A Whirlwind 50 Hour Trip to Chicago – Day 1

19553905_10154511663915974_1785449452011117391_nI’m writing this on the plane going back home from a short trip to Chicago. This was a shorter trip than Sharon and I would normally take so there had to be a good reason behind it. Just like our trip to New York in January, we traveled to Chicago because Sharon used her Ticketmaster skills to get us tickets to see “Hamilton.” Getting tickets for the show in Chicago was a little easier than for New York, but not much. To make things more complicated, we needed to change the dates of our tickets due to some conflicts that came up and then we had to shorten the rescheduled trip due to other commitments. Thank goodness I booked the original airline tickets with Southwest so I didn’t have to pay to change the flights. Even with it being a short trip and all the changes we had to make, we had a blast and are so glad we went.

Knowing we had such a limited amount of time to see the city, we narrowed down what


we wanted to see ahead of time. The only activity we knew we definitely wanted to do was TILT at 360 Chicago. Thanks to the help of our readers, we were able to get some great suggestions of other things we could potentially do during the trip.

Here’s a rundown of how the weekend went…

After getting through an uneventful flight on United, I was glad that I paid the extra money to avoid basic economy seats. We then took the the train from O’Hare airport to our hotel. This was really easy to do and cost us $5 each for the 45 minute ride. I knew we’d have a morning flight so I tried to arrange for early check in at our hotel, the Kimpton Hotel Allegro. They informed me they were totally booked the night before so they couldn’t guarantee it for us. Luckily, when we arrived around noon, the hotel did indeed have our room ready. We went upstairs to drop off our bags and decided to go out and have some lunch.

When we had asked about places to go in Chicago to eat, several of you said to go to Lou Malnati’s for pizza. You did not steer us wrong! It was only a ten minute walk from our hotel to Lou’s. When we arrived, we were told the wait was 25-30 minutes but we could order our pizzas then, while waiting for our table, so we wouldn’t have to wait so long after being seated. This system worked well, and Sharon ordered herself a cheese deep dish pizza and I went for the Malnati Chicago Classic (Lou’s lean sausage, some extra cheese and vine-ripened tomato sauce on Buttercrust).

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Our first time having Chicago deep dish pizza while in Chicago

While I really liked the pizza, I’m not a true fan of deep dish pizza. Maybe it’s because I’m from the NY/NJ area but I feel like I shouldn’t need utensils to eat a pizza. If I can’t fold my slice (with pepperoni!) in half before I eat it, then it just isn’t pizza to me. Sorry, not sorry.

At this point, between having to get up at 6AM and the carb overload from the pizza, we were both in need of a well deserved nap. We were very thankful that our room was ready, as we headed right up and managed to get a solid 90 minutes of sleep (isn’t our travel life glamorous?). By the time we woke up, it was time for the social hour in the lobby. The Kimpton hotels hold this event daily in all of their hotels from 5-6PM and our hotel was offering a free glass of Prosecco (or two or five). Apparently free booze is a good promotion because the lobby was PACKED!! We managed to grab a seat on one of the couches and mingled with some other guests. This was when we found out that both the Red Hot Chili Peppers and The Grateful Dead (or Dead and Company) had concerts in town that evening and these concertgoers were using the social hour as their pregame.

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It was time for us to head off to the theater to see “Hamilton,” although we did take time to stop by Daley Plaza to get a picture of the Picasso sculpture. Little did we know that the last Friday of the month is the Chicago Critical Mass Happy Friday bicycle ride. There seemed to be an never-ending stream of bicycles of all types going around the plaza. Sharon weaved her way across the road but I’m a larger target so I waited until it finally ended before crossing the street. Sharon, of course, being Sharon, had to videotape the moment…

I don’t really have to much to say about “Hamilton.” It was wonderful, as always. I’m not a theater critic and I don’t think that’s what you are reading this for. If you’re interested in my opinion, let me know cause I can talk forever about the show. 🙂

After “Hamilton” was over, we were both wide awake and a little bit hungry. I pulled up Yelp! and checked for places that were open late. One of the top hits was a tiki-bar called “Three Dots and a Dash.” Sharon has recently started collecting tiki mugs so I immediately knew this was the place we were headed to.

It was a pretty close to the theater, definitely not worth getting a ride for, so we walked over. The bar was located in an area of clubs, bars and live music venues and was really popular on a Friday night. We walked to the place location on the map but didn’t see a tiki bar. We thought maybe we had missed it, so we turned around, and nope, still no tiki bar. Tried the side street and it wasn’t there either. The only other place we could check was this alleyway. Now it wasn’t a scary alley, as there were lights and people there, so we headed down and shortly thereafter we saw two tiki torches by a door. We walked up and the guy at the door said “Three dots?” I nodded and he pointed over to a line on the other side of the alley and said “Over there.”

The line was only about 10 or 15 people deep and we headed over to wait. As we walked, the doorman, who was about the size of The Rock, stopped us. He looked at us and said “You’re cool, just go on in.” I must have had a puzzled look as he kinda pointed the way and said “Enjoy!” Now lets get something VERY CLEAR here. I’ve never been cool in my life, anywhere. Neither has Sharon. Even moreso not at a club that has a doorman and a line but if the huge man with an earpiece says I’m cool, then I am in no position to argue this fact with him. Sharon said it was cause of her gray hair and being so short, maybe they thought she was a little old lady in the bad lighting of the alleyway, and if so, that’s cool too.

We walked back to the door and told the doorman, “He [pointing to The Rock] said we could just go on.” The doorman let us through so we went through the door and down the stairs to another hallway. Where is this place? Eventually we approached a Tiki God statue and the host stand. We asked about food and were told that they were very busy so they could put us on the list but no guarantees. We decided we wouldn’t push our luck and just went to the bar. Whoa, the place was packed with people who were all 20-25 years younger than us. They also had a DJ playing but there wasn’t a dance floor, thank goodness. The music was loud but not too loud. It kept you from hearing other conversations but you didn’t have to yell to speak to the person next to you or to order a drink. It was an interesting type of music, too – sort of dance music but with a tropical flair. We liked it!

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Bartenders at work at Three Dots And A Dash
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The Rum Barrel (L) and Trader Vic’s Mai Tai (R) at Three Dots and a Dash
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Sharon’s newest addition to her tiki mug collection. Photo courtesy of threedotsandadash on Instagram

We managed to use our elderly knowledge to find a few seats at the bar, and looked at the menu. Of course this place specialized in tiki drinks that all came in specialized mugs and they also had a three page rum menu. After sampling some of the drinks (and buying one of the mugs to take home) we hung out a while, just watching the bartenders make drinks. We both enjoy doing that, since we spent the better part of a decade and a half hanging out at an interactive comedy club/bar and used to watch the bartenders who worked there. After chatting with one of the bartenders on and off for over an hour, I decided to make an order off the rum menu. I could see he was happy to make something else besides a tiki drink. After finishing our drinks, we walked back to the hotel and thus ended our first day. Not bad for being in town for only 12 hours. Stay tuned to see what the next day will have in store for us.

Click here for Part 2!

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