The gastronomic offer of Chicago is very wide. I suggest you try these 3 restaurants, very different from each other. I divide them by category
As I already told you, if you are in Chicago you cannot miss tasting the Chicago style hot dog. If you have followed my advice, you have certainly already tried it during the Millenium Park tour. However, a visit to Portillo's, the temple of the hot dog, is a must! In this historical place, the authentic hot dog is served respecting the ancient recipe that includes these among its ingredients: mustard, seasoning, celery salt, freshly cut onions, sliced ripe red tomatoes, kosher pickle, and peppers piled on a perfectly steamed poppy seed bun. Even the package is absolutely traditional: the hot dog is kept inside a paper wrapper, rigorously inserted, in turn, in a paper bag.
The restaurant is very rustic and does not include table service. As in any self-respecting fast-food restaurant, you queue, order and pay, sit down at a table and wait to be called to pick up your order.
Don't be frightened by the queue that you will surely find at your arrival (at any time), the staff is very efficient and you will be served in a moment.
If you want to spend an evening in a fashion club in the city, tasting excellent dishes of Italian cuisine, you must reserve a table at Siena Tavern. Reservation is mandatory if you want to find a table. If you are staying at the Westin River North, the restaurant is very close, just 4 minutes on foot. The restaurant is very nice, with fashionable furnishings, frequented exclusively by locals enjoying their night-out. The restaurant is welcoming with those sofas instead of chairs... The cuisine is excellent. The chef was able to amaze us with excellent cold cuts accompanied by an excellent fried dumpling, then continuing with truffle dumplings and to conclude with delicious mini donuts... to die for! The memory of an excellent dinner and the desire to return will accompany you for a long time.
For your American dinner, I recommend Ditka's: owned by the famous Mike Ditka's former football player, star of the Chicago Bears. It seems not at all difficult to find him at the restaurant: we missed him for a few minutes. The restaurant has a typical American atmosphere, of those restaurants/clubs that you often see in movies. Stylish furnishings, all in polished wood, memorabilia and photos of the world of football on the walls, impeccable and super attentive service from the waiter who will follow you throughout the evening. The food is in perfect American style: starting from hamburger to prawns served in style with lots of steaming melted butter. The cuisine is excellent and the dishes are very accurate. Try it if you want to ensure an all-American dining experience!