A Chicago Bucket List

While I was making lists of all the things I have to do to get ready for my move to Maine, I thought I’d come up with a fun one—my Chicago Bucket List. As the title implies these are all the things I need to do before I leave my Chicago hometown. Now I’m sure every Chicagoland native has their own bucket list, or things that must be experienced in Chicago. Most of those things I’ve already done, and am okay with not repeating. This is my list is of things that I have to experience at least once more before I leave:


  • Go to Cityscape Bar. This bar is located at the top of the Chicago Sun Times building which has a Holiday Inn Express on the upper floors. This bar sits on the corner of the 15th floor with floor to ceiling windows that offer a spectacular view of the Chicago River and downtown skyline. A nice glass of Malbec and a pretty view—what more could you want?
  • Make a visit to “The Lake.” This is what Chicagoans call Lake Michigan. Most people will tell you to visit Montrose or North Avenue Beach, but I like to view the lake up near Northwestern University in Evanston—just north of the city. It’s quieter and offers great, off-in-the-distance views of the city.

Chicago Bucket List

  • Eat Chicago-style pizza and hotdogs. Chicago-style pizza is deep dish pizza. It’s delicious, and only a handful of places get it right. Giordano’s is usually my go-to for guaranteed good, deep dish pizza. For hot dogs nothing hits the spot quite like Portillo’s. A Chicago dog is typically topped with yellow mustard, chopped white onions, pickle relish, a pickle, tomato slices, and pickled peppers. I usually opt for an abbreviated version with just mustard and onions.
  • Visit the Intelligentsia Coffee Bar. This is one of the best coffee brands of all time. They take their coffee very seriously, and it’s a very cool coffee bar to visit.
  • Donuts! When I moved downtown last summer I visited a lot of donut shops. Honestly I was on a quest to find something comparable to the Holy Donut in Portland, ME. Alas it couldn’t be found, but I did come across some other great donut shops in the process: Do-Rite Donuts, Glazed and Infused, and the Doughnut Vault were among the stand-outs.
  • Museum Day. Chicago has a lot of great museums: The Art Institute, The Field Museum, The Museum of Science and Industry, the Shedd Aquarium, and The Adler Planetarium to name a few. I’ve been to all of these museums several times, and will have to visit at least one of them again before I go.
  • Bookstores. Naturally I have a few favorites in this department as well. Again I’ll have to visit at least one of these before I go: Myopic Books, Open Books, Market Fresh Books, and The Book Cellar.
  • Go to my neighborhood pub during a ‘hawks game. Hockey is the only sport I can watch on TV and not get bored. And watching a Blackhawks game in a room full of people who love Chicago hockey is an awesome experience to be a part of.

What are some things on your bucket list before you leave your current city?