There are two things about the Windy City you need to know: the wind keeps blowing and the people keep smiling. Seriously, the people are so nice! And Chicago is all about YOU. In every facet of its being, the city reaches out to interact with you, so dive in and experience city life differently with these 5 ways to spend a week in the Windy City.
1. Dine with Death
What’s Chicago’s take on the classic “dinner-and -a-show”? They make dinner part of the show! After all, nothing adds flavor to a delicious 4-course meal like murder. My brother and I went to The Dinner Detective Murder Mystery Show at the Knickerbocker Hotel (how fantastic is that name?!) a few months back and had a blast. The actors in this whodunnit were exceptionally interactive and had us all looking like the cry-laugh emoji by the end.
Shows can be a bit pricey so make sure to check Groupon for discounts!
2. Play some Volleyball on Lake Shore Drive
When the sun’s out and the temperature’s over 60, you can bet your bottom dollar there’ll be someone playing beach volleyball on Lake Shore. Swing by for a pick-up game or bring a picnic basket and enjoy the gorgeous view. With Lake Michigan on one side and the beautiful Chicago skyline on the other, who could ask for anything more?
3. Go undercover at SafeHouse Chicago
The name’s Bond. James Bond. Transform into a secret agent and dine the way they do. Brand new to the city’s restaurant scene, it opened this January, SafeHouse Chicago brings you into a world of espionage and danger so beware of double agents! From the moment you walk in (it’s the red door), to the time you make your getaway, you’ll be in the world of Bond, Agent 99, and Agent K.
So put on a swanky suit, take on a secret agent name and make your way to the SafeHouse for a terrific night. And don’t forget to get your cocktails shaken, not stirred. 😉
4. Laugh your butt off at Second City or grab a seat at a local play
This is the city that brought us some of the best SNL talent and of course, the fabulous musical Chicago! Comedy and drama are kind of their thing. Seats are hard to come by as shows are bought out months in advance, so if you can’t get in, don’t fret. Chicago’s got plenty to entertain you. Every one is different but there’s lots of experimentation going on with user experience in smaller, local productions. I sat in on a one-woman play once where we, the audience, were bystanders trapped in a room with the character in one instant, and in another instant, we were accused of being part of the angry mob outside, the cause of the woman’s conflict.
5. Pizza, Dogs, and Chocolate Cake Shake: The Trifecta
New York has Halal Guys, Chicago has Portillo’s. Portillo’s brings you the best of Chicago–hot dogs and the Masterful Chocolate Cake Shake. It’s literally a giant slice of chocolate cake blended into a gigantic chocolate shake. Bring a few friends to split the sweet. You can thank me later.
For some delicious Chicago-style deep dish try Lou Malnati’s or Giovanni’s or venture into the side streets for something a little less touristy.
There’s always more to do in Chicago and the outer cities so go out and explore one of my favorite cities in the world. ♥
Did you enjoy the post? Want more? Sign up for my newsletter for exclusive content from my trip to Chicago and the other amazing places I’ve been!