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Chicago Questions (1 Viewer)

Beef Ravioli

Footballguy
I have driven through Chicago on multiple occasions and went downtown with some friends for less than two hours once. I have no idea where we were. It was probably 15 years ago and he took us in the ESPN restaurant.

It will be me and the wife. Want to stay in the city. Looking for shopping, dining, a play or concert, safety, and a Cubs game. Which airport do I fly into or does it matter? What part of town to stay in?

As always - thanks in advance!

 
If you are not renting a car, and you can get a flight to Midway, you are almost downtown. O'Hare is quite a bit outside of town. There is mass transit back and forth, just need to factor in time.

 
If you are not renting a car, and you can get a flight to Midway, you are almost downtown. O'Hare is quite a bit outside of town. There is mass transit back and forth, just need to factor in time.
We would prefer to not have a car. Would like to walk or take transit wherever we go. We may drive (and then park it for the most part) there as it is under a six hour drive but if we can find a deal on tickets, we will fly.

 
How much you want to drop on a restaurant?  I have been wanted to go to Alinea for a long time.  But lots of other great places.
It would vary from day to day. We plan on staying 3 or 4 nights. Probably one night we would like a $50 to $60 a plate (100 - 120 for both of us) and then the other nights would be places we find online for reviews, anywhere from $15 to $30 a plate. We are foodies but have a limited budget.

 
It would vary from day to day. We plan on staying 3 or 4 nights. Probably one night we would like a $50 to $60 a plate (100 - 120 for both of us) and then the other nights would be places we find online for reviews, anywhere from $15 to $30 a plate. We are foodies but have a limited budget.




 
I have only been to Chicago when I was on business and someone else paid - so we went fairly expensive.  Alinea is a destination type place that my wife and I want to do for something special.  

I did enjoy the Billy Goat Tavern for their cheeseburgers and there was an italian place in behind the Hard Rock hotel and below the bridge that was fantastic.  Wish one of the Chicago guys could tell me what the name of it was - really want to go back there.

 
Midway is closer to Chicago but both O'Hare and midway are easily accessible to downtown via public transit. Flying into midway might save you 10 minutes or so on the same transit line. If that is important to you, fly into midway. 

Staying in river north or magnificent mile areas will get you close to most of the usual tourist types things and that's where most hotel rooms are. 

 
We would prefer to not have a car. Would like to walk or take transit wherever we go. We may drive (and then park it for the most part) there as it is under a six hour drive but if we can find a deal on tickets, we will fly.
You don't need, or want a car. Fly to either airport. Stay most anywhere downtown, best might be near Michigan Ave, "Magnificent Mile" or Millennium Park.  You can't walk more than a couple blocks without passing a great restaurant or two, great shopping on the "Mile"; two great theaters are Goodman and Steppenwolf, but there are dozens of great smaller theaters who do a great job. There will be good live music nearly every night of the week somewhere downtown. Wrigley is a short cab ride, bus ride or red line ride from downtown, very convenient.

 
You don't need, or want a car. Fly to either airport. Stay most anywhere downtown, best might be near Michigan Ave, "Magnificent Mile" or Millennium Park.  You can't walk more than a couple blocks without passing a great restaurant or two, great shopping on the "Mile"; two great theaters are Goodman and Steppenwolf, but there are dozens of great smaller theaters who do a great job. There will be good live music nearly every night of the week somewhere downtown. Wrigley is a short cab ride, bus ride or red line ride from downtown, very convenient.




 
You can also do good work with AirBnB too. The shopping in Chicago is mostly overrated as an activity but everything else is pretty tremendous. Theatre - both with established, like Steppenwolf and Goodman, and smaller - can be top notch activities for an evening out. Second City can be a blast too. There are abundant and plentiful venues for live music - Green Mill is good for jazz, for example - of every type. Restaurants are top notch too. The city makes a point of making really good food affordable and an experience like around West Loop, Bucktown, Logan Square and Wicker Park (not so much River North). 

 
Midway is closer to Chicago but both O'Hare and midway are easily accessible to downtown via public transit. Flying into midway might save you 10 minutes or so on the same transit line. If that is important to you, fly into midway. 

Staying in river north or magnificent mile areas will get you close to most of the usual tourist types things and that's where most hotel rooms are. 
This. Often which airport highly depends on where you are flying from and which airline. For example Southwest flies only into Midway, Spirit into OHare. Get whichever is cheaper or on your preference of airline. Time to downtown is negligible. 

Not only don't you need a car, you don't want a car. It will cost you $50/night to park your rental and there's nowhere you'd really want or need to drive to. 

Summer in Chicago is glorious. Make sure to carve out half a day for the lakeshore/millennium park/rent a bike up and down the lakeshore. Beautiful. 

 
This. Often which airport highly depends on where you are flying from and which airline. For example Southwest flies only into Midway, Spirit into OHare. Get whichever is cheaper or on your preference of airline. Time to downtown is negligible. 

