Having lived in Chicago, there's so many good eats I could recommend. You have so many true Chicago classics done really... really... really well. Below are my ultimate favorite - things I plan my schedule around (just so I can knock out as many as possible).
It's Chicago, so of course there's deep-dish pizza, hot dog (don't you DARE ask for ketchup), and Italian food... oh, there's also tacos!
Deep dish pizza @ Lou Malnati's
Chicago style dog @ The Weiner's Circle (photo: ChicagoFoodAuthority)
Bucatini @ RPM Italian
Tacos (along with shot of whiskey and beer special) @ Big Star
Salumi platter @ Purple Pig
(1) Deep dish pizza @ Lou Malnati's
There are thousands upon thousands of articles written about which deep dish pizza place in Chicago is the best. Giordano's, Pequod's, Gino's East, Pizzeria Uno... have each topped an impressive "Best Deep Dish Pizza" list. For me... I have to go with Lou Malnati's. Everything about this big piece of cheesy, tomato sauced filled slice of pie is incredible. It doesn't hurt that their trademark is their buttery crush - appropriately named "Buttercrust." Oh... and if you get sausage on your pie (as you should)... know that it's actually a thin patty of seasoned meat that covers the entire pie.
(2) Chicago style dog @ The Weiner's Circle
Inevitably when you ask someone for a Chicago hot dog recommendation - someone is going to mention The Weiner's Circle. They'll also recommend that you ask for the $20 chocolate shake. I can't really tell you if the hot dogs at The Weiner's Circle is actually good or not... partially because I've never had it sober. The Weiner's Circle - a hot dog stand on Clark Street in the Lincoln Park neighborhood - is where people go after a night out! You stand outside in the Chicago cold, surrounded by a rowdy crowd that gets more and more excited by the staff's foul and aggressive language. It's an authentic Chicago hot dog that comes with a truly authentic Chicago experience - what more can you ask for?!
(3) Bucatini @ RPM Italian
RPM Italia is my go-to restaurant in Chicago. I know I will have an incredible meal there regardless if I'm going for a family dinner, a date, a group celebration dinner, or eating by myself at the bar (yes, I've done all that before). Everything at RPM is delicious - the burrata, the 600 day aged prosciutto, the bistecca, grilled giant prawns, and all their pastas. My favorite... Mama DePandi's Bucatini. It is so simple, and so delicious. Go on a cold night, get the bucatini and a nice glass of Montepulciano or Barolo... it is as good as it gets.
(4) Tacos (along with the shot of whiskey and a beer special) @ Big Star
Before you judge me for recommending a taco joint in Chicago... you should know that it's nearly impossible to get into Big Star without a long wait. It is good. And it is worth it. You can sit outside on the patio or inside. More than likely, you'll end up standing by the U-shaped bar - with one friend holding a pitcher of margarita and another holding onto the plastic tray of tacos. Here's my pro tip: once a week Big Star Wicker Park will open its vaults to share some bottles from their personal collection. Each bottle is limited. Get the whiskey and a beer... because who wants to wait around to order a second round?!
(5) Salumi Platter @ Purple Pig
The Purple Pig is one of the most popular dining destinations on Magnificent Mile. Pork is the natural star of the Purple Pig’s menu. I don't even know where to begin with all the pork dishes that they offer... milk-braised Berkshire shoulder (mashed potatoes, crispy lentils), pork spare ribs (Amaro BBQ sauce, farro, roasted red peppers), pork gyro (tzatziki, pickled banana peppers, and Fried Smashed Potatoes), pork belly (ginger glaze, carrot and espresso), just to name a few. They are most well-known for two things: their crispy pig's ears and their salumi platter. Both of these are a must for me! The crispy pig's ears is a delicious crunchy snack. Perfect to start off with - as you drink your wine and decide on what other deliciousness you're going to order. The salumi platter is to die for. So delicious. It is the absolute perfect thing to share with a few friends over a bottle of wine as you all settle into dinner. If I've managed to convince you to go... then go early! I mean... like RIGHT as it opens early. Pro tip - sit at the bar! Oh and save room for dessert (if you can)!