Kidding Around in Chicago

Chicago Postcard

One of the things I’ve learned since moving to NYC and making annual extended summer jaunts back to Michigan to visit family and friends a part of our lifestyle is that it’s pretty easy to wear out your welcome when you crash at someone’s house for too long (even, or especially, if it’s your parents’ house). So when my husband mentioned he had to be in Chicago for work the last week of July, and the boys and I could tag along if we wished, I jumped at the chance. It would give us an opportunity to get our fix of some of the basics of city life we missed, plus it would let us live on our own terms for a few days, as opposed to what has become our summertime normal of constantly trying to squeeze ourselves into someone else’s lifestyle and avoid making too many waves (or too big of a mess).

To the delight of our oldest, my husband booked us tickets on the Amtrak into Chicago. My oldest lives for the railroad and dreams of being a train engineer, so while driving would have put us at our destination quicker, we couldn’t pass up the opportunity to let him ride the rails (plus it did save us the cost and hassle of parking downtown).


Train Ride

Train Snack

Our train delivered us to Union Station in downtown Chicago around dinner time on a Sunday evening. Loaded down with luggage, we elected to grab a taxi to get us to our hotel. Similar to our experience at NYC airports, there was a taxi line outside the station to help manage transportation needs for all arriving passengers. Depending on how much luggage you have and where you are staying, the station’s location makes walking or a quick transfer to a Chicago Transit Authority (“CTA”) bus, subway or elevated train convenient options to consider.

My husband’s employer had him booked at the Hard Rock Hotel, which, while not the most kid-friendly choice, did offer an amazing location that was walking distance to Millennium Park, the Magnificent Mile, the Loop, Navy Pier (ok, Navy Pier was a bit of a hike, but we walk A LOT in NYC, so by those standards it wasn’t too bad), and so much more. Another upside was the ping pong table in the lobby that kept my boys occupied for a good ten minutes or so each time we entered or exited the building.

On the downside, the hotel room had the requisite ridiculously overpriced minibar/fridge, which was made worse by the fact that a giant tray of snacks sat in plain sight on the credenza and charges for the items “are automatically billed to the room when one of the motion sensors on the tray is activated”. That’s right, motion activated sensors on that $10 mini can of Pringles. You can imagine the conversation I had to have with the boys. “Please don’t touch anything on the tray. We will get charged if it is moved.” “It doesn’t matter if you don’t open it.”  “Seriously. Don’t touch it.” “I DON”T CARE IF YOU JUST WANT TO LOOK AT IT, THE TRAY DOESN’T CARE IF YOU JUST WANT TO LOOK AT IT. DON”T TOUCH THE TRAY.” They eventually got the point, but that didn’t stop them from conducting all their activities and storing all their stuff right next to that tray. As a result every time we entered the room I held my breath as they carelessly dropped their belongings practically RIGHT ON TOP of that tray of goodies, my mind screaming FOR THE LOVE OF GOD, PLEASE DON”T TOUCH THE TRAY.

I’m sure you care more about how we spent our time outside the hotel than my battles with the mini fridge and snack tray, so I’ll get on with it and give you the rundown of our Chicago itinerary.

Day 1 – Because of my oldest son’s obsession with trains, I knew we had to start our trip at the Museum of Science and Industry.  Located about eight miles south of downtown in the Hyde Park neighborhood, the museum is a little out of the way, but well worth the trip. Using the Metra commuter rail system, we were able to get to the museum quickly and inexpensively from the hotel by walking just a few short blocks to Millennium Station and catching a train that dropped us a couple blocks from the museum entrance. Kids 11 and under ride free, so our round trip cost was only six dollars, and more importantly my son got to ride a DOUBLE DECKER TRAIN FOR THE FIRST TIME EVER.


Metra 2

Metra 3

We probably could have ended our day with that ride and been all set as far as he was concerned, but once we made it into the museum and he started making his way through the exhibits he realized the train ride was only the beginning of something really, really good.

When we arrived, there was a ridiculously long line to purchase tickets, but thankfully the museum offered self serve kiosks in addition to the ticket desks. With no line at the kiosks, we had our tickets and were into the museum in less than five minutes. Because we only had a few hours available for the museum, we passed on paying for upgrades to gain entrance to a handful of special exhibits. There was more than enough to keep us busy with the general admission exhibits! Here’s a few of our favorites:

  1. All Aboard the Silver Streak: Pioneer Zephyr
  2. Farm Tech
  3. Genetics and Baby Chick Hatchery
  4. Science Storms
  5. The Great Train Story
  6. ToyMaker 3000: An Adventure in Automation
  7. Transportation Gallery

Pioneer Zephyr

Hall of Transport

Steam Engine

We could have easily spent an entire day at this museum (in fact, my oldest begged for a return trip each day), but with other commitments had to high-tail it out after a late lunch from the surprisingly tasty, variety-filled (I actually found satisfying meat, dairy and gluten-free options for me), albeit overpriced, cafeteria.

