Solo Travels: Chicago, September 2023

Hopefully the first of a solo travel series!

Welcome to my second substack… read here for more information!

Intro to Solo Travels Series

When I finally moved into one full-time job this year, I started to have the idea to take at least a weekend trip each month starting in September.

This plan is unfortunately already on hold for next month as my car is currently in the shop and I am awaiting nerve testing to see if I need a surgery - but I’m hoping that all works itself out and I can resume this plan by November.

Many factors went into this idea:

• I’ve recently realized that I’ve not enjoyed my life for quite a while; so I’m intentionally making an effort to try to enjoy at least part of my twenties.

• I’m strongly considering moving out of Nebraska, but I want to be thoughtful in deciding where. So I’m mostly trying to travel to places that I am curious about moving to.

• I want to grow. I don’t think traveling is 100% necessary for growth, but I’m in a place where I need to prove to myself that I can follow through on my plans and take care of myself a bit. So solo traveling is a way to rebuild that trust in myself.

For each trip, I want to write up some things that may be helpful for others who are traveling or curious about traveling more. I’ll try to break up the sections to make these as easy to skim as possible.

First Solo Trip: Chicago

So, I made plans and went on my first solo weekend trip.

Hannah in front of a blue, hazy skyline of Chicago with the lake behind her.

For my first solo trip, I chose Chicago. This might not be the best first solo location for everyone, but I think it was the right place for me:

• I have friends that live there that I had plans to see.

• I’ve been there before (twice, though the last time was a decade ago).

• It’s relatively close, in the same time zone.

• I could easily go there again.

Why were each of these important?

• Having friends that lived in Chicago made me feel a bit safer being on my own. If some disaster happened, I knew that they could try to help me navigate it. It also gave me an easy answer to the question “What are you doing here?” from random strangers. (I’m not a great liar, so “Just seeing some friends” was easy enough - I know if I keep doing solo trips, there will probably be situations that I’ll need to have a lie ready for questions like these, but I was glad to not need one on my first trip.)

• While I was 8 and 15 on my other trips to Chicago, I did at least have a familiarity with what Chicago is like, which I think helped ease some of my anxiety. I had a general layout in my head of what the place was like (although Google maps has helped me have this same feeling for other places I’ve traveled to as well).

• I’m not sure if the proximity to where I live actually made that much of a difference for my trip or not. I think staying in the same country was helpful - I didn’t have to navigate the language, the currency, visas, norms, jet lag, or things like that. But before I left, I kept seeing “stay close to home!” as a common piece of advice, and I’m not sure why. If there’d been an emergency, I don’t think there would’ve been that much of a difference if I’d been in Chicago vs. say, NYC or LA.

• For me, I wanted to go somewhere I could easily return to. I didn’t want the pressure of having some once-in-a-lifetime trip that I needed to make sure I made it to all of the must-see sites. There were places on my list I didn’t make it to, but since Chicago is relatively close and not horribly expensive to get to, I’m not upset about that. If I’d gone halfway across the world, I’d probably be more upset about it.

Lessons Learned

Honestly, I did not do a great job of planning for this trip. I’d booked my flights and accommodation, but then I didn’t end up having very much time to actually plan out what I wanted to do and see.

You can somewhat see the mural on this building along the riverwalk: “Bodéwadmikik ethë yéyék/You are on Potawatomi Land” by Grand Portage Ojibwe artist Andrea Carlson.

So, some of these weren’t so much “lessons learned” as much as they were a failure in time management, but here are some things I didn’t consider:

• Transportation: If I would’ve had a bit clearer itinerary for at least the areas I was going to be in each day, I could’ve saved a little money on the Ventra card. I bought an unlimited card for all of the days I was there, but I ended up mostly walking from place to place and not taking the train.

• Food: Without planning ahead, I hadn’t really budgeted for food. If I start traveling for longer periods of time, I should plan cheaper, more sustainable options (my hostel had a kitchen, leftovers, and there were grocery stores nearby - but I mostly just ate out). This is probably the biggest area to plan for future trips (at least what cost to expect in the area and what options are available).

