-D experience! We watched BBC Eath’s Shark’s and the 3-D glasses, bubbles, music, chair mechanics, etc. made it an experience to remember. Also, be sure to catch a couple of animal spotlights! 

There are no hard copies of maps, spotlight times, etc. Be sure to plan your Shedd Aquarium visit prior to your arrival. 

Know Your Limitations

Roaming around in a new city can be fun and exciting with so many novel places to see and events to experience but know your limitations. Do not cram too many stops in one day. Take breaks when you need them, refresh, hydrate, have a snack and once everyone is revived continue on. If everyone is tired then be okay with calling it a day, remember there is a lot to see so much so that you can start noting places to see and things to experience on your next visit. 

Seek more Diversity in Multicultural Opportunities 

Large cities are no strangers to ethnic neighborhoods. Why not expose the kiddos to more culture diversion by stopping off at Lincoln Square, Greek Town, Polish Downtown/West Town, Little Italy, or Chinatown?

We opted for Chinatown where the children enjoyed having lunch at Rotary Sushi Bar, perused the shops, and left with a souvenir to commemorate the day. 

We had an amazing time visiting Chicago and are already planning our next trip! 

So what cities are on your list? Just because school has started doesn’t mean the exploring, weekend getaways, and overnight excursions have to stop! 

One thought on “5 Tips for Visiting Chicago with Kids

  • Perfect! I’m taking the family with me on a business trip next month and this has given me some great new ideas for my kiddos’ first trip to The Windy City! 🙂

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