We live in Tri-Taylor, a literally tiny triangle-shaped neighborhood in Chicago. We’re nestled between the Medical District and Lawndale with big trees, lovely stone houses all in rows, and Italian residents who have been in the neighborhood for seventy years. It’s a wonderful place to come home to, especially now with the trees all budding and the air all sweet and the stray cats looking not menacing but actually soft. It’s a neighborhood sort of hidden away with a handful of little restaurants and cafes that Isaiah and I sampled all in the first week we were here. We live here in Tri-Taylor. We could feasibly just live in Tri-Taylor. The grocery store is only a few blocks away, there’s a coffee shop, a bakery, a pizza place, and a mexican place all within short walking distance, and our church meets in the building where we live. There is no real need to leave.
But we do. We leave. We don’t only live in Tri-Taylor. We live in Chicago, all of it. Or, at least, we are trying to.
We leave Tri-Taylor frequently because this city is HUGE and WONDERFUL! There is too much to see and try to only just stay in our little comfortable triangly neighborhood forever. So Isaiah and I drive our little blue car around and find other little homes in the city. Coffee shops, restaurants, parks, libraries, little corners all across Chicago that have sort of become ours. I have a developed fondness for lots of neighborhoods across this city. I’m getting to know what to expect to see on the streets that cross our town. I watch the neighborhoods blend together, transition from one to the next, each with a different vibe, melody. I’m starting to feel like a resident of all of Chicago, and I love to feel that way. But I feel differently when I remember that there are huge swathes of Chicago that I’m missing all together, huge pockets that I’ll never see, entire lives that are entirely different than mine based on income, based on skin color, based on things outside control. I traipse around the city eating pie and reading novels while kids get shot sitting on their porches, while mothers mourn their sons, while families’ homes are foreclosed on and there is nowhere else to go. I’m a resident of some of Chicago, of the soft parts, the fun parts, the shiny parts. There are parts I’ll never know at all.
I feel grateful beyond grateful to have the time and resources right now in life to facilitate exploration. Isaiah and I both have jobs that give us free time in daylight hours. We own a car. We have a little budget for occasional fun purchases like coffee or burgers. But as I explore the joy that Chicago has to offer, I can’t help but feel the privilege of this lifestyle. I see the people tired at the bus stop, waiting to go somewhere, and I wonder where they are going, whether it’s somewhere exciting or dull, when the last time was they wasted time in a coffee shop just because it’s Wednesday. This city is huge and heartbreaking, with massive inequality and a bewildering sense that I’m living in the top half of the pile. It’s a massive privilege to eat a doughnut in Wicker Park for fun, and I’m all sorts of grateful and all sorts of heartbroken when I let myself think about the people who live in a very different sort of Chicago than the one I live in. There is no way to fix that just in myself. So I just remember. I try to see. I weep with those who weep, even though my weeping does precious little. And I keep exploring.
Here’s a little list of a few neighborhoods and the places in them that Isaiah and I have been siphoning into our ever-widening feeling of home in Chicago. None of these places are special, necessarily. It’s not like we are trying to find the most secret and remote places to be. In fact, most of them are quite known, popular even. But they’re ours still, ours because we return to them, again and again. As if they were a 30-second walk from our home. As if we lived just around the corner. Because we sort of do. Or we try to imagine that we do, that Chicago is just one big corner, that it all, all of it, is home.
University Village/Little Italy: This neighborhood is my most-frequented of the list, as it is the broader name of the area where I live. Taylor Street is at the center of it all, in fact 5 of the 6 places on this list can be found on Taylor. It’s not a destination neighborhood by any means. People aren’t coming here on Friday nights in droves like they would to Wicker Park, but still it’s vibrant and comfortable and the food is GOOD.
- Chilango. My favorite place around for Mexican food. I’ll frequently stop in here for a $2.50 taco as a snack. Try the chicken. It comes topped with delicious pickled cabbage, perfectly seasoned.
- Conte Di Savoia. This Italian deli/grocery is a neighborhood pillar, always full at lunch time. I love it because it sells a perfect $1.50 cappuccino right next door to a Starbucks, and the cookie case is always on point.
