The weekend after our Yosemite getaway, we took an excursion to the concrete jungle of Chicago. One of my best friends from home is attending her doctorate program there, and of course with all the drama of 2020, she happened to have some time off from her collegiate demands and invited us out for a visit. I was thankful she could join us in our adventure because navigating the big city with a mobile toddler by myself felt really daunting. And also I love her, so it was a win-win on all counts!
The original plan was to fly out Sunday afternoon for an evening arrival into Chicago. Ha! The adventure all started right there. We got to our assigned gate just in time for boarding to start… except that boarding never started. I got a sinking feeling. As the clock approached the departure time, I realized we might have to try again on Monday. The flight had a “creeping delay,” which meant there was a mechanical issue that could be a quick-fix or a complete disaster. I’ll let your imagination decide what happened in this instance. I decided to wait it out, but only for two hours because of our connecting flight through Denver. I had zero desire to get to Chicago at midnight and then take two trains to get to Alese’s apartment all alone with a toddler. No thanks.

So the next morning, we tried again. And guess what? Our plane from the day prior was so broken that they were flying a new-to-us-airplane into Kalispell for the displaced passengers. Hooray! The flight went out a few minutes late, which meant that our connection in Denver was starting to look dicey. I don’t claim to be an airline expert, but I do know a thing or two. And I know that 15 minutes is not enough time to make a connection in Denver when you land 23 gates away from your next flight. Yikes. Then add in a toddler and all of our bags, since I had opted against checking bags this trip. All aboard the Hot Mess Express! Choo choo!
I, again, looked like a pack mule. I explained to Gavin that we needed to run. “Run?” he asked with raised eyebrows. “Yes, run run run run run!” He heeded my command… for all of ten strides, complete with his rolling backpack in tow. We did the best we could, but it was a lost cause. I was secretly hoping for some sort of delay of our connecting flight to give us a few extra minutes of wiggle room, but that wasn’t the case. We missed it. I slumped my shoulders and approached the agents to ensure they could roll us over to the next flight. The gate agents were extremely friendly and they waited as long as possibly could for us. They honestly seemed more upset than I was about missing the flight, which brought me some comfort. They transferred my reservation to the next direct flight to Chicago, which gave us about two hours of time to relax.
I was sweating profusely and out of breath when Gavin said, “Hungry.” Poor dude barely ate breakfast and it was nearly his nap time now. “Let’s find food,” I said, and he nodded in agreement. We happened to be next to the hot dog restaurant so that’s what we ordered. But dude. I ordered him a plain hot dog, so no bun and no toppings. That sucker cost me $10! DO YOU KNOW HOW MANY PEOPLE I CAN FEED WITH $10 OF GROCERIES?! I was so irritated, but I also had my puppy-dog-eyed-toddler staring at it like he hadn’t eaten for weeks so I didn’t protest. He only had two bites of the hot dog before requesting fries and milk. Face palm. I obliged his requests, simply because his schedule gets turned all kinds of wacky when we travel. If he is fed and rested, I can basically eliminate 99% of meltdowns.
We reached the gate for our second attempt into Chicago with my hands full of more food for Gavin than myself. We were listed 12 and 13 on the standby list for a flight that only had 14 open seats remaining. I checked in with the gate agent and anxiously watched the monitors while I waited for my seat assignment. I noticed a trickle of crew members approach the podium, flashing their badges and adding themselves to the standby list. I turned my gaze to the standby monitors and watched our names fade further down the list to 17. Eighteen. Nineteen. Twenty. I yawned, patted my face, and crossed my arms. We are making it to Chicago today, dangit! The gate agent starting assigning seats, making it about halfway through the list when she started paging standby passengers by name — this usually means that not everyone on standby will get a seat and the seats available are slowly dwindling. I followed along with her pages and the names on the monitors around us. I started losing hope until I heard my name. I practically jumped out of my seat. I approached the podium as she gracefully tapped away at her keyboard with a sense of urgency and my gaze widened with anxiety. And then. She smiled and handed me boarding passes. “Thank you so, so much!” I said. Gavin and I boarded the flight without incident and were finally Chicago-bound!


