We’ve been visiting the city of Chicago with our kids since they were babies. I’ve always loved big cities. And so do my kids, especially my oldest daughter. So the first time we visited Chicago when they were old enough to remember it, they were floored.
Chicago has just about everything that could possibly exist for a fun-filled few family days in a big city! It’s become one of their favorite places to visit, and I know will quickly become one of yours, too!
Getting to Chicago
For us Michiganders, we can get to Chicago in one of two ways very easily: we can hop on a short plane ride (seriously, only like an hour!) or a quick four-and-a-half-hour road trip. Personally, I prefer the road trip method because I love taking road trips with my kids.
And honestly, between getting to the airport early, and the process of flying and going through security, baggage claim, boarding earlier, etc., flying doesn’t actually save you that much time vs. driving there from Metro Detroit.
Planning a Visit
We’ve gone to Chicago with just the four of us (my husband, daughters, and I) and with extended family (grandparents, cousins, etc.). Both ways offer tons of opportunities for family fun, and it can work as a vacation destination with extended family. But, it will require a bit more organized planning with a larger group, like any major city destination. Think larger party reservations, etc.
As far as time limits, believe it or not, we’ve gone and spent only one night, and still made the most of our weekend there. We successfully accomplish this by arriving earlier in the day and leaving later the next day.
We’ve also gone and spent multiple nights there as well. Either way, again, you’ll just have to organize and plan your activities accordingly. If only staying one or two nights, I would never over-schedule ourselves so that we feel overwhelmed by too many activities. And I would always, no matter how many nights we’re there, schedule in some down time to just roam around the city and take in the towering skyscrapers, beautiful architecture, and busy city life that’s always a treat to see and be a part of!
Regardless of who we’re going with and how much time we’re there for, my plans for us are usually the same:
- One or two restaurant visits for a late lunch or dinner (I never try to over-schedule us with restaurants on any trip as it can take up too much time, and the cost can add up.)
- One family activity per day
- Save some room in our evening or early morning schedule just to walk around and grab coffee, dessert, etc.
- One or two hours of shopping, as there is some amazing shopping to do in the city of Chicago!
Chicago Itinerary Options
The Best Chicago Restaurants (start here!)
Breakfast | Wildberry Cafe | 196 E. Pearson St. | 312-470-0590
This famous Chicago brunch house is well-known for its breakfast items and has many kid-friendly options such as pancakes, omelettes, waffles, etc.
Breakfast, Lunch, or Dinner | Grand Lux Cafe | 600 N Michigan Ave. | 312-276-2500
Grand Lux Cafe has a similar atmosphere and menu to the Cheesecake Factory we’re all familiar with (they’re the same company), so it’s very family-friendly with plenty of favorite options!
Brunch | Starbucks Reserve | 646 N Michigan Ave. | 312-283-7100
Starbucks Reserve is a pretty cool restaurant to visit, as there are only six in the entire world! It’s a five floor Roastery that serves so much more than just lattes and macchiatos. You can watch coffee go from bean to cup and order a sit-down breakfast or a tasty pastry made fresh in-house.
Something to note about coming here: there’s a lot of walking between the floors, so lots of stairs and elevators. Bring a stroller accordingly. Also, it’s definitely more on the upper end of the taste-bud spectrum, serving things like lox and avocado toast. I remember my daughter wanting a bagel, them not having it, and me having to go to a regular Starbucks down the street for said bagel after grabbing our own food.
But, it’s still a landmark here, and definitely worth visiting. Plus, it’s gorgeous and a great place to sit if you can even get some kid-free time here!
Dinner | Lou Malnati’s or Giordano’s
These are two of the most famous Chicago pizzerias serving up multiple pie options, including the famous Chicago Deep Dish. We personally love both. My recommendation if you plan to dine at either is to call ahead for reservations, as they do book up fast. Though for a smaller party, it is easy to get on a wait list for same day. Both pizzerias have multiple locations, so check their website for the one closest to you.
Favorite Chicago Attractions (choose a few!)
Chicago Children’s Museum | 700 E Grand Avenue, Suite 127 | 312-527-1000
Located on Navy Pier, another premier Chicago landmark, this museum has so much to do, especially for younger kids. Bonus: they even offer free museum days on some days of the week, so check their website if you plan to come here!
