To me a perfect family vacation is one where the kids are allowed to be kids, they stay entertained with little work on my part, I don’t lose any of my children, and I don’t have to sell my firstborn to afford it.
I didn’t think that a big city would ever fit this mold. I mean I can’t even keep track of my kids in my own house some days and paying to take 5 kids to anything adds up quickly. That was until we moved just a few hours from Chicago. We have explored many of the things to do in Chicago with kids and even tried out a few things that maybe weren’t the best options. . . I’ve never heard “my legs are tired” so many times in my life!
Chicago is a family-friendly city but that doesn’t mean that everything is made for families. You may be tempted to make your Chicago sightseeing plans based on the typical traveler’s guide, but not all of these are kid-friendly; and while there are some choices that would be “good,” there are others that would be “better.” When you travel with kids your time and money are precious. By making your plans based on these tried and true suggestions you will rest assured that you are investing in the “better” things and not wasting your time and money on things that are just “good.”
Chicago is made for families. . . and reliable walking shoes and strollers. I have compiled a list of 8 things you shouldn’t do while giving suggestions of what you should do instead.
Of course, when you’re on vacation, it is also important to know where you should really spend your money. There are tons of cheap things to do in Chicago with kids but I have also highlighted a few things that are worth splurging on to make sure that you get the full Chicago experience.
1. Don’t Visit the Willis Tower Skydeck
- 1. Don’t Visit the Willis Tower Skydeck
- 2. Don’t Walk the Magnificent Mile
- 3. Don’t Drive in Chicago
- 4. Don’t See a Broadway Show
- 5. Don’t Visit Navy Pier
- 6. Don’t Pack a Sack Lunch
- 7. Don’t Do An Architecture Tour
- 8. Don’t Go to the Art Institute
Popular. Long lines. Lots of waiting. Impatient kids. Hungry kids. Expensive.
Instead, Have Dessert at the Signature Lounge (Splurge)
I think this is one of the best-kept secrets of Chicago. The Signature Lounge is on the 96th floor of the Hancock building which has views that are comparable to those at the Willis Tower, AND you can sit down and enjoy the view while you have a drink, appetizer, or dessert (each adult must-order a beverage). These can run anywhere from $10-$20 which may be more than your average donut, but the view makes it worth every penny and you can take a load off those feet for a while and enjoy a cold drink.
Children are allowed in the lounge and they even have non-alcoholic beverage options. The limeade we had last summer was out of this world! Also, don’t forget to take the little miss to the potty to check out the best view in Chicago hidden in the women’s restroom windows.
The pictures don’t do it justice. Sorry guys, you will never see the real thing, the men’s restroom does not have this view.
2. Don’t Walk the Magnificent Mile
LOTS of walking. Tired little feet. A limited selection of kid’s stores. Expensive shops. Crowded streets.
Instead, Play at Maggie Daley Park
Those little feet would much rather be running around the massive 20-acre park made especially for kids. Named after Maggie Daley, the former first lady of the city who died in 2011, this park (which used to be a parking lot) is a dreamland for any kid and is at the top of my list of things to do in Chicago with toddlers. There isn’t any better way to get those wiggles out.
You could spend the entire day in the enclosed 3-acre play garden or venture out and do a little rock climbing or mini golf (for an extra charge). Picnic tables are available and there are even some water features in the play garden to cool off during the hot summer months. If you are there during the winter months, you will definitely want to check out the “skating ribbon” that winds around the park creating an outdoor ice skating experience. Although there are options to spend money here, you don’t have to spend a dime to experience this unexpected big city gem.
3. Don’t Drive in Chicago
Congestion. Aggressive drivers. Pedestrians. Taxis. One-way streets. No parking. Expensive parking. Anxious kids in the back seat.
Instead, Ride the Train or Divvy Bikes
If you want to avoid the headache that is driving in Chicago, travel like the locals and ride the ‘L’ train or pick up a divvy bike if you have older kids that can handle a full-size bike.
The ‘L’ is a very clean and well-thought-out public transit system. For my train-loving toddler, it is always the highlight of our trip. The ‘L’ takes you within walking distance of any key place you wish to go in the city and kids under 7 ride free. We often get a hotel room by the airports (cheaper rates) and ride the train downtown. I don’t have to close my eyes while my husband drives like Jason Bourne and my kids enjoy the city from the train windows.
I can’t wait until all my kids are old enough to handle the Divvy bikes. This is my favorite way to see the city because you can go where your walking legs can’t. For only $10 a day, you can hop on a bike and ride the trail along Lake Michigan or the city streets. The only catch is that you have to check into one of the stations every 30 minutes, but this is easy with the hundreds of stations all over the city. There is nearly one on every block.
Riding Divvy bikes out to the Alder Planetarium will give you the best views of the city.
