A taste of The Windy City

Boston was Simon’s city of choice, and Chicago was mine. After drooling over countless photos of towering skyscrapers floating above beautiful clear waters (and even painting my interpretation of the skyline), I was ready to experience this city for the first time in all of its high-rise, deep dish glory.

When we first stepped off the blue line train into the middle of the Loop, we both did a double take. “Hold on, wait, are we in downtown San Francisco?”

Chicago was like no city I’d ever seen. There was so much skyscraper. So much city. I was thrilled to be in the center of action again, delighted to eat all the foods, visit all the museums, and spend a warm summer day in the park.

Things I loved:

• Grant Park. It stretches across the urban center and offered a perfect spot to rest my feet after a long day of walking. Also there is so much public art!

• The city bike system. The Divvy/Lyft bikes made it so easy to get around without having to walk! We rode them from the museum campus to the marina around sunset. Crossing the river was such a thrill.

• World-class museums (and the super convenient bus shuttle!) We visited the Museum of Science and Industry (it was okay), the Shedd Aquarium (worth seeing the penguins), and the Field Museum (so many great exhibits!) We didn’t make it to the Art Institute but I’ll definitely be back!

• Lincoln Park Conservatory. The nicest indoor botanical gardens I’d ever visited.

Things Simon loved:

• Del Seoul. A Korean fusion restaurant by Lincoln Park with amazing tacos and banh mi sandwiches.

• Giordano’s meat-lovers deep-dish pizza. (Never have I wanted a salad more after eating my first and only slice.)

The Architecture

Okay this deserves a section of its own. Let me indulge.

As much as I resisted my undergrad education, I’ll have to admit it did foster a deep appreciation and admiration for architecture. And Chicago is the beating architectural heart of America. Modernist skyscrapers, Art Deco treasures, cheeky Post-modern high-rises, and abstract contemporary architecture come together to create an iconic skyline that wraps around a bizarre river that flows in reverse. The undulating shapes, crazy ornamentation, and even those twin corn cobs they call apartment buildings play on architecture tradition and tell the story of Chicago, the Second City.

Witnessing the triumph of engineering was a also marvelous sight, as our architecture river cruise guide told us all about how newer high-rises had to add cantilevers to maneuver around underground transit, and how the trunnion bascule bridges use massive counterweights to operate. The architecture and engineering innovation in this city was on a whole other level, and it was awe-inspiring to see this concrete jungle present itself in all of its majestic towering glory.

My favorite part of Chicago

Beyond the dazzling buildings, I’m a sucker for gorgeous well-designed outdoor public spaces. This Riverwalk. Just wow. The way it connects the river to the metropolis above, and offers locals and tourists a shared public space that is welcoming, functional, and entertaining. In the short time I spent walking along the promenade during my first encounter of the Riverwalk, I was in love. I was thrilled to be a part of the vibrant crowds gathered along the riverfront to celebrate the end of the pandemic, the beginning of summer, and the reawakening of the human spirit after a long dark proverbial winter.

Nighttime was especially magical. Live music, riverside patio dining, illuminated waters, and dreamy boat tours that took you around under the glittering night sky. We grabbed dinner to-go, and caught the Art on theMART outdoor art gallery show that projects exhibitions onto the massive Merchandise Mart building. What a way to showcase art and share it with the public in a setting that is so uniquely Chicago. If I lived here I’d spend every summer evening here, taking in every chaotic but harmonious sight and sound.

In our short three days in Chicago, there was so much I didn’t get to see. (Frank Lloyd Wright stuff, skydeck views, walking tours, nice sit-down meals, Navy Pier, the offbeat museums) But it was enough to make me fall in love and want to come back to experience this one-of-a-kind city again and again.

#waterandaview forever