Our Weekend in the Windy City: My First Trip to Chicago

Despite growing up in a small, rinky-dink town in mid-Michigan surrounded by trees and cornfields, I have always been obsessed with big cities. I’ve been to New York City twice, and despite the fact that Chicago is just across the lake, I had never been (and I had wanted to go for almost as long as I can remember).

Unfortunately, no one in my family shares my love of big cities. Somehow, none of my close friends do either. Or, if they do, they never have the time or the money to go. My cousin Chad lives in NYC and has been gracious enough to let my stay with him and show me the city on two different occasions, but I that still left me in a little bit of a pickle when it comes to traveling to other places. Long story short: Chicago has always felt so close, but so far away.


I met Wajid in December of 2017 and we have always talked about going to Chicago together. Despite the fact that he’s from Kashmir, which for reference is over 7,000 miles and an ocean away, he has been to Chicago a bunch of times to visit his close friends who are currently working there as post-docs. He knew the ropes of getting there and navigating the city, including fun places to visit, the best restaurants to eat at, etc.


The funniest, smartest, most patient man I’ve ever met.

Because Wajid is here on a scholar Visa (which sounds very fancy, but is fitting because he is truly the most brilliant person I have ever met!) our time together is finite. If there was one thing I really wanted to prioritize before he has to go, I wanted to experience Chicago with him and I am so genuinely grateful we had the chance to do that. It was a weekend and an experience that I will always remember.


Scheduling the trip was kind of tricky because we’re both super busy people. He works at MSU as a post-doctoral researcher and a lot of his work is very time sensitive—i.e., running experiments, working on getting papers published, etc. He also is the most hardworking person I’ve ever met, so as much as I wanted to go, I knew that, ultimately, his work had to come first and I didn’t want to stress him out about it. 

If getting a trip planned around both of our schedules wasn’t hard enough, the weather this spring was throwing another wrench in our planning. We finally were able to nail down a date in late April and from there he booked the train tickets and I booked the hotel and bought our City Passes.


I spent the weeks leading up to our Chicago trip planning things out. I bought a ridiculous amount of new clothes, made sure that my nails were done, my lashes were filled, etc. Not only had it had literally been 10 years since I had been on a trip, but I’m also naturally the most ~extra~ person ever so I had to make sure that every detail was accounted for.

As our trip started getting closer and closer I started feeling increasingly overwhelmed. I was stressed out about the logistics of the trip, I was stressed out about the work that I needed to get done before we had to leave, I was stressed out about what I should pack. I got so overwhelmed that I started feeling like I shouldn’t have even bothered planning a trip if I was going to feel so stressed the entire time.

Wajid has always been the yin to my neurotic yang and was able to help me relax and reassure me that everything would be okay and I that I would get everything done I needed to and have the best trip to Chicago ever—and he was right.

(Side note: I’ve become less reactive and much more pragmatic since I met him, so hold on to your hat because I’m going to be a hot ass mess without him).


I was so excited for our trip that I couldn’t sleep the night before. I literally felt like a kid on Christmas. 


I had never been on a train before and it totally exceeded my expectations. I had no idea that there would be wifi on the train or that there would be a place to charge my phone and computer. I worked the entire train ride, so it went by so fast. The closer we got to Chicago, the worse the weather started getting and by the time we reached Union Station it was snowing and sleeting. 


To be entirely honest, there could have been locusts swarming Chicago and I wouldn’t have cared. I was so excited to be there with him, it didn’t matter to me what the weather was doing.



I was in charge of booking the hotel and, naturally, I chose the fanciest hotel possible. We stayed at the Chicago Athletic Association and, while it was a great hotel and we loved our stay, I would probably opt for something a little less expensive/pretentious on my next visit there. 


January, February and occasionally late April!


After we dropped our things off at the hotel and took a little break, we headed out for our first tourist-y experience: Shedd Aquarium.

I had always wanted to go to Chicago and I had always wanted to go to an aquarium so I literally could not wait for this and it didn’t disappoint.


