I have been working for over 25 years in the market research industry. During that time my travels have taken me to both cities for industry conferences, training sessions, board meetings, new business development calls, hiring trips and client meetings.
Both cities have a lot to offer:
- Great hotels
- Cutting edge restaurants
- Museums
- Sports teams
- Great nightlife
- Located on the water
- International airports
- Premier skylines
And plenty more.
For me one of these cities stands out more than the other. I really like staying at the Chicago Marriott on Michigan Avenue. It is located a few blocks from the water and is in the heart of the Magnificent Mile and one of my favorite hotels. I also like the architecture a little bit better in Chicago and love how Chicago has integrated the water into the city where NY really hasn’t made the most out of the waterfront area (of course my opinion). Both cities have all the major sports represented but I do like Wrigley Field the best out of any of the stadiums with Madison Square Garden a close second.
For me my decision is easy. I like Chicago better than New York.
Now your turn:
- The question is which city do you like better?
- What city would you rather travel to?
- What city would you rather go to conduct business?
- What hotel do you usually stay at?
- Which city are you more comfortable in?
- Whicy city would you rather live in?
- Have you lived in either city?
I look forward to reading your comments.
John Garvey says:
Merrill:
As you are a native of the Boston area of course you are going to say Chicago. You’d never be allowed back into MA if you said NYC.
As a native New Yorker (yes, they do still exist and Westchester is upstate) and someone who has been to Chicago numerous times for both business and pleasure I have to say NYC is the better city. Chicago is great but as Sinatra said “If I can make it there I’ll make it anywhere” Sample bias, you bet.
Rachel Campbell says:
Chicago! Hands down…best Pizza, best Hot Dogs, best jazz music, best landscaping, places to see, free attractions; Lincoln park zoo is FREE and beats all of the zoos around me with the animals and the landscape…
You can easily spend a whole day lounging at Lake Michigan…I honestly don’t think there is a single thing I don’t like about Chicago (other than the fact that I don’t live there).
*sigh*
Beth Rounds says:
Chicago. I grew up there and I love it! Although we moved to Minneapolis 25+ years ago, I am always happy when I am back in Chi-Town. Lake Michigan is beautiful and traveling up the North Shore is just wonderful. It may not have the same energy as New York, but it is tops in my book.
Christine Cook says:
New York! It’s 1.25 hours from Philidelphia which is my hometown, the folks and all the cousins. Never lived in NY but it’s a great place to visit. On the other hand, I did the Chicago living right on Michigan and Lake for a year. Too cold for this kid! NY for business…the Marriott Marquis at Time Square. It’s the best! You can also drive 2-3 hours from NY and be in so many places…DC, the shore, etc… I vote NY.
Jeffrey Lorber says:
I am an expert on both, having lived in NYC for 10 years and currently in Chicago. So let’s break it down:
NY has: Yankees, much better pizza and hot dogs, prettier woman, Broadway, slightly better weather, New Years Eve at Times Square, Macy’s Thanksgiving Day Parade, did I say the Yankees?
Chicago: Cleaner, less intense, better public transit (cleaner, safer) friendlier, Da Bears, less traffic (but still bad), much better drivers, great airports.
Both: Great museums, great buildings, great parks, lots to do great sports.
But please, a hot dog with a jalapeno pepper, a tomato slice, and a pickle! What is Chicago thinking?
And you cannot compare NY C’s Ray’s Famous to Chicago’s crappy “deep dish” whatever.
NYC wins by a nose.
Merrill Dubrow says:
Interesting since my vote doesn’t count it is tied 2-2.
This will be a close race.
Merrill
Matt Gershner says:
Listen – I really like Chicago – it’s one of my favorite places to visit. It has some great restaurants (including NoMi – my favorite restaurant) and one doesn’t need a car – a big plus to a New Yorker.
However, you can’t compare the second city to the first city. You say “Lake Michigan,” and I say “Central Park, the Hudson, Battery Park, Coney Island, etc.” The Bronx Zoo, the Botanical Gardens, Lincoln Center, Broadway (Chicago has to wait for the tour of “Chicago” to see the show), Times Square, the Met, MOMA, and Guggenheim are just some examples why we’re the center of the universe.
Our sports teams (and yes, we have many, many more) have won quite a few more championships in comparison. The Blackhawks haven’t been seen in decades, the Sox have won 3 Series in 103 years, well, the Yanks have won 26. Heck, even the Mets have won 2 Series since the last time the Cubs won over 100 years ago.
We have the headquarters for all major media outlets, NBC, CBS, ABC and even Fox, although Chicago has Oprah and Jerry Springer.
And then we get to pizza. While we have the original, flat crusted wonder that is pizza, Chicago’s version can generously be considered a round casserole with the same ingredients. No competition there.
In the end, if Chicago wants a piece of NYC, it can always have Staten Island – most NY’ers wouldn’t mind.
