The Top 10 Things You Have To Do In Chicago Before You Die


Visiting a world-class city like Chicago can be almost overwhelming.  There’s so much to do and you may have little time to do it in.  But if you have to pick and choose, there are some experiences that you just can’t miss.

Whether you’re a visitor or a new Windy City resident, you shouldn’t go to your grave without doing the following:

  1. Eat Deep Dish Pizza

One of the first things that springs to mind when you think of Chicago is probably deep dish pizza, so this obviously has to be on your list.  Whether you decide that you love it or hate it, you can’t leave without giving it a try.  Delicious pizza pie can be had at a great many of the city’s pizzerias, so don’t feel you have to go with one of the hyped spots – in fact, you may want to nicely ask a local if they’ll tell you their favorite.

  1. Go to a Cubs Game

With not one, but two baseball teams to call its own, Chicago is most definitely a town that loves America’s Pastime.  Ask any Chicagoan and they’ll tell you whether they’re a die-hard Cubs or Sox fan, but if you don’t have a loyalty for either team, you ought to go to a Cubs game just for the experience.  Wrigley Field is one of the oldest baseball stadiums in the country and is still one of the only ones that relies on a hand-turned scoreboard.  And before you make a joke about their underdog status, check out the infamous story of the Curse of the Billy Goat.

  1. Have a Drink at The Signature Room

Chicago has one of the most historic and most beautiful skylines in the whole world, so it would be a shame if you didn’t see it from on high.  You could visit the viewing areas of the Willis Tower or the John Hancock Center, but why pay to get a view alone when you canpay for a cocktail and get the view for free?  The Signature Room at the top of the Hancock Center allows you to do just that.

  1. Visit the Neighborhoods

Chicago is not just Downtown…in fact if you talk to a local, they’ll tell you that they hardly ever venture to the Loop unless they work there.  Part of what makes the city so special it its many diverse neighborhoods, so you’d miss out big time if you didn’t check a few of them out.  A few of the most interesting are Wicker Park, Lincoln Park, Andersonville and Pilsen.

  1. Hear The Blues

Though blues music may have been born in the Mississippi Delta, it was raised right here in Chicago.  Many musicians migrated to the city in the first half of the 20th century, resulting in the creation of another hub of the music genre.  Nowadays, you can catch great live blues any night of the week, no tickets necessary.  Stop in and pay a modest cover charge at places like Kingston Mines, Blue Chicago., Rosa’s Lounge or Buddy Guy’s Legends and you’ll get a taste of the real deal.

  1. Shop Till You Drop

If you’re coming in from out of town, make sure you bring an extra bag for all of your new purchases.  Chicago is chock full of amazing shopping opportunities for those who love a little retail therapy.  Of course you have to check out the Mag Mile (otherwise known as Michigan Avenue) but be sure to also visit the unique luxury shopping district on Oak Street as well as the funky boutiques of the Bucktown neighborhood.

The Top 10 Things You Have To Do In Chicago Before You Die

  1. Catch an Improv Show

You may not know this, but many of the funniest comedians of all time got their start performing improv comedy in Chicago.  Legendary icons like Bill Murray, Chris Farley, Stephen Colbert and Amy Poehler (among many, many others) are all alumni of Chicago’s Second City improv theater, which puts on shows every night of the week.

  1. Take a River Boat Tour

The Windy City has a rich and storied architectural history and is home to some of the most renowned buildings in the world.  There are plenty of ways to see the famous structures, but one of the best has to be from a boat cruising down the Chicago River.  You’ll hear some fascinating history while you take in the unparalleled views of the city.

  1. Check Out a Museum

The Windy City is home to some of the world’s best museums, so while you may not have time to see them all, you should see at least one before you leave.  Go for the Art Institute, The Field Museum of Natural History, The Museum of Science and Industry or the Adler Planetarium.

  1. Do Some Fine Dining

Obviously you have to try Chicago classics like deep dish pizza and Italian beef, but you’d be remiss not to do some fine dining as well.  The city boasts a staggering number of renowned chefs and critically-acclaimed restaurants, like The Girl and The Goat, owned by Top Chef winner Stephanie Izzard and Spiaggia, run by James Beard award winner Tony Mantuano and a known favorite of President Obama.

There you have it!  Now just save this list and start planning your time in Chicago, because there isn’t one of these experiences that you can afford to miss.

About the Author:  Liz Kores is a proud Chicagoan who wouldn’t trade her city for any other in the world.  As the Managing Director of the Oak Street Council, some of her favorite activities involve shopping and dining out.  Liz is also on the Chicago Fashion Incubator advisory board and is a frequent guest author on fashion and travel blogs. For more info, visit