- Arrigo Park. Wide open space with a goofy statue of Christopher Columbus, lots of dogs to watch, and lovely homes all around. Isaiah and I walk here just to walk here all the time.
- Roosevelt Library. It’s tiny, charming, and I recognize all the librarians. What’s not to love?
- Chez Joel. Delicious french food. It’s our go-to when we are feeling fancy. Our favorite thing to is come here just for dessert with friends. Isaiah is especially fond of the creme brulee.
- Big G’s Pizza. The best slice in the neighborhood, and I know my pizza. Also, sometimes they play movies on the tv in the shop too. It’s very satisfying to eat good slice and watch Bruce Almighty at a pizza shop, I’ll tell you from experience.
Andersonville/Uptown: Isaiah lived in uptown last summer, so we like to find our way back as frequently as we can. The north side has a really different feel than the west side where we live. I can’t even put my finger on it. Younger people, maybe, less long-time residents, less old Italian ladies? I don’t know.
- The NeoFuturists. If you live near Chicago and have never seen the Neofuturists’ weekly show “Too Much Light Makes the Baby Go Blind,” get there asap. Like next weekend. This is some of the most inventive theater I’ve ever seen and it happens literally every week of the year. Every time I visit the Neofuturists, I leave feeling ready to keep making art, keep sharing myself, keep loving the world.
- La Colombe. Get ready, because I’ll be mentioning three La Colombes. There are three locations in Chicago, and they all basically feel to me like the perfect coffeeshop. Wood tables, gorgeous coffee bars, some of them intentioally without wifi to promote an unmediated chat with a friend or quiet contemplative latte-enjoying. This location, in Andersonville, is the largest and my favorite. for its huge windows alone.
- Village Discount. A GREAT thrift store with just the right amount of grunge. Isaiah and I visit every time we are in the area. Rows and rows of very various clothes, and a huge selection of shoes, one of my favorite things to thrift. A very different feel than goodwill. There are other locations in the city, but I’m not sure where exactly.
- Montrose Beach. My favorite beach in Chicago! The biggest perk, FREE parking, a hot commodity in Chicago beachfront life. Another perk, a fantastic long concrete pier shaped like a question mark snaking out into the lake, a perfect place to sit with feet dangling over the edge watching the urban fishermen waiting for a catch. There’s also a bird sanctuary and actual uneven ground to walk on. A very good place in the universe.
- Baker and Nosh. A dreamy, dreamy bakery. The kind that makes you want to drop everything and just bake bread for the rest of your life, brioches, baguettes, sourdough, croissants. The best place for a light breakfast or for grabbing a daily loaf. I only wish we lived closer.
Wicker Park: The quintessential “hip” Chicago neighborhood that actually isn’t overrated if you don’t let it be. Isaiah and I hang out here more than we ever thought we would because it’s pretty close to home and there is simply a lot to see and do there. I’ve felt it shifting in me from a cool place to a comfortable place, which feels pretty nice. I like being there during the day when things are relatively calm. Weekends and evenings get crazy.
- La Colombe. The second La Colombe on my list, and I’m not sorry. It’s nestled under the blue line, and it’s sort of delightful to sip coffee in the shade and hear the trains roar past. Try the draft latte, it’s my favorite. Milky and light, it’s like a coffee milkshake without the ice cream.
- Taco Bell Cantina. Okay, so it’s just a regular Taco Bell EXCEPT, you can buy a slushy with a shot of TEQUILA OR RUM in it. I KNOW! The funnest thing for a friday night with no prospects. Trust me, it’s the best crappy cocktail you’ll have.
- Stan’s Donuts. Classic. I remember coming here for the first time during college and thinking it was just the coolest in the world. Now I use it for very specific moments of self-care. The doughnuts, especially the custard-filled ones, are decadent and soft, just how a doughnut should be. I’m not saying they’re the best doughnuts in the city (I feel like I haven’t decided that yet), but they sure do the trick.
