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3 Days in Cheyenne’s Chicago

Aug 3, 2019 | USA | 2 comments

1,026 days. That’s how long it had been since I left Chicago from the best fall break almost 3 years ago. It’s no surprise that I was long anticipating a visit not only to Windy City, but also to one of my best friends, Cheyenne. We met at Sewanee, studied abroad the same semester, in the same country, and even spent spring break together in Mallorca.

We hadn’t seen one another since last May, when we graduated from college. Since then, she’s started her career in nursing, and I was in Ukraine. So much has changed, and yet so much has stayed the same.

Because Cheyenne’s a working girl now, I had some time with her, and some time to explore Chicago on my own. Which is definitely a good thing, because I take forever in museums and it’s just better for everyone involved if I go it alone in a place as magnificent as The Art Institute. Here is everything I did, from touch down 3 days ago to this morning, as I type this post!

airport transfer

Remember when I talked about how to find super cheap flight deals? And I was high-key freaking out over a $48.30 plane ticket on American Airlines? Yeah, that’s the flight I took on Tuesday to O’Hare, at a bright and early 5:50am. I did enjoy seeing the sunrise from my window seat, though!

Once I got to O’Hare, I went straight to the CTA that would take me to central Chicago. From there, Cheyenne picked me up at Division station on the blue line. Getting on the train was relatively painless. It did take a few minutes to find, so just head to the basement and you’ll see more signs for trains to the city. I’d expect to spend about 30 or more minutes en route.

My ticket was $5, which is a little on the pricey side, but standard for airport trains. It took a couple of minutes, the swipe of my credit card, and I was on the train headed for my BFF.

If you’re coming from Midway, just take the orange line instead of the blue. Cheyenne does it all the time. Easy, peasy!

white and black floor tiles close-up photography at Chicago O'Hare
Photo by Evan R on Unsplash

CTA public transit

Now that I’ve given you the low-down on public transit from the airport, know that you can use the Chicago train system to get just about anywhere. It’s $3 per ride if you buy separate one-way tickets, or you can pay $10 and get an unlimited 1-day pass.

Relative to other metros and subways I’ve taken, Chicago’s service has trains further apart. You can’t necessarily assume that there will be another train in 2 minutes. The least amount of time I waited between trains was easily 4 minutes. It’s no big deal if you’re not in a hurry and know that in advance.

silver train near station in Chicago
Photo by Stephy Miehle on Unsplash

regional bus system

Leaving Chicago, I’m taking the Megabus to Milwaukee. Literally, right now. I bought a ticket to Milwaukee leaving at 7am for $10.99 since another good Sewanee friend and former Res Life boss is there. Then, this afternoon I’ll take another at 1:50pm to Madison.

Why Wisconsin? Well, my usual response when anyone asks me, “Why (insert destination here)?” is, “Why not?”

Anyway, I’m visiting a friend that you’ll probably recognize from my study abroad series, and we’re having a long overdue reunion!

Here are my two cents about the Megabus. If you’re doing two separate routes like I am, just add your second ticket to your first on the same reservation screen. If you don’t, you’ll pay the $2.50 processing fee twice, when you could have just paid it once. Also, I got great deals without buying super in advance. I didn’t get mine until Tuesday, after I’d been in Chicago for a few hours.

Oh, and get there at least 15 minutes early, especially if you don’t reserve a seat. I didn’t pay extra for one, and don’t think it’s worth it to pay for a seat. The bus ignition was on at 6:57, and we left at 7:00:00 on the friggin’ dot. They will leave you behind if you’re not already on!

where I stayed

Since I lucked out by having one of the best people in my life based in Chicago, I had a cozy air mattress complete with fluffy blankets in Pilsen. Cheyenne and Francisco’s apartment is adorable. They have the cutest little balcony off their kitchen, which is where I know I’d write with a cup of coffee every morning. That is, if Cheyenne would let me work as much as I usually do…

Sometimes, it takes the important people in our lives to show us that working until 11pm is, in fact, not normal. Hm.

