We (meaning Melissa) slept in the first morning until about 11:30 or so (Jay and I were up, bright eyed and bushy tailed by 8ish). We had a 2 o'clock reservation for Chicago's Historic Architecture Boat Tour (by that other group, not the Chicago Architecture Foundation or whoever is the official guide company of the city). First things first, we had to eat breakfast/lunch. Jay drove us in the G35 to a place called Jerry's on Madison.
We ordered beer cheese as an appetizer, which comes with big soft pretzel pieces, little pretzel sticks, and some kind of fried pita to dip in the cheese. It was pretty good. For lunch, they have an endless list of sandwiches to choose from. The menu was so overwhelming, we ended up choosing blindly. Melissa got the largest burger I've ever seen, and it was topped with avocado, cheddar, and bacon (she designed it personally) with fries and mac n cheese as her sides.
Jay ordered one of the specials - chicken shwarma sandwich with peanut pasta salad and potato salad. I ordered the John W I think, which was a turkey, brie, and something else with honey mustard, side order of fries and mac n cheese. All three were phenomenal. I highly recommend Jerry's to anyone who finds him or herself in Chicago.We were running late, thanks in no small part to Melissa's aptitude for sleeping late. We drove back to Jay's to grab jackets and waved down a cab to take us as quickly as possible to the North Pier to ship off. The company recommends that you arrive 30 minutes before departure time. We showed up at departure time.
The boat was nearly full, so we decided to reschedule for the 3 o'clock tour so that we could get choice seating. With 45 minutes to kill, we just wandered around the nearby streets. We met Gus, an 11-month-old French bulldog who went crazy if you scratched his back. His legs just gave out and he'd lay in an ecstatic crumpled heap on the grass until you stopped. Then, we meandered into Flamingo's, a hole in the wall restaurant, the ethnicity of which we could not determine. We got a round of drinks while a group of four next to us watched the Milan football game and accosted the bartender when he changed the channel out of the blue.
Once 2:30 rolled around, we headed back to the pier to disembark. The tour guide was a bit too educated, or so it seemed, on all things architecture and Chicago. She talked a mile a minute, taking breaks every time we passed under one of the many bridges of the Chicago River to gasp for air and sip her Starbucks iced tea. Between rambling on about the origins of the city's nickname - "The Windy City" - and telling cheeky anecdotes about previous passengers, we we realized we did not receive what must have been obligatory pre-tour literature on Architecture 101. The terms she used, the architects she mentioned, and the styles and theories she discussed were so far beyond what your average layman would ever understand, I'm not sure why they thought she was a good choice for the emcee. We were lost for the majority of her ramblings on conceptualism and postmodern flying buttresses. Fortunately, the real joy of the tour is the open views you get by taking the water route through the city. One thing Chicago has to offer that most other big cities don't is this open vantage point. Cities like NY and Atlanta and LA don't offer good views of their prominent skyscrapers because you can only reach them street-side, and you are too close to see much of anything. Pictures of the tour are on my flickr page.
After the tour ended, we walked up to the famous Navy Pier and got a fantastic view of the Chicago skyline across Lake Michigan.
After wandering through the tourist trap on the Navy Pier and buying some world famous Garrett popcorn, we hopped in another cab to the building formerly known as Sears Tower (now, Willis Tower) to go up to the skydeck. The building allows people to purchase tickets to go up nearly to the top of the tower and walk out onto fully enclosed glass balconies - glass ceiling, walls, and floor - to get a bird's eye view of the city. It was about 6pm when we got there, and the wait was about 2 and a half hours, so we abandoned that plan and headed for the L (name comes either from the fact that it is elevated or electric, we're not sure which, and it might be both). 
The Blue Line took us back to Wicker Park (Damen stop), where we promptly collapsed on the couch and relaxed a bit before a late dinner.Dinner
There is a pizza place near Jay that comes highly recommended. It's called "Piece," and it is apparently always crowded. They brew their own beers - we tried several of the brews, including the Goldenarm, the Worryin' Ale, the Wack Job, and the Full Frontal Pale Ale, all very good. After an hour wait, during which we made friends with a big group of girls who ended up being seated next to us, we sat down and ordered a customized pizza. This place doesn't offer the traditional Chicago deep dish with a 98% risk of immediate heart attack, but that doesn't mean the pizza wasn't top notch. We got a medium, feeds 2-3, red-style pizza with garlic, onions, green peppers, mushrooms, and spinach.
It turned out Saturday night is live band karaoke, so we were treated to some quality amateur performances on stage. Live band karaoke means instead of a monitor and a DJ playing songs, you choose your song, and the band behind you plays the music while you read lyrics off a piece of paper. The people who went up were, for the most part, actually pretty good.We headed home after that and called it a night around 11:30-12ish, don't really remember exactly when. Sunday on a Wrigley Rooftop was just around the corner, and we wanted to make sure we were well-rested. Stay tuned for Sunday's adventures, hopefully to come tonight.
It is currently Monday morning. I'm writing this while Melissa showers. Next up, we decided to finish our trip with one grand finale in Canton, OH at the Pro Football Hall of Fame. We reserved a Hall of Fame package at the McKinley Grand Hotel. The package includes two tickets to the hall, a welcome gift, a free breakfast, a 10% discount at the Hall's museum store, all tax and gratuities, and access to one of Canton's nicest hotels - 24 hour fitness room, indoor pool and spa, and more. See some of you Maryland folks in a day or so, then back in Phoenix on Wednesday for the SLA Conference from Thur-Saturday.
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