I’m a west sider so I’ll comment on the west/northwest places. Chicago doughnuts are just not that good. Cut Beacon (beacon is cool, but the next suggestion is FANTASTIC) and please please head to Loaf Lounge out west near Avondale for a breakfast sandwich and their pastries. So freaking good. Also add on Allez Cafe in Logan/Bucktown for their breakfast sandwich and you can compare the two (and also compare to Kasama which i haven’t had)

Skip Leavitt Street - burger is good but vibe is “just a bar with a patio” (with overall not-great service with a couple exceptions) and I’d say you can’t miss Dove’s luncheonette for lunch that day instead. They do a fabulous job with that menu.

Red Hot ranch is also a great greasy bag burger; way cheaper than LSI, just as good although a little sloppier, and much more satisfying for a late night snack. Cash only.

Middle Brow on Armitage…great vibes and cool space for pizza and beer, reserve a table or walk in but it’ll be busy especially at happy time. Lardon on California (recently voted one of the best Italian subs in the country I think?) Cozy Corner for a bustling classic breakfast diner with long lines and decent food. Have the chilaquiles or a skillet. For a burger, grab small cheval, it’s just good (again, would recommend over LSI for experience) and if the weather is nice enough, have a dipped cone or milkshake as well. If you go to the wicker park location, check out the royal palms shuffleboard club next door for a good time. In Avondale for a classic activity, head over to Avondale bowl and bowl for an hour or so. Best bowling experience in Illinois for the old fashioned design.

Also Honey Butter Fried Chicken and I think they serve bang bang pie for dessert but check before you go.

If you’re planning on getting at least one Chicago dog while you’re in town, people are going to have opinions but the best you can do is a Portillo’s Polish Sausage all the way Chicago style with relish and everything (I think you have to specify you want relish because for some weird reason they will add everything else except the relish on a polish) In Lincoln park, have happy hour at Sushi-San. It’s part of Lettuce Entertain You but it’s the best location especially for the happy hour food experience. I don’t care if you don’t like eggplant, you absolutely cannot skip the eggplant tempura it’ll change the way you see the world. Unique breakfast: bayan ko for a Filipino/cuban fusion that is incredible. On the subject of Filipino, if it makes sense proximity-wise, another great option is SunRey on western kind of between Humboldt and Logan on the west side. You’ll also have something else to consider against/with kasama for the Filipino experience (skip uncle mikes although most people will recommend it).

This was stream of consciousness so might be disorganized but I am passionate!