Second City, The Windy City, My Kind of Town... no matter what you call it, here are some things that I would absolutely not pass up on your day in the best city in the world, Chicago! Here's a list of my all-time faves.
1.) Take an architectural boat tour of the lake and river. I think would be an excellent use of your time if you are interested in the history and details of Chicago's architectural beginnings.
2.) The Willis Tower (true Chicagoans do not refer to this building by what it's named today. It will always be The Sears Tower to us) is the tallest building in the city, but my choice is The Hancock Building. The views of the lake are beautiful and it's near all the amazing shopping on Michigan Avenue.
3.) The museums in Chicago are unsurpassed and rich in history and activity. For the art lover, The Art Institute is stunning. For the science buff, take a cab to Hyde Park and visit the Museum of Science and Industry. They have the most amazing exhibits and are well worth the drive.
4.) The Art Institute is smack dab in between Millennium Park where you can see the "Bean" sculpture, and Grant Park, known for Buckingham Fountain. They're easy to get to and nice to walk with some great photo ops of the city.
5.) No trip to Chicago would be complete without deep-dish pizza and, believe me, Chicagoans a very loyal to their favorites. Personally, nothing beats Lou Malnoti's... but a close second is Giordano's.
6.) Chicago is known for its steak houses. My two favorites are Chicago Chop House and Gene and Georgetti's ... you cannot go wrong with either one.
NOTE: If you see a street vendor with real, Chicago-style hot dogs, get one! However, and I can't stress this point enough... DO NOT ASK FOR KETCHUP! Everyone will know you are a tourist and you will fall prey to scrutiny and evil glares. Besides, ketchup on a hot dog is just gross. Do it like a real Chicagoan and you will love every mouth-watering bite.
Jennifer Conforti: I was born and raised about 35 miles northwest of the city of Chicago in Palatine, IL. Just a 40 min ride on the train and I was in my happy place. Chicago is teaming with life and love. It truly is the City of Big Shoulders and if you ever have the chance to go, just do it.