Las Vegas might be flexing with its 11,500 annual shows, but if we’re talking actual theater – you know, the kind where nobody’s pulling rabbits from hats or dancing with feathers – New York is still the uncontested champion with a whopping 10,000 live shows per year! The rest of the world practically bows down to NYC as the theatrical mothership. But hold onto your playbills. Did you know that Chicago has over 1,400 annual productions, making it America’s theatrical runner-up? (Sorry, D.C. and Houston, you’re still in the game, but sitting in the cheap seats.)
As any good friend knows, I practically came out of the womb humming showtunes! Theater ranks sky-high on my “must-have” list for potential forever homes. Sure, New York dazzles, but it’s about as close to family as Mars is to Venus. Now Chicago? That’s been our curiosity cat for ages, especially after Doug’s cousin David and his wife Dawn talked fondly of their life downtown as cool urban professionals.
Fast forward to today, and the dynamic Jones duo has relocated to the ‘burbs with their twin tornados of awesomeness, Olivia and Eloise! We thought we were excited about Chicago, but “moochdocking” in their driveway turned out to be the headline act of our trip! Their house? HGTV-worthy. Their hospitality? Five-star hotel level.
Unlike those chaotic family reunions where conversations last about as long as a commercial break, we finally got quality time with these advertising powerhouses (seriously, they’re like Mad Men but with actual ethics and better wardrobes). Their daughters? Imagine if politeness, creativity, and hilarity had babies – that’s them. Not to mention, that Baily had their full attention and couldn’t have enjoyed herself more.
Sliding into their routine felt like slipping into the comfiest pair of designer shoes – walking to school with Bailey, attending a local fall festival, touring each other’s domains (their gorgeous home vs. our rolling one), and simply connecting over good food and better conversation. In just days, we built a friendship bridge you could drive an RV over. We had the best time with them.
We also had a very special visit with Doug’s Aunt Patsy (David’s mom).
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Towards the end of our visit, with David and Dawn working and their kids at school, we fit in one perfect day in downtown Chicago.
We trained it downtown like proper commuters and started at Union Station, where I nearly strained my neck gawking at that 115-foot barrel-vaulted ceiling. The Great Hall was filled with natural light – magnificent.
Next stop: Willis Tower (still Sears Tower in my rebel heart). Monday, shoulder season, meant no lines. As we made our ways towards the elevators, there were displays on Chicago history and the history of this incredible building. Then the high-speed elevators whisked us up 103 floors to Skydeck Chicago with its Ferris Bueller-approved panoramas spanning four states (Illinois, Indiana, Wisconsin, and Michigan) on a clear day.
The only wait was for “The Ledge” – those glass box balconies that extend four feet outside the building. It’s here that you can stand 1,353 feet above ground like you’re auditioning for a superhero movie. Nothing says “I love you” like watching your partner turn slightly green while pretending they’re totally fine with floating above certain death!
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From Sears Tower, we wandered Chicago’s architectural wonderland like kids in a concrete candy store. This city is basically architecture’s Broadway – from the birthplace of the skyscraper to stunning modern minimalist designs from architects like Mies van der Rohe who famously said “Less is more”. Chicago’s architectural innovation is nothing short of world-class.
Although in typical nomadic fashion we ate from our backpack, food options bombarded us – deep dish pizza joints and fancy world cuisine restaurants – all vying for our attention. We passed so many theaters, museums, and jazz clubs I started mentally calculating how many years I’d need to experience it all. We also passed the elevated tracks of the “L”, one of the oldest and most extensive rapid transit systems in the U.S., dating back to 1892. At one point, I literally spun around like a tourist cliché trying to absorb the city’s magnificence, probably looking like I was auditioning for “The Bear: A Musical.”
The crown jewel? Our architectural boat tour along the Chicago River – 90 minutes of floating education that should be mandatory for all visitors. We learned how the Great Chicago Fire of 1871 essentially gave architects a blank canvas; how the city’s explosive economic and population growth during the Industrial Revolution drove building innovation; and how squishy Chicago soil led to steel frames that created the world’s first modern skyscraper in 1885. This allowed buildings to reach unprecedented heights. This boat ride is like floating through an architectural textbook, except more fun and with great photo ops.
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Beyond our home town of San Francisco, few cities have tugged at our nomadic heartstrings, but Chicago might just be relationship material. The Jones’ suburban-to-downtown setup mirrors our old East Bay-to-SF dynamic, hitting that sweet spot of familiarity. Sure, we visited during the Goldilocks season (late September – not too hot, not too cold), but we’d seriously consider braving a few months of whatever Chicago weather throws our way to explore this area a little more.
The next time you’re flying through O’Hare on business, you might think about tacking on a few extra days to explore this architectural playground. The only way to improve your Chicago adventure would be staying with the Joneses – but we value their friendship too much to turn their home into a VRBO (or their driveway into a Boondockers Welcome) by passing out their address to our blog readers.
Thanks Chicago and thanks Jones’ for a wonderful stay. We’re hoping for an encore soon!
Did you know that the oldest and largest aviati
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