Not only don't you need a car, you don't want a car. It will cost you $50/night to park your rental and there's nowhere you'd really want or need to drive to. 

Summer in Chicago is glorious. Make sure to carve out half a day for the lakeshore/millennium park/rent a bike up and down the lakeshore. Beautiful. 




 
Do you live there?

 
We would prefer to not have a car. Would like to walk or take transit wherever we go. We may drive (and then park it for the most part) there as it is under a six hour drive but if we can find a deal on tickets, we will fly.
No car then Midway is closer but both have L service directly into the city. Go with cheapest fair or preferred airline and don't worry about airport as much.

 
It would vary from day to day. We plan on staying 3 or 4 nights. Probably one night we would like a $50 to $60 a plate (100 - 120 for both of us) and then the other nights would be places we find online for reviews, anywhere from $15 to $30 a plate. We are foodies but have a limited budget.
Depends on what you like. If you want the Chicago stuff then you need a Deep dish, Chicago style dog, and Italian beef for some meals though you can do those as lunches and then look for nicer places for dinner. There are more than a couple of threads on discussion, debate, ideas on places and dino posted a couple for you to look thru.

 
Just looked, no that wasn't it.  It was under one of the bridges over the Chicago River - AND I believe I stayed at the House of Blues - not the Hard Rock.  I remember walking across a cement plaza and taking steps down to the river level and taking a left - the restaurant was right there with a very few small tables right on the river.  

I looked on Google Earth maps but didn't see any restaurants I think it would be - pretty sure it was under either the Clark St./Dearborn or N. LaSalle or N. Wells St. bridges.   

 
Bella Bacinos?
Damn ...no.  Looks like a very similar menu though I don't remember any deep dish - it was all thin and crispy that I recall and a great antipasto app menu.  

Pretty sure it was on the other side of the river from Bella Bacinos with no street-facing front (just river) and had all kinds of old Sinatra photos (pretty sure taken at the restaurant with the owners).  

 
Damn ...no.  Looks like a very similar menu though I don't remember any deep dish - it was all thin and crispy that I recall and a great antipasto app menu.  

Pretty sure it was on the other side of the river from Bella Bacinos with no street-facing front (just river) and had all kinds of old Sinatra photos (pretty sure taken at the restaurant with the owners).  
#####?

 
Are you talking about River Roast?
That location looks an awful like what I remembered.  How long have they been there?  

I remember the inside not being real big either and kind of long like the pictures show.  Could be the location and that restaurant I went to is no longer there - I'm talking like early 2000s.  But the italian place looked like it had been there for years.  

 
Flatwater? 
Again, that outside location looks familiar but definitely not the restaurant.  It was an old school italian restaurant and definitely not fancy decorations (ex. kind of lame wood paneling walls).

Sorry for the goose chase - but it seems like that place isn't around anymore.

BUT it was definitely in one of those walk-down locations by the river with a few outside seating tables.  

Bummer, thanks for those trying to help.

 
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Again, that outside location looks familiar but definitely not the restaurant.  It was an old school italian restaurant and definitely not fancy decorations (ex. kind of lame wood paneling walls).

Sorry for the goose chase - but it seems like that place isn't around anymore.

BUT it was definitely in one of those walk-down locations by the river with a few outside seating tables.  

Bummer, thanks for those trying to help.
what was your waiter's name?  That might help me.

 
Damn ...no.  Looks like a very similar menu though I don't remember any deep dish - it was all thin and crispy that I recall and a great antipasto app menu.  

Pretty sure it was on the other side of the river from Bella Bacinos with no street-facing front (just river) and had all kinds of old Sinatra photos (pretty sure taken at the restaurant with the owners).  
Bold - Are you sure you were in Chicago?

 
Here's a question - do we really need 4 different Chicago TV shows?

http://www.usatoday.com/story/life/tv/2017/02/28/review-chicago-justice-****-wolf-robert-bianco/98458174/

NBC is promoting a 4 show cross-over event. 

Another question - @Christo - when you going to appear on one of these?

 
Here's a question - do we really need 4 different Chicago TV shows?

http://www.usatoday.com/story/life/tv/2017/02/28/review-chicago-justice-****-wolf-robert-bianco/98458174/

NBC is promoting a 4 show cross-over event. 

Another question - @Christo - when you going to appear on one of these?
Law and Order 2:  Fuhgeddaboutit Bugaloo

 
Going to be in Chicago Friday - Sunday. Is Second City the best comedy club there, or is it just the one everybody has heard of? Maybe a nice dinner spot near there since we could be in the area all day (Yanks/Cubs during the day, a stop at North Ave Beach to re-enact the Frank Gallagher scene, dinner, then Second CIty...solid day/night?).

Then on Saturday we'll be doing the Chicago tourist thing. If there was one restaurant you Chicago guys would recommend (thinking high-end steak, Italian, or Asian) in the downtown area, what would it be? Also a recommendation on a cool rooftop bar with a sweet view, preferably one where we could watch the Yanks/Cubs game Saturday night, would be most appreciated.