Amy Shields says:
I happen to have been blessed with the opportunity to spend a decent amount of town in both of these fantastic cities. Since I opted to move to NY in January of this year, I guess my choice is obvious! While I agree that Chicago is a fabulous city, it’s just too cold for me and doesn’t offer the same easy access to the history of the east coast. For me, NY is more than just the unmatched energy of the residents (which is definitely present and which I personally thrive on)….but also has world-class parks, amazing cultural attractions, a passionate spirit of volunteerism/activism, an unmatched diversity of cultures/lifestyles, AND a wealth of nearby destinations (and public transportation systems). I moved here to take advantage of all it has to offer and since January, here are a few things I have done: Take the train to Philly and DC and a commuter plane to Boston; attend several plays; walk more miles than I can keep track of; hang out at numerous street fairs, restaurants, etc; drive to Rhode Island for the week-end; attend MANY professional sporting events (Knicks, Yankees and Mets).
As far as I’m concerned, there’s no place like NYC; it is the mecca of all that is good!
Dan Womack says:
I’ve gotta cast another Chicago vote. I’ve chosen not to live in a major city but have always said if I had to live in one of the 5 largest metros and had a choice it would be Chicago. Tough to say exactly why, but I’ve always had good experiences when visiting Chicago. I love the people there…and the food!
Paul Kirch says:
I’ve spent a great deal of time in both and for me, nothing compares to NYC. I loved Jeffrey’s comment about Chicago deep dish pizza, which in my opinion is ALWAYS a disappointment. Broadway, great restaurants, better weather, etc. NYC is one of my all-time favorite cities, and though Chicago is a great place to visit, there’s no place like the Big Apple.
Throw San Francisco into the mix and it would be a harder debate. SF is my old home and one of the most amazing cities I’ve spent time in. Ok, I know that’s not the debate. Go NYC!
krista joyce says:
Chicago baby! I travel to both cities for business & leisure & its true NYC is its own animal but I love the charm of Chicago – its sports, food, comedy scene & activities are way better (and friendlier) than my visits to NYC.
Plus, I’m moving the family to Chicago next month
My husband and I are in Chi-town right now house hunting as a matter of fact – Wrigleyville is stupidly fun!!!
Karyn Picchiotti says:
CHICAGO is the best!
New York is too:
–noisy
–dirty
–congested
–hard to get around
Chicago:
–is lively
–is diverse
–has Lou Malnatti’s
–is CLEAN
–is FRIENDLY
–gas is less expensive
–has better looking men (sorry Jeffrey)
–people are warm, friendly and helpful
Michelle Elster says:
I love to visit NY but I live in Chicago. I think it comes down to where you’d rather be MOST of the time and Chicago wins, hands down.
Merrill — you’d knew I’d chime in on this one.
Heather says:
Oh–great one. Do I keep this long or short…maybe I’ll just give the other side to everything Gershner said. Starting with the “many, many” more sports teams–if I am correct, it’s only 3 more.
which city do you like better? CHICAGO!
What city would you rather travel to? NYC–because that means I am leaving eventually
What city would you rather go to conduct business?–Chicago, I think it is easier to get people to warm up to you here
What hotel do you usually stay at? i haven’t really stayed anywhere in ny because i lived there but we usually had our events at the Parker Meridian or Grand Hyatt because of location. We’re trying out the Ritz Carlton battery Park this weekend which I am very excited about to have a full “downtown” experience instead of the standard midtown craziness.
Which city are you more comfortable in? NYC–it was my home for 12 years and I still feel like a pro there
Which city would you rather live in? CHICAGO
•Have you lived in either city? BOTH!
I have to put my OVERALL vote in for Chicago. I lived in NYC for 12 years and have been in Chicago now for about 6 months. Hands down I have been much more active in Chicago than I ever was in NY. I feel people take much more advantage of the lake front as well as anything outdoors, since the nice weather is limited to a few months. While I thought there were a lot of social sport leagues in NYC, nothing compares to the level of participation you get at them in Chicago.
Also, the street festivals. NYC “has” them, but it’s the same food vendors, soap and sock vendors and crafts you see every weekend. In Chicago, the neighborhood fests are all quite unique with regard to what they offer from vendors, but also musical selections and other entertainment.
On a grand scale, I would put Chicago and NY side by side, similar to how many have, with the basics (food, museums etc). But overall, there are a lot of extras Chicago has that NY doesn’t when it comes to actual living.
Bob Graham says:
Let me begin by saying that Chicago is one of my favorite cities and I love going there, but if I have to choose between the two, New York is my hands down favorite (sorry, Michelle).
My feelings are best summed up by Oliver “Daddy” Warbucks in ANNIE. Right before he launches into “NYC” he says “After you’ve been to New York City, everywhere else is Buffalo!” (and I have live in both New York City and Buffalo, so I know whereof he speaks).
For me, NY is the excitement of the theater district, the cosmopolitan atmosphere, the quickening of the pace, the diversity of the neighborhoods.
According to Soxology.com, NY has 10 Red Sox Bars (!); Chicago has 4. NY also has better Irish bars with authentic Irish Music. NY has McSorleys and St Andrews (with its unparalleled selection of single malt scotches). And pizza, you would have to try very hard to find bad pizza in NY (I haven’t found one yet (not that I’m looking).
