[Note from Todd: Sage went on a trip to Chicago a week or so ago and when she told me about her adventures, I insisted she write them all up as a guest entry. Enjoy!]

I’m sitting on the couch and I’m wailing, “But I don’t LIKE travelling by myself. Why did I say I’d go? I hate being a tourist and there’s nothing else to do in a strange city. I wish I could spend the next six days getting WORK done instead of going to stupid CHICAGO.”

“How about this,” says my partner Todd, “How about we give you a Photo Treasure Hunt? That gives you a reason to wander around the city.”

As much as I want to continue wailing, I have to admit that it’s a pretty great idea. So I get on the plane armed with books about Chicago’s history and a list of photos to gather (which are scattered throughout this entry) and a library to visit so I can tell all of you about my adventures.

I grew up in California. I’ve lived in Missouri, New Mexico, Michigan, Massachusetts, New Hampshire, and Pennsylvania. But I’ve never been to Chicago. I’m going because my musical improv troupe has been accepted into the Chicago Musical Improv Festival. Which means we get to go to Chicago and get on stage and make up a 30 minute musical on the spot. I can’t wait for THAT, it’s the rest of the time away from home I’m dreading.

When the plane lands I head for subway station, which is connected to the airport. I find the transit pass machine without any trouble, and put my debit card in so I can buy a seven day pass. The machine says it can’t read the card. I try a credit card. Same thing. I try a second credit card, no luck.

I wonder (most of me hopes) if all of my Canadian cards will fail in Chicago, and I’ll just have to get on the next plane back to Toronto. But as a last ditch effort I try the ATM machine, which works. Now I have two twenties, the machine takes cash, and the transit pass costs $33. I’m set!

Except the machine doesn’t give change.

I head to the first Dunkin Donuts I’ve seen in 14 years and buy an apple fritter so I can get change. (I feel incredibly disloyal saying this, but good lord was it better than Tim Hortons.) I go back to the machine, get 90% through the process, and realize I got the wrong change. I die laughing, go to a convenience store where I buy the first Mr. Goodbar chocolate bar I’ve seen in 14 years, get the correct change, and buy my transit pass.

It’s the best introduction to Chicago I could have had. I haven’t owned a smartphone in four years by choice, so I couldn’t call anyone for advice, I couldn’t look anything up, I had to deal with this small speedbump all by myself. And I do, and it is easy, and silly, and I feel tremendously pleased with myself.

The train is much narrower than Toronto subway cars, and almost empty. It runs on an elevated track far above the road (a response to the number of people who were being killed by trains on the street level in the late 1800s). I watch out the window as we pass through neighbourhoods filled with houses built in the sixties, then eventually wander into the city itself. People live so close to the tracks that you can practically reach out and touch them.

The train pulls into Roosevelt Station, a hub connecting three different subway lines, and I get off and start walking, looking for breakfast. My backpack, the only luggage I have, is incredibly heavy. I pass an inordinate number of fitness centres, a few restaurants that will open in an hour for lunch, and finally I spot an open restaurant – The Borghoff, a German restaurant where you can buy Spatzleknodel should you so desire. (I do not desire.)

But beggars can’t be choosers, so I run inside and drink three cups of coffee in fast succession and order a halibut sandwich. When it arrives I discover that living in Canada for the last fourteen years has definitely changed my ideas about restaurant meals. This would have been the perfect lunch in 2003, but today it seems like enough food for three people, and the texture of everything on the plate is best described as slurgy. But I feel much better with a full stomach.

The check-in for my AirBnB is 3 PM, so I have a few hours before I can settle in and unpack. Using the maps I printed before I left Toronto I walk east towards Lake Michigan. (The buildings surrounding me were built over a hundred years ago, and I tried just now to find you some facts about the awe-inspiring architecture and history, but these specific buildings aren’t even on any lists of beautiful Chicago buildings, because the ones that took my breath away are ordinary compared to the REALLY transcendent buildings downtown.)

I walk towards the water, and I see two middle aged men sitting under a shady tree. Two geese (each about the size of a two year old child) come stomping over and stand in the shade. One of them abruptly sits down and they both glare meaningfully at the men. No fools, the two men immediately gather up their belongings and leave the only shade in sight to the geese, who have wingspans of six feet and have been known to beat people while biting them, sometimes in gangs of two or three.

The water is an absurdly lovely blue, with no piers, just anchored boats bobbing in the water.

I find my own goose-less shade under a far away tree, and sit happily reading about Chicago in the 1960s. A shy young woman with a camera around her neck comes up to me. “Hi,” she says, “I like your hair and the way you’re sitting under that tree. Would it be all right if I took your picture?” I grin and say yes, and she takes the photo and we wish each other well and she walks down the shoreline.