  • I had planned ahead and packed to save money for breakfasts, but my hostel actually ended up providing breakfasts!

  • A lot of my list of recommendations of “things to do” in Chicago were actually just restaurants too, so I think I just need to make sure I balance that out some for future trips - like finding must-see places that aren’t just rooftop restaurants.

• Travel day: I sometimes forget to eat lunch in general, so I hadn’t figured in that after getting up at 4 a.m. for my flight there, I would probably be pretty hungry by the time I got into the city around 11. Whenever I fly somewhere, I usually take a bit to adjust to a place (I’m not really sure if this is anxiety or what), but also being hungry during this time made that worse for me on this trip - instead of taking a few minutes to ground myself, I had to go find food right away.

• Sights: I had a list of some places to go, but many were spread out across Chicago, and I ended up mostly within a walking distance from my hostel. Overall, if I’d planned better, I might have been able to make it to some of the places outside of that walking radius.

• Open Hours: I also didn’t consider that some museums would be closed on Mondays and Tuesdays, and some had very limited hours. This was more of my lack of time management to plan ahead for this trip, as this is pretty obvious, but if there are places you want to visit, check out their hours. (Luckily, I had done this for the Art Institute, and knew before I left that the Bean was under construction.)

• Weather: I luckily did think ahead enough to pack a rain coat, but it rained a good portion of the time I was there. Many of the places I planned to go, like parks and gardens, weren’t as enjoyable in the rain. So having rainy day alternatives is probably a good idea if a lot of your plans are outside.

• Sunset: Similarly, look up when the sun sets if you have outdoor plans. I assumed the sunset was about the same time as home since it’s the same time zone, but I actually had no idea that the sun would set about 40 minutes earlier there than it is at home right now. (For someone who’s traveled a decent amount, this actually made me feel a bit silly that I didn’t know this!)

• Walking: If you mostly walk places, be sure to break in your shoes. (This one is a bit gross.) I wore newer shoes, and I ended up with a blister on one of my toes that became pretty painful, since I only had the same pair of shoes to keep wearing. My toe was actually bleeding by the time I took off my shoes at airport security for my flight back, so if I’d stayed any longer, it probably would’ve actually messed up my trip a bit. I’d packed band aids, but maybe the blister band aids would’ve been good to have too.

This isn’t really a lesson learned, but to un-glamorize travel a bit, this is just a reminder that if you have anxiety attacks, they can happen anywhere.

One night, I’d dropped my new phone (it’s only barely scratched because my real case hadn’t come in yet), but since my nerve issue is why I’m dropping things, I spiraled - worrying about needing surgery, the recovery time, and how much it will cost, and how that would mean I probably cannot travel as much as I’m hoping to this year.

So there I was, on the Magnificent Mile, in a full-on panic attack.

Here I am crying in the middle of Chicago, but trying to take a goofy photo to better document my travels… I’m about embracing the cringe right now.

I walked to an area where there were streetlights and more people. Even though I didn’t really want to be seen, that felt a little safer than the darker side streets I was on initially. I was able to ground myself pretty quickly - the irony of crying on the “Magnificent Mile” helped a bit - but I just wanted to point out that mental health while traveling, especially alone, is still important.

After that, I do think I got a bit of pity privilege though (like pretty privilege, but instead of being hot, it’s me clearly having just stopped crying), as the host at the rooftop restaurant I went to let me through to take photos without buying anything at the bar. :)

The view from Cindy’s rooftop, where the dinner menu had no meals under $20, so I’m guessing the food lives up to these views.

General Itinerary and Costs

We hate talking about money in this late stage of capitalism, but especially with travel, I think it always seems so expensive and unattainable. I always wish travelers would just say roughly how much things cost so I could try to see how I could afford it. So in that spirit, I’ll share an overall cost for parts of my trip, with notes on how I could maybe save more in the future.