4. Don’t See a Broadway Show
A small selection of family-friendly shows. $160 nosebleed seats. The stress of keeping kids quiet. Late shows. Tired kids. See the show on tour.
Instead, Go to a Cubs Game (Splurge)
If you really want the full Chicago experience, your money would be much better spent going to the iconic Wrigley Field and seeing a Cubs game. At these games the noisier the kids are, the better! Since moving to Illinois my son has become an avid Cubs fan (especially after winning the world series in 2016) and has made it mandatory to attend at least one game a year.
If you want to get the best prices on tickets don’t go to a Cardinals/Cubs game and make sure to wait until the 2nd inning to buy tickets from scalpers outside the park. This will test your negotiating resolve and leave some money in your budget to buy that Chicago dog during the game. Just be advised that even with scalping this may qualify as a splurge if you have lots of kids to get in, but it’s still pennies compared to a Broadway show.
Nothing to do. Long walk. Expensive
Instead, Visit a Museum
You will never be bored if you take advantage of the array of museums Chicago has to offer. This is by far one of the best things to do in Chicago with kids. They are world-renowned museums for a reason. You could literally spend an entire day at any one of these museums and not see everything. They are massive.
Our favorite museums include (in order):
- The Museum of Science and Industry
- Shedd Aquarium
- Field Museum of Natural History
- Alder Planetarium
As mentioned in this article, you can use your CityPASS to be admitted to any of these museums. However, if you plan ahead, you can also use one of the best-kept secrets: the ASTC reciprocal pass. This museum membership, bought at a participating museum near your home, will allow you to enter all of these museums for FREE along with hundreds of others in the United States. It has saved us hundreds of dollars in the last year. However, the pass does not include the Shedd Aquarium. Illinois residents can still see the aquarium for free, along with all other museums, on free museum days that are held throughout the year.
6. Don’t Pack a Sack Lunch
Instead, Eat the Food that made Chicago Famous (Splurge)
I don’t know any kid that doesn’t love pizza, and Chicago is famous for its deep dish. Of course, every pizza joint will claim that they are the best and only authentic Chicago pizza, but our favorite is Lou Malnati’s. The “Malnati salad” is topped with the perfect sweet dressing. Their pizza is pretty excellent too, just make sure you order ahead of time as deep-dish pizza can take up to 45 minutes to bake.
If you need something quick, grab a Chicago dog from one of the food trucks next to Millennium Park or share a big bag of Garrett’s popcorn, just be prepared with lots of wipes for those cheesy orange fingers. Eating your way through the city may qualify as a splurge if you go all out, which I recommend that you do. If you stay for a week you could easily try a new pizza place every day. When it comes to seeing Chicago, eating the food they are known for is part of the experience.
7. Don’t Do An Architecture Tour
Fascinating and informative, but not for kids. Just an expensive boat ride.
Instead, Visit Lincoln Park Zoo
If you are looking for cheap things to do in Chicago with kids, Lincoln Park Zoo should be at the very top of your list. You don’t get any cheaper than FREE! You will forget you are sitting right along the shores of Lake Michigan in downtown Chicago as you check out some impressive wild animals.
This zoo has pretty much any animal your kids would want to see including a lion, gorilla, zebras, bears, giraffes, and penguins, just to name a few. This is pretty impressive for a place that doesn’t charge a dime to get in. However, if you don’t mind spending a little, there is the option of a 5-D virtual submarine ride, or a train and carrousel ride. You could easily spend half of the day here and if you visit at night during the holidays they have zoo lights to make the experience even more memorable.
8. Don’t Go to the Art Institute
Quiet space. Expensive admission. Lots of running space. Kids getting lost. Adult atmosphere. Priceless works of art. Don’t touch!
Instead, Stroll Through Millennium Park
Let’s be honest, all kids want is a license to run around and be loud, and this park has LOTS of running space comprising of 24.5 acres and filling up the entire block between Michigan Avenue and Columbus Drive. You would never guess that this area used to be covered with unsightly railroad tracks and parking lots.
My kids couldn’t get enough of their reflection in “The Bean”.
Some notable (and free) places you’ll want to visit in Millennium Park are Cloud Gate (otherwise known as “The Bean”) and the Crown Fountain. Both are iconic works of art that have become symbols of the city. If you visit during the summer be prepared with an extra change of clothes for the kids when you visit the Crown
Fountain. It’s hard for a toddler to resist splashing in the shallow reflecting pool at the bottom of two 50-foot glass block towers with projected LED screens.
Millennium Park is also a great place for cultural events so make sure and check out the special events calendar online before you go.
Now that you have a narrowed-down list of the best things to do in Chicago with kids, your next challenge may be trying to pull your kids away from each one as you move on to the next. The best part about a family vacation to Chicago is that your kids will hit the pillow hard (like a coma, hard) after a long day of seeing the city and THAT really is every parent’s dream vacation.