A quick return trip on the train brought us back to Millennium Station where we met up with my in-laws and sister-in-law who had just arrived for an overnight stay to join us at a Cubs game later that evening. Millennium Station is located directly underneath Millennium Park, a relatively recently built (10 years ago) cultural center and “town square” of sorts. We spent some time walking around, enjoying the people watching, and taking in some of the park features such as Cloud Gate (otherwise known as “the bean”), the Lurie Garden, and Crown Fountain (aka “the spitting fountains” per my boys). Before leaving, we stopped for a rest at the Jay Pritzker Pavilion and took in a rehearsal by the National Youth Orchestra for a performance later that evening.


Milennium (2)

After that, it was time to get ready for a ball game! My husband and boys are big baseball fans and we purchased a ballpark passport earlier this year with the goal of eventually seeing a game in every ballpark across the country. We were hoping to stamp out two parks on this trip by catching both a Cubs and a White Sox game. Unfortunately, the MLB scheduling gods were not working in our favor, so we had to settle for just a Cubs game. But really, no Cubs game is just a Cubs game. It is an event, a social outing of epic proportions.

One of the oldest ballparks in baseball, and still using a classic hand-turned scoreboard (for the time being, due to forthcoming renovations), Wrigley Field is the quintessential friendly, neighborhood ball park where everyone is welcome. (It certainly didn’t hurt our cause as outsiders, Detroit Tigers fans to be exact, when my mother-in-law made quick friends with the Cubs fans surrounding us by telling them the story of her grandfather, who played for the Cubs from 1911-1917.) The park is easily accessible from downtown using the subway/elevated train system, and I like to think we rode in with a bit of winning magic for the struggling Cubs, as they walked off the field with another one in the “W” column that night.


Wrigley 2

Family Selfie

Day 2 – We started day two with a trip down to the Museum Campus, a 57-acre park that is home to the Adler Planetarium, the Field Museum of Natural History and the Shedd Aquarium, as well as Soldier Field, home of the Chicago Bears football team. It offers sweeping views of Lake Michigan and the juxtaposition of the downtown skyline, crowned by the Willis Tower. You can get to the Museum Campus via car/taxi, Metra train or CTA bus. Biking to the Museum Campus along Lakeshore Drive is another great option. Leaving from one of the many bike rental vendors between Navy Pier and Millennium Park, it’s an easy two to three mile ride along the shores of Lake Michigan. A water taxi that operates between Navy Pier and Shedd Aquarium, which I experienced on prior trips, is another nice option to get you to the Museum Campus.

Museum Campus 2

Museum Campus

Museum Campus 4

We elected to spend our time on the Museum Campus at Shedd Aquarium, the largest indoor aquarium in the world. The Shedd Pass Plus ticket option we chose gave us full access to the exhibits, as well as the choice of one add on from the live aquatic show, Jellies special exhibit, Stingray Touch experience or a 15 minute 4-D movie. Of course my boys went with the 4-D movie, which was a cute spin off of the Ice Age series. We spent several hours at the aquarium and lingered at some of our favorite exhibits:

  1. Amazon Rising
  2. Waters of the World
  3. Wild Reef

If possible, try to plan to visit in the morning, as the aquarium is an extremely popular attraction and lines often form outside the building in the afternoon due to capacity constraints.


Shedd 3

Shedd 2

After whiling away our morning checking out ooh and aah worthy sea creatures, we headed back to our hotel to chart out our plan of attack for the rest of the day (I’m not really a pre-planner when it comes to being a tourist, flying by the seat of my pants suits me best, as I like to go with what I am feeling in the moment). My husband had evening meetings, so I knew I had several hours of daylight left to keep my boys interested and occupied and I wanted to find something to do that would let them “be boys” for a bit and get their energy out. After a bit of online research, I came across Bobby’s Bike Hike. I was drawn to Bobby’s because of their one-of-a-kind kid-friendly bike tour, Bobby’s Tike Hike, appropriate for ages 10 and under. However, we had already missed the time slot for this once daily tour, so I signed us up for the Museums and Parks at Sunset tour, a two hour tour starting at 6pm, that indicated it would accommodate young riders.

With a plan for the evening and some time to kill, the boys and I headed for a walk up the Magnificent Mile along Michigan Avenue. To the delight of my boys, our walk started with a crossing of the Chicago River over the drawbridge connecting South and North Michigan Avenues. We reached our destination, the Water Tower Place (essentially an upscale mall), just south of the John Hancock Tower, without any major side excursions and made our way to the LEGO store. I actually tried to get my kiddos to help me face my fears and join me on Tilt at the John Hancock Observatory before heading to the store, but they were having none of it. With two boys, it’s hard to skip or postpone the obligatory trip to the LEGO store, kind of like trying to skip or postpone the American Girl store (which, by the way, is adjacent to the LEGO store) is impossible when you have girls in tow. We killed a good hour in the store, as my boys love the wall of bins filled with what seemed like every type and color of block available. They spent that time creating their own custom masterpieces (a replica of Chicago’s elevated train loop for my oldest and a playhouse for my youngest), which we were able to purchase for significantly less than the prepackaged kits.