I do want to share the caveat that I’ve been saving money up thinking I was going to have to have neck surgery and yearly MRIs, so I’ve been doing quite a lot to intentionally save money for about a year and a half. (Maybe that’s another post - but also, choose sanity, don’t work 60 hours/week.) As I’ve found out I won’t need neck surgery, at least for the next many years, I started to budget out a general idea of spending that savings to travel more over the next year. However, I’ve recently found out I may actually need a nerve surgery on my arm, and when I returned to Omaha my car immediately had to go to the shop — so money absolutely stresses me out, and I have trouble spending money ever, with how much I always seem to end up needing to spend on medical bills. But logically, I know it’s also a good idea to spend money on something enjoyable for once (I think).

Flights: United

Flights are always the most expensive part of traveling for me. I paid just over $250 for these flights. This allowed me to bring a carry-on and personal item (I usually don’t check a bag unless they gate-check my carry-on for free).

I did have some flexibility in my dates, which helped me find this price. Most of the major events in Chicago in September were on other weekends, which I think is why that weekend was significantly cheaper when I booked.

Potential to save:

• Airline - I chose to pay a bit more to not fly with Frontier, as I’ve had bad experiences flying with them before (I likely won’t fly with them out of Omaha again, as they only fly back into Omaha every few days).

• Planning ahead - I was unsure about some work events and scheduling things, so I only booked the trip about 3 weeks in advance. Of course, that made the flights more expensive.

• Frequent flyer programs - if I do end up traveling more, I think I’m going to need to find a credit card with miles or some kind of frequent flyer program. These seem to be the best way to save, and since flying is the biggest expense, I think that’d make a bigger difference. (If you have any tips on this, feel free to share!)

Accommodation: HI Chicago Hostel

I stayed in a hostel - this was also a first for me! Hostels are considerably cheaper than hotels if you’re traveling alone, so I wanted to try this out on this trip. I actually liked it quite a bit!

I stayed at the HI Chicago Hostel in the Loop, and it was about $200 for the three nights. I was in an 8-bed room. The website said there were mixed-gender bathrooms down the hall, but we actually had a bathroom and shower in our room, as well as more showers down the hall, which was a welcome surprise.

The hostel also provided breakfast (fruit, croissants, pastries, muffins - smaller stuff, but much better than my mashed up pop-tarts I was planning to eat). They had kitchens on every floor and a good-sized laundry room too. They also had a bag check if you came early or were leaving after the check-out time (for $3), which was super helpful.

Here's a few views of the hostel! I'd read to make yourself a bit of a cave with a bottom bunk by hanging up a sheet, and the front desk gave me an extra blanket - so even in a room with 8 beds, I had some privacy! There was also this dining area with massive windows and a common room with couches, a TV, pool tables, various seating, and more of the massive windows.

Potential to save:

• More beds: I spent a little more to get a medium-sized dorm with 6-8 beds instead of the 10-bed room. Now that I’ve stayed in a hostel, I think I’d just stay in the bigger room for a bit less money.

• Membership: The HI Hostels also had a member rate, and the membership was something like $15/year. If I keep traveling to cities they have hostels in, I’d probably get the membership to save a little extra.

• Other locations: The hostels I’ve looked at internationally have been sometimes around $8/night, so I’m not sure if US hostels are just more expensive or what the difference is, so I think the location could help with the cost.

Transportation: The L

I spent around $20 on Ventra cards for the unlimited fare. In total, I think I took the L 5 times, so I would’ve saved money if I’d just paid the $2.50 for each trip. I liked knowing I could take the L if I needed to, but especially in other cities where the transit is more expensive, I think planning for how much I’d actually use it would save money.

If you know me, you know I love public transportation though, so all my love to the L - it even goes right into the O’Hare airport.

Here’s the blue line from O’Hare. :)

Airport Parking: Omaha

Since my flight times weren’t very convenient to get a ride from anyone, I parked my car at the cheapest airport lot. I downloaded the online coupon as well, so this was $20 for the 4 days.

