Chicago, Illinois

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What's it like to live in Chicago?

What's the best and worst things about living in Chicago?

As someone who has lived in DC, Portland, NYC, and Cincinnati, here's my perspective:


Best value for your dollar, Chicago has tons of great amenities at cheaper cost than other major American metros

Top tier big city experience: Housing is relatively affordable, the CTA is great, and we have amazing cultural diversity

People here aren't jerks. I think Portlanders were more surface nice, but you always felt like you were in some sort of crunchy Olympics to be more green and more liberal

Best architecture of any American city, arguably the best skyline of any global city

Each neighborhood is so different and yet still so very Chicago, you can plan your free time around exploring the different parts of Chicago and never run out of stuff to do

Robust white collar jobs market paying VERY competitively

We will live like kings when the water wars start

Chicago pizza

What are the best and worst things about living in Chicago?


Architect - Hard to deny there is any skyline better than Chicago and every building is beautifully made

Cost of Living - It is pretty good I feel like. It can be way worse in other big cities like SF, NYC, LA, DC, etc. Of course the reason why it is so good is because more people move out than in every year.

Food - There is a lot of fantastic food here and I love Chicago pizza. I don't even necessarily love deep dish but they just flat out make pizza here perfectly.

Jobs - There is a lot of jobs and opportunities I feel like over here.

Public Transit/Walkability - You don't need to have a car to live in the city of Chicago with the CTA. You can also use the Metra for suburban level areas.

What is it like to live in Chicago (city)?

Winters are cold as hell, but there are some surprisingly mild days interspersed. Spring is rainy, windy, and chilly, but absolutely gorgeous towards the end. Summers are hot and humid but with some nice cool weather mixed in. Fall is wonderful.
Lake Michigan is a treasure. Lots of public beaches and parks along it. The water is a really beautiful cerulean color sometimes and seeing the skyline on the lakefront by night is a must.
Chicago is a city of neighborhoods. Downtown (the greater Loop plus River North) is tall and dense, kind of like Manhattan but emptier (especially at night). Outside of that, however, the city is divided up pretty precisely into neighborhoods, each with their own architectural styles, socioeconomic/racial/ethnic demographics, histories, points of interest. They are fun to explore - Hyde Park is very academic and cerebral; Wicker Park and Logan Square are trendy with lots of thrift stores and funky restaurants; Bronzeville has important Black historical and cultural institutions; Boystown is the lgbtq hub of the city. The downside is that they can also be a little insular at times and there are pretty glaring inequalities between neighborhoods, especially on the South and West sides.

What is it like to live in Chicago (city)?
Profile photo for Basim Ali
Basim Ali
, lives in Karachi, Sindh, Pakistan
Updated May 28, 2021
Chicago is hands down one of the best cities in the states.

Cost Of Living: First off, Chicago is incredibly cheap. It’s significantly cheaper than NY, LA, SF or even cities like Seattle and Boston. (It’s cheap compared to most major North American cities. It’s still obviously going to be more pricey than middle of nowhere Texas). Most cities with a relatively cheap cost of living either don’t have well paying jobs, or they don’t have jobs at all. Chicago on the other hand is the 3rd largest city in America, and it has a very diversified economy. Despite this, it remains affordable for such an important city. Even in the desirable neighborhoods in the North Side of the city you can very easily get a studio for $1000 a month.

Things To Do: Chicago has more than enough things to do and there’s something happening every single day in the city. The Magnificent Mile is one of the best shopping streets in America, trumped only by Fifth Avenue. Other places to visit include the Navy Pier, Millennium Park, Grant Park, Buckingham Fountain and one of my personal favorite things about the city: the Riverwalk. The Lincoln Park Zoo is incredible as well (and it’s free). In addition to this there are many river and lake cruises that offer stunning views of the skyline. In the summer the lakefront bursts into action. Throughout the warmer months, there are parties and festivals on the gleaming beaches in the shadow of Chicago’s cloud piercing skyscrapers.

In this video I share the 35 things you need to know before moving to Chicago.