- Buffalo Exchange. It’s a resale shop with a high concentration of Madewell, JCrew and Zara, so what’s not to love? I come here when I’m looking for a specific piece and not faring well at traditional thrift stores. Found my perfect navy sweater here. Also, they buy high-quality used clothes, so if you’re trying to KonMari your life bring a garbage bag of reject clothes and try your luck.
- House Theater. This is some of the best theater in Chicago. Everything they do is wonderful. My little college theater ensemble sort of idolized their work and would frequently take field trips to see it (indlucing a ten-hour epic including mexican food, giant dragon puppets, and little foxes.) You seriously can’t go wrong with these very special artists.
- Craft Pizza. The best wood-oven pizza I’ve had in Chicago. Period. It’s perfect, and I know my pizza. This shop on Damen is relatively new and fairly small and making excellent pies. I passed it often and always wanted to try it. When I did I was NOT disappointed.
- Jeni’s Ice Cream. You guys, it’s the best ice cream. Period. It’s really expensive, but it’s worth every bite, go ahead and treat yourself, right now, I mean it!!!
Ukrainian Village: This neighborhood is one of my favorite places to be. It neighbors Tri-Taylor (except for a brief industrial corridor, whatever that is), and is a true gem. You can’t go far without running into a gorgeous old Ukrainian church, and new restaurants and shops are popping up ever week to supplement the ones that have been there forever. Some good friends of mine are moving into the neighborhood pretty soon, so my exploring this area will only expand!
- Dollop Bakeshop. This coffee shop/bakery opened very recently, and I must say that it is nearly perfect. It’s in a corner, so floor-to ceiling windows make two walls of the shop. It’s bright and warm, with wood tables and flowers all around. The coffee is well made and the pastries are fresh from the oven. One time they gave me not one but THREE samples of the new snickerdoodle cookie they were working on.That’s pretty much a whole cookie! I’m sold.
- Roberto Clemente Community Academy. This is the school I worked at for my recent teaching artist apprenticeship. I taught theater skills in two ninth grade english classes for six weeks. The kids were both the hardest and best thing about it, and I was constantly challenged and learning. I’m hoping this is the start of more chances to teach and learn. Who knows?
- Star Lounge. This coffeeshop run by Dark Matter coffee makes one of the most velvetty lattes I’ve had in Chicago. And the croissants are HUGE, the mark of a very good place. The downstairs is busy and great for people-watching, while the upstairs is quiet with plenty of space to work. Try it, you’ll like it.
- Sprout Home. THIS STORE IS VERY DANGEROUS FOR ME. I’ve written about it here before. It’s the perfect plant store, where the air smells fresh and there are blooms and green everywhere you look. Each time I go I want to spend about three-hundred dollars. There is an indoor section with houseplants galore as well as curated home goods like candles and dishtowels, and a newly stocked outdoor section that is like an explosion of springtime. I hear they’re opening a whole homegoods store across the street. That will REALLY be my kryptonite.
West Loop: I like to call west loop “Fancytown” in my head, because that’s how it feels. All the best food lives here, as well as a lot of cool businesses and residences and such. It’s often nearly impossible to find parking, but it’s worth it to try if you need a little fancy in your life.
- La Colombe. The third one on the list. This one feels the smallest but still does the trick. They’ve got some pretty cool red tiling going on in the back of the shop, and all the same happiness as the other two locations. You can’t go wrong with any of the three.
- The Allis. Located on the ground floor of the exclusive Soho House, this cafe is the epitome of fancy. You can do a pricey but decadent full-service afternoon tea if you’re feeling REALLY fancy, or you can come in for the morning to enjoy a pot of tea or a latte or some eggs on a comfy chair in some really fancy company.
- Little Goat. This restaurant is run by the same chef as The Girl and the Goat across the street and features some very fun more accessible options for the young an dlimited like you and me. I once had a chocolate cheez-it cake here and tried a sip of a goats milk latte. Find your way here here if you need to live a little.
