Chicago Bucket List

After a very long application process and excruciating waiting period, I was accepted this past February into the MBA program of my dreams, which means I’ll be moving to Seattle in two months (holly guacamole!). During my four short years in Chicago I’ve seen so many bands and landmarks, consumed pounds of hotdogs and pizza, downed buckets of beer and cocktails, and danced the night away with some of the coolest cats in town, but I now feel immensely panicked by all the things I still have yet to do. Thus, my Chicago Bucket List. Here’s the list that I’ve been working on since March. I’ll chronicle my adventures obsessively on Instagram in case you’re afraid of missing out. **Disclaimer: This is my personal Chicago Bucket List, not like.. what I think all people coming or leaving Chicago should do…. maybe I’ll make one of those once I’ve left**


Annual St. Paddy’s River Dying: I went out once for St. Paddy’s in Chicago, just one time,  and passed out by noon. A day drinker, I am not. And somehow, while I was out, I missed the river turning green. So this year I made the pilgrimage downtown, sober and alone, to see that dang green river. I was skeptical, because how cool could a vibrant green river be? A lot of rivers are naturally green. But this was definitely different. Hanging out below the Marina City towers, yelling at the rowers, watching the boats go back and forth, it felt very “Chicago”, so I loved it. Plus, prime people watching. It’s impressive how many people can manage to get drunk by 10am. While a very stereotypical Chicago activity, totally worth it.

Expat: Rosé snow cones. NEED I SAY MORE. I’ve been following them on Instagram for at
IMG_8551least a year and been completely obsessed with their snow cones, but was always “too
busy”. Don’t be too busy and miss out on this lovely al fresco pop up. We went around 6 on a Saturday and there were still quite a few tables open, not sure if that’s how it always is, or it was good luck, but who cares

Books: Rare, Medium, Well Done: This store sits unassumingly on the corner of Wellington and Clark and has probably been passed by hundreds of Lake View residents thIMG_7494at never entered. From the outside it doesn’t exactly look like a functioning business. There are books in seemingly random placement, some on shelves, some on the window sill, books on top of books on top of other books in perilous stacks. But, the store is in fact op
en and now I’ve been. Inside, it’s as chaotic as it appears from the outside, but organized chaos (far right side is fiction and literature). Books are super cheap and if you have the time it’s fun to just hang out there and parooz. Hours (approximately) 1pm-7pm Monday-Sunday (maybe). Don’t just a book (store) by it’s cover (I’M SO FUNNY).

Mindy’s Hot Chocolate: Another place I severely loathe myself for not visiting during the polar vortex. Their hot chocolate is actually worth all the hype, and their brunch is to die for, so just go.

Big Joe’s Turtle Racing: I had a lot of logistic questions about turtle racing before I did it, so if you’re a turtle race “virgin”, then this is the post for you. Arrive EARLY, while the turtle races start every Friday at 9pm, the place is packed by 8:30pm. Another incentive to arrive early is the lottery system. For every drink you buy you getIMG_7481 a certain number of tickets (like 6 or 7) and every ticket gets you closer to racing your very own turtle. There are new races every 15 (or so) minutes and they draw 5 tickets per race, and if you’re one of the lucky 5, you’re assigned a turtle. The turtles are all at the center of this large pool table under a cake cover and the turtle wrangler lifts the cover and lets the turtles go wild. If your turtle wins or gets second place… you get like a shirt and some booze.

If you’re just a spectator it can be difficult to get up close to the turtle table, there’s a lot of crowding and pushing once the turtles take off, but there’s a live video feed around the bar as well. Big Joe’s is the perfect spot to start your weekend off weird. Side note: at one point people came in to sell pieces of pizza and tamales, so don’t come completely full like I did and be super upset that everyone around you is eating pizza.

Garfield Park Conservatory: I’m mad at myself for never having gone here before, I definitely could have used the plants and warmth during the polar vortex. I’ve been to a few conservatory’s in my day, but I would have to say this one is the grandest of the grand. You’ll find every different kind of climate beneath the beautiful dome of glass. While I love the city, the concrete can be suffocating, and the conservatory is a great way to “get back to nature” without having to stray far from the CTA.


Navy Pier: I was a tourist in Chicago long before I was a resident, but still never made it to Navy Pier. All I’d ever heard was that there wasn’t anything to see, the food was bad, and it was hard to get there. But this past year I started seeing articles about the renovations going on and decided this would be the year to go if I were to go at all. I liked it! In spite of going Memorial Weekend when there were tourists crawling all over the city, I didn’t feel suffocated by them at the pier. The sidewalks are large, there are tons of bathrooms, plenty of seating, beautiful views, beer, and free live music! I didn’t make it to the new Ferris wheel because the line was insane (it was opening
weekend after all ), but I’ll definitely go back. The highlight of my journey was the ‘Original Rainbow Cone’ kiosk with its famous well.. rainbow cone. Would go back just for the ice cream tbh.

Milk Room: Anyone who has lived in Chicago for any amount of time has either heard of Paul McGee or had one of his masterpieces at the ever popular Three Dots and a Dash and/or Lost Lake. So when there was word that he was behind another project, there was obviously a lot of buzz behind it. A bar with only 8 seats and slim reservation windows, drinks that ranged anywhere from $20-$45 dollars, which contained some of the rarest fine liquors in Chicago, if not the world! I present to you the Milk Room, a speakeasy located in the Chicago Athletic Associate Hotel. I’ll start off by being completely honest in saying that I think the experience was somewhat lost on us due to or lack of spirits expertise and knowledge. But this also didn’t affect our experience, we had a great time, I just think someone with that background would have maybe appreciated it more.

There’s only 5 or 6 cocktails on the menu, but they are STRONG and all dramatically different and unique. We tried 4 of them, and wish I could remember their names, but as I said they were strong. The drinks aside, the ambiance alone is worth the visit. When the beautiful glass doors close behind you it feels like you’re transported to a different location entirely. There’s no noticeable trace of noise from the rowdy Game Room next door, soft blues playing in the background, soft lighting, it feel like the bar is just open and there for you. Great place for a special occasion with someone you really like to talk to.

On a final note, if you’ve never been to any of the Chicago Athletic Association’s bars or restaurants I highly recommend them all. When I return to Chicago as a tourist in the future, I fully plan on busting the bank and staying here. In the meantime, I’ll just be lounging in the library pretending to be a guest.


  • Tourist Traps…

Chicago Pizza Tours:

Frank Lloyd Wright Tour:


Segway Tours:

Night Architecture Tour:

Navy Pier Ferris Wheel:

  • Places to Eat…

Flub a Dub Chubs:

China Town:

Fire cakes:

Hampton Social:


  • Places to Drink…

High Tea at the Drake:

Pump Room:

Richard’s Bar:

.50c night at Darkens:

Mezcaleria Las Flores:

Lagunitas Tour:



Got suggestions? Please post!