It's been almost 2 weeks since I took a quick trip to Chicago aka "Chi-Town." And for those unfamiliar, that's pronounced "shy-town". I wouldn't call it that, though. It's not popular among the locals. Why do I mention any of this? Because back in 2007 or 2008 I was in New Orleans for a college trip and saw auditions for the show Street Smarts. My friend and I decided to try out. Why not? Making it onto this show may or may not have been quite the accomplishment. One of my questions was "What city is also known as Chi-Town?" I was stumped and ended up saying "well, definitely not New Orleans" and gave a sheepish grin. I did not make it onto the show (lame) but she did get a second audition. I came back to school and was telling my roommate all about it. This roommate often wore a Nike shirt that read "Chi-Town." She busted out laughing and asked me how on earth I didn't remember. Slightly embarrassed and feeling like an idiot, I explained to her I always thought it was pronounced "Chee-Town." Yes, face palm.
It was this same friend and another college friend that I flew out to meet in Chicago. They were celebrating her birthday and I decided to crash their party. I have desperately been missing travel. It's been a combination of Covid and my breakup. My boyfriend was my travel buddy for a few years now. I loved spending hours planning a trip for us. I would read blogs and check Pinterest for tips and ideas. I would make notes and check out hotels and Airbnbs. I loved it. Correction: I LOVE it! I have missed the planning and coordinating and stress. I have missed the hustle and bustle of the airport. Does the airport also stress me out? You bet it does. Not knowing where everything will be or if I'll be have to get on a tram or how long security will take. But, finally, I got to go on a trip. Of note, I was very excited for this trip. Excited, a feeling that did not exist for me for a few months. I was not the one doing most of the planning for this one and I did not care. I was just excited to be back in the air and heading to see some longtime friends.
our itinerary
friday
2:15 pm - arrive @ O'hare
catch an Uber - pickup was at Terminal 2
stay @ LondonHouse Chicago, Curio Collection - LOVED this hotel and the views, though the elevator keypad was a little finicky
3 pm - order room service because your flight was delayed, then less delayed (United's words), then delayed again
3:30 pm - eat THE BEST Parmesan Truffle Fries with Black Garlic Aioli and enjoy the view
6:30 pm - eat @ Michael Jordan's Steakhouse - the double smoked maple glazed bacon-get it
8:30 pm - take a minute to enjoy the snow falling in the city
9:30 pm - catch a show @ The Comedy Bar - they serve food and drinks
saturday
9:30 am - catch the bus- Don't ask me for tips. I will get you lost.
10ish am - breakfast @ Ann Sather-the cinnamon rolls are considered a side and are pretty delish
11 am - walk around Wrigleyville - baseball fans can check out the Baseballism store - I like some of their more subtle designs
Noon - tour of Wrigley Field - fun for baseball fans, even for this St. Louis Cardinals fan...shhh!
1 pm - head back toward the hotel
2 pm - check out The Bean - a fun place to take pics
3 pm - free time - we got some hot chocolate, did a little shopping, and I went to clean up/nap
5 pm - architectural boat tour with Wendella Boat Tours - highly recommend. The nighttime views of the city were worth it! Dress warm! I had on boots, wool socks, fleece leggings, sweatpants, long sleeves, fleece zip up, Land's End coat, and North Face beanie.
7:30 pm - eat @ Rosebud (Italian) - my friend got the risotto. I feel the need to say that because for some reason I feel like I'm always hearing people critique "the risotto" at any given place. Side note, there was an episode of Psych where someone poisoned the food critic with the risotto.
9 pm - close out the trip on the 96th floor @ The Signature Lounge - my ears immediately started popping in the elevator
This was a fun trip catching up with old friends and teammates but went by too fast! Obviously we could not do everything. That's what makes cities so fun. There are so many options and each trip can be different. Before I got there they went to museums, the Shedd Aquarium, and Giordano's. I love pizza but am not crazy about Chicago deep dish. Please don't disown me.
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