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I spent the first 25 years of my life in NYC and still have family I visit regularly there and have lived in Chicago for the past 20 years, so i consider myself native level fluent in both cities. I missed NYC when I first moved to Chicago, but after a couple of years I came to realize that my life in Chicago no longer translates to NYC. My mortgage for a four bedroom home in Wicker Park (which is similar to a hybrid of Williamsburg, Park Slope and East Village) is only slightly higher than my rent for a one bedroom walk up on the Upper East Side. And Wicker Park is a far more progressive neighborhood than dull UES. The smallest bedroom in my house is the same size as the bedroom I had in Manhattan, and I turned that bedroom into my closet. I literally have too much stuff to ever return to NYC because no home in an equivalent neighborhood is large enough to accommodate me anymore. Maybe a $10 million brownstone in Brooklyn Heights or $25 million brownstone in Greenwich Village? My home has a garden, roof deck, backyard, but here's the best part - I'm STILL within walking distance of everything from sushi to Indian food to live music venues to clubs. I haven't had to give up much of anything about what I loved about living in NYC to have all of this in Chicago and a whole lot more. I'd have to give up 75% of my worldly possessions to find a place to move back to in NYC. Yeah NYC may have more "stuff" but let's be honest, here. Most people living (not visiting, LIVING) are too busy hustling to afford their studio apartment to take advantage of half the stuff they brag about having access to in NYC. Don't lie to me because I was one of you. You've been to Joe's once since you moved here. You still haven't been able to get reservations to any of the top restaurants yet. You can count on one hand the number of times you've hung out in any part of NYC other than your own borough or below 59th street in Manhattan. You only go to Katz's to flex when your friends or family are in town. And you still haven't gotten around to seeing a Broadway play, ballet, or the symphony. You spend your average weekend doing the same thing most people in most cities do - you join your local gym, meet your friends at the closest bar on your block, get General Tso's chicken on DoorDash, and watch Netflix while eating it. Your life would translate just fine in Chicago. For a good chunk of you, your life would translate just fine in Cleveland. Posers.

I moved to Chicago about 2 years ago, initially, I was living in Albany Park when my lease ended I moved to Gold Coast and I love it. Not sure I will remain in Chicago but if I will not leave this area. Lincoln Park, Old Town, and River North are all amazing areas with lots to do, and see, and all within walking distance of each other.

Great tips!! Keep posting!

I lived and raised a family in the southwest of Chicago, behind Midway airport, safe and friendly neighborhood.

Lived in Chicago for six years was the best city I have ever lived in by far

Stay away from the south side

If love diversity like me then move to Albany Park

I use to love visiting Chicago in the 80's and early 90's. Now I want nothing to do with it.

1300 for a studio? Psh...tell that to inflation. Lol...there ain't a studio in any area north of the river under 1600 (for a livable unit). But realistically about 1800-1900 is more the average range.

Any where but Chicago . Ghetto up and comming . U haul is the answer . Their,rape ,car jacking , murder , high taxes . Come on man .

schools, crime and winter are major deal breakers.

Hi I saw your video here and I wanted to ask, if moving to Chicago, are there many job opportunities there? Thanks a lot.

5 DOLLR TACOS????

Chicago in its hay day had just under 4 million people in the 1950’ 1960’s. NYC City Annexed its 5 Burroughs because they were afraid Chicago would take over them in population. If Chicago were to annex the 100 plus villages and smaller cities they would 100% percent take over NYC in population or be pretty dam close.

At 11:20 - Palmisano Park in Bridgeport. It sits where a quarry once stood.

NYC is nice to visit. Yet my condo on the lake front in Chicago is so much less in price.

Cincinnati looks great at 3:30!

Please help me to find someone who live in chicago

Ethan and I still want to move to Chicago some day and If I don’t Ethan will be lol

New York is the better city overall.

I'll choose New York over Chicago. I had more fun in NY than Chicago.

Awesome video, very helpful My personal pick would be 1. Lincoln Park 2. Downtown 3. West 4. North 5. South

You tell us to grab a slice yet you don't provide us with the pizza... Smh

I’m gonna go ahead and say it- at least post pandemic there’s really nothing to do downtown. I moved to Chicago as a grad student (still finishing my MFA) in 2020, I originally moved to the south loop, then lived in the Pittsfield- a cheap building for students, young professionals, and other lower income people next millennium Park- before moving to streeterville (the worst area in the city in my book) for the better part of 2021, then finally moving to Lincoln Park, where I reside now. While living in the loop, I found multiple expensive restaurants, the infamous shops, closing early, and overall lights very little barring the park- more so grant, aside from skating at the ribbon, and I don’t like millennium- with streeterville, being the most egregious example of where I lived. The near North in general is very, very vapid and touristy, but Streeterville is where you live in the area if you’re an old person who wants to be a little bit away from the bars, so I quite literally as a 24-year-old had nothing to do in my neighborhood. I wouldn’t include Chinatown as part of downtown- most people here in the city, considered to be the near south side- and have other issues with this videos Examples, of what constitutes which region. Personally, if you want ‘adventure’ as this video puts it, you’re better off on the near west side, near southside or south loop, and the far north, for Chicago I would put it this way, downtown is simply a business district- at least, following the lightfoot administration- where are you go home after work.