We spent hours and hours there exploring the whole place and it was a great way to kick off our trip. I absolutely love how excited Wajid gets about seeing and learning new things, and his enthusiasm and willingness to always try new things makes him the greatest companion for museums and adventures. 


After we left Shedd Aquarium we headed back to the hotel where we hung out for the rest of the night, with the exception of making a trek out in the shitty weather for some Nando’s, which was a first for me. We tried taking a stroll after we ate dinner but it was freezing cold and sleeting, so we decided to call it a night.


We had the absolute best weather on the second day of our trip. We genuinely could not have asked for a more beautiful day. The sun was shining, the sky was clear and blue and it was not too hot or too cold. It totally made up for the shitty snow the previous day, not that either of us were bothered by it anyway.


We started our day at Goddess and the Baker because I had seen it on Instagram and wanted to try it. Wajid is literally the best sport about going along with stupid things I’ve seen on the internet.


After we had breakfast we walked over to Millenium Park where we got photos in front of the Bean (!!!) and Michigan Ave. God bless his soul for always taking a million gratuitous photos of me and making sure they hit all my good angles.



We spent a lot of time wandering around the park, taking pictures and taking in all the sights.



I bought this Gucci bag specifically for this trip, so yes, you will see it in every single photo and no I am not sorry in the least.


Our next step was the Navy Pier, which was one of the things I was looking forward to the most.



We did just about every quintessential Navy Pier thing you can think of, including an architecture tour of the city, riding the Ferris wheel, walking the pier and shopping. Bonus points that they have a botanical garden of sorts!



After we left the Navy Pier we went back to our hotel for a while before heading out for the Skydeck. We tried to do some shopping in between because I ripped my pants (because of course I did) but we spent too long at Sephora (because of course I did) and I ended up not having any time to get new pants before all the stores closed.


Seeing Chicago at night was amazing, no matter how long we had to wait in line (or how many times) and God bless Wajid for putting up with my grouchy ass.


After we left the Skydeck, we hoofed it back to our hotel to eat Shake Shack and watch Game of Thrones on my laptop because the hotel didn’t have free HBO, but not before stopping at the Chicago sign on the way back because I really wanted to see it and Wajid is the sweetest and always humors me.



Our third and final day in Chicago started with coffee at the coffee shop in our hotel, followed by the Field Museum, which was arguably one of the best experiences of the whole trip. I am a huge museum nerd, and this was honestly the coolest museum I have ever been to.


I am definitely not everyone’s cup of tea to travel with because I enjoy doing super touristy things, spending all day at museums, etc. Thankfully, Wajid enjoys museums just as much as I do and was happy to spend all day wandering around learning. Science, bitch!


We had to hurry through the museum because our train left at 4 p.m., but we could have easily spent all day at the Field Museum taking everything in.


I honestly owe Wajid an apology for taking the absolute worst pictures ever. He takes the best pictures of me and I am the worst.


You’re Joe Meteorite, and I’m Joe Dirt!


Wajid does a lot of work with tobacco plants so I asked him nicely to pose in front of this fake plant for a picture, which I know he didn’t want to do but did anyway.

After we left the Field Museum, we headed did some more shopping (the Michigan Ave. Sephora was the most glorious Sephora I have ever been in and I couldn’t stay away—plus it was during the spring sale, so I bought way more than I should have. You can read my blog post about it here). 

After that, we got some Thai food and headed back to Union Square to catch our train.


Looking much less enthusiastic on the way home.


I had the best time ever in Chicago. This trip exceeded every single expectation that I had and is something that I will always remember. I couldn’t have asked for a better trip or a better travel partner. 

One thought on “Our Weekend in the Windy City: My First Trip to Chicago

  1. sallyhenspeckle says:

    I’m glad you got the chance to stop by. I tell people from smaller towns that they don’t know what they have. I’m a Chicago native and I appreciate the lack of lines, waiting, traffic and crowding. I moved to the country. Michigan is beautiful, I used to go every summer to camp and I think that fostered my love of the country.


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s