36 Hours in Chicago

A couple weekends ago, my sister, a close mutual friend of ours named Christina–we became friends at U of L, where she’s graduating in May, and she works at the same law firm as my sister–and I went to Chicago. We left Louisville at 7:40am on Saturday and got back after midnight Sunday (or Monday?), just in time to get a couple hours of sleep before we had to go to work and class, respectively.

Why would we do this crazy adventure, you ask?

There’s a lot of festivals in Chicago, many of them centering around food, and I was looking them up back when I thought I was going to be living there. One in particular caught my eye and even after I accepted my job here in Louisville, I knew that I wanted to go to this festival. I also knew that my sister and Christina would both be willing to come with me, if the flights were cheap enough.

So, we bought our festival tickets, booked a couple of cheap flights through Southwest, and not long after, we were headed up to spend roughly 36 hours in Chicago.

Just to go to Donut Fest at the Lincoln Park Zoo.

Confession time: I love donuts. No matter what variation they come in–beignet, zeppole, Chinese, or a good-old yeast donut with chocolate glaze and sprinkles–I love them. The best donuts are the ones that you get fresh out of the fryer, top them with powdered or regular sugar, and pop them straight in your mouth.

My sister and Christina are also donut fans. Additionally, we all love the zoo and with the local zoo’s penguin exhibit being closed for over a year now (my sister is a bit obsessed with penguins), this was just too good of an opportunity to pass up.

All this being said, there was one slight problem: the time frame. We only had about 36 hours up there, including time spent sleeping. If you’ve ever been to Chicago, you know that you can’t possibly conquer this city in that short of a time.

But we definitely gave it our best shot. Here’s how we spent 36 hours trying to eat, drink, and see the best that the Windy City has to offer.


We left Louisville at 7:40am. This meant that we had to arrive at the airport by 6:40am; this might sound like cutting it close, but SDF isn’t like O’Hare or JFK.

We made it through security with a few minutes to spare and headed to Starbucks. However, the line was almost out the door and since we only had about 15 minutes until boarding began, we knew we wouldn’t have enough time to wait in line, wait for them to make our order, and then get to our gate.

Thank the coffee gods for finally bringing mobile ordering to the SDF Starbucks. Christina and I placed the orders through our respective apps, strategically planning it so that we could the maximum amount of bonus stars, and just a few minutes later, we were headed to our gate.

My favorite view

The flight was fine and thanks to Google Maps, we found our way to our hotel with no problems.

Until we got to the entrance and saw a crowd of protesters out front. Apparently, we chose to visit during a weekend when there was a hotel workers’ strike. Hotel security was out front and they let us through, but we made sure to ask about an alternative entrance. We also grabbed plenty of extra toiletries that were left in front of the elevator on our floor, just in case. I mean, what if we wanted to take ten showers over the weekend?

After getting our room keys and leaving our bags with the bellhop, we headed out to the zoo. We were balling on a budget, so we planned to take the bus up there.

Only to find out that we went to the wrong bus stop. The one we wanted was another block down the street.

Undeterred, we decided to just wait another ten minutes or so. To amuse ourselves, we took photos with some cute doors that were part of an art installation at the park. We’re pretty sure that a girl and her mom were taking senior photos there too, so that was a bit awkward while we tried to stay out their shots.

Then things kind of went to crap. Not major-crap, but definitely minor-crap. Major amounts of frustration occurred.

Did you know that there was a marathon in Chicago a few weeks ago and many of the streets were shut down, causing detours for the bus routes? Yeah, neither did we.

We got halfway through our journey, but after trying to transfer buses only to find that we weren’t even at the right stop for the second one (I think, I still don’t really understand the issue), we decided to say, “Screw it.” We swallowed our pride and called a Lyft, since it was after 11am by this point. We landed about 8:30 local time, so we had been in Chicago for about 3 hours and had spent most of that trying to get to the freaking zoo.

Luckily, the donuts and the animals more than made up for it. We were at the zoo until 4:30 and no, we had zero regrets about that fact. Our plans were kind of loose, time-wise, and there were SO MANY ANIMALS that we wanted to see. Seriously, I highly recommend this zoo. As an added bonus, it’s also free, in comparison to the $16.25/adult that our zoo charges.

I love grey wolves. They’re perfectly camouflaged, but you can spot one in the bottom right corner.
Some penguins during a feeding demonstration.

