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Vacation: New York or Chicago?

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So, I am planning on going on my first real vacation in the last five years in September. I am trying to decide between NYC or Chicago. I was looking at Chicago, because I want to see the Foo Fighters in concert at Wrigley. My other option is NYC, which is my favorite city in the world. I haven't been to NYC since I was 15 (18 years ago). Also, I was planning on going to NYC the weekend of 9/11 to go to a Yankees game, and JR Cigars is having a cigar cruise on the Hudson. Help me make a decision.
 

bostoneo

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Going to Chicago myself labor day weekend, been there once before maybe 8yrs ago, and had a blast. Can't vouch for NYC, never been there yet.
 
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Even though I'm on Long Island, I love NYC. Actually The Cigar Inn is doing a cruise "Smokin' on the Hudson" in September I think. I'll post up the link below for you to check it out. A little pricey, but what you get for it seems beyond worth it and a steal IMHO. Plenty of NYC lounges to check out for smokes and you could get an easy trip to NJ for JR Cigars too.

http://www.smokinonthehudson.com/
 
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My wife travels to both cities for work quite a bit and said she likes both, but Chicago much better.

I've only been to Chicago and really like it. I'm actually catching a Cubs/Royals game there in Sept with my father. I can't wait to go. Have fun wherever you go!
 

Cigary43

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Been to both cities numerous times. Here's a breakdown on both...

NYC....parking is outrageous if you're staying at a hotel...the fees alone will have you pi$$ing blood after day 3. Taxi drivers are the equivalent of terrorists...take your seat belt and tie it around yourself..twice. If you can check the Waldorf out...I've been there when their pricing is so good it's a crime not to stay there...Suite for $295 per night and I'm talking a real suite that is almost 1000 square feet. Use different search features for the Waldorf as each place has different pricing...it takes time to go through them but it's a room you'll never forget.

Chicago....the food is great..so many places to eat and grab some pizza at Lou Malnati's...you'll thank me. Lots of things to do..Science and Industry...Miracle Mile...Cubs Game...more food....Chicago Dogs....Ditkas.
 
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This is false. New York pizza is far superior.
Oh snap...this thread is doomed! :facepalm: :LOL:

I do enjoy both cities. Made many visits to Chicago in college, and it's definitely more affordable and less intense. NYC offers more in the way of things to do, based on sheer size. But riding the subway there (the only really affordable way to travel) makes me want to kill people! :punch: So it all depends on what your tolerance level is...;)
 
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Best pizza in New York is Di Fara in Brooklyn. Hole in the wall but the best if you make the pilgrimage.
Best sicilian in New York is L&B Spumoni in Brooklyn.

However, in order to avoid the trek and to add a NYC pastime, take a stroll across the Brooklyn Bridge on the pedestrian walkway and grab a pie at Grimaldi's. Most of NYC pizzerias are mediocre. You have to check out one or all of these establishments for a true thin crust experience.
 
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as a chicago native, i like ny style pizza better. i know, that is sacrilegious... or sacri-licious... however, im not that picky, as the only time i have pizza is when i help someone move. i mean, its food. quit being a whiny little girl and eat your food.
both cities have cult followings of their sports teams. both have good and bad, such as museums, historic landmarks, architecture, tourist traps, insane traffic during rush hour, and gangs. i think there are less jerks in chicago than nyc.

i think it comes down to:
1. do you like to eat? chicago portions are larger, which is why we are one of the most (if not THE most) obese city in the US (move over, Houston!). We have Au Cheval (rated by food network to have the best burger in the US) and Gibson Steakhouse (the only restaurant group in the US to have their own USDA certification)

2. will you have time to herf? if so, chicago bros will meet up (as long as you give us enough lead time). not sure about the NY guys - @ENV will probably meet up with you, call you a fag, then leave - HA!


 
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I think I'm gonna go with NYC. My company is having a cigar event there on Sept 12, so I figured that would be a good time for me to go on vacation. I think I am going to stay at the Waldorf as the rates are decent. I need food recommendations, and places I should see (besides cigar stores).
 

ENV

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Best pizza in New York is Di Fara in Brooklyn. Hole in the wall but the best if you make the pilgrimage.
Best sicilian in New York is L&B Spumoni in Brooklyn.

However, in order to avoid the trek and to add a NYC pastime, take a stroll across the Brooklyn Bridge on the pedestrian walkway and grab a pie at Grimaldi's. Most of NYC pizzerias are mediocre. You have to check out one or all of these establishments for a true thin crust experience.
I'll add Louie and Ernies in the Bronx. Also Johns on Bleecker is fantastic
 
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