When we finished up, a pre-bike ride snack was in order, so we stopped at Wow Bao, a Chicago-based chain selling steamed Asian buns, dumplings and other Asian fare in a fast casual setting. A few buns were the perfect on-the-go snack as we made our way to Bobby’s Bike Hike.

When we arrived at Bobby’s we were informed that the potential for storms and rain showers had left us as the only reservations for our sunset ride, but they were willing to ride if we were. Without hesitation I said “Let’s do it.” The thought of getting rained on a bit didn’t seem nearly as bad as the thought of trying to keep the boys entertained and away from the tray of minibar offerings in our hotel room for the rest of the night.

Because we were the only riders, our fantastic guide, Tim, gave us the option of choosing our route for the evening. I mentioned we might try to head up to the Lincoln Park Zoo the following day, but was unfamiliar with the area and he immediately planned a route that would get us acclimated while keeping us biking exclusively on paths and trails. We had a blast riding along the shores of Lake Michigan north of Navy Pier. It was a great time of day to see and experience how Chicago locals enjoy the parks and beaches around the lake. From biking and running to more beach volleyball courts than I could keep track of and group yoga sessions on the beach, we were surrounded by activity. When we reached Lincoln Park, we crossed into the park and enjoyed a leisurely ride around the zoo before heading back south to check out a famous statue of Abraham Lincoln. It was about that time our luck finally ran out and the summer storm that had been threatening trapped us in the middle of a torrential downpour. While we never made it to see Abraham, through the quick thinking of our trusty guide, we were able to take cover under the Ulysses S. Grant Memorial until the weather cleared. About twenty minutes later, a little wet, but no worse for the wear, we emerged and finished our trek back out of the park and down the shoreline. The boys had a blast biking the paths covered in water left behind by the storm. More than once I wished I was capable of taking photos while riding my bike (I am a definite two hands on the handlebars kind of girl), because I smiled the whole way back as my boys sped through the puddles, feet up and out.


Day 3 – Day three dawned with my boys begging to ride bikes again, so I ditched my original thought of taking either the bus or taxi up to the Lincoln Park Zoo and we headed back to Bobby’s Bike Hike to rent bikes. Now that we were “experienced” Chicago bikers, the boys and I were ready to set out on our own. The late morning bike ride had a much different feel than the evening ride, as the paths were much less crowded and the parks were now filled with kids participating in summer camp activities as opposed to adults blowing off steam at the end of a long work day.

Lincoln Park 3

Lincoln Park (2)

Lincoln Park

When we arrived at the zoo, a 35 acre gem that is free to the public 365 days per year, my first thought was Yes! It’s shady. I am actually not a big fan of zoos for a variety of reasons, one being that I always remember the zoos I visited in the past as being sun-scorched and hot. (OK, I’ve really only been to one or two other zoos in my life and I think my dislike of zoos is actually a result of some long buried adolescent angst resulting from someone in grade school comparing me to a hippo. But whatever, it was the heat. That’s my story and I’m sticking to it.) In any event, the Lincoln Park Zoo provided a lush, beautiful setting that I had been unaccustomed to in other zoo experiences.

Zoo 5

Zoo 4

Aside from checking out the animal exhibits (the primate house, giraffe, and Bactrian camels were favorites), my boys enjoyed a ride on the children’s train (of course) and on the endangered species carousel. After a couple of hours my boys were ready to hit their bikes again, and were on a quest to find the Abraham Lincoln statue that had eluded us the prior evening.

Zoo 3

Zoo 2


When we finally made it to the south end of the park, there he was! To our delight, while checking out Abe, we ran into Tim, our tour guide from the night before, who had just arrived at the statue with a large group of sightseer’s in tow. My youngest actually begged to join up with “Mr. Tim” and his tour group, but luckily I was able to pull him away without a major meltdown with promises of a ninja warrior show at Navy Pier.


To end a great morning on our bikes, we stopped at a self-serve frozen yogurt stand conveniently located near the entrance to the pedestrian bridge that would take us out of Lincoln Park, over Lakeshore Drive, and back onto the lakeside path that would get us to our bike drop off point and Navy Pier. It was the kind of self-serve place with several flavors and dozens of toppings, perfect for allowing the boys to create their own custom fro-yo masterpieces.



