Since this is your first trip you'll be in a great location for a lot of what you are looking for regarding bars, food and nightlife. I think you'll be at the epicenter of the Viagra Triangle and close to Michigan Avenue.

While I agree Navy Pier is touristy, the walk is nice and the skyline views from the end are worthwhile.

Definitely do the Cubs (this from a Sox fan). The area surrounding Wrigley is worthwhile.

Lots of good museums to see in the city and I'd suggest an architectural river tour.

Recently disowned, no doubt. ;)

Well
 

I agree, but none-the-less, many may find it appealing.

While Navy Pier to chicago is clearly a tourist trip, but Fisherman's Wharf to San Francisco is not.

There are a lot more to see and do in Fisherman's Wharf than Navy Pier. I have been to SF many many times, but I never got tired or sick of it. Whereas Navy Pier once is enough.

The OP may find more objectivity when reading one of the many Chicago travel guidebooks or by visiting the Metromix, Time Out Chicago or Chicago Reader websites. That's what I suggest. About Navy Pier ... it's a huge attraction, not just to tourists ... and if you spent a couple days there you probably couldn't fit-in all there is to do. The panoramic views of Chicago's lakefront from the pier are spectacular. But do some more independent investigation to find things that interest YOU and not the rest of us and check back to ask some specific questions. mid-September is usually an excellent time of year to be in the city. Thanks.

I'm not sure what makes Fisherman's Wharf any less of a tourist trap other than the fact that it's easier to leave. Both have spectacular views, both have tons of tourist crap. Fisherman's Wharf has better food.

Yes, but Navy Pier has better Shakespeare. And I'm still hoping the Fritto Misto that I had at Scomo's a few years ago has worked it's way out of my arteries.;)

How old are you?

Right. You like Fisherman's Wharf because you've been a tourist in SF. I lived in SF, and I assure you that no locals go there unless they are entertaining out of town guests...and probably not even then.

There is a restaurant in Water Tower Place called FoodLife that is really cool, also Garretts Popcorn has amazing cheese and caramel corn.

Delta747

I really, really apologize in advance for what I'm about to do, but here it goes anyway.

I'm a fan of a band based out of Chicago. Their fan forum has an absolutely phenomenal post/thread about what to do in Chicago, written by some long term residents and Chicagophiles.

I don't know if you will be able to read it without registering, but here is the link to the thread.

FWIW, I get to Chicago at least once a year, and my visit is not complete (and I've completed quite a few visits over the past decade) without a stop at Lou Malnati's for deep dish. That is sure to raise the hackles of some of the locals (I know, Gino's), but to each their own :)

It works without registering.

Some good stuff in that thread - thanks for the link.

Hardly. I know plenty of locals, myself included, who rate Malnati's well above Gino's.

I presume you're talking about Gino's East - are they even in the mix anymore? And is Gino's (the one on Rush that the Dept. of Health closed down a time or two and is not related to Gino's East) still open?

Yeah, Gino's East. They're back in the location on Superior just east of Michigan and I've seen crazy lines.