- Goodwill. Here lies the best goodwill I’ve found in Chicago. I literally found a perfect Theory dress that fit me like a glove for only $10 the other day. I could hardly believe it! It’s pretty small and almost always crowd it, but the things you can find there are worth the work.
Loop: Ah, the crown jewel of Chicago, where all the hustle and bustle and middle-aged lawyers are. Isaiah and I like to find our way to the loop often just to remember it’s there, that this is the city we live in. It’s sort of especially fun to carve out little pieces of home among the towering buildings and sculpted parks.
- Cultural Center. This is one of the best places in the loop. A gorgeous building, basically an indoor park, free and open to the people, with art galleries, like really great ones, and plenty of places to sit and be quiet, and gorgeous mosaic work and even free foreign films sometimes. It’s the best. You’ll know it by the big metal bull out front.
- Va Piano. I like to meet my friend Annie, who has a fancy marketing job, for lunch whenever I can. This is where we always go. We split a pizza and eat it all, slowly, as we talk, enjoying the din of all the people hurrying through their lunch break around us. It’s the perfect sort of casual lunch place in that it just works. They make the food quickly and serve a lot of people really well. And, when you’re done you can help yourself to free gummy bears as you pay! It’s the best part! Free gummy bears!
- Art Institute. In college we got to go free to the art institute any time we wanted so I’ve been there quite a bit. Now I have to carefully wait for the free days for Illinois residents if I want to go. Museums tire me out quickly if I’m not careful, so I like to spend my time there revisiting old favorites. I like to sit in front of “Song of the Lark” or anything Degas, or find my way to some Marian icons or renaissance religious art. It is best for me if I stay in one place, one small area, for a while and see what I can find in just what’s in front of me. To try to take it all in is too complicated, too much pressure. Just one thing at a time.
- Three Arts Club Cafe. This is a place to go when you need to feel very fancy. That’s how Isaiah and I like to treat it, for those times when we’ve been feeling glum and we need to be somewhere beautiful for just a little while, even if we only eat french fries there. It’s inside a Restoration Hardware store, which is a little weird, but the ambiance is amazing. It’s like sitting on a terrace but indoors and wonderful. You won’t regret it if you find your way there. Don’t leave without also working your way up to the garden area on the room. Someday this summer we want to bring books and sit there with some white wine. It’s that sort of place.
- Dollop. Nestled by the Harold Washington Library under the El tracks is my favorite loop coffee shop, Dollop, sister to the one in Ukrainian village with the big windows. They serve metropolis coffee and even make some pretty great sandwiches. There’s a big chair by the door that is very comfy, and they have a pie cookbook that they sell there that I like to look through. And it’s by the library, a testament to the true reason we like it a lot.
- Harold Washington Library. It’s a big, big, big library, you guys, so obviously we love it. The best part is the winter garden at the very tip top, a quiet, lovely place to read and be a person, and I would go there every day if I could probably. I also always like to wander the stacks in libraries, and this is a very wander-able one. Also, the building itself is pretty fabulous with the red brick offset by the green whatever spikey things at the top…? You know what I mean? It’s the greatest.
- MCA. Confession time. I’ve never actually been inside this museum. I know, I’m the worst. It’s on the list because the summer I interned at Lookingglass I sat on the stairs of the MCA every day while I ate lunch and I watched all the people walk by while I sipped my ginger ale and it was a really special thing for me to do. It was the first time like I felt like I had a place that was mine, especially mine, in the big, intimidating city. I went there every day, back again and back again, until I owned it. I still own it in my mind. A little piece of me is sitting there on the steps of the MCA, a museum I’ve never set foot in. And I like knowing that. Even if I never sit there again, that little piece of Chicago will always be mine. Isn’t that all we can really hope for?
For other City-ing ramblings, click on over here! I love living in Chicago, and I’m learning more every day. I won’t ever pretend to be any sort of expert because I’m not, I’m not, I’m not. I’m just living here and saying what I see. The little bits of things I’ve collected as I’ve walked and wondered. Chicago is too big to ever know and aren’t you glad that’s how it is? I’ll keep city-ing and city-ing as long as I’m here! Thanks for reading, friend.