Chicago is a city that has been on my husband’s “family trip” radar for years. For us, it’s about a five-hour drive, so it makes for a perfect short getaway with our sons. With our oldest now 18, we want to squeeze in as many family road trips as we can before he leaves the nest.
Here’s an overview of how our family visited Chicago, including the top things to do, how much it cost, and my words of advice to fellow family travelers.

Monday (Spring Break for us – early April)
We drove straight off the highway and visited Millennium Park first, where we saw the infamous “bean,” then we walked a block or so to Lakefront Trail, which lines Lake Michigan. The water was clear, the area clean, and the air cold. At a busy crosswalk light, I mistakenly said that the traffic was “biting at the chew” instead of “chewing at the bit”; it was so cold that my face, and perhaps my mind, began to freeze.

We returned to our car to find our hotel, only to discover it was just a few blocks away as well. In hindsight, we should have parked at the nearby 24-hour lot and then walked around the parks and trails. We stayed at the Best Western on Michigan Avenue, with a spectacular view of the high rises, a glimpse of Lake Michigan, and even the Ferris wheel at Navy Pier in the distance.
For dinner, we walked to nearby Aurelio’s Pizza. There, we got our first-ever deep dish Chicago-style pizza (the server joked that only tourists order it). It was worth every calorie.

We finished the evening out with another walk along the lake, making our way over to the planetarium and then back to the hotel. By this point, our 16-year-old son commented, “Everywhere I look, people are running.” It was true – running clubs and single joggers alike were always within sight.
Monday’s bill:
$7 street parking for two hours
$50ish for dinner for four at Aurelio’s
Tuesday
I woke on Eastern time at 5:00am (not unusual for this writer/farm girl, haha), looked out the window and saw someone jogging. If I had reservations about visiting Chicago because of the violence it’s known for, the early morning runners soothed my fears.
When my family woke, we ate at the Best Western (a nice surprise, since they didn’t advertise the free hot breakfast). From there, we walked to the Field Museum; this was an absolutely lovely stroll. It was a foggy morning, and we only had to cross over Michigan Avenue to get to a park trail that led us right to the museum’s doors.

You can Google the details about the Field Museum; in short, if you’ve never been there, it’s worth a visit. I particularly loved the many displays of bird species and the sacredness of the Egyptian mummies, not to mention the famous Tsavo lions (their story inspired the 1996 movie “The Ghost and the Darkness”).
After the museum, we walked to the Fine Arts Building (built in 1885) on Michigan Avenue. My husband has a knack for finding unusual things to do in the cities we visit, and this was a real treasure. We found ourselves in this particular building because of a business on the ninth floor called Performers Music, which has scores of sheet music. (Our sons play piano and trombone.) The store itself is a gem, but I would be remiss not to mention the building itself and the elevator, which is still worked by an operator.




Tuesday’s bill:
$140 Field Museum, four tickets including one special exhibition
$50 lunch at the museum (you could eat for less, and even bring your own food)
$110 dinner at The Burger Bar (I regretted this choice after getting the bill, but if that’s in your budget, then go for it – the food was delicious, just more than what we normally spend on a meal)
Wednesday
By this time, my family had a giggle at every car horn because it was so constant compared to what we hear in our Kentucky town. I noted that pickup trucks were few and far between, and the runners continued running.
We visited the Museum of Science and Industry, which was a 10-15 minute drive from the Best Western. I don’t want to diss the Field Museum, but it’s worth noting that the science museum was much more interactive and entertaining in general. We saw dissected bodies, explored how storms work, and walked through a mirror maze that led us to a section all about symmetry and design in nature. There was even a handmade dollhouse that made the little girl in me squeal with delight and awe.

We returned to Aurelio’s for dinner because between the convenience, food, and price, it was worth going back to.
Wednesday’s bill:
$80 Museum of Science and Industry
$22 parking at the museum (worth it – the garage is under the museum, I don’t know if there are other options for parking)
$40 lunch at the museum (kid’s meals for all of us, but filling)
$60 dinner at Aurelio’s
Thursday
On Thursday morning we had our last breakfast at the hotel, then hit the road to return home to our dogs and chickens. (Special shout-out to my father-in-law for farm-sitting for us!)
Thursday’s bill:
$75 total overnight parking near hotel
$490 for 3 nights at the Best Western
So that’s a family trip to Chicago in a nutshell! It’s a great city, and there is plenty to see and do if you stay longer.
If you’ve been, tell me your favorite things to do in Chicago in the comments section below!
Happy travels,
Cherie Dawn
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