Chicago is one of my favorite cities and while there's a lot of blogs about Windy City experiences here on AAATravelViews, I'd like to add a few of my recommendations:

Attractions
My absolute favorite place to go in Chicago is The Second City, an improv theater that’s been around since 1959 and features some of the best up-and-coming comedy sketch artists.  This is where Joan Rivers, John Candy, Bill Murray, Dan Aykroyd, Eugene Levy, Gilda Radner, George Wendt, Shelley Long, Mike Myers, Steve Carell, Tina Fey, Stephen Colbert and Jane Lynch got their start. The shows are adult-oriented and hilarious.  A typical evening begins with scripted comedy shorts and skits, while the second half of the show has the audience giving suggestions for improvisations. 

The first time I went to Second City I met one of the cast members in front of the theater, Holly Wortell, who later appeared on Life With Bonnie.  The box office was closed but she offered to let my family and I in the show with a cast pass, we were taken to the front row and had a great time. At intermission Holly came out to say hi and introduced us to Chris Farley, who later used my name in a skit, which is still a high point for me.  Second City is a Chicago landmark everyone should visit.

If you are like me and you enjoy the campy, silly stuff you should try The Untouchables Tour.  The guides act like old-school mobsters with the accents and white ties on white shirts.  First we stopped at a church where there was a mob shooting, and I stuck my finger in a bullet hole.   Then we went to the sight of the Valentine’s Day Massacre, it’s now a nursing home parking lot.  The tour also passes the Biograph Theater where John Dillinger was shot and goes by Mrs. O'Leary's cow farm, where the Great Chicago Fire started.  Ironically, it's now home to the Fire Department Academy.

Restaurants
Billy Goat Tavern is famous for two things:  it was the inspiration for the famous “cheezborger, cheezborger” skit on Saturday Night Live. In the SNL skits it was called the Olympia Diner.  It also has an infamous connection to the city.  Owner William Sianis brought a pet goat to Game 4 of the 1945 World Series at Wrigley Field.  Sianis and his goat were thrown out of the game.  Sianis was so mad he put a curse on the Cubs.  They lost the game, the World Series and the Cubbies, sadly, have not won a pennant since 1945.

The Rock 'N' Roll McDonald’s is the third busiest McDonald’s in the world.  The first floor is a typical McDonald’s, but there are two other buildings connected to the store - a music exhibit which is mostly Elvis memorabilia and a McDonald’s Museum.  My favorite item on display was the original Ronald McDonald doll, which I had as a kid and it instantly brought back a ton of fun memories.  I also liked the Happy Meals display showing highlights of the toys, many of which I had at one time.  When I am sick my comfort food is still a Happy Meal with a vanilla shake.

Ed Debevics is a greasy spoon diner and a longtime favorite in Chicago.  Their motto is “eat and get out.”  The first time I visited I was shocked at the service.  The waiters were rude and they didn’t seem to care about me.  Then I realized the rudeness was part of the fun and started throwing insults back at the servers. The food was pretty good; I had the All American Grilled Cheese Sandwich.  It was made with Velveeta cheese, and it was just like my mom used to make, perhaps even better. Just don’t tell my mom I wrote that. I also got a hot dog, fries, and an Ultimate Black Cow, which is a root beer float.   I would suggest Ed Debevics to anyone --just make sure you understand the rudeness is all part of the experience.
 
Art Work
If the weather allows, check out these two outdoor experiences. As fellow AAATravelviews contributor Greg Weekes noted in his blog about the Navy Pier, the Bob Newhart statue in Gateway Park is cool, especially for fans of The Bob Newhart Show.  Donated by TV Land in 2004, the statue is a life-size replica of Bob Newhart as Bob Hartley, the Chicago psychiatrist.  The statue has Bob sitting on his chair looking over at a 70’s-style couch. The sculpture is a great photo op, as you can sit on the 'couch'.

I also stopped by the Daley Center to see the Pablo Picasso sculpture 'untitled' but most people call it “the Picasso.”  Every time I see it I  think about The Blues Brothers movie.  If you remember, the Brothers end their 'mission from God' near the landmark when they run into City Hall to pay the taxes on their childhood home.

Any more fun Chicago spots?