Bike Ride

Bike Ride 2

After dropping the bikes off, it was a quick walk to Navy Pier, where I had purchased tickets for the 2pm matinee of Cirque Shanghai Warriors at the Pepsi Sound Stage. The show offered the perfect opportunity to rest our bodies while engaging our senses after an activity filled morning. It was thrilling and funny and kept the boys on the edge of their seats for the entire 75 minute performance.

From there, we couldn’t miss a ride on the famous Navy Pier Ferris Wheel, which at 150 feet tall is the visual focal point of the complex and offers sweeping views of the Chicago skyline and Lake Michigan. I have to admit, the ride was a bit of an anxiety-inducing experience for me, and I think I held my breath the entire seven minute ride.

Navy Pier

After grabbing a quick snack, I planned to end our day at the Chicago Children’s Museum. The museum is open until 6pm during the summer months, and I thought a late afternoon visit was a good choice for a couple of reasons, one being that I wasn’t sure how long the museum would hold my nine year old’s attention and the other being that I hoped the crowds would thin out later in the day. My hunch about the crowds ended up being right on and we enjoyed having the place virtually to ourselves and not having to spend more time waiting our turn than actually taking part in activities. On the other hand, my concern about the museum holding my nine year old’s attention turned out to be unfounded. Both boys had a fantastic time, and were so engrossed in the exhibits that we missed out on seeing a large portion of the museum and literally had to be escorted out because we lingered a little too long after closing time. Some of our favorite experiences included:

  1. Circus Zirkus
  2. Waterways
  3. Skyline
  4. Kovler Family Climbing Schooner

Childrens Museum

I would be remiss if I didn’t also mention the human wrecking ball station that was set up the day of our visit. It involved the kids flying off a platform on a rope swing in an attempt to knock down a large pyramid constructed of cushions and pillows. It was a HUGE hit (no pun intended)!

Day 4 – Day four dawned with the prospect of an early afternoon train ride back to Michigan and just a few hours to kill in the morning. The Chicago History Museum was promoting a Railroaders exhibit and free admission for the kids, so that’s where we headed. When we arrived and I realized it was located at the southwest corner of Lincoln Park, I decided in hindsight it would have been a good addition to our day of visiting the zoo and biking through the park.

While the Railroaders exhibit was mostly photography based, which can lose kids pretty quickly, it also featured a small wooden train table that kept my youngest occupied and an area that replicated the interior of a caboose where my oldest could try on authentic railroader clothes and pretend he was living life on the rails.

We all enjoyed the Chicago: Crossroads of America Exhibit and my husband and I spent some quiet time learning about the life and death of Abraham Lincoln and Lincoln’s Chicago. The museum did a good job of creating kid-friendly experiences throughout the galleries through the use of History a la Cart interactive stations staffed by museum volunteers. My boys had fun at the station that taught them about the various types of bridges used in the Chicago area and allowed them to build and test their own bridges on a model of the Chicago waterways.

They also had a great time at the “just for kids” exhibit, Sensing Chicago. While it was a small area and I was skeptical it would keep their attention for long, the boys really got into learning about what makes a Chicago style hot dog special, testing out a high wheel bike, and creating custom digital postcards detailing their favorite parts of their Chicago visit (the photo at the top of this post is an example). It was interesting for me to see the unique highlights each of my boys took away from the experience, despite sharing an identical itinerary.

Hot Dog

Hot Dog 2

When if was finally time to bring our visit to an end, a couple of Uber* rides later, we were back at Union Station, tired and a little cranky, but filled with new stories and experiences and ready to relax on the return train ride.

 *If you aren’t familiar with Uber, it’s a must-have rideshare/taxi service app, especially when traveling in larger cities. Rates are comparable, and sometimes less than taxi fares (as was the case in Chicago due to a 25% off promotion), and it’s like having your own private car service, which can come in handy when there is no taxi to be found or you need a certain sized car due to excess passengers or luggage. Although I will say, Uber Chicago needs to get their act together. Every prior experience I have had with Uber, in both NYC and DC has been flawless. Courteous, knowledgeable drivers showing up when and where they promise in clean, impeccably maintained vehicles. Not so much in Chicago. Not sure what is going on there, but I hope Uber can get a handle on it, because it is normally a service I love to recommend.








    1. Andrea

      Thanks! That is a huge compliment to come from a former Chicagoan! We loved our time in the city and are so happy to share our adventure.

    1. Andrea

      Lol! I think I have a sickness 🙂 When I moved to NYC three years ago, I spent the entire summer running around the city with my boys. When I finally started meeting people and shared how we were spending our summer, they looked at me like I was crazy and often said, I’ve lived here my whole life (or ten years, or whatever) and haven’t seen or done most of what you did. Of course now that we are settled, when my kids want to go anywhere farther than a few blocks away I squish up my nose and try to convince them that the park around the corner is our best option :). Thanks for taking the time to check out my piece!

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