Lawndale

Ur gonna get people killed telling them to move to the southside

damn this was a stellar video

Born and raised in Chicago .... the best place to live in Chicago is Florida...... the taxes and fees are a killer .... Chicago is trying to be NYC and failing miserably.. But I love my city

Could you do a video about "o" Block where little Dirk and them are from?

You are great at wasting time speaking nonsense :)

Why did you show Atlantas skyline? @7:55

Hi are you still doing this?? I tried your links but it seems they're down

I do wish that obnoxious T**** tower was deleted or sold. I've seen a lot of people pose across the river from it and have their picture taken using particular hand gesticulations.

I've lived in both the north and south sides of Chicago. I live in the suburbs now, but if I were young, living in the city is fun. The problems Chicago faces is faced by all big cities. Watching Chicago evolve into what it is now, it has turned for the better. If people think it's "bad" now, they never lived here in the 80s. If you want to live in a major metropolitan city, Chicago beats LA and NYC in terms of costs, but not overall choices in things to do and see.

My wife and I will be moving to Chicago in a few years. We cannot wait!

My soul recoils in horror at the thought of having to live in a cold, dystopian place like that...good thing I live in Albuquerque where the sun shines and the people aren't sociopaths.

The 666 ok sign thumbnail..why does everybody do that now?

nvsafety issues are annoying

Anyone know how the wrigley field ticket raffle works? Or where I can find more information?

Don’t ml s to Chicago guys. We’ve got enough yuppies here, no offense. Yuppies are only tolerated in a few areas here. Very few, honestly. Stay away if you’s a yuppie. Okay? Thanks

As someone who lives in New York City and has toured Chicago, the two are like sister cities, but they have their differences. Chicago downtown is like Manhattan and downtown Brooklyn, while Chicago’s suburbs are like the other boroughs of New York City.

I loved living in Chicago, but the winters are brutal! I couldn't do it again.

Your descriptions of New York sound like someone who only knows it from bad movies or a tourist who never left Times Square (that happens a LOT!). Your food mentions are bagels, pizza and cheesecake? New York has EVERY KIND OF FOOD. From almost anywhere in the world. You could eat at a different restaurant every day and never get through all of them (also because restaurants are opening and closing all the time). Of course, this requires venturing out to the boroughs other than Manhattan (which people absolutely need to do). Queens has the best food anywhere. I'm not sure I can finish the video after this extreme oversight. I lived in NYC for almost a decade and I miss it terribly. It's unique in the US.

I'm planning a trip to Chicago and am a smoker (cigarettes), I see that Chicago is a smoke free city...can you really not smoke in the city. I know you don't like smokers but it's a drug and I'm hooked hahaha. Any help would be appreciated.

My son lived all over Chicago and I’m glad he finally left the city and made the move to Vero Beach, Fl. I never understood why or how anyone could live in an area so loud with the L trains and the constant yelling and loud vehicles and the high crime rate…and the worst weather…

I moved here 10 years ago from the South and while staying with a friend on the Northside while apartment hunting, I discovered the Southside which reminded me of the South in some areas. I've got a one bedroom with free assigned parking space, central air , wah/dry in building and there is no comma in my rent and I'm not in the hood. Found it on Craiglsit while they (independent landlord) were remodeling the building. Best decision I ever made.

I pay 8k in DFW TX property tax … education is low, healthcare, food, etc all lack in Texas. It’s very diverse tho, but lacks culture. Its weird. Either way, I’m hoping I’ll be moving back home to Chicago after 20+ years. Taking a wife and 2 kiddos.. 3 Texans who will be shocked for the good while living there 😎 Affordable homes and affordable food something N.Texas doesn’t know anything about

Your perspective of New York seems like it came from a tourist who literally just rode on those big red tourist buses, went to see time square and then went home. I was hoping youd be more objective. But your job is to sell properties in chicago so I’m not surprised that this comparison isn’tfair

I will say something tho, logan square is not considered the west side.... the south side gave us the first lady and president Barack Obama... besides the 1st ferriswheel or the 8hr workday or elevator or house or jazz music, it was the birthplace of the skyscraper. The architectural offices of Skidmore Owings Merrill that are hq here also built the current worlds tallest building in Dubai. So even the richest royal crown prince still has the tallest buildings in the world designed by Chicagoans....

Tell us about your comparison between Chicago and say Houston or Dallas? Since your from texas, this should be interesting