I want to give people my quick welcome to Chicago tour, 2 different sets and just a bunch of random places. Note, these are for people who drink and eat pork but there are non-alcohol and other meat alternatives to these. Most require reservations but are usually easy to get for the top set.
The 'Welcome to Chicago' I prefer:
Violet Hour - There is a speakeasy type place in Wicker Park. They require a reservation, and have a dress code of no sports stuff etc. But they have super fancy cocktails. Just amazing staff and service. They have a very old drink called a 'Flaming Heart' that is my favorite, but can be hard to find someone to make it.
Big Star - You can then go straight across the street , or put in your res there before you go to Violet Hour. They also have a window they do a Pork Belly taco out of that is very very good if you cannot get a reservation. Mexican food with a ome good paloma.
Piece - The alternative, it is around the corner from there that does a great thinner style pizza, and you want to get it with Doug Sohn of Hot Doug's sausage, if that is your style. The sausage is great.
The alternative 'welcome!':
Three Dots and a Dash - This is a tiki bar in the Near North side area near downtown. They have super fancy tiki drinks with incredible presentation and flavors. Very unique.
Xoco - Right around the corner, this is Rick Bayless's Mexican place. You could go to his more upscale places like Frontiera or Pompolbomo, which is Michelin starred. But at Xoco, you get the limonada that is incredibly tart and get a sandwich called an Ahogada, which is pork carnitas in a super spicy tomato/chile soup, get it as hot as you can handle. It's incredible.
And other great places scattered all over, but i love the places clustered around Fulton Market.
Peaquods - Both Northside and in Morton Grove. Best pizza anywhere, it's a pan-style, not dissimilar to my favorite style of Detroit. Though Burts Pizza in Morton Grove is close.
Publican - Fulton Market, One of the best menus of just great food, another Paul Kahn resturant. Lots of seafood and pork here. They also have a separate Publican Quality Meats which has ALMOST the best sandwiches anywhere.
JP Graziano - Fulton Market, the BEST sandwich anywhere. Italian grocery store that is just making great great stuff.
Girl and the Goat - Fulton Market, If you have 6+ people, you can split a goat leg here, if you can get a reservation. very tough to get in.
Smyth - Fulton Market, Three star restaurant, very very expensive, but great flavors and presentations. I went for Alan Turing's birthday one year, and they made me a crypt text 'thank you for coming' just for me. Has a great bar in front, the Loyalist.
Alinea - Fulton Market, Three star restaurant, even more expensive, but so unique. Arguably one of the best places to eat in the world. Has sister places of Next (just as expensive food!) and The Aviary (fancy cocktails).
Off color - West of Bucktown, Some of the best beer in the midwest of many different styles.
Hopbutcher - in Ravenswood area, Has Belgium style beer and mussels that are fantastic.
Manny's - near UIC, a traditional Jewish deli. Pastrami is excellent, it's a seasoned beef sliced super thin.
Tamale Spaceship - Food Truck, started by a guy who used to work at Frontera that does tamales, just great stuff.
Tons of smaller chains that are good: Ricobenes, Portillos, Harolds, Cafecito, Ginos, etc.
I need to expand this list out, but hopefully this is enough to get out there and try stuff.