Field Museum | 1400 S Lakeshore Dr. | (312) 922-9410
The Field Museum is one of the most renowned museums in the country, and is home to the largest natural T-Rex fossil in the world—Sue, at almost 90% completed! It’s a true landmark and a must-see. My kids adore visiting here, and always find so many cool things to learn about.
Harry Potter Magic at Play | 835 Michigan Ave.
This super fun Harry Potter exhibit opened this year on Michigan Ave. It’s an interactive Harry Potter-themed play area with rooms themed right out of the books and movies. Tickets should be pre-purchased ahead of time and are available on their website. This exhibit is only in Chicago until Labor Day!
Millennium Park | 700 E Grand Avenue, Suite 127 | 312-527-1000
Millennium Park is an icon, and holds one of the most famous Chicago landmarks: The Bean. It’s an artistic sculpture that flocks tourists from all over. But this park has so much more than just a bean-shaped sculpture. Check their website for current events and happenings. Some of their daily offerings include multiple themed playgrounds for kids, gardens, and plenty of activities and outdoor space for families to enjoy!
Shedd Aquarium | 1200 S. Dusable Lakeshore Dr. Chicago IL 60605, 312-939-2438
The Shedd has one of the largest indoor aquariums, with many large marine life unique to it. Make sure to catch the dolphin show and visit the whale and penguin exhibits on site!
Chicago City Pass is a pass that allows you to pick between five main attractions in the city of Chicago for the price of two—plus an extra three added on! You have nine days to use it, but many people will choose to do Shedd Aquarium and the Field Museum on the same day since they’re right next to each other and share a parking lot.
In my opinion, if you’ve never been to either one, it’s a much better option to do each one on separate days, so you can take your time at both. They will each take up a good chunk of your day as there’s a lot to do and see at each one, and they’re excellent attractions, so trust me: you’ll want to make the most of them.
Make Some Time For Shopping
There is so much great shopping to be done on the Magnificent Mile! The directory linked lists all of the different shopping districts and store locations, as well as store directories.
There are so many places to go shopping. I mean, truly the sky—or dollar in this case—is the limit. My own kids’ personal favorite place to shop here is the American Girl store! They look forward to coming here and count down to it. They even make a list of what they’ll be buying their American Girl doll the next time they visit the store in Chicago. The location is also pretty great, as it’s right on Michigan Avenue, and an easy walk or Uber ride away.
There are lots of other kid-friendly stores, as well as some strictly for us mommas. And don’t knock some of the retail stores we already know and love from Metro Detroit or our local malls; retailers garner special pieces strictly for larger cities, and Chicago is no exception.
Some of my favorite and most unique pieces have been purchased here, from some of the same retailers in our own malls, but the items are unavailable in the Metro Detroit area. Even if all you do is walk around and do some window shopping, it’s worth checking out all the shops located along the Magnificent Mile.
End Your Chicago Trip at Navy Pier
There is so. much. to. do. on. Navy. Pier. Quite honestly, you could easily spend a whole day and evening here. And we have before. There’s a ferris wheel, tons of restaurants, exhibits including the Chicago Children’s Museum I mentioned earlier, ferry rides on Lake Michigan, and so much more! And in the summer months between Memorial Day and Labor Day, there are fireworks on Lake Michigan.
But one of our favorite things to do here is grab some ice cream in the evening after dinner and just walk around the gorgeous pier once it’s all lit up at night. Events and dates change here all the time, so be sure to check the website.
Bonus Tips to Chicago
- Like any major city, the majority of transportation is done by walking and/or using public transport such as buses and Ubers. It’s very difficult to find public parking spots due to crowded city streets, so once you park your car in your hotel, it might very well be the last you see of it until the end of your trip.
- Try to find a hotel as close to Michigan Ave. (aka The Magnificent Mile) as possible. Most of the tourist sites and attractions are located there. It will allow you to walk to many of your destinations and avoid having to get a taxi or Uber.
- If you have younger kids, bring a stroller since there’s so much walking, especially on busy public streets.
- Chicago can be a tad overwhelming trying to get so much done in one city. We’ve visited so many times now and have yet to do all that we want. My suggestion is to have each family member pick one main activity they want to tackle and add it to your list. Once you tackle the one must-do for everyone, you can add more or choose to save some for the next visit. The nice thing about visiting the city of Chicago is that it’s not too far for us Metro Detroiters, making it the perfect short weekend family getaway!