When I think of fun restaurants in Chicago there are so many it will be hard to list all here. There are the High Class ones, not that I would think that was fun, but some do because it's not a part of their world normally.
There are the Hot Dog Joints which are truly Chicago at it's finest. You usually see some heavy set guy, with a heavy Chicago accent barking out orders to the guys (usually Mexicans now) behind the counter. Or the Hot Dog stands where the guy can hold five dogs at once and fill each one with ketchup, onions, mustard, relish, and hot peppers, or whatever else the people have ordered.
There are the Greek places, where you have generations of Greeks keeping the same menu, same place, same workers for thirty years or more. They usually are stuck in the neighborhoods away from the hustle and bustle of the City Dwellers, and only satisfy the families who have gone to them for years.
There are the Italian, Polish, Indian, German, Mexican, Japanese Steakhouses, Chinese, and other Authentic Old World Restaurants where the owners make sure everything is authentic and up to par to their standards. Chicago has an eclectic slice of fun restaurants, you just have to define what you think is fun.
There are also the Chop Houses, the Sports Bars, the Cabarets, and the ever popular Dinner and a Show Theater. I will try to highlight the ones I like the most, and have the most fun at. Sometimes it's not the food, but the ambiance, other times it's only the food, and some it's a little of both.
1. My all-time Fun Restaurant Tony and Tina's Wedding
I was never this sappy until I became a married man, but this is a lot of fun for the whole family. The food is decent, and you get an authentic Chicago Italian feel to the night. I grew up with an Italian Grandma, and laughed the whole night here. The soup is great, try the lasagna, not top notch but it will stick to your bones. The veal Parmesan isn't spectacular but adequate. The wine is good, and fun will be had unless you don't have a pulse.
2. Maxwell Street Jewtown (It's not an Anti Semitic name because a Jewish man called it that)
This isn't a place to take your children, but it is distinctly Chicago. What Jew-town is (as it is affectionately called by its patrons), is a place where you go to eat the best Polish Sausage, Pork Chop, or Italian Beef sandwich you ever had. There are only two stands left now, but they give you the foot-long polish, or most tender Pork Chop, these are piled up with the best tasting grilled onions you'll ever eat. The fires are attached to the Polish and are one whole potato sliced in front of your eyes. There is no room to sit, all you do is order it at a window and then return to your car. On the way back you will be inundated with runners selling watches, movies, magazines, and the occasional jacket or t-shirt, this is why it's called Jew-town, you can negotiate the price. The first time I heard about it, I thought we were going to Skokie for some Kosher food. The food isn't Kosher, and it has nothing to do with Jews, but it is a fun unforgettable experience.
3.Ditka's
Da Coach! If you want true Chicago fare you go here. The Pork Chops which will cause your arteries to harden as you eat, the ribs are slathered with enough sauce to take a bath in, but cooked slowly to make as tender as possible. There is also a chance you will see a Celebrity or two, as this restaurant is a hangout of most of the Chicago Bears, Cubs, Bulls, and not a few announcers. There is also the ambiance that is distinctly Chicago. You may even see Da Coach enjoying his favorite salad and beer.
4. Calvins BBQ (formerly Smokin Woody's)
If your looking for traditional hickory flavored Ribs, Chicken, or pulled pork sandwiches. Then this is your spot. There are many I could have put here, but Calvin lost his lease and needs the business. When you instantly know your in a rib-house. There are the grills, the smoky smells, and the overall ambiance of true Chicago Rib place. The owner is a transplant from St Louis, but don't let that fool you. He knows what Chicagoans like in their ribs. The meat falls off the bone into your mouth. No matter how much you may be tempted to try the pulled pork sandwich, of the southern fried chicken, go for the bucket of rib-tips first. They are heavenly.
5. Fogo de Chao
This is a Brazilian Steakhouse. It's truly a one of a kind experience. It takes you to the Brazilian Frontier. Dine in a beautiful restaurant resplendent with pictures of Brazilian Cowboys cooking over open pits. They call their style Gaucho. It is a tradition handed down by the European immigrants who settled Brazil. The meat is carved right at your table to make for a festive evening.