Former art student and young bohemian checking in here-
We have to keep in mind an art student's/ artist's budget. , which rules out Gibson's, Green Zebra (though in my experience, many art students lean towards vegetarianism, so if you were to splurge, this may be the place), and Trotter's to Go, Yoshi's, and even Fox and Obel.
There is a handful of artist faves, which may not be my first choices in seeking the kind of adventurous fare that I prefer, but offer reasonable, vegetarian-friendly, and most importantly- centralized locations convenient to galleries and other hip parts of town.
Downtown (near Art Institute)-
Exchequer- favorite drinking haunt of School of the Art Institute students, classic Chicago pub grub, not great, but serves decent deep dish pies, fried fare, and classic sammies like ruebens. The French onion soup is great and the spaghetti and meatballs is old school good.
226 s Wabash
Oasis Cafe- It's former location was covertly hidden in the back of a jeweler's mall, which was a huge part of the draw- we artists love our exclusivity. Its veg-friendly, most importantly. Falafel's fine, shwarma can be good, and two dollar lentil soup with pita is many art student's life support on cold afternoons. Its not the same since it relocated to its current fast food mall spot, but the food hasn't changed much.
21 n Wabash
West Loop (bourgeoning gallery district)-
two Mexican spots:
Perez- Mostly a gringo spot. However, the salsa negra here was my first and is tangy, smoky, and delicious. Weekend specials rock- Birria, a rustic goat soup, will make a mess of your Friday night’s best as you de-bone chunks of meat plucked from spattering greasy broth, but that is my kind of thing. The shrimp ceviche is super fresh and at $2.50 on a tostada, its hard to beat. Their shrimp soup features the largest low budget, high quality prawns in town.
853 w Randolph
deCero-
A trendy newcomer with Modernist decor, hip Latin American soundtrack, and a small plate approach to mix and match tacos.
814 w Randolph
Wicker Park (hip neighborhood)
Sultan's Market-
Again, not the best, like Salam in Albany Park, but conveniently located near the hub of the neighborhood. Falafel is pretty darn good. Veg-heads love the salad bar in particular.
2037 w North Ave.
Handlebar
Just down the street from Sultan’s, it’s a bike culture stronghold and features a fairly healthy, fish as only flesh alternative, mostly vegetarian menu. To my tastes, the samosa appetizer is the only standout, but the simple fare is a nourishing alternative for many neighborhood folks. Good beer specials.
2311 w North Ave.
Irazu-
This has been a particularly heavy trafficked spot amongst the art community in my days. The Costa Rican food is hearty and fairly simple combinations of meat, beans, rice, and plaintains. I like the burritos- the chicken is my favorite of its kind with carmelized bits of skin and onions nestled amongst the juicy dark and white meat. Burritos are equipped with requisite avocado, which is always a plus. The veggie burrito has sautéed mushrooms and black beans, which is a different twist to most of its kind. The Costa Rican sandwich is always popular. They have excellent jugos- slushy smoothies made in a range of tropical fruits; their oatmeal shake is legendary.
1856 n Milwaukee
Pilsen (upcoming art district)-
Skylark-
My personal favorite bar in town. Great beer list. Tater tots with a trio of condiments. Really good fried chicken, mac and c, and greens dinner. I like it.
2149 s Halsted
Hope this is a help.