When it’s time to check into my AirBnB room, I head back to the subway, taking the Red line to the Blue line, and then ending up at the Damen station. I’m realizing already that my bad habit of taking taxis everywhere when I travel by myself is one that both limits my ability to understand the city and my independence, not to mention costs the earth. Being able to zoom around on the very well laid-out train system is another massive boost to my confidence.

At Damen Station, I wait for the bus. And wait. And wait. And wait some more. (People in Toronto actively hate the transit system. I am the only one I know who sincerely loves it, and I attribute that to having grown up in America, where sometimes the buses are 90 minutes apart. The Damen bus takes twenty minutes, compared to Toronto’s five.)

When I arrive at the building, no one answers the door. I’m flummoxed. I check the AirBnB information I’ve printed out, and there’s nothing about which buzzer to hit so I try them all just in case. Nothing. I walk back to Damen Avenue, the nearest big road, and look for a payphone. To my happy surprise, I find one almost immediately. I put in two quarters and dial the number for the AirBnB host. Nothing happens, except the payphone is two quarters richer. I go inside the nearest convenience store and explain what happened, and ask permission to use the store phone. The very nice clerk gives me his phone instead, and I call. The host says she’ll be waiting outside for me when I get back, and she is, and from there the check-in is easy.

Inside the room I use the Chromebook and the wifi to briefly check in with Todd, then head back out to grab dinner before telling a story at the Storylab storytelling show.

It’s slurgy again. I finish about half and then walk to the Storylab venue and am very excited to see that four of my musical improv troupe members have shown up to see me tell a story. We chat before the show, and when it starts I tell the story of how Todd and I met and we watch the rest of the storytellers. By the end of Storylab, I am so exhausted from my very full day that I go to the restroom and briefly fall asleep in the restroom stall before sitting bolt upright and reminding myself that I have to stay awake long enough to get back to my room.

I sleep beautifully that night and when I wake up I use the wifi to look up unique places to visit in Chicago. I find The 606, a brand new elevated hiking trail that runs for two miles above the city (which was originally a disused train line that the community was hiking along anyway, the city just decided to make it official and safe). The 606 is within walking distance, and after a croque monsieur (traditional French sandwich with ham, mustard, and melted swiss – more slurge) I start down the path. Even on a Friday morning The 606 is filled with locals, and I’m the only one who’s excited when a train zooms right over us.

The sides of the trail are covered with delightful flowers.

I see a sign for the “Humboldt Overlook” and decide that it will be my stopping point, so when I get there I laugh out loud to find that it’s just a road.

A road that someone loves looking at so much they’ve even brought cushions so they can marvel over it for longer. (“Look, Jimmy! Another Toyota Camry!”)

Canadians tend to close their drapes even if they’re on the 44th floor facing a massive park, but some of the ingenious Chicagoans are using The 606 as their own gallery space – one would like you to know how many trophies they’ve won:

And another is displaying their art:

At the Humboldt Overlook I return to street level and happen upon L. Frank Baum’s house, the one where he wrote The Wizard of Oz. (It’s now a multi-unit set of townhouses.) Outside, an old man is bossing a young man as he re-paints a fence. The old man doesn’t like the placement of the Halloween yard decorations either, and orders the good-natured young man to fix them. I turn to walk down the sidewalk and Chicago says, “Surprise!” and presents me with these vibrant purple flowers, complete with color-coordinated bugs.

Back at the start of The 606, I’m just around the corner from the Bucktown Wicker Park Library.

The library is only twelve years old, but looks like the 1980s libraries of my childhood. Dark wood, carpet, few windows. Cozy. Downstairs it’s happy chaos, children everywhere, running and screeching with glee.

The computers are hidden at the back of the first floor. On October 3, there’s a Science Fiction Board Game Night for grown-ups, which I would DEFINITELY attend if I were in town. I am tickled to see that the library has a robust collection of mobster books.

I am embarrassed to admit that if I were able to get a book from the library, this is the one I’d choose.

Upstairs, there’s a reading room filled with men that is so silent I’d have terrified everyone if I’d done so much as cleared my throat. I sit in a peaceful chair for awhile, looking over the photos I’ve gotten so far today, then go downstairs to the lobby. I find a display of vintage toy cars collected by a library patron, and suddenly remember that when I was eight I asked to have my collection of opals, picture jasper, and amethysts displayed at my local library, and when I walked by that display I felt FAMOUS.

I hop back on the train and arrive at Blick Art Supplies in no time. I find a replacement for my almost-full notebook (the one I write down notes for entries like this one in) and as I’m checking out the clerk mentions that they are (this is going to sound made up but I swear it’s true) having a Pet Shelter Puppies And Eat Free Cookies Day as a celebration of some kind of anniversary of the art supply store, so I end my visit with a puppy cuddle and a lemon tart.

As I’m leaving