OLD TOWN

  • Old Jerusalem - BYOB Middle eastern on Wells St. Chicago has a thing for BYOB, there are tons of gems throughout the city that will let you bring in your own alcohol and you only pay a small corkage fee (I'm pretty sure their's is only $2). Aside from saving money on booze, all of the food is moderately priced, with no entree topping $14. The best items on the menu are the appetizers, in my opinion, and when I went with my family we ordered one of each appetizer and had a proper feast. I highly recommend their grape leaves- which are vegetarian AND the best grape leaves I've ever had. If you are really looking to eat on the cheap- try one of their pita sandwiches, as they all fall under the $10 mark. I love that this is a family run place. Oh, don't forget to try a piece of their baklava too! 

SOUTHPORT CORRIDOR

  • Pasta al Gusto - BYOB Italian on Southport. I crave this place. All of the pastas come in huge portions, all are freshly made, and they do not charge a corkage fee. Two people can eat, and be so satisfied for under $30. Depending on what kind of night you want to have, you can bring one or two bottles of wine, share an appetizer and each get a pasta dish. My favorite is not actually on the menu, but I always ask for Penne alla Vodka with broccoli and spinach added. This place is best for a casual dinner with friends, although would make an awesome date spot if you are both feeling a more casual vibe. 

THE LOOP

  • Cafecito - Authentic Cuban cafe in the heart of downtown. Inevitably, you will find yourself, at some point or another, either a) showing out of towners The Bean or The Sears Tower or b) wandering around the Loop during work looking for something that isn't a chain restaurant. In either cases, I recommend Cafecito. They are famed for the Cuban Sandwich, which is $6. My suggestion is the Black Bean Soup $3 (get a large) and ask for a side of avocado slices. Of course, a Cafecito (aka, Cuban coffee, or, shot of espresso with sugar in it) is necessary to pick you up after such a heavy lunch, but it's so worth it. As a Floridian, I know good Cuban food, and one of my gripes with Chicago prior to Cafecito was the lack thereof. There are 2 in the Loop, one on E. Jackson/Wabash and one on Wells/Madison.