But above all else, New York has New Yorkers and I love ‘em! I love their passion their openness, their resiliency and their ability to take everything in stride. When I lived in NY I remember the City being shut down because of a huge snowstorm. The next day, people were cross-country skiing down Broadway. I even love it when I get yelled at for wearing a Red Sox hat, because it always leads to a robust and spirited discussion. People from other parts of the country don’t understand New Yorkers. How they can argue face to face and still be friends (as long as you don’t say anything about the other guy’s mother). But I find that when New Yorkers argue vehemently, they get it all out of their systems. People in the South and Midwest seem content to hold it inside and hold grudges. New Yorkers would rather be upfront and in your face, and I love it!
So sorry Chicago, you are a great city and one of my favorites (I tell people that my current home of St Louis is Chicago on a smaller scale) and you have much to offer, especially compared to LA–sorry, Ed–and San Francisco the “charms” of which have always eluded me (ever try to find a decent Irish bar in SF? It’s a futile task.), but when it comes to American cities, you are number 3 and NY is number 2 (and if you have to ask who my number one is, you haven’t been paying attention).
Ruthann Chesnoff says:
I have been to Chicago several times and enjoyed each visit. Really was surprised how beautiful it was and loved the water being so close to the fabulous shops. Great restaurants and friendly people.
But I have to say I love NY. I was born there and even though I have lived in New Jersey for 40 years I still have the adrenalin flowing every time my car enters New York.The energy that exudes from the diverse population with all the hustle and bustle is just wonderful. I also love the location so close to everything,beaches theater,museums and of course New Jersey. New York wins hands down.
John Joseph says:
This is a great debate. Having come from Michigan and worked for a Chicago based company, I know that city very well. Working for a New York company now, though and traveling there often means I am as qualified as anyone else to express an opinion. I love NY! Even if I had to live in the region and commute, I could get used to it in NY ( I would live in NJ) rather than Chicago where the commute to the north shore suburbs can be long and hard.
The excitement and energy in NYC is at such a higher level than Chicago just because of sheer numbers and it’s true: if you can make it in NY, you can make it anywhere. I love the NY Palace, especially when someone else is paying for it.
Sports teams are a draw……………nightlife options better in NY. So much of the decision depends on whether you can live in the city or have to commute to the suburbs.
Bill Dunn says:
Am I the only one around that has never been to either city?
Merrill Dubrow says:
Bill wow – seriously? That should win a prize.
Both have alot to offer.
Merrill
john says:
NYC – nice place to visit, wouldn’t want to live there
Chicago – great place to live, not a great tourist spot
I value longevity over sparkle. Chicago wins.
Karen Flannery says:
First – Bob Graham I thought we were friends – no more after you chose NYC.
Chicago is the best.
Yes NYC is great. The theater, the energy – My favorite hotel is the Marriott Marquis.
Chicago offers the best region theater in the country (Goodman, Steppenwolf). The restaurants are great and we have Oprah. We also are the home town of Barack Obama. Where else can you go to a sold out baseball park to see a team that has not won the World Series in over 100 years. In any other cities the seats would be empty.
The architecture of Chicago wins hands down. We have the tallest building in North America – the Willis Tower – which Chicagoan will always call Sears Tower.
New York is fun to visit but I want to live and play in Chicago.
Malcolm Williamson says:
Chicago has the metro downtown vibe and really friendly midwest folks… Really great combo.
NYC is made of awesome and there’s no other place like it.
I couldn’t make a choice.
How about Chicago from June thru Nov and NYC Dec thru June?
David Lester says:
Having lived in NY (westchester) as a teen and just visited Chicago for business. My answer would be Ft Worth.
Erin Weinland says:
Count one more for Chi-town! I lived there for 6 years, and have only visited NY. The neighborhoods, the beautiful lake front (although it can’t beat the ocean), the great restaurants, and of course, the Cubs and Wrigley field.
For travel, especially business travel, Chicago also wins for me. It’s so easy to get in and out of the airport. My favorite hotel is the W, either by the lake or in the loop – they’re both great. It’s really the city that works!
Leslie Case says:
Have to say NYC ! Charlie (my son) says it hands down has the best pizza. He and friend Jeremy say they love the crowded streets.. and their ice cream. And there’s just something about that NY-er demeanor !
Dan Prince says:
Chicago–by a Magnificent Mile!!!!
Kelly Heatly says:
I want to wake up in a city that never sleeps… (Sorry, I couldn’t resist.)
I’m from Dallas, but travel to both cities for qual work. However, no matter how early the flight, how crowded LGA is, or how congested the traffic, NYC has a completely unmatched energy and vibe the moment you step foot in it. It’s more than just museums, restaurants, and sports. No offense to Chicago, but there is simply no comparison to the Big Apple.
I think I value sparkle over longevity (per John’s comment above).
Daniel Allen says:
I am a native Chicagoan and I spent 25 years of my life there. My kind of town, Chicago is…