If you don’t have a loved one in Chicago, then check out the Airbnbs in neighborhoods just outside of downtown. I really liked Pilsen and Chinatown, but take your pick!

On my first trip to Chicago, Cheyenne and I were with my mom and grandma. We stayed in the downtown Marriott because of my Mom’s account with them. We had a lovely stay, but know that even if a room is listed as large enough for 4 people, it’s a tight squeeze. Also, parking is a nightmare. And a ghastly one, at that.

Pilsen Chicago mural

where to eat + drink

The Wormhole Coffee

My first evening in Chicago for this trip, I went out solo after a nice nap from my 3am wake-up call. Since Chey and I planned to watch The Bachelorette season finale and we knew she wouldn’t get home from work until midnight, I knew I needed caffeine. Besides, I had some articles to take care of and wanted a jump-start to work.

I decided to take the train up to Wicker Park. I love this area. As soon as I got off at Damen, I was surrounded by streets full of cute little restaurants and coffee shops. I made my way into The Wormhole, and was not disappointed. Since I was feeling indecisive this night, I asked the barista for his recommendation.

I went with the Cool but Rude, a latte with ginger and curry. Wow. The way those flavors exploded in my mouth was delicious. I’d have another in a heartbeat.

latte with art

Native Foods Café

Allow me to preface this by saying that, on my first trip to Chicago, Nashville didn’t have a lot of delivery options. Of course, that’s changed in the past few years. But my first non-pizza delivery experience was in Chicago, and Native Foods was the restaurant.

My vegan meatball sub was a highlight of my time there. That being said, I knew Native Foods had to be a stop on this trip. And it just so happens to be down the street from Wormhole.

From the moment I stepped in, their staff was so friendly and accommodating. I got the vegan beef brisket burger. I know, right? How in the world does something like this even exist?

It was incredible. I liked it better than the meatball sub. You’ve got to try this place, vegan or not! They’re so inventive.

veggie burger and french fries


Cheyenne wanted to try this place forever, so we finally went while I was in Chicago. I was very impressed! I got the fried avocado grilled cheese, made vegan. It came with spinach, tomatoes, mushrooms, onions, and the fried avocado with cheese on sourdough.

The way the veggies meshed with the less healthy sandwhich ingredients made it a good balance. Chey got the biscuits and gravy. This place is technically veg-friendly, so you can get dairy cheese and eggs here. I’d definitely go back, and highly recommend it.

sandwich and french fries

Rock Bottom Brewery

I’m not a big drinker. I do, however, enjoy the occasional beer, especially if it’s a local brew. It’s all about the cultural experience for me. I didn’t plan on getting a beer at Rock Bottom, when Cheyenne and I met up with Theresa, her friend from home whom I met in Mallorca. It felt so, so good to catch up with her after two years of each of us doing our own thing.

Had I not seen a light beer I wanted to try, I would have gotten the mojito. Yum! I just love that blend of fresh mint leaves and lime. But, I was surprised to see a locally-brewed light beer with citrus notes that sounded appetizing. I’m a diehard Guinness girl, so I usually don’t like a beer I can see through. This one delivered, though! I’m thinking about it right now…

The Chicago House of Za

The Chicago House of Za blew all of my expectations completely out of the water. It’s a 100% vegan pizza restaurant that serves traditional Chicago-style pies.

I don’t discriminate against a delicious, all-vegan restaurant. But, I’m going to be honest. I saved the best for last.


I ordered The Wes, deep dish-style. It comes with seitan sausage, carmelized onion, mushrooms, and cashew cheese. It. Was. Heavenly.

If you’re ever in Chicago, you should definitely check this place out for some incredible plant-based food, friendly staff, and the coolest atmosphere.

closeup of pizza slice

what to see + do

Pilsen murals

Cheyenne lives in Pilsen, and I loved being based in this neighborhood for my trip to Chicago! There were gorgeous murals everywhere, so I highly recommend checking the area out for the art alone. While you’re there, go to The Museum of Mexican Art and try out some food from locally-owned grocery stores and restaurants!

