This is how we choose our travel destinations. Grant randomly searches GoogleFlights and finds a spontaneous sale on a nonstop weekend flight to Chicago in November. He turns to Emily and me at dinner in Cafe Coyote (San Diego) and goes “want to go to Chicago? He waited a few seconds to make sure no one objected and the response was pretty quiet. Which was his queue to proceed with “I am going to book three flights.” Once again no major objections. And just like that…we are on an adventure to Chicago.
If we didn’t live in San Diego- I would want to live in Chicago. Grant and I both love everything about it. Everything except one thing. The winters. For comparison, San Diego at the time of departure was having a heatwave and clocked in at 92 degrees. Chicago was a cool 32 degrees upon landing at around 11:00 pm.
We chose not to rent a car so we were going to rely on Ubers and walking this trip. We learned the hard way downtown Chicago is no place to try to park a vehicle overnight. Very costly. The flight got in late, but we knew of a spot called Sienna Tavern that is open late. Nope…I did it again. It’s Bar Sienna that is open late. Hence, the hiccup that I caused when we first landed.
We travel frequently, but for some reason, navigation has been something I have struggled with recently. Old age? When we went to Alaska— I had us going to a glacier that caused us to miss a reservation. While most make more texting typos as they age I take us out of the way to places we don’t want to go but have a small relationship to the place we do want to go. If this doesn’t make sense just keep reading. Sienna Tavern closed at 11:30 pm, but Bar Sienna, a sister restaurant with a similar menu, was open until 2 am. I might have accidentally put the wrong restaurant into the app and I might have had the Uber driver take us to the closed restaurant. No one was pleased and so we departed only to call another Uber to get us to the right spot. A $20 mistake Grant let me hear about.
The good news was that it was a short distance later and the kitchen was still open. The server that we got wasn’t pleasant, but according to Grant, the Sangria was delicious. The decor was nice and the DJ made it feel like a Friday night. We scarfed everything down and proceeded to check into our hotel.
The next morning we got up bright and early to head to Navy Pier. Instead of heading right over, we had to stop and find the coffee addict Emily her Starbucks. Just an FYI— if you drink coffee I think you're an addict so she’s not really one. The problem was that even though they may appear on every corner— that does not mean that they are open. So we scoured around downtown Chicago looking for an open Starbucks. After attempting to go to three (all closed) we called it and went to the Navy Pier.
Good news! The Starbucks there was open and Emily got her pick-me-up drink. We moved quickly to the Shoreline Sightseeing boats to partake in the Chicago Architecture Tour. It was a unique way of seeing all of the buildings and the tour guide did a nice job babbling on about the buildings for the length of the tour. I can say that I am none the wiser, but am more appreciative of the hard work that goes into buildings.
Lunchtime was upon us and so we knew that when in Chicago get pizza. We attempted to find a new place, but due to time and limited options, we settled on Lou Malnati's. A tried and true reliable deep dish— this restaurant did not disappoint. Note to self: skip the pasta even if it sounds good. I ate it but didn’t love it.
From there we caught the matinee showing of a sketch comedy show at Second City. The group may have had the “B-Team” time slot, but they were still a hoot. For some reason, showing up on the later-side works at a place like that and we were ushered to the front row. After the show, we wandered around the area, walked through Old Town Chicago, and snapped some fun shots of the river at night.
For some reason, I kept being put in charge of navigation and so I put in our hotel— Hyatt. The problem was that there were probably about 30 Hyatt’s in Chicago…so I may have taken us to a Hyatt that was not ours. No matter— we dropped off the pizza we had been carrying and hightailed it to our last show of the night and our main attraction— Teatro Zinzani.
We had seen this show a few times in Seattle, but each time it’s a bit different. The best way to explain it is Absinthe (raunchy variety show in Vegas) meets dinner theater. If you haven’t seen Absinthe think random comedy, singing, acrobatic acts plus a four-course meal timed with the show. Everyone enjoyed the 3-hour dinner show but was a bit worn out after a busy day.
The bed was calling, but we knew snow was in the forecast. We waited impatiently for the white stuff. I changed into pajamas and Grant changed into his onesie. When he gave Emily and me the green light that snow was falling we made our way down to check it out. Afterward, we returned to our room to call it a night.
The next morning I woke up Emily with an alarm that I somehow set. My bad! Sorry. We fell back asleep and then got ready for brunch. The night before I found a restaurant called the Dearborn that was close to where we were staying. We ordered, ate some yummy food, and then parted ways to the airport.
Again…somehow I got roped into calling the Uber. I think it had something to do with me being the only one willing to take my hands out of my pocket to call the Uber because it was so cold. I put in the airport and we were on our way to Midway… oops…. I did it again, but at least caught myself this time. Cancel that one. Put in O’Hare and…we were on our way.
In the future, I have lost navigation privileges, but I have a sneaking suspicion that banishment won’t last too long. Especially if it’s cold outside.