The First Night In Chicago

On my way from work to John’s apartment to pick him up, it occurred to me that this weekend was going to be a kind of a dream come true for me, as I’ve been wanting to go to Chicago for a weekend of fun with friends for 10 years now.  My first time to the city was in 1996 as an intern at the Democratic National Convention, and I fell in love with it during that two-week stay there.  I got to know the city well through that trip and the subsequent 6 trips to the Windy City.  At the conclusion of this long weekend trip, I have spent over a month of my life in Chicago, and have enjoyed just about even minute of it, even when I was stuck there after 9/11 left me stranded there while traveling for business.

However, all of my prior trips to Chicago were for reasons other than for pure pleasure, and even though I have had a lot of fun, this was the first time I was going to be able to enjoy the city without taking time out for seminars or meetings at ungodly early morning hours!

We flew from Providence to O’Hare on United airlines.  I don’t think I have ever flown United before: very comfortable seats, with enough leg room even for me.  Things got off to an adventurous start with Erock getting stopped at security for having a pocket knife and a Swiss Army Knife in his luggage, both of which he had forgotten he had.  Of course, that would have been bad enough, but he had also decided to bring a small bottle of Jack Daniel’s with him to have in the room for any "pre-game" warming up, and that was the first thing the security guard saw when she opened his luggage.  Of course.

Erock was then subjected to further indignity on the plane, as his overhead reading light was constantly flickering on and off.  We were already cracking up before we even got to Chicago, to the point where we woke up John from what he described as a "very nice dream."  That’s how he described it and that’s all we want to know about it!

Once in a Chicago, we got the fine opportunity to experience Chicago traffic, battling to get downtown requiring a long, painful ride in a crowded cab’s backseat.  Once to the hotel, I was greeted by a front desk workers told me she thought I was handsome – and she wasn’t even working for tips.  Also, membership has its privileges: we got the roll-away bed for free thanks to my Priority Club gold status, saving us $30. 

The compliments at the front desk must have flustered me, since as I was leading the way to our room, I told the guys that we were in room 2117.  So we got off at floor 21 and as we joked about our room key "issues" in Philadelphia, with our keys needing to be reprogrammed nearly every time we went to use them.  So in goes the first key card… and it doesn’t work…. then in went the second one… that one also didn’t work… and then the third…. another failure.  We were both cracking up AND appalled.  Then I looked at the card containing the key cards and realized we were on the wrong floor.  I called it a practice run. 

We dropped out stuff off in the room (the right one) and went out for some real Chicago-style deep dish pizza.  We attempted to go to the original Pizzeria Uno’s, but they said it was a 2-hour wait and it was already 9:00 p.m. Chicago time (which meant 10 p.m. East Cost time… we were REALLY hungry).  We tried Pizzeria Due, which is practically across the street and had only a 30 minute wait, and we ordered our pizza when we put our name in. The pizza was delicious and will be reviewed separately.

From there we went to Blue Chicago, a touristy yet authentic seedy little blues club where we caught some great live music.  After catching a full set, we decided to move on. Just as we left the club we were confronted by a large black man with shoe polish and a milk crate.  He was trying to hustle a shoe shine out of me and next thing I knew I had white shoe shine goop on my left shoe and had him shining my shoes.  He then asked for "ten dollars a shoe and a nice tip" which is obviously a ludicrous amount.  I gave him a few bucks and moved on.  Have to say that the shoes did look good though….

As we were trying to figure out where to go next, the rain was starting to get heavier and we wandered by a place called "Rockit."  Entranced by a large group of people singing along to "Sweet Child O’ Mine" by Guns N’ Roses, we went in to check it out. We decided to hang out in the less-crowded and darkly decorated (had kind of a industrial house of horrors feel to it) bar/lounge area instead of the crowded and too-loud upstairs bar/dance area.  After a few great songs including "Girls, Girls, Girls" by Motley Crue,  "AC/DC’s "Back in Black," and another GnR classic, "Paradise City," the music took a turn for the worse, as they devolved into a series of retro 80’s pop songs that weren’t doing it for us any more.   That wasn’t before a classic music-geek moment where we were in an argument over whether or not "Let’s Get Rocked" by Def Leppard was on Hysteria or not.  Erock and I knew it wasn’t, though John insisted it was.  A quick Google search on my Treo resolved the issue.  I should have bet a drink on it.

By about 2:o0 a.m. we were pretty much done with our first night in Chicago – it had been a long day and was technically 3:00 a.m. for us.

We went to bed with a very funny conversation spurred by John’s long and wet-sounding belch leading to Erock’s question of "what are you doing over there, eating p*ssy?"  John, being the token gay in the room, responded with "Ewwww… that’s what it sounds like?" and I answered him with "Only if you’re doing it right!!!"  There was then a comparison to that activity to eating Italian beef sandwiches in terms of physical similarities.  I don’t know how else to say that without getting this blog banned by corporate firewalls…

One thought on “The First Night In Chicago”

  1. My thoughts on day 1 in semi-chronological order:

    I have never had so many occasions where I needed my pocketknife since getting home from Chicago. F.U. TSA 😛

    I really felt like I was stuck in a bad 3 Stooges episode with the whole reading light thing, but it definately provided some good laughs.

    I’ll save my thoughts on Pizzeria Due until Derek posts his review, but let me just say that I never get pizza at Pizzeria Unos (the chain), but I am drooling just thinking of the sausage pizza we had. (Note: meal#1 in Chicago with sausage for me)

    Blue Chicago was an eclectic crowd of locals and tourists. It was a bit odd hearing the German tourists in a Blues bar. The band was rather ethnically diverse as well, including a Japanese guitarist who had some great blues chops. After half a set the vocalist came out and did another 5 or 6 songs, but I thought they were better off without her. Oh, and the bar had no Jack. Jim Beam and Coke works just as well for me though.

    Rockit left me quite underwhelmed. It is a dance club upstairs and the downstairs is a converted warehouse-style bar-and-grill that tries a bit too hard to set a mood by having lit candles all around the room. Let’s just say Erock wasn’t feeling the “rock” in Rockit. Couple that with a waiter who didn’t have a clue what the hell was going on. This bar didn’t have Coors Light or Tanqueray as John and Derek found out, but John found he likes Amstel and Derek went with the Sapphire so all was good there.

    At this point I am a bit worried that there is an alcohol crisis in Chicago. First no Jack, now no Tanq.

    After this it was the first of many long-but-doable walks back to the hotel to attempt to rest up for our first full day.

Comments are closed.