Explore Chicago: The Four Seasons With Kids

We head to the Windy City in the 2021 Toyota RAV4 Prime

Once upon a time, we could get away as a couple whenever we wanted wherever we wanted. Early mornings, late nights, breakfast in bed, shows, clubs, parties—you name it, we enjoyed it. But for a while now, we’ve had to play by a different set of rules in our travels: our kids’.

This can be a bummer to some, but we’ve grown accustomed to it. And quite frankly, wouldn’t have it any other way. Of course, ours are already a bit older; two teenagers and a nine-year-old, so it’s not like we’re hauling toddlers around anymore. The fact that we get to show them the world, cultures, etc. while we have a good time as a couple—we love it.

Following the first heavy months of the pandemic and after not leaving our home for essentially four months, we need to escape our four walls. Given the fact that more than half of our family’s birthdays are in the Fall, we thought it was the perfect opportunity to travel, albeit it as safely as possible. Our destination: Chicago.

The Windy City is a no-brainer for us for many reasons: tons of delicious food (pizza!), pretty architecture, good shopping, top-notch hotels, and last but not least, it’s only a three-hour drive from Indy. Maybe even less depending on traffic.

Considering the fact the pandemic had forced us to cancel our wedding anniversary trip to Europe back in April and a couple of other trips we had planned, we had the desire and budget to splurge a bit this time around. Hey…you can’t take it with ya.

We quickly chose the Four Seasons Chicago. We’ve been lucky enough to stay at several of their properties around the world for work and pleasure, and they never disappoint. Second, they had a clear and comprehensive health policy in place. Third, they had literally just remodeled the property and it looked stunning. And last, their new restaurant, Adorn, established by a chef I admire and the recipient of the James Beard Award, Jonathon Sawyer, had just opened its doors in the lobby of the hotel. What more could we ask for?

Our ride to Chicago was the impressive 2021 Toyota RAV4 Prime, which, believe it or not, has basically reached unicorn status in the U.S. Its plug-in hybrid capabilities and utter efficiency had made it a best-selling nationwide, so much that people are paying ridiculous markups for them.

Under the hood of the Prime is a 302-hp, 2.5-liter four-cylinder engine aided by an electric motor and battery pack, which helped us achieve over 32 mpg during our stint from Indy to Chicago. It’s a comfy ride too, which is expected from a practical and utilitarian ride like the RAV4.

The Prime variant is all about efficiency, building on the traditional RAV4 by offering the capability of driving fully on electric power (when charged), and also on gasoline under hybrid power (fuel and battery). When fully charged, the battery offers a 42-mile driving range, which is one of the highest available from a non fully electric vehicle.

Upon arrival, we were welcomed by valet parking at the ground level, who quickly gathered our luggage and whisked our RAV4 away. Inside, a Four Seasons staff quickly greeted us and checked our temperatures, and asked us a few health questions. Following the check-up, were entered the magnificent atrium, which was covered in gorgeous marble from floor to ceiling. As expected, check-in was a breeze, and we were escorted to our suite on the 43rd floor.

When we travel with all of our kids, we oftentimes get two adjoining rooms, this way they have their own area, bathroom, TV—and so we don’t have to look at their mess—let’s be frank. This time, however, only our youngest joined us, so a traditional suite worked out just fine, with a separate bedroom and living room area with a pull-out couch. This gave our daughter her own bed, her own TV, but wasn’t too far removed where she felt lonely or we couldn’t check up on her. Plus, we didn’t have to splurge on a second room.

Saving on that additional room came in handy, of course, because that freed up more budget for things like room service, spa, and a little shopping on Michigan Ave. If there’s one thing that I’ve always enjoyed at the Four Seasons, it’s their kitchen. From the Poke Bowls to the salads, steaks, and of course, desserts, they’re always excellent (except for those pancakes in Whistler that one time) and a great alternative to getting dressed and going out. Sometimes all you need is room service and a good TV show, no?

Another detail that I love about the Four Seasons is its amazing Concierge. They were aware that we were celebrating two birthdays, so they left us some decorated cupcakes and other sweet treats. In addition, they had a kid’s robe ready for my daughter, as well as kid slippers and a welcome goodie bag. This cute little tote had a Four Seasons stuffed animal, a cool face mask, coloring activities, and more.

After unpacking and settling into our suite, we decided to order some room service and have a relaxed lunch while enjoying the incredible view of the Chicago skyline and Michigan Ave. After a quick nap, we headed down to the incredible pool, which turned out to be empty. Talk about having the pool all to ourselves! We were over the moon.

Fun fact: while watching Home Alone 2 at a later date, we noticed a scene where Macaulay Culkin jumps into the pool at the Plaza Hotel in NYC. Actually, that pool belongs to the Four Seasons in Chicago, and not the Plaza. Now, my daughter can see she had the entire Home Alone 2 pool all to herself!

There is normally an entire room dedicated to kids at the Four Seasons, but sadly it was closed due to the COVID-19 pandemic. Also, they even offer an ice cream trolley to come directly to your room and make you an ice cream sundae right in front of you. Our daughter, who is a bit of an old soul, was content just lounging in the room drinking soda while wearing her robe and slippers.

When it came time for dinner, we ordered delivery pizza from Pequod’s, as we typically do regardless of where we stay and paired it with a nice bottle of bubbly.

After enjoying a beautiful sleep on my favorite hotel linens (which you can actually buy for your home), we woke up a room-service breakfast and a couple of mimosas. Our daughter, of course, stuck to OJ only.

Following a quick trip down to the spa for a little couple’s time, we hit Michigan Ave. and spent most of the day window shopping. This helped us build some appetite, of course, which was perfect because we had dinner reservations at Adorn. A couple of hours our suite was perfect to take a bath, get some rest, and get ready for dinner.

As expected from Chef Sawyer, our dinner did not disappoint. It was dreamy. Adorn’s menu is a perfect mix of elevated cuisine with homey, soulful American food. Fried chicken, Brazilian steaks, the most stunning french fries I’ve ever had, and a variety of seafood and vegetarian dishes that were to die for. Oh, and an edible candle…

At the end of our dinner, Chef Sawyer came out to say hello and talked to us about the couple-week-old restaurant then. It was the cherry on top of a magnificent evening.

The next day was our last in the Windy City and the awesome Four Seasons. We hopped back in our Toyota and drove back home. This time, it was the Prime’s smooth ride and quiet cabin that came in extra handy, comforting us as we made our way back to our normal life at home.

With so much uncertainty in the world right now, we don’t know when we will be able to get away again and do so safely. What we do know, is that when opportunities come up, you have to make the best of them, even if they’re not exactly on your terms.

If you plan on visiting Chicago with or without kids, we highly recommend the Four Seasons, and of course, Adorn. The location, the people, the property, and the excellent service will make it well worth its price tag.

Safe and happy travels.