Architecture is good, just walking around and taking in the city is too. I could easily spend a day on the “L” just riding around. I’m a bit of a travel / transit geek, and if there was a nice branch of the library, I’d visit that too.
You’re already doing the MSI, where there are several train engines.
As mentioned, the architecture tour is on a boat.
If the weather’s nice in October, you can rent a Divvy bike and ride the 20+ mile lakeshore trail.
In October, there are always “Haunted Chicago” tours - usually on a bus.
The el is self-explanatory.
Yeah, that description stuck out to me as well. It’s just downtown. I don’t really think of it as a neighborhood, either, just part of the business district.
I personally would say Hancock, go up at night and grab a drink or three on the 96th floor. No admission fee, the drink prices are comparable to any other downtown watering hole, and you have a beautiful view of Chicago.
Meanwhile, what Sears/Willis has going for it is the plexiglass (or whatever material it is) ledge which you can stand on and see a clear nearly 100 stories below you. I personally do think it’s pretty cool. That said, if you’re with someone and want to enjoy a good time and chat over drinks, the Hancock wins hands down.
This. If you asked for fifty suggestions – no problem. Just one? A little guidance, and we’ll zero in on something for you.
An outdoor day to go with your indoor (museum) day? There are at least fifty things to do in just one lakefront park, Lincoln Park:
The Zoo, Conservatory, and South Pond Boardwalk are close together; a bit north, are the Lily Pond and North Pond – very nice excursion if the weather is good; all embedded in a classic of traditional grand urban park design, with modern extensions.
Library?!
You will be in the neighborhood for sure, to visit the Harold Washington Library Center at 400 S. State (State/Van Buren El stop).
That would be the “nice” library to see!
Hancock view is along the lake shoreline and the surrounding buildings are residential.
Willis view is more varied, with Loop office buildings on two sides, views of Grant Park and the Museum Campus, and of railyards/South Loop/UIC.
The Signature Room (restaurant, dress code) and Signature Lounge (bar, no dress code) are actually both above the observation deck - it’s on the 94th floor, and they’re on the 95th and 96th floors respectively. I went to the Lounge last Wednesday to watch the fireworks - it was actually pretty cool seeing them from a few hundred feet above. The main limitation of the Lounge (or Room) vs. the observation deck is you don’t really get to roam around - you get seated wherever they feel like putting you. It’s fine if you just want to go up high and don’t care what specific view you get; if you care about the 360º view you’ll have to go to the observation deck.
The times I’ve been in the Lounge, people freely wandered to look out the different windows. That was always daytime though so I don’t know if it gets more crowded at night or there’s some other barrier to doing so.
The REAL sticker is that the ladies room gets a big window looking out and the mens room doesn’t. Unfair!
My bad.
Again, all great suggestions.
To provide a little clarity on my itinerary, it goes something like this (all times local):
Friday 10 October, land at ORD at 0725. Head downtown, dump stuff at hotel for storage since check in is much later. I’m staying at the Travelodge Downtown on E Harrison St.
No plans so far for Friday until the evening, when I’ll apparently have a beverage at the Signature Lounge.
Saturday morning until about 1500 - 1600ish, MSI.
Saturday 2005, train to New Orleans.
About moi, and my interests: Former travel agent, aviation / train geek (not a foamer), currently involved with civil aviation, like interesting buildings, would happily wander around a library for hours (or an interesting grocery store), very willing to take transit or walk around.
Basically need to kill Friday, and the odder the experience, the better.
Thanks again.
At the Museum of Science and Industry:
Here ya go:
Cool, that pooches some of Friday! 
The bit I liked about the Sears Tower (as it was called when I went) was that it had a pretty detailed legend explaining which buildings you were looking at in each direction.
October in Chicago is not a fun time to be on the water.
Says you.
In that case - check out Belmont Ave in general and Uncle Funin particular.
Have not been here - but plan to check it out next time we’re in town: Three Dots and a Dash - tiki bar http://threedotschicago.com/ – 435 N Clark
How about the Billy Goat Tavern? I recommend the original location: 430 N. Michigan Ave at Lower Level
Head out to Gorilla Tango Friday night for one of their geeky parody burlesque shows?
No good. Uncle Fun closed a while back. I just rode past it.
Nth on Hancock over the Sears Tower. Much more interesting view.
OK, so *after *the Signature Room, if you want an odd experience, I bet this gig is going again in October.
A friend of mine is a standup comic who usually hosts this burlesque/standup comedy show. I don’t get why somebody decided interspersing women taking off their clothes to music with standup comedy had some gestalt synergy, but there it is. Two hour show - 10 to midnight. Three women take off their clothes to music, two or three comedians do sets. Small room. Reasonable price ($10 I think?).
One quick bump with an odd request. Anyone out there want to skip work on Friday the 10th of August, and run me out to Fermilab? Not paying for a cab, dammit! I’ll pop for gas, and lunch.
As a civil aviation buff, you might want to see how they’ve been developing the former Meigs Field into parks and stuff. A nice place from which to see the city (and the lake) without being IN the city. Should have some fall colors on the trees.