By this point, the marathon was over, so we caught the bus back to our hotel. There, we watched some Love It or List It and Christina and I took quick naps, before heading back out for dinner.

While Chicago has an awesome food scene–one of the main draws for me, personally–none of us were hungry enough for some deep-dish or anything equally as heavy. So, we decided on the one cuisine that can be counted on to have something for everyone: Italian.

We ate at Eataly and as someone who had never been to one before, I’ve gotta say: it’s a dream come true. The only drawback was that I was flying home, so I couldn’t stock up on all the pasta, olive oil, and cheese that my heart desired.

Instead, I got my cheese kick from a mozzarella “bar” that consisted of balls of fresh mozzarella along with roasted tomatoes and basil pesto. For my entree, I tried ravioli with a charred shishito pepper and butter sauce. I’m a notoriously picky eater and avidly avoid anything even remotely spicy, so I was annoyed when I learned that I couldn’t get it without the pepper. But the waiter convinced me to take a chance on it, saying that it was actually very mild.

I’m glad I listened, because the butter from the sauce really tempered the spiciness, so that it was just a pleasing warmth lingering on my tongue. It also forced me not to scarf down my food, which had the added benefit of actually making me feel more full at the end of the meal.

Ravioli with charred shishito pepper butter sauce from Eataly

I still got gelato afterwards, though, because I have zero self-control when it comes to that stuff. I got addicted in Italy and I haven’t looked back. My sister and Christina also bought some wafer cookies, as well as some chocolates to give our flight attendants on the way back home.

After Eataly, we went to Sugar Factory. It’s a crazy, candy-focused place that is known for their celebrity-loved Couture Pops, but they’ve also got some pretty wild drinks. I tried the Grape Crush, which is grape soda mixed with vodka. Not a combination that I’d ever bothered to try before, but I like grape and I like vodka, so why not, right?

It’s now one of my favorite cocktails. I prefer to not be able to actually taste the alcohol in my drink, and the in-your-face sweetness from the artificial grape accomplished that quite nicely.


Also, since you can’t find the drink prices online, here’s a tip: the Grape Crush costs $12 while one of their goblet drinks, made with dry ice, gummies, and 8oz of alcohol, starts at about $30. Personally, I’ll take the Grape Crush any day of the week.

We headed back to our hotel a little after 11pm, ready for some much-needed sleep before starting our day bright and early once again.


We woke up, packed, and were out and about again before 10am. First stop: Super Target.

Confession time 2: I love Target. Christina is also a Target fan, even more so than me, and since the closest Super Target probably is the one in Chicago, we knew we had to make time for a visit.

Two-story Target? Heck yeah!

Of course, we didn’t know that our pre-Target Starbucks run would take us past a crime scene.

Yeah, you read that right. On our way to get Starbucks before going to Target, we walked past a cop talking a couple guys on the street. We then passed a corner surrounded in crime scene tape and a news crew diagonal from said corner. It wasn’t until I looked it up later that we learned that we walked right past the place where a man was stabbed and critically injured the night before.

While at Target, we realized that the tote bag and 2 backpacks we brought weren’t going to fit everything we had bought between Target and Eataly. The only logical course of action, obviously, was to buy a set of luggage. They were actually on sale and my sister’s been wanting new luggage for a bit, so we took that as a sign.

And thanked God for Southwest’s generous checked baggage policy.

We then returned to our hotel to re-pack, this time using our new suitcase when we were divvying up everything. We had planned to store our bags with the bellhop again, since the guy from the day before was really friendly, but were told to go to “Luggage Storage.” Reasonable enough, sure, but not when we found out that it was going to be $3/bag. Plus there was a lady, whose purpose the staff seemed confused about when we asked them later, “directing traffic.” She was beyond rude to us and quite frankly, it soured my mood for a little bit, which I didn’t appreciate.

After finally getting our bags settled, we headed to breakfast at Chicago Waffles, which again, I highly recommend. The portions were generous and the food was delicious, even the space was a bit packed. My mood brightened as soon as I took a bite of my liege waffle and the accompanying meat-lovers hash.

Liege waffle and Meat Lovers hash from Chicago Waffles

Then we took a Lyft back to Lincoln Park Zoo, since I had decided that I needed to return and buy the red panda stuffed animal that I was still thinking about. We had a river and lake tour scheduled at 1pm and were taking the bus down, so we had to hustle. I’m proud to say that we were in and out within ten minutes. We even made it to the bus stop with a couple minutes to spare.

