What should I do in Chicago?

If you can do Second City, definitely make a go of it! I have seen them twice on tour and it was wonderful; I nearly pissed myself laughing.

Imagine (and I know this is difficult) if SNL were still fresh, hip and genuinely funny. That is Second City.

Will you be in the city or the sprawling suburbs?

In the city you can meet up with some of us for drinks at the aforementioned Peninsula or maybe a place like Resi's Bierstube for Bavarian beer.

As I live in Chicago and spend a lot of time in NY, I feel reasonably confident that a NY'er should hit the following places:

Manny's Deli - authentic corned beef, pastrami, latkes, etc - makes Stage, etc look like the tourist traps they are. Seriously, go here. Super cheap.

Frontera Grill - best mid-fancy Mexican ever. Sister restaurant Topolabambo is super upscale and also excellent but I like Frontera. IMHO, NY has nothing like this. Very reasonably priced.

Spiaggia - super high-end Italian. Obama's favorite special ocassion restaurant and truly superb food and views of Lake. Seriously expensive and no cheap way to go

Blackbird - as good as the reviews say - and if you don't go crazy on wine, surprisingly reasonable.

Randolph Wine Cellars - excellent wine bar at other end of street from Blackbird. Great hangout (and a free parking lot - a rarity for chicago). Lots of by the glass and - key - 1/2 price bottles on Tuesday!!!

Velvet Hour - upscale cocktail bar in Wicker Park. Fun scene but a bit pretentious (what we here sometimes call, a bit too NY)

If you're cruising Rush/Oak area, eat at Le Colonial - upscale Vietnamese. Mid to high prices but lunch can be very reasonable. Attached to Le Passage, a throbbing bar scene at night

Weiner's Circle - nothing better at 3 am. Cheap

With all due respect, I generally disagree with all other recommendations in this thread, except I do like the Peninsula bar. (and - I know its heresy - but NY pizza is far better than Chicago glop)

collect obama souvenirs...

Go to The Publican, Paul Kahan's (Blackbird and Avec) new gastropub. You could sit there all night and just keep ordering.

Check out the Underground Wonder Bar on E. Walton, great music. Also, Swirl on Hubbard is a cool wine bar with good jazz as well, my buddy Dave plays with Trio Mare on Fridays when he's not playing on the road.

Alinea is good if you are into that budget.

Originally Posted by goodlife

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NO!

I agree it is a better view than the Sears Tower, but the observatory is not the way to go. There are long lines and I think there is an admission charge. It is a much better idea to go to the bar at the Hancock. It is the same 360 degree view, just one floor difference but with booze and no cover. The connected restaurant also does a decent brunch if you are being accompanied by minors.

I recommended the Hancock observatory for the college students visiting. I wouldn't recommend the snooty, overpriced bar & restaurant for them.

Originally Posted by spertia

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Nooooooo! As a New Yorker, you'll be glad you didn't. Hell, as someone from ANYWHERE else, you'll be glad you didn't. I swear, Chicago deep-dish pizza has got to be the most overrated thing about the entire city. And yes, I've tried all the "classic" places in town and have been severely disappointed.

Again, I recommended Chicago deep dish for the college students visiting.

Weiner Circle and the new Paul Stuart store.

Originally Posted by Mauby

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I recommended the Hancock observatory for the college students visiting. I wouldn't recommend the snooty, overpriced bar & restaurant for them.

Snooty maybe, but wouldn't it be smarter for a college student on a budget to take the $15 they would pay to get into the observatory and buy a cocktail, leave a tip, pocket a buck or two, and get the same views while avoiding a long line of obnoxious tourists?

Originally Posted by goodlife

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Snooty maybe, but wouldn't it be smarter for a college student on a budget to take the $15 they would pay to get into the observatory and buy a cocktail, leave a tip, pocket a buck or two, and get the same views while avoiding a long line of obnoxious tourists?

I hear ya. I thought college students got a discount to go to the observatory with their ID. Maybe they don't anymore. They'll get plenty of crowd and obnoxious tourists on either level though.

Originally Posted by jefe

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I wouldn't recommend the Belmont station for Second City... that's a helluva walk. Try Sedgwick off the brown/purple train or North & Clybourn off the Red Line.

You're right. WTF am I thinking of that's off Belmont? I'll look tomorrow and heck just to make sure I'm not insane.

There are plenty of comedy clubs to go to with cheap ($20ish) tickets like IO, 2nd city, or annoyance theatre.
Chicago pizza is great but try to avoid the most of the bigger chain places as they won't be as tasty and will be filled with families with little kids. (if you end up real far north in the city ginos north is good and has a cool art deco interior)
Also, pick up a copy of the chicago reader (or go to their website-lots of show/restuarant reviews)

Check any one of these out:

http://www.mkchicago.com/
http://www.bokachicago.com/
http://www.grahamelliot.com/

Originally Posted by deaddog

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As I live in Chicago and spend a lot of time in NY, I feel reasonably confident that a NY'er should hit the following places:

Manny's Deli - authentic corned beef, pastrami, latkes, etc - makes Stage, etc look like the tourist traps they are. Seriously, go here. Super cheap.

Frontera Grill - best mid-fancy Mexican ever. Sister restaurant Topolabambo is super upscale and also excellent but I like Frontera. IMHO, NY has nothing like this. Very reasonably priced.

Spiaggia - super high-end Italian. Obama's favorite special ocassion restaurant and truly superb food and views of Lake. Seriously expensive and no cheap way to go

Blackbird - as good as the reviews say - and if you don't go crazy on wine, surprisingly reasonable.

Randolph Wine Cellars - excellent wine bar at other end of street from Blackbird. Great hangout (and a free parking lot - a rarity for chicago). Lots of by the glass and - key - 1/2 price bottles on Tuesday!!!

Velvet Hour - upscale cocktail bar in Wicker Park. Fun scene but a bit pretentious (what we here sometimes call, a bit too NY)

If you're cruising Rush/Oak area, eat at Le Colonial - upscale Vietnamese. Mid to high prices but lunch can be very reasonable. Attached to Le Passage, a throbbing bar scene at night

Weiner's Circle - nothing better at 3 am. Cheap

With all due respect, I generally disagree with all other recommendations in this thread, except I do like the Peninsula bar. (and - I know its heresy - but NY pizza is far better than Chicago glop)


Generally agree with the above. Two notes: (1) Ashkenaz on Cedar is a superior Jewish deli. (2) While New York bests Chicago re pizza, they both take a backseat to New Haven. Something similar can be found at Coalfire on Grand.