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Gotta be south loop
my bf lives right between Roosevelt and Printers Row and it is my least favorite neighborhood in all of Chicago 🥲 feels sketchy, unexpectedly expensive, very busy roads/less walkable, no good restaurants
South Loop will be your best bet - by far.
Get yourself walking distance to Roosevelt Red Line. All the stores are in the South Loop. Your partner will need to hop on 55. should be 35-40 minutes depending on the time of the day.
South Loop puts you both in a good location for you to catch the Red Line and for your partner to drive 55 out to Lemont. He will be going against traffic so the commute should be under an hour in the mornings provided normal conditions. Outside of the South Loop, you begin to compromise on various points that are important on your list.
oof rough. South loop sounds good, Fulton market area is also up and coming, I’m not really familiar with the commute as I own a car but just some ideas.
West loop along the blue line wouldn’t be awful either. (Depending on which red line stop you work off of) I drive to Westmont and Lombard pretty often and find living less than a 2 min drive away from the expressway makes it less painful. If you’re open to leaving the city, oak park and forest park have some decently priced rentals but you should find places along Madison in those suburbs if you want to stay under the 10 min walk. I don’t like south loop due to all the congestion for drivers. It becomes very gridlock during rush hour.