Top 10 Things to Do in Chicago

Chicago. Home of the Cubs, the Chicago dog, Deep Dish Pizza, and the blue blue waters of lake Michigan. A city destroyed by fire and reborn from the ashes (thus the name Second City). A city known for its architecture, innovation, jazz, comedy, and, fun fact, the place where the brownie was invented. I took it at a slower pace than usual, spending 5 days leisurely seeing the sites and making my home base at the modern and trendy downtown Godfrey Hotel (highly recommend). Here are my Top 10 things to do in Chicago – just some repeat-worthy highlights!

1. See a Chicago Cubs game at Wrigley field and buy extra time by touring the stadium for some behind the scenes selfies https://www.mlb.com/cubs/ballpark/ Wrigley field has superfans (and so do the Cubs), but even if you’re not one of those, or even that into baseball (me, and me) this is an experience worth having. But if you’re going to buy tickets in advance, do some research on the seating and score something in the shade. It can get hot in the Windy City.
   
   
2. Do your own food tour. Chicago is known for alllll the things, like Italian Beef (Al’s!) https://www.alsbeef.com/, Deep Dish Pizza (Giordanos!), (https://giordanos.com/, popcorn (Garrett’s! mix the cheddar with the caramel, then do like I do and eat them separately anyway) https://www.garrettpopcorn.com/, dogs (a dog with all the Chicago fixins’ means mustard, dragged through the garden (aka lots of veggies) and celery salt as the secret ingredient), and Michelin stars. Rather than buy into a food tour official (they do offer them) I decided to make my own way through the eats. There’s so much to choose from that the narrowing down process can be intimidating. So, do your research and do you, then weigh in on the age old battles of who has the best (insert food item here) in Chicago.
   
   
3. Have a laugh at the Second City comedy club https://www.secondcity.com/ The birthplace of improv, this comedy empire (because it’s so much more than a performance space) has been in continuous operation since 1959 and counts among their alumni comedic greats like John Belushi, Dan Akroyd, John Candy, Steve Carell, Amy Poehler, Stephen Colbert, Gilda Radner, Bill Murray, Harold Ramis, Tina Fey and on and on. They have nightly shows.
   
   
4. Ride the L (originally short for “elevated” ) train https://www.transitchicago.com/howto/riding-the-train/ because it’s cool to take public transportation. And Chicago’s is easy to understand and use and also useful. A winning combo you don’t always get in a major city.
   
   
5. Hang in a hammock along Lake Michigan’s waterfront walk at the Tiki Snack Shack https://tikisnackshack.com/ Somewhere between Navy Pier and Promontory Point along the lakefront paved walking path, there lies a floating Tiki bar with a perfectly placed shaded hammock facing the blue water of the lake that one can peacefully relax in while sipping any beverage on the menu. This was repeat-worthy.
   
   
6. Leap tall buildings in a single bound at the architecture center http://www.architecture.org/ and explore all the phenomenal structures that man has built, seemingly defying gravity and other forces of nature. The center is small, but plan to spend an hour or more deep diving into the tallest and most unique buildings in the world, and the really actually quite riveting history of Chicago’s structural stories. Hint: if you book the river cruise through them on their website, you can add on entrance into the center for $5 and that’s good for any time entry (doesn’t have to be on the day of the cruise).
   
   
7. Everyone will tell you to do a river cruise. My top tip? Cruise the river at twilight (and book with the Architecture center). Trust me,  THE most magical moment is when dusk falls on the city. There’s a hush you feel on the river, watching the building lights wink on and set the waterfront aglow as day transitions to night. You almost want to hold your breath it’s so beautiful. You won’t be disappointed with this open-top 360 view of the towering skyline soaring above you while you learn all about the styles and types of architecture that make Chicago notable and memorable https://www.architecture.org/tours/detail/chicago-architecture-foundation-center-river-cruise-aboard-chicagos-first-lady/  Hint: pack and bring a picnic of cheese and charcuterie that you can create at nearby Pastoral https://www.pastoralartisan.com/ at their Loop location. It was an added treat to be dining on the water.
   
   
8. Sip and savor the view from one of the many rooftop bars. There are SO many. The rooftop at the London House https://londonhousechicago.com/rooftop/ and Cindy’s Rooftop Bar http://www.cindysrooftop.com/ (overlooking Millenium Park) were among my favorites. I also recommend the food at Cindy’s (lobster roll! Yum!) and the view from London house by night.
   
   
9. Be one with the bean (actual name: Cloud Gate) in Millennium Park. https://www.chicago.gov/city/en/depts/dca/supp_info/chicago_s_publicartcloudgateinmillenniumpark.html Cloud Gate is that enormous bean shaped liquid-mercury-like reflective art piece you see all your friends post pictures with when they visit Chicago. So it’s one of those “postcard” moments you just have to check off your on Chicago bucket list. It’s art! And while you’re there, Millennium Park has a lot to offer, so explore.
   
   
10. Sing along to a Broadway musical https://hamiltonmusical.com/chicago/ I grew up on New York City Broadway so Chicago had some big shoes to fill in the theater department, but let me tell you, the performance of Hamilton I saw knocked my socks off. Chicago, you are my Broadway home away from home. Bravo! And if you’re still in the mood for music after, take in the jazz scene at Jazz Showcase https://www.jazzshowcase.com/ Reaaallly good stuff.

There were so many other things I did – like taking long walks along the lake, absorbing architecture inside and out, taking the L to Chinatown, and exploring Navy pier. And I still didn’t see it all. My advice, if you don’t see something you love above, ask any Chicago native, they are always willing to share. But whatever it takes, get ye to Chicago and create your own Top 10 things to do in Chicago list!