2021 FT Analyst Living in Chicago

Using the Loop as your reference point for most of this. I'll caveat that i'm a more recent transplant, about two years have lived there - There's so many cool neighborhoods like ukranian village, logan square, etc. that i haven't experienced. Below some general thoughts from where I looked at and/or lived:

Further away from the loop, to the north of the downtown - Wrigley field (and Wrigleyville generally), Lakeview, Lincoln park, etc. Lincoln park is a really nice area - there's some affordable stuff there (also very expensive stuff - but whatever). Bus lines and CTA lines down into the city - also get proximity to the lake which is awesome in the summer.

As you get closer to the loop, again from the north, you have the gold coast, streeterville, river north - gold coast is largely IMO older money so I'd avoid that at the start

River north is the 'hot' neighborhood - it's walk able (generally) into the loop for work, tons of bars, nightlife, premium buildings with tons of amenities... with prices to boot. If you have a roommate or two, the costs won't be astronomical but if you are trying to live by yourself, we lived in a convertible (think one bedroom minus a bedroom door) that was ~2400 a month by the time we were done with utilities, etc. On the plus side, though, you have tons of access to the river walk - access to the loop - access to the lake as well, and all are generally walk able depending on, of course, weather. The one downside is depending on where you are, a lot of tourist traffic since Michigan avenue isn't too far off.

West loop - think extremely yuppie. People who outgrew river north or similar, moved to the west loop. Cool neighborhood. Lots of food. Less high rises - more mid rise type living (although there are certainly high rises). Really fucking expensive, although I'll note that my view is in about 6 months it will be less expensive. On par with river north, or worse honestly depending on the buildings. Issue with the west loop is that you generally are further away from the lake front, etc. still very walk able into the loop. Live here currently - it's a nice area.

South Loop - somewhat similar to the other two, just... literally south of the loop. Easier access to all the museums, the park, lake front, etc. from here. Walk able into the loop. Prices are better than river north or west loop - less 'known' food spots but still plenty of stuff to do and proximity you are still close to everything. It's fine. They have a trader joe's so... that's good.

• Do not live in the loop. Just. Don't. Do. It. That's all.

• L is simple to navigate (the train), just know your general line colors. Blue goes to o'hare, orange to Midway airport. Brown/Purple/Red go north towards wrigley, etc. (red also goes south pretty far). Green goes from west (through west loop) all the way down south through mccormick center, etc. Pink.... takes you near a Costco. That's all I got there. Metra can take you down to University of Chicago.. probably other places. Bus system is actually pretty solid - learn those, cheap, easy, effective. Don't drive to O'hare at rush hour.

• My last tip is walk the city as much as you can. Get to know the neighborhoods, explore out the various CTA lines for new or cool areas - there's a lot to see/do, and it varies so much depending on where you are. Enjoy!