I think you owe my employer some money, because this is going to take a while. But whatever, slow day so why not help you out. Let me know if you have any questions or whatever.
OK, pizza... phew, here goes...
Every Chicagoan you ask is going to tell you a different place is best. I'll list some of the big ones.
Lou Malnati's - One of the most known places. They are located all over the city and the burbs, and can slightly differ from place to place. Some people say this is Chicago Deep Dish at it's best, others think it's nothing more than decent.
Pequods - One of my favorites. But it's extra heavy and sometimes you really gotta be in the mood for it. They carmelize the crust, so it looks burnt but tastes amazing (in my opinion).
Unos (on Ohio - the rest are crap IMO) - The first place to server Deep Dish. Some say still the best.
Gino's East - Another popular one that has turned into a chain like most of the others I mentioned. Just make sure you go to the downtown location, just like with Unos.
Spacca Napoli (on the Northside) - Very very good, traditional thin pizza.
There are sooo many more popping into my head right now, but I wouldn't know where to stop if I got started. Chicagoans take a LOT of pride in their pizza, so you seriously have endless options.
Other Food
So many foods are perfected here, that this could get really long. There is a reason Chicago has a huge obesity problem. I'll name some fun, mostly quick cheaper places/foods.
Weiner's Circle - Go get a char dog at 2am on Saturday here. But only if you can take the workers giving you a ridiculous amount of sh1t. This is a cash only dog/burger stand on the Northside. Last time I went there, I went to the counter only to hear "Are you gonna fvckin order, cracker-a$$ mothafvcker!? And don't you dare forget to tip, b!tch!" And for a little added fun, order a Chocolate Shake. Little hint, they don't serve chocolate shakes, but with a $20 tip, the large black women working there will give you a "chocolate shake"...Yeah...
Italian Beef - The italian beef in Chicago gets possibly just as much discussion as the pizza, when it comes to who is the best. I'm gonna get a headache just going through all of those, so I'll list a couple and you can look into them if you are interested. Portillo's (some argue their beef is too commercialized, but they have good food all around, not just beef), Al's Beef, Mr. Beef, Johnny's, Jay's, here comes that headache....
Hot Doug's - Sausage superstore. Go here if you wanna try something different and also clog your arteries. So good.
Kuma's Corner - Ok, this is a heavy metal restaurant (not my thing), that plays heavy metal music (not my thing), with food named after heavy metal bands (not my thing), and a really small place with a usual 2 hour wait (not my thing). Yet, I would eat here every day. The burgers are incredible, with some insane toppings. Just thinking about their burgers on pretzel bread with a cold Gumballhead beer is making my mouth water right now.
Harold's Chicken - If you don't mind going into the hood a bit, Harold's is some damn good chicken! Not sure if you listen to Hip Hop, but Wale called Harold's out for being overrated. He got treated to some heavy verbal abuse at his next concert here for that one haha. This is the only thing in this whole posting that I am mentioning on the South Side, by the way.
Greek Town/China Town/Etc - We have very sectioned areas that offer different types of food. Greek, Chinese, Italian, German, it's endless.
Ok, I think I'm gonna stop with the food now. You have a ton of good options there, plus there are so many places that I'm sure you will find ones just walking around that you wanna check out.
Tourist Attractions
Summer in the Chi is my heaven. There is nowhere I would rather be.
Beaches - Main ones to hit are North Ave beach and Oak St beach. If girls are what you are looking for, and you don't mind crowds, go to North Ave beach. More specifically, go near Castaways. It is a bar on the beach that is basically a beached boat. It is also by a huge area for beach volleyball. The women flock to this area. Just watch out, there are also a ton of high school chicks that are seemingly old enough (man, that was close...). Couple warnings, cops WILL bust you for drinking on the beach itself, and gangs have actually been somewhat of an issue. Just keep your eyes open and don't be stupid (this goes for anywhere in Chicago. Not sure if you have seen the number of shootings, but it's nothing to mess with). Don't be so obviously wasted or you will be a target for police, theft, etc.
Navy Pier - Like a boardwalk. Has a few rides, shows, beer garden, etc. I personally think it's a bit overrated, but tourists love it. Does have an incredible view of the skyline from the huge Ferris Wheel.
Willis (Sears) Tower - Tallest building in the world until a little while ago, and still the tallest building in the US. Freedom Tower in NY is going to be taller, but only because of the antennae. Willis Tower will still have the highest floors in the country. They have a fairly new attraction at the top of the tower where you can stand on a glass floor that extends out past the building.
http://2.bp.blogspot.com/-l1I1DNFXz...lis-Tower-Skydeck-Sears-Tower-in-Chicago4.jpg
*There is also an observation deck at the top of the John Hancock building, as well as a nice (expensive) restaurant on the 95th floor with panoramic views of the city. I think it's impossible to take a date there without her begging you to fvck her after. Probably not the place to go with your buddy.
Architectural Boat Tour - Actually a really cool tour. You ride on a big fairy boat along the Chicago River for about an hour and a half and it takes you around to some of the most incredible buildings. One of my favorites.
Museums - Chicago has some very nice museums if you like that sort of thing, or the weather isn't so nice. Field Museum, Museum of Science and Industry, and Shedd Aquarium, are the must-sees.
Wrigley Field - Love them or hate them, the Cubs ballpark is history. It's second in age only to Fenway park, but in some ways has the feel of being much older. If you love baseball, Wrigley is a must-see, in my opinion. And the stadium is surrounded by bars. I wouldn't spend the night at these bars though. Unless you want to hang out with 21-year-old douchebags all night, and individual girls that are out with 5 guys.
Magnificent Mile - If you want to shop, you are golden right here. This is the name for Michigan Avenue starting at Oak Street at the North (By Oak Street Beach and Hancock Building), and down to the Chicago River at the south. This area is covered in hotels, high end shopping, etc.
Millenium Park - Couple Chicago landmarks here. Pritzker Pavilion
http://www.checkonsite.com/wp-content/gallery/jay-pritzker-pavilion/800px-gehry_pritzker.jpg , Cloud Gate or "The Bean"
http://culturalcapitol.files.wordpress.com/2009/12/cloud-gate-09_0114_melody-mudd2.jpg , as well as some other stuff. Again one of those things where it isn't much to "do", but whatever.
Second City Comedy Club - Located in Old Town, a ton of big name comedians got their start here: Peter Boyle, John and Jim Belushi, Dan Kroyd, John Candy, almost everyone ever on Saturday Night Live, Steve Carrell, Stephen Colbert, Bill Hader, etc. Right down the street is also
Zanies Comedy Club. They also have very good comedians, such as Seinfeld, Chelsea Handler, blah blah blah... If a comedy show is something you wanna do, let me know cause I have a couple friends in the business that can give good recommendations about all of the places around here.