There is a mural of the one and only, Selena Quintanilla, on the side of a small local business. You must go see it, and while you’re there, get some delicious lunch!

pink mural of Selena Quintanilla


If you’re anything like me, then seeing all the Chinatowns is on your list. When Cheyenne told me that Chicago has its very own, I was definitely down to see it. From the architecture, the colors, the food, the bubble tea shops—it’s all magical. I would go back to Chinatown in a heartbeat, and would stay there if I were looking for an Airbnb.

arch entryway into Chinatown Chicago

The Art Institute of Chicago

Seeing art museums is one of my favorite things to do, hands-down. This is precisely why I knew I needed to wait until I was alone to visit the glorious Art Institute.

I’m self-aware. I know I’ll take forever. And this museum was worth every, single second.

Like I did at the Met, I stood at Monet’s work for at least 20 minutes a piece. I didn’t actually research about the Art Institute before I went, just to have everything be a pleasant surprise. Boy, am I glad I did! I was blown away by the iconic pieces in this museum, its architecture, and the thoughtfulness of each display. I’d go again right now, if I could!

Monet's Irises
I was in Monet heaven

The Bean + Millennium Park

If Chicago’s on your radar, then you probably already know about The Bean. Thanks to The Vow, it’s become a hallmark of wistful romance. Know before you go that it will be crowded, and if it’s sunny out, it’ll probably be hot. If you’re traveling solo, then you should ask someone that seems trustworthy enough for a photo. I did, and I’m glad I went back to ask!

Another cool thing about this area is the building to the right of the Bean (see cover photo). It’s shaped like a vagina, because it was designed by a female architect who said that all other skyscrapers, well, aren’t…

#Representation, ya know?

What a fun fact and true story!

The Bean in Chicago

Navy Pier

I FINALLY MADE IT TO NAVY PIER! I was ecstatic. Since I last visited Chicago on fall break, it was a tad nippy outside. And, since Navy Pier isn’t exactly right in downtown, it was a trek from where we were. This time, I knew, beyond a shadow of a doubt, that I was determined to make it to Navy Pier. It delivered, for sure!

I contemplated going up in the ferris wheel, but decided against spending the $18 to go inside. Maybe next time, though…

Navy Pier ferris wheel

Solo in Chicago?

Yes, yes, yes! I had a blast on the treks I took around the city alone. Because Cheyenne was at work all day long my last day in the city, I saved things like a visit to The Art Institute and Navy Pier to do solo. I also went out to The Wormhole, Native Foods, and Myopic Books on my own.

I felt safe in Chicago, aside from your average incident with unwanted attention, which happens everywhere. Enjoy Windy City at your leisure, ladies! And, as always, be safe!

girl in front of Chicago skyline and Lake Michigan
A friendly couple from Chattanooga took this lovely photo of me. Wonderful people are everywhere!

This post was an absolute thrill to write. My return to Chicago was long overdue, and my reunion with Cheyenne even more overdue than that. I had a blast enjoying the city with her and Francisco, but also on my own. I hope reading about my experience helped you find some delicious vegan food to try, and see some highlights of the city. Once you book that flight, the rest is good times and smooth sailing from there!

If you liked this post, don’t forget to Pin It!

Chicago Bean with "3 days in Chicago" written on it


  1. Robert

    Excellent post and photos for first time visitors to the Windy City. We are yet to visit from the west coast of Canada, but one day very soon! Spotted your post on Pinterest & have pinned for future reference. Thanks 🙂

    • Sarah

      Thank you and I hope you get to visit Chicago (safely) soon! 😊


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Hi, I'm Sarah

Girl on boat with turquoise water in background

Welcome to my oasis! I am a writer and budding entrepreneur with a love for caffeine, capital gains, and seeing the world. If I'm not writing, you can find me reading a good book, trying out a new vegan recipe, or adding to my coffee mug collection. My goal in life? To see every country in the world. Come along for the ride!

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