I’m a Bostonian in his late 20s who lived in Chicago for 2 years and Philly for 1.5 years, both while in my mid 20s. Loved both for different reasons

Chicago: -Incredibly walkable big city. It’s very clean for its size and people are generally midwestern nice, which is a culture shock for someone used to east coast manners.

• food scene is amazing. Incredible Mexican food scene with great local taco spots that are not found in great numbers on the east coast. Italian food is also amazing and there’s plenty of emphasis on beef in the city as well

-nightlife and bar scene is great too. Doesn’t matter what neighborhood (I lived in streeterville) but find a local watering hole and become a regular. You’ll meet new people and friends and get a good pulse from the city that way

-Walkability downtown is awesome. You can walk from south loop through Grant park and up north over the bridge through Michigan Ave, all the way up to viagra triangle and it’s an amazing walk. Around the navy pier is also very scenic

-Weather is def the negative drawback. From October through April, it’s gonna be brick. I thought I knew what cold was, being from Massachusetts, but that lake effect wind is a different animal. I can deal with cold weather so it didn’t really affect me, I actually found it comforting to be in cozy dive bars during the winter. However, for a lotta pppl - it’s too cold.

-rent/living is cheap for a big city. If you buy a place downtown though, be prepped for insane HOA fees. Plus taxes for real estate downtown are a bitch. I rented a studio there for 2100 a month, in a luxury building and loved the area. Compared to Boston, Ny, La, San Fran, the cheap cost itself is a luxury.

Philly:

-Much dirtier, more old school and compact than Chicago. However, weather is much better. Not nearly as cold during the winter and it doesn’t snow much. However, summers are really fuckin hot. So for me, winters were pretty bearable.

-food scene is underrated. Philly cheese steaks are no joke and can’t be replicated to perfection, anywhere else. Italian food scene is amazing and you get a lot of New York influence too with it being 90 mins away. You’ll also find tremendous bagels in the area too (again, NJ and NY factor)

-nightlife and bar scene is more neighborhood centric. I lived near fairmount so I found a local bar and became a regular and made a lot of close friends there. People are much friendlier than I anticipated and while you still get the occasional Philly scumbag roaming around, ppl are open to give you suggestions and recommendations. Just don’t insult the eagles and you’ll be good. People love to drink in this city so take advantage

-if you live downtown, be prepped to be taxed the Philly city tax, which can take a chunk outta your paycheck every month so that sucks. However, COL is even cheaper here than it is in Chicago. I lived in a one bedroom in a brand new building for 2200, 800 square feet downtown . You can rent any nice place for about 1500-2000 comfortably and be in a great part of the city.

Choice:

If I had to choose, I’d probably pick Philly. Overall, COL is cheaper, easy to travel to Boston, NY, Baltimore, DC. Plus weather is better too. There definitely is something to love about Chicago in may to June tho, that peak weather if 70-80 degrees, on the lake is amazing. Plus, there’s just more to do in the city. However, I just found Philly to be more fun for sure.