There have been some solid suggestions so far, but I'll add a few more.

If you're looking to stay touristy, then go to Harry Caray's, Navy Pier, Uno's, etc. Fogo de Ciao is an all your can eat steakhouse that isn't about quality, but trying to get your large intestine to burst.

JW's is a hot steakhouse. Gibson's atmosphere is very nice imo.

Just go to a Tapas bar/restaurant-act like you know what its about and they'll all like it. Sangrias and ton of obscure appetizers is really all you need to know.

Touristy-Dick's last resort. Raunchy and fun at times, out ot town girls/buddies may enjoy it.

Touristy-Howl at the moon. Standard dual piano bar that usually stays packed from those staying downtown.

If you want to travel a little north to old town, there are some nice restaurant spots here. I suggest Topo Gigio's for a nice italian meal, and then headover to 2nd City for a chill night that won't empty your wallet. Old Town Pub is a cool little hangout as well.

If you are staying out late, you could do better than Barleycorn on Clark, but it'll do. Then just head to down to Deja Vu for lol retards till 5am (if that's still the closing time)

Bucktown bars for the 26+ crowd. Stanley's off Sedgwick for Sunday brunch and bloody mary bar. Also a good amount of cougars to be found there on a given weeknight.

S+G's (can't remember what this stands for) on Southport for weekend breakfast-go with a skillet and nothing else. There are some alright nightspots on weekdays on Southport as well. Seconded on Wishbone breakfast-I've seen abotu a half dozen celebs there in the 15-20 times I've been there.

Visitors, please treat yourself to a Chicago Style Hot Dog..... whether it is at a chain like Portillo's, or a neighboorhood Hot Dog joint.

Bun, dog, onion, tomato, mustard, pickle, celery salt,relish, sport peppers

I've spent many drunken nights here, didn't think anyone would mention it.

The rest of your suggestions were good as well.

Agree. Chicago style dogs are very good.

FYP.

More seriously, Chicago is great. I'll probably go there for my MBA, but man, is it cold. The 3 non-cold months are fantastic, but the other months are just brutal. I've never been quite sure how people manage.

My favorite Turkish food was a little place near Ukrainian Village, but I can't remember the name right now.

Don't understand the recommendations for Japonais. It's pretty and trendy, but the food is only okay IMO. Not bad, but expensive. My favorite sushi place is Meiji, a little west of downtown. If you want authentic Japanese food, like sukiyaki, try Chiyo. It's a little out of the way and not that well known but really really good. The sukiyaki was comparable to the ones I had in Tokyo.

I personally prefer Tru to Charlie Trotter's, although both were certainly tasty. Haven't tried Alinea yet. Another excellent restaurant if you're not looking for the 9 course $120 meal is Blackbird. Great food, although it's certainly not cheap either. Just not as expensive.

Some personal notes on other places mentioned in this thread:

Whoever recommended Pequod's for deep-dish pizza is right on the money, although if you're going to a chain my favorite is Lou Malnati's.

I also live near Wishbone and agree that it is awesome. Sunday brunch is really crowded, so if you are there on a weekend Saturday is better.

Custom House has good food. As stated previously, the menu is more than just steaks but the steaks are great.

I don't really like Navy Pier - it's just too touristy. There are better ways to spend your time.

Big Herm's. God I miss that place.

I really need to move somewhere I can get good breakfasts.

Gibson's

and this:

dean,

you live close to one of the locations of Orange, and I believe you live close to the Bongo Room.

7ontheline,

sounds like we should hang out sometime. we've probably been in the same restaurant a few dozen times already, might as well sit at the same table and grab a beer. i've been hoping someone would suggest someplace that does non-sushi japanese, so thanks for that!

i went to Trotter's last night and it was better than i remember either of my other trips being. i think i still prefer Tru, but there's something to not feeling like you're going to explode at the end of the meal... regardless, the Trotter's menu right now was really tasty.

casau,

i think that chalkboard might have closed? haven't checked right now, but i think i read that somewhere, and it was disappointing since i heard it was quite good.

couple of other random things:

in andersonville (where the Hopleaf is), there is an italian bakery run by a young italian (american?) couple. everything is more expensive than you'd like, but everything i've had has been excellent. they fill canolis fresh for orders, and they are really, realy good.

in lincoln square, bistro campagne is great. traditional french bistro fare (with a couple not so standard things thrown in), a great beer list, a fantastic atmosphere, and realy nice outdoor seating when the weather is good.

I lived near there for four years, but always ended up at Marge's instead. It broke my heart when Marge's closed. One great thing about the city is the neighborhood bars.

Dublin's on State and Maple for great food and beers.

i think sushi samba is the best sushi in chicago - i like it better than any of the nobus i've been to.

for french le bouchon is great. not glamorous at all - small and crowded - but great food.

sweets and savories on fullerton - which is a bizarre name because as far as i could tell it's just a restaurant - is a random place i went to a few months ago and thought was very good.

macello on lake street is a place a friend of mine opened over the winter. pretty amazing country italian.

M Henry in Andersonville (north of nearly everything else, on Clark) is my favorite place for brunch in the city. Absolutely delicious!

Lula Cafe in Logan Square is a really interesting restaurant. They basically have 2 menus - cheap & expensive. Both options are good, depending on what sort of meal you're looking for and everything tastes great.

If you want real improv comedy, go to iO (formely ImprovOlympic), right across the street from Wrigley Field... it's different from Second City in that 2nd City is sketch comedy that is pre-written, whereas at iO, everything is made up on the spot.

I lived in Chicago for 3 years and have just left a couple days ago... already miss it.

I'll add a +1 for the Chicago Architectural Boat Tours, they are a lot of fun. Did one last summer in late August on a perfect sunny, warm afternoon. Great way to spend a few hours and learn about the city.

I've visited a decent number of restaurants since I moved here almost 2 years ago, glad I found this post though. I will have to try some of your suggestions. Places I have liked are Roy's and Blue Water Grill. I know Roy's is not native to Chicago and I don't think BWG is either, but loved both of my meals there.

I seem to like Gino's deep dish for whatever reasons, but Lou Malnati's is close.

As far as improv goes, I just saw a show on the NW side of the city called Too Much Light Makes the Baby Go Blind. You can't make reservations so you have to get in line ~1 hr before the show (30 min before they let you inside) but I had a pretty good time. They do 30 skits in 60 minutes in a random order based on audience input. I think I still like Second City more though.

I'm sure I have more input but gotta run for now.