Top 5 Things To Do and See in Chicago

As a born and raised Chicagoan, I’m pretty persnickety about what passes for essential Chicago tourism. Yes, the Magnificent Mile is pretty but  this glitzy stretch crammed with designer shops really doesn’t define the Windy City or its sensibilities.  So I’ve compiled a list of the top 5 things that in my opinion, truly reflect Chicago history and attitude. 

1.  Pizzeria Due:  Deep dish Chicago style pizza is an absolute must. You may think you’ve tasted it before but if you’ve never been to Chicago, you’ve never experienced true deep dish pizza. It is dripping with cheese, it weighs about 5 pounds and it neatly reflects brash Chicago style and heavy Midwestern palates. The iconic Pizzeria Uno chain is credited as one of the first to serve the delicacy. Pizzeria Due is just as iconic and is my personal favorite because it’s slightly less crowded than the original.

2. Untouchable Tours:  No matter that Al and the most notorious hoodlums are gone, this is a gangster town, always will be. Review the recent mayoral election if you don’t believe me.  With guides dubbed ‘Southside” or “Ice Pick”, this is the most entertaining and authentic tour of Chicago gangster landmarks. With shiny spats and Tommy guns in hand, “da guides” will escort you to the site of the St. Valentine’s Day massacre and everywhere in between.

3. Willie Dixon’s Blues Heaven Foundation: This is the home of the blues but you’ll never learn any real blues history at cheesy North side blues joints.  At the Blues Heaven Foundation, you’ll view the actual recording studio for Chess Records, hear live blues demonstrations and buy CDs for Chicago blues icons like Muddy Waters, Howlin’ Wolf, Koko Taylor, Chuck Berry and the legendary “father of modern Chicago blues,” Willie Dixon.  You’ll learn how blues became rock n’ roll and how the genre informs most contemporary music today.

4. Chicago Cultural Center:  In the shadow of sparkling new Millennium Park and the legendary Art Institute of Chicago, the Chicago Cultural Center sometimes gets overlooked but it’s a very regrettable mistake. Boasting the world’s largest stained glass Tiffany dome and gleaming Carrara marble, the cultural center is an architectural marvel in its own right but there’s so much more. Art exhibits, concerts, films, lectures and festivals are presented almost every day of the week and all for free.

5. Chicago Lake Street Bridge:  This is another overlooked treasure.  It stretches over the Chicago River and offers the most magnificent views of the skyline.  This is the only downtown bride that survived the Chicago Fire. It’s rarely as crowded as the Michigan Avenue Bridge so stroll slowly across it and grab a big eyeful of Chicago.