The river and lake tour was a highlight of the trip for me. I love architecture and on that front, Chicago delivers like few other cities I’ve visited. Our guide, Andrew, was also awesome and made the history of Chicago interesting for all of us.

Then there are the pictures that we were able to get. I’ll just let 2 of the 600 or so speak for themselves.



Following the tour, we headed yet again to Starbucks to use their bathroom and wi-fi. We then went to Millennium Park, where we got the requisite photos of the Bean.

A relatively tourist-free photo of the Bean
Tourist-filled reality








We wandered through the rest of Millennium Park and then Grant Park, since they were on our way back to the hotel, and relaxed for a bit by Buckingham Fountain.

Buckingham Fountain, Grant Park

This is when we found out that our flight was delayed. Needless to say, none of us were thrilled, especially when the delay got pushed back multiple times, finally setting on an hour late. Instead of leaving at 10:20 and getting home at 12:30am, we were now going to leave at 11:20 and get back to Louisville at 1:30am. Just in time to get home around 2am and be up for work at 6am. We had been prepared for a 12:30am arrival time, but getting it pushed back by an hour just made things worse.

Luckily, Chicago has no shortage of places to kill time. We ended up at Bulldog Ale House, on recommendation of the concierge at our hotel, where we stopped to see if we needed to pick up our bags, since our flight was now delayed and we didn’t know if the place would be open when we were ready to leave.

The same bellhop from the night before was there and he told us to just grab our bags from the luggage storage people and he and his coworker would be happy to keep them for us, free of charge. Since we didn’t want to go to dinner with all our luggage, this was a life-saver for us.

At Bulldog, we ordered a lot of apps and a couple apps while we watched the Bears-Packers game. It was a great way to end our trip and honestly, if it wasn’t for the fact that we were trying to figure out if we should start making backup plans in case our flight was cancelled–remember, this was right before Hurricane Florence landed–it would have felt like a regular night out.

We went back to the hotel after dinner, picked up our bags from the bellhop, and caught a Lyft to the airport. We had planned on taking a train, but once our flight and therefore our departure to the airport got delayed, we decided that it was too much of a safety risk. It certainly wasn’t worth saving $15 if it meant sacrificing our peace of mind.

The TSA agents were some of the rudest I’ve ever encountered, save for a security agent in Germany who yelled at me in German despite my clearly not knowing the language. I was tired and quite frankly borderline bitchy by this point, but I knew that I wasn’t going to risk getting in trouble and missing my flight just because of two rude, condescending TSA agents. So, I contented myself with writing a complaint to TSA while waiting for our flight. I still haven’t heard back; raise your hand if you’re surprised. I’m not.

My sister and I always bring some (store-bought, in their original, unopened container) chocolate or cookies for our flight crew. It’s something that I read about in a travel group I’m part of, Girls Love Travel (GLT), and it seems to really brighten the crew’s day. This particular crew was especially grateful, given the late hour and all the issues with the flight. The pilot said we could have whatever we wanted and what we wanted at that point was room to stretch out, so we asked if there would be open seats.

He said yes and we breathed a sigh of relief. Then we headed to the back of the plane, betting on the fact that few people would be willing to venture so far. I scored myself a window seat, popped in my earbuds, and pulled my sleeping mask out of my purse.

I was asleep before take-off.

So, was it all worth it?

Given the public transportation issues, flight delays, and lack of sleep, was this trip worth spending hundreds of dollars just to spend 36 hours in Chicago?


I love travelling, no matter how long or short the trip. And I adore Chicago, so much so that I was (and kind of still am, if I’m being honest) hell-bent on moving there. I prefer spending more than a weekend somewhere, so I can explore it more, but weekend trips are awesome for nearby places that you can visit again if you want to.

Or if, you know, you have a job that requires you to actually be there, in-person, 5 days a week. Heads up: don’t expect to be able to use PTO right away, since you’ll likely have a probationary period. In other words, don’t go booking anything longer than a weekend trip until you’ve finished said probationary period, which is 90 days at my job.

So yes, it was absolutely worth it. Like I said, I love travelling and I’m never going to stop, no matter where I’m working or what the PTO policy looks like. Travel is a major passion of mine and I’ll always make things work so that I can purse that passion.

I know this was a long post, so if you stuck around this long, thank you! If you want to leave a comment below, I’d love to be able to thank you personally.

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