Activities:

Many of the places I chose to go to were free - like the Chicago Cultural Center, Museum of Contemporary Photography, Lurie Garden, Navy Pier, Milton Lee Olive Park, Millennium Park, Ohio Street Beach, and Harold Washington Library. & There’d be a few more parks on this list if it hadn’t rained around 60% of the time I was there.

I really loved Lurie Garden, Ohio Street Beach, the Contemporary Museum of Photography, and visiting Exile in Bookville - all for free! The Chicago Cultural Center was neat, but I'm not sure I really understand the domes. Milton Lee Olive Park was nice, but online it seemed like it might be the best view of the city, which I'm not sure I'd say is the case. The Art Institute also has a free terrace you can visit for good skyline views without paying for a ticket!

The Art Institute of Chicago - $32.

Outside of flights/hostel, I think this was the most expensive part of my trip. I had just missed the visiting Van Gogh exhibition, but I still spent the better part of that day going through the galleries - my camera roll is mostly filled from the Art Institute. I could probably do a whole other post on what’s there, and I might!

I’ll probably share more about some of the art later, but here’s Andy Warhol’s take on the Mona Lisa, almost like I visited the Louvre.

The American Writers Museum - $14.

While this museum probably only jives with a certain crowd, it is a crowd I’m part of, so I enjoyed this museum. If you like to read, especially about writers and writing, then you’d probably like it as well.

The photo ops here were a little odd, or maybe just hard as a selfie (the words projected on the wall here don't make a lot of sense projected onto my face, but it said "stand here!") - but the artwork of some of these writers, like this artwork of James Baldwin, was super cool in my opinion.

Food:

I ended up spending less than $100 on food - my estimated goal was to spend less than $150, so I spent less than I thought! I try not to over-budget for food on trips, unless it’s an expensive area or I’m going to fancier places, because no matter where you are, you’ll need to eat. (Basically, the idea is that this mostly comes out of my general monthly budget for food, not a trip budget.)

I did spend $20 on one meal to get deep dish pizza since I was in Chicago. I also met up with a friend at a place that I spent about $20 at, but we chose to go there because it was the Hanabusa Cafe (which if you didn’t catch it while reading, is basically my name).

Side note: in middle school, I went to a performing arts camp where another camper’s last name was Hanabusa, so I knew it was a Japanese word, but I hadn’t had Japanese soufflé pancakes before. They were pretty good!

So without those, I spent around $60 on food, which all in all isn’t too much more than I’d probably spend at home to eat for 4 days.

My deep dish pizza and the Hanabusa cafe (which these are actually on the same street)!

Packing:

Luckily, I’ve traveled a decent amount, so I’ve built up most of the things that make traveling a bit easier, like a carry-on backpack (similar to this), a clear TSA toiletry bag, dry bags, and I usually travel with my Beats (which are sadly actually sort of flaking, but they still work).

For this trip, I also bought a padlock (about $3) for the hostel, and cheaper packing cubes ($11 on clearance), which ended up being super useful living out of the locker in the hostel. I’d probably get better quality packing cubes that compress more, especially if I end up traveling in colder months packing sweaters/coats, but those worked great for this trip.

I also somewhat impulsively bought a Fjallraven Kanken, these bags originally created to prevent back problems in Swedish schoolchildren (in arctic green).

• It’s embarrassingly expensive, especially when you consider that I’ve been looking for a new laptop bag for months and refused to buy one over $50, but since Charlie was wearing this lil bag in Heartstopper, I just had to get one.

• HOWEVER, these bags are waterproof, and since it was raining most of the time I was in Chicago, this bag actually saved my belongings! And when I wore the bag correctly (with the straps pulled tight), my neck actually didn’t hurt at all, so there may be something to these arctic fox bags preventing back problems.

Here I am with my impulsively purchased but beloved Fjallraven kanken at the Art Institute.

Since I’m not sure if I’ll be able to take more trips or if I’ll need surgery and/or a new car, I’m not sure how to wrap this up. So… thanks for reading! I’ll probably write more for this space soon. :)

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