The summer of 2022 has been one of the hottest ever in Austin, TX, and a hot Austin with a toddler has been pretty much… unbearable. We’ve made the most of dining out, water play, and indoor activities, but half way through the summer I had a major urge to plan a cool weather vacation. I came up with a simple list of criteria (direct Southwest flight, good public transit system, walkable, NO CAR SEAT REQ!) and all signs pointed to Chicago (Midway).

Let’s touch a bit on the no car seat thing. Toddler travel can be tough because toddlers are toddlers, but lugging around a beast of a convertible car seat is an underlying pain almost anywhere you visit. A convertible car seat *almost* makes a rental car mandatory. And outrageous rental car prices and paying for hotel parking just aren’t where I want to spend my dollars. 

Back to Chicago! We flew out on a Thursday morning and curb checked two suitcases and the travel stroller. I prefer to curb check, especially when flying without Kody, because there usually isn’t a line and it allows me to get rid of the heavy stuff ASAP. When we landed, Kody handled the suitcases and I took care of the stroller and navigation. I didn’t really put much thought into how we’d get to the train, but I remember it being pretty easy during my last visit in 2014.

The train station was a decent walk from baggage claim, but the signage was great and all walkways were enclosed. We purchased our Ventra tickets and, within minutes, we were on the Orange line. After 25-ish minutes on the train, we hopped off at State/Lake. And this would be our biggest challenge of the trip – not all train stops have elevators! We acted quickly and I carried Ez and the folded stroller. Kody was a champ and lugged our luggage with ease. From there, we walked another 15 minutes to the Sheraton Grand on the Riverwalk. The walk was pleasant: sidewalks were great, pedestrian crossings were timely, and the weather was perrrfeccctt! Side note: the elevator thing wasn’t a big deal the rest of the trip, it was merely an unanticipated challenge with luggage.

The hotel checked us in early and honored our request for a high floor away from the elevator (win!). Ventra tickets work on the bus, which was the best way to get to our first stop: The Lincoln Park Zoo. The vibration of the bus lulled Ez to sleep and we found ourselves at the zoo with a peacefully sleeping toddler. A quick change of plans led us to a quaint Italian restaurant where we casually sipped on very large dirty martinis and warm (warm!!!) calamari and prawns. Ez continued to sleep, so we continued to dine. It was a super peaceful impromptu date night that couldn’t have been better timed.

We set the theme of the trip: public transit to and walking home from our destination. We soaked up about two miles of city life, stopped at Whole Foods to grab a pizza dinner for Ez, and settled back at the hotel after a seemingly full day stuffed into a half day. I noticed the hotel had an indoor pool before we left, which was the perfect way for our late napper to burn off some energy and sleep soundly in a new city. 

Saturday was be our best day, a day where we’d clock over 20,000 steps! I packed a bunch of non-perishable snacks and Ez had fun working his way through the snack smorgasbord for breakfast while Kody and I did a little unintentional intermittent fasting before lunch. We hopped back on the bus for a do over of the zoo where I learned that 3-½ might just be the most perfect zoo age. Seeing giraffes, rhinoceroses, and polar bears was special for all of us! Ez snuck in a train ride and convinced us that he needed a pumpkin bubble machine glow stick before lunch. I hadn’t made lunch plans other than “find hot dogs nearby with a decent rating” and was pleasantly surprised when Google maps led us to hip Chicago’s Dog House on our way to the train. 

After we loaded up on hot dog goodness, we took the train south to Summer of George for an architectural boat tour. It was just as awesome as I remember it. Kody’s brain was filled with architectural facts by the time we finished and I loved how it super-charged his Chicago experience from that point forward. My big tips here are to buy boat tour tickets on Groupon (half the price!) and to plan this early in your trip so you have a greater appreciation during your city strolls for the remainder of your visit. 

After the tour we ditched public transit and walked to Buckingham Fountain and Play Garden. Ez was obsessed with the playscapes at Play Garden and could have spent an entire day there! I loved seeing him turn into a super climber and could tell he was feeling confident and independent. This park is a must if you have preschool/elementary school aged kids.

Kody’s only restaurant request was something that felt like the Sopranos would eat there. A quick Google search led me to La Scala and it was a perfect vibe match and wonderful for classic Italian.

Sunday came with a super slow start. In the moment, it didn’t feel like we accomplished much. But looking back, the few hours we spent at the Navy Pier checked a ton of boxes. As soon as we arrived, someone pulled us aside to let us know that Blue Man Group would be performing in a couple minutes. They pointed us toward a lake front stage where we sat in the grass and watched a short and sweet performance. Afterward, we encountered several other stage setups with live performances. There was so much happy energy at every turn! We worked our way to the Centennial Wheel and experienced the city from a birds eye view. And that was about the time all of us hit a tired tourist wall.

Because we traveled mostly by foot, it was a vacation that celebrated the journey while being rewarded with the destination.