Chicago Travel Diary: 5 Days in the Windy City

two of the tallest buildings in chicago

Last month, I went to Chicago for a work conference. I feel so lucky to have had the opportunity to visit one of the greatest cities in the world. Now that I’m back in LA, life feels…different. Like, things are moving faster. Or maybe it’s just me, I’m different since returning. There’s a saying that goes something like “travel changes you.” I’m not exactly sure what changed in me, but I guess I’ll figure that out over time.

Chicago Travel Diary

Deep Dish Pizza

My first deep dish pizza in Chicago

I ate my first Chicago deep-dish pizza in Chicago. I’ve eaten deep-dish pizza at a few so-called authentic Chicago pizzerias here in LA, including Numero Uno, but ain’t nothing like the real thing. It’s a similar feeling to eating New York-style pizza in New York – it just tastes better there.

Architectural Boat Tour

As touristy as the architectural boat tour is, it was so much fun. In fact, it was one of the best parts of the trip. Who wouldn’t enjoy a boat ride where you get to drink wine, champagne, and look at cool buildings? We went to the 7:30 pm tour around sunset, which is the best time to go. Good thing I had my scarf with me because it got chilly out there.

All the Food and Wine

rosé all day

Speaking of wine and champagne, the other best part of the trip was eating and drinking with my colleagues. The conference sessions were great and informative (and the whole reason I was there in the first place) but Chicago is a city that begs to be explored. Food and alcohol tend to create bonds and break barriers, and people I barely spoke to in meetings or over email became much friendlier over margaritas and Rosé. Also, for some reason, I’ve been drinking Rosé exclusively since returning from Chicago. #roséseason #margaritasforlife

Check out my other travel diaries.

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