ETA - where do we go downtown to watch the Derby Saturday? Staying at The James in River North so we'll probably be in that general area if that helps

 
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I'm going to be there May 14th-19th.

What's the pizza joint I HAVE to try?  Looking at Lou Malnati's and Pequod's...but if you Chicagoans suggest otherwise, let me know.

 
Going to be in Chicago Friday - Sunday. Is Second City the best comedy club there, or is it just the one everybody has heard of? Maybe a nice dinner spot near there since we could be in the area all day (Yanks/Cubs during the day, a stop at North Ave Beach to re-enact the Frank Gallagher scene, dinner, then Second CIty...solid day/night?).

Then on Saturday we'll be doing the Chicago tourist thing. If there was one restaurant you Chicago guys would recommend (thinking high-end steak, Italian, or Asian) in the downtown area, what would it be? Also a recommendation on a cool rooftop bar with a sweet view, preferably one where we could watch the Yanks/Cubs game Saturday night, would be most appreciated.

ETA - where do we go downtown to watch the Derby Saturday? Staying at The James in River North so we'll probably be in that general area if that helps
Second City is your best bet.  Most historic and gets great talent.  Buy tix in advance.  Many good restaurants very close by on Wells St.  You asked for a rooftop bar to watch Cubs, but there is a good rooftop near Second City at the Hotel Lincoln, with great views of Lincoln Park, Lake Mich. 

I'm out of touch on what is good foodwise in River North nowadays. Unless you need advice on donuts - I've been to all of those strangely enough. Kids will make that happen. 

 
Going to be in Chicago Friday - Sunday. Is Second City the best comedy club there, or is it just the one everybody has heard of? Maybe a nice dinner spot near there since we could be in the area all day (Yanks/Cubs during the day, a stop at North Ave Beach to re-enact the Frank Gallagher scene, dinner, then Second CIty...solid day/night?).

Then on Saturday we'll be doing the Chicago tourist thing. If there was one restaurant you Chicago guys would recommend (thinking high-end steak, Italian, or Asian) in the downtown area, what would it be? Also a recommendation on a cool rooftop bar with a sweet view, preferably one where we could watch the Yanks/Cubs game Saturday night, would be most appreciated.

ETA - where do we go downtown to watch the Derby Saturday? Staying at The James in River North so we'll probably be in that general area if that helps
I'm partial to Improv Olympic, but you'll probably be fine at Second City. It's obviously very well known, and the location should fit well with your other plans.

I don't go out much for high-end dinners in Chicago too often, so not sure I can help much there. I'm sure you can ask around or look online for reviews to find something. Tons of good options usually, especially if you are looking for steak obviously.

I'm old and boring now so probably not much help on the other stuff either. Sorry.

 
if the choices are Lou and Pequods then I would agree. There are a number of new joints open though that are getting good reviews. I saw something recently about a new one in Logan Square that is supposed to be really good. 
Can't go wrong with Lou or Pequods. Add to that, I just had Piece the other day. They make a hell of thin crust. Only problem with it is Rick Nielsen profits off of my patronage.

 
I'm partial to Improv Olympic, but you'll probably be fine at Second City. It's obviously very well known, and the location should fit well with your other plans.

I don't go out much for high-end dinners in Chicago too often, so not sure I can help much there. I'm sure you can ask around or look online for reviews to find something. Tons of good options usually, especially if you are looking for steak obviously.

I'm old and boring now so probably not much help on the other stuff either. Sorry.
Monteverde just got a James Beard award, right? Tough to pass on that. There are a ton of great places off Randolph. I'm partial to Avec and Blackbird.

 
The James hotel is right next to Pizzeria Due. Used to be a pretty darn good pizza, though I can't speak for it nowadays. 

 
Monteverde just got a James Beard award, right? Tough to pass on that. There are a ton of great places off Randolph. I'm partial to Avec and Blackbird.
those are great, but not sure I'd call Avec a high-end choice. Especially if he's looking for steak, Italian, or Asian.

I'd probably go as far as saying if you are coming from NYC area, you really shouldn't be getting Italian in Chicago unless you're going to Spiaggia.

 
The James hotel is right next to Pizzeria Due. Used to be a pretty darn good pizza, though I can't speak for it nowadays. 
original Uno or Due are solid choices downtown. I'd even recommend them over Malnati's personally.

 
those are great, but not sure I'd call Avec a high-end choice. Especially if he's looking for steak, Italian, or Asian.

I'd probably go as far as saying if you are coming from NYC area, you really shouldn't be getting Italian in Chicago unless you're going to Spiaggia.
Good point about Avec. I was just thinking about it as good food.

 
For steaks, I currently am a fan of Prime & Provisions on LaSalle/Wacker.

ETA: Haven't been to Second City in a while, but the shows are typically very good.  However, to say the seating is cramped would be a major understatement

 
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