I got back from the the trip, and thank you all for your great suggestions. I couldn’t get to nearly half the places that I wanted to, but had a great trip. You Chicagoans live in a beautiful city.
The trip invariably began with an airport delay. However, it allowed to me to have a very engaging hour-long conversation at an airport bar with a recently-elected member of the MLB Hall of Fame. I could probably start a separate thread on that, but I think that there was an expectation of privacy since he is a semi-public figure.
As I mentioned, I was there for a conference, but was able to sneak away in the evening to Portillo’s after a couple of drinks at one of the local watering holes. It was the Thursday after-work happy hour so not too different than what we do in NYC. I went with a local who was at the conference and worked in the area. I ordered the Italian beef sandwich with sweet peppers and a hot dog. To be honest, I felt the beef sandwich was a bit dry. The next day, someone else told me that I should have asked for them to dip the sandwich, or at least ask for the au jus on the side. I guess I’m more accustomed to Philly Cheesesteaks that are greasier. The hot dog was great, but I’ve had very good replicas here as well.
The conference ended on Friday afternoon, so I made my way to the Embassy Suites on State and then met one of my banks for dinner at a place called Chicago Cut. Had a really good dry-aged steak and sides but nothing different than I what I get in NY. But that huge meal got me very tired, so never made it back out of my hotel. Forgot to mention that I only slept about 4 hours the night before.
I woke up early Saturday, ate the very generous breakfast buffet, and walked over to the Michigan Ave. / DuSable bridge. I took the Chicago Architectural River Cruise. I found it absolutely fascinating! The history and beauty of the buildings, the humor of the tour guide, all were incredible. He didn’t stop talking for 90 minutes and yet probably left out a whole lot of the history. The views of the city and buildings from the river were spectacular. It was cloudy, but I actually think that it helped since I could see all of the buildings without squinting.
After the cruise, I walked along the River Walk and stopped for a drink at one of the bars. It was getting a bit chilly by the water after a while, and I wanted to watch the FA Cup Final, so walked a different route back towards my hotel. While Chicago is a great walkable city, I do have one complaint: When walking down sidewalks in the opposite direction of a street’s one-way car traffic, the cross street signs aren’t visible. So you have to actually cross the street and then look back to see the sign. I like to “learn” the street names while I walk so had to do a lot of rubber-necking.
By the time I got near my hotel, I saw through the window of a bar that the soccer match had already started (my watch was still on Eastern time) so went inside. Had a couple of drinks at the bar - called Rock Bottom Brewery - and watched the rest of the match. I was planning on then heading to my hotel to change, and then over to Chicago Pizza and Oven Grinder Company for that Pizza Pot Pie that some of you mentioned. However, the girl next to me at the bar told me that the wait would probably be pretty long, and I was already hungry. She told me to go to Gino’s East, but then I remembered some of you mentioned Lou Maltani’s.
I’m so glad I listened to you guys, because that was one the most memorable meals of my life. It was crowded as well, so the waitress took down my name and handed me a menu. Apparently they want you to order while waiting since the pizza takes so long to make. While waiting in the bar area with the menu in hand, I noticed the portrait of Babe Ruth wearing a Maltani’s jersey. I found that to be very cool, and took it as a symbolic nod to me, being a Yankee fan. It just so happened that the seat at the end of the bar opened up, so I sat down. I was lucky that I was alone. The bartender took my order, based on his suggestion of the sausage pie with butter crust. I ordered a small size, since the Personal looked a bit too small, with the thought that I would probably waste some. I drank a Lagunitas while waiting and had a friendly discussion with the guy next to me, who happened to be an upstate NY municipal judge, and also alone. We has a nice talk about a variety of issues (legalized marijuana, painkillers, the state of the Onondaga tribe of NY, etc.). We were both on our second beers when the food finally came out. We both completely stopped talking while we ate, as I think we were each in our own private paradises. The crust, the sauce, the cheese; simply amazing. I ate the whole thing and was stuffed.
I walked back to the hotel to take a quick nap before heading out again in the evening. But all that food and drink really drained me. I watched the Preakness and then passed out. I woke up at around 8pm, took a shower, and headed back out. The streets were lively so I kind of walked around aimlessly, taking in the city a bit more. I went back to Rock Bottom to watch the Cavs-Celtics game. I met a couple of guys at the bar and had a couple of beers while debating Lebron vs. Jordan. It was a nice evening, but didn’t do much else.
I originally planned on checking out of my hotel and then take in another one of your suggestions today. But the weather was crappy, and there was talk of bad storms approaching. Since I have some important meetings tomorrow morning in NY, I decided to head to ORD early and change my flight to an earlier one. Got lucky and flew out around 2:30pm.
Thank you again for all the great advice. I’ll be back soon, as I don’t think I could go a whole year without that Lou Maltani’s sausage pie! I may bring my kids out there during the summer.
