There are some good recommendations in this thread. Here is what I would do:
Spend a lot of time in southside, lives there for two years and I miss it everyday.
Southside
For breakfast I would go to STIR. Southern style fare. Awesome bourbon collection and great breakfast/brunch items. You also get a small buffet included if you purchase an entree. $2 mimosas. The next day I would go to State Of Confusion. Way better brunch buffet, boozy, great food, the whole nine. I would also recommend Bluegrass Grill if you just wanted an absolutely perfect breakfast and didn’t want to booze it up. I’ve never seen it when there isn’t a line. I’ve been there many times waiting in line before the sun is up waiting on the staff to open it up...
For lunch, I would go to Main Street Meats and order the burger. It’s the best one I’ve ever had. (Tremont Tavern in Northshore is in my top 5 too). If you like divey type places, The Pickle Barrel is my favorite bar in Chattanooga. They smoke in there but you can sit up on the roof/patio to avoid that. They have a great cheap menu and in an awesome space. Pepper jammer burger is my go-to. The Terminal (right beside Stir) would be a good option too for lunch as would. FEED would also be a good lunch option.
For supper, I would have to recommend Alleia. The best bolognese I’ve ever had. Can be a pricey place, but when me and ole gal go we can get two orders of bolognese and a bottle of wine and I’m out the door for $70 including the tip. I would also go over the Flying Squirrel for drinks/cocktails before you go out to eat supper or afterwards for a night cap:
Northshore:
For breakfast, go to FOODWORKS. Dollar mimosas and very well done food. High quality stuff and not terribly expensive.
For lunch, River Street Deli. Order whatever the special is. Or go to Tremont for a very solid burger and a beer.
For supper, there are some good options depending on what you’re in the mood for. Brewhaus is good if you’re into that type of thing. German style food and good beer. Foodworks does a very solid supper too if you didn’t do breakfast there and want to try it out. Beast + Barrel is solid. Alimentari and IL Primo are two very highly rated pasta shops over there. I’ve never been because if I’m eating pasta it would take a freight train to pull me out of Alleia.
Let me know if you have any other questions or anything else I could help with. Sent from my phone so I apologize for any misspellings and formatting.
Thanks