We landed just shy of 5 P.M. and met up with Alese in the baggage claim area before hopping on the train. Gavin was so excited for the train ride. Within an hour, we had reached Alese’s neighborhood and stopped off at her apartment to drop off our bags. I dove into the couch as if it was the ocean, the cushions splashing around me. I didn’t want to move. So we started talking dinner plans. I live in Montana and while there are enough restaurants to suit my stomach, the multitude of eatery options in the city were overwhelming. Alese suggested Jerry’s Sandwiches, but I just can’t eat deli meat since having Gavin. “No, listen,” she said. “They have literally everything you would ever want on a sandwich.” I was intrigued so I read through their menu online, and holy crap, they really did have everything. We called in our order for pickup and got ready for a nice little jaunt to the restaurant.
I absolutely loved walking through Alese’s neighborhood. The homes were beautiful, the families we passed were kind, and the crisp, fresh air felt oh-so-good. While I’m definitely a mountain girl now, there’s always something a little nostalgic about being in a big city. I grew up dreaming of living in places like this. We continued on the sidewalk and turned a corner to be met with dangling white lights and the serene fountains of Lincoln Square. The area was welcoming, quaint, and cozy, especially on a late-summer night. Families were playing outside together, couples were holding hands, and friends were laughing in this outdoor space. That’s what I love most about big cities: the people. I love how so many people from so many different walks of life can share the same space, ebbing and flowing in harmony.
We picked up our sandwiches and made our return trip back to the apartment, the delicious smells putting some pep in my step as I dreamed of devouring every last bite. But once we got settled and actually started eating, I realized that my eyes were definitely bigger than my stomach. Not long afterwards, we made a plan for the next day and settled in to bed.
The next morning, we took our time getting ready and preparing coffee before heading to the aquarium for our reservation. We took a little walk along Lake Michigan, which was beautiful, and saw Navy Pier in the distance. Unfortunately, the water taxis weren’t running because of the pandemic and even the Pier was closed. Bummer. So we carried onward to the aquarium entrance. Because of the COVID-19 pandemic, Shedd Aquarium is operating on a reservation-based system with timed entries for guests. I don’t like crowds, so naturally that’s why we decided on Shedd for the main attraction in the first place for this trip. When we arrived at the aquarium there literally wasn’t even a line. We walked right up to the queue, the visitor agent scanned our admission tickets, and off we went to explore. I was impressed with the one-way flow through the exhibits and the regular cleaning of high-touch surfaces.

The only downside was not getting as close as I wanted to at certain exhibits, but still, we saw anemones, belugas, dolphins, sea otters, penguins, and more. Gavin favored the anemones, pointing his tiny finger while his jaw dropped dramatically to floor. I thought for sure he would love the penguins, but he was only interested in going up and down the three stairs that led to that exhibit. Face palm. The stingray encounter was open and had a great, big hand washing station at the entrance and exit of the exhibit, with an attendant present to ensure proper washing (both for the animal’s safety and our own). This was hands down Gavin’s favorite exhibit because he loves the water. I don’t think his arms were quite long enough to touch the stingray despite my best efforts of hanging on to his thighs as I dipped him over the edge of the pool, but he enjoyed watching them swim by and splashing in the water. All in all, we spent just under two hours at the aquarium. I’d like to go back when Gavin is a little older and has a broader attention span.
We met up with Alese at a local coffee and sandwich shop where she was studying for an upcoming quiz. The weather was turning warmer, so we decide to visit Millennium Park because duh, you can’t go all the way to Chicago and not see the Bean. The walk was long and hot, but Gavin fell asleep thanks to the lull of heavy traffic. All but one entrance to Millennium Park was open, with a Parks and Recreation staff member manning the gate to ensure you were wearing a mask upon entrance. For outdoor exhibits I get a little irked about the mask-policing, but I just try to remember that everyone has different opinions and comfort levels when it comes to the virus. I could just as easily avoided the park and the mask requirement, but I wanted Gavin to see the Bean, so on the mask went. Barricades were set up all the way around the Bean and the adjacent areas of the park. I still got some pretty photos despite the less than flattering barricades and overall everyone in the park seemed to be having a good time and adhered to the mask policy. We sat in the shade and enjoyed the fresh air while Gavin slept in the stroller. This was such a perfect day with beautiful translucent leaves waving at us under the sun. I could sense the nearing end of summer and the transition to fall.


Once Gavin woke up, we made our way to the Chicago River Walk. I highly recommend checking that out if you’re ever in town; that place should be as much of a staple as Millennium Park. The air was much cooler on the water and there were so many boats and people to watch, with trendy bars, restaurants, and coffee houses every inch of the way. I assumed that since the water taxis were out of service that the architectural boat tours would also be closed, but that was not the case. I definitely would’ve booked a river tour had I known, but that’s what I get for not doing my research ahead of time.

We hopped the train and headed back towards Alese’s apartment to get a light snack, refresh ourselves after walking for hours in the heat, and pack our bags for the beach. Yup, Chicago has a beach, complete with sand and whitecaps! The walk to get there was quite a distance while pushing a stroller on cracked sidewalks, but seeing Gavin’s stoke level once we arrived at the beach was totally worth the effort. I immediately took off his shoes and socks, and he was off the races. The sand was cool to the touch and so refreshing after walking a couple miles. The breeze was picking up now and Gavin was running in and out of the water, soaked head to toe and squealing with delight. We didn’t have any sand toys with us, but that didn’t deter him from finding ways to entertain himself. I was waiting for him to get bored so we could make a swift and tear-free transition to dinner. Then my stomach starting grumbling and I could only put that off for so long. I know I said earlier that Shedd was the main attraction on our itinerary, but let’s be real. Deep-dish pizza was the real showstopper. So we said our goodbyes to the sand and waves and headed for the bus stop a few blocks down the road en route to authentic deep-dish pizza at Lou Malnati’s.


Gavin learned all about crosswalks on our way to the restaurant and eagerly looked for the “red hand” the entire way there. Even on the bus, he would peek out the window and make sure I knew where every “red hand” was. “Mom, red hand! RED HAND!” he’d say repeatedly with wide eyes and mouth agape. He was becoming quite the city slicker for only being in town for the last 24 hours. We arrived at the restaurant and wanted to sit outside, but we weren’t willing to wait 30 minutes to make that happen, so we sat in a high-top booth inside. Gavin didn’t even need a booster, he just sat right up to the table and started coloring. When did he get so tall? He looked like a boy sitting there and my heart felt both insane pride and tragic loss. I imagine I will have that feeling many times over as he continues to grow and age.
As we perused the menu, Alese said she was getting a salad. A salad!? But there was a method to her madness since she’s been here many, many times before. The pizzas are huge and so are the salads, so she suggested that we share them. That turned out to be the best idea of all time. So we smashed the Combination Platter appetizer and the Malnati salad while waiting for the deep dish pepperoni and sausage pizza. But I have to tell you about the salad because it was honestly the best salad I’d ever eaten in my life. The secret had to be the dressing, a sweet vinaigrette that I honestly wanted to drink. Gavin helped himself by fishing pieces of romaine right out of the serving bowl. My stomach was starting to feel satisfied when the pizza arrived at the table, but there was no way I was going to stop eating now. The smell alone got me salivating all over again. I wish I would’ve gotten Gavin’s reaction to the pizza on camera because he was completely awestruck, his eyes even larger than the pizza itself. I cut him a few pieces and he went crazy inhaling it, I could barely keep up with cutting the pieces fast enough.
I took a deep breath and sat back, rubbing my stomach and smiling. Now that was a good meal. I was thankful we needed to walk back to Alese’s apartment so I wouldn’t feel so guilty for indulging. And just like that, our time in Chicago was coming to a close. Alese was gracious enough to do a load of laundry for us so I didn’t have to carry around my sweaty clothes on the trip home. The following morning, I organized our clothing piles and packed our bags for the journey to the airport. “Train?” Gavin asked. I put him in the Tula baby carrier and confirmed his suspicions about our transportation. We took the bus to the train to the airport where we said our goodbyes to Alese.
I really didn’t want to leave. At this particular time, I felt like I needed Alese and Alese needed me. I met Alese at my very first ever restaurant job back in 2008 at the Chili’s in my hometown. She’s seen me through all of my biggest phases in life, from a college graduate, to a single woman, to a married then divorced woman, and now as a married-again woman and mother. She helps me stay connected to myself as “Megan”, not just “Mom/Megan”. She’s the most intent listener and the biggest empath with the biggest heart. We weren’t keeping in much regular contact over the years… until 2020.
Everyone is struggling this year, myself included. I certainly never anticipated what this year would bring. But thanks to quarantine orders we were both facing in completely different cities in completely different states, Alese and I were able to reconnect. We checked in with each other over texts and FaceTime calls, sharing life and supporting each other through the bizarre 2020 tides. For that I am so thankful. She visited us in Kalispell in July, and now here we were seeing her in Chicago. Certainly 2020 brought a lot of turmoil; but amidst the chaos, 2020 brought back a very special friend.

Beautifully written. I’m so glad you enjoyed your trip sorry about the difficulty getting there. I certainly will follow your blogging. Smart move getting off social media. ❤️
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