Three months ago I moved away from Chicago and let me tell you - I miss it like all hell.
There's something about the energy of Chitown that is unlike any other US city you'll visit. It's big enough to always have something going on, but small enough to navigate some really great spots within a short weekend visit.
I spent five years living in the trendy Bucktown/Wicker Park neighborhood of Chicago (I'm super partial to these areas as you will see), and working Downtown in the historic Wrigley Building on the Magnificent Mile. Coming from someone who loves non-pretentious places, good + cheap eats and drink, and live music, take my advice for your next trip to the Windy City.
Best Places to Eat & Drink in Chicago that Won't Break Your Bank - Or It's Too Good You Have to Go
1. Pub Royale in Wicker Park - $$
Incredible, amazing Indian food. Arguably better than Rangoli, imo. YOU MUST GET THE BUTTER PANEER. And a mango lassi.
2. Little Goat Diner in West Loop - $$
Upscale diner food with a Thai twist, brought to you by Top Chef Stephanie Izard of Girl & The Goat (also a great place, hard to get into. Book on Opentable months in advance). The Tonkatsu sandwich is absolutely to die for and big enough for two people to share - trust me on this one. Also the best bloodies in the city.
3. Northside Bar & Grill in Bucktown/Wicker Park - $
I will say this upfront - the food is bad. Their Happy Hour, however, is what dreams are made of. From 5-7pm every Monday-Friday Northside has 1/2 off appetizers (Nachos are decent), and $5.00 22-ounce pours of craft beer. Simply the best draft deal in the city! I miss it so much.
4. Fat Rice in Logan Square - $$
Teensy weensy modern Chinese restaurant on the outskirts of the hipster Logan Square neighborhood. Opentable reservations are absolutely necessary. There is a small bar next door they will shuffle you into until your table is ready. Let me tell you - the food here is beyond phenomenal. The Fat Rice bowl is just okay - the small appetizer plates are where it's at. The eggplant in particular.
5. Piece Pizza in Wicker Park - $
Unlike the traditional "Chicago-style" pan pizza, Piece only serves thin crust pizza... and it is absolutely life-changing. The flavors are unbelievable. They also brew their own beer here. On Sundays they do a take-out special for $25 - Large pizza and a growler pour of their own brew.
6. Dusek's in Pilsen - $$
Okay, Dusek's has amazing food and atmosphere, you'll read that everywhere. But the real catch and reason to eat here is because it is right next door to Thalia Hall, Punch House and Tack Room. Thalia Hall is a historic music venue that has many great acts running through it - Punch House is an excellent, retro craft cocktail bar underneath Dusek's - and Tack Room is a Piano Bar next door to Punch House. You see where I'm going here: Cocktails, Dinner, Show, Piano Bar. Also, I've never laughed harder at a Piano Bar in my whole life.
7. Furious Spoon (several locations) - $
The absolute best, most amazing ramen you will ever eat in your entire life is the traditional Tonkatsu bowl. You cannot miss this, especially if it's cold out.
8. Stan's Donuts (several locations) - $
There is no other donut place like Stan's. I will say this about a lot of places in Chicago, but for all that I am and have, you can take my word for it on Stan's. Best donuts in the city. I'm partial to anything "blueberry" flavored, where they've drizzled a fritter or an old fashioned (my absolute fave) with their house-made blueberry glaze. Will blow your mind.
9. Bangers & Lace in Wicker Park - $
I love Bangers and Lace. I think it's lost traction over the past five years since I first moved to Chicago, but it's still one of my favorite places to go. Amazing beer on tap, great rustic atmosphere, delicious food and it's on Division St in Wicker Park within walking distance from the rest of the nightlife on that strip. I will always love this place!
10. Antique Taco in Wicker Park - $$
There are so, so many places to get good tacos in Chicago - Big Star, Arturo's, Takito... the list is endless. I love antique taco though because they are incredibly creative with their menu and never fail to deliver on quality. They are more expensive than your average taco though, so be aware of that. This is a total white person taco Mecca. If you're craving super authentic Mexican tacos, I recommend Arturo's on Western/Armitage.
Hope this was helpful... let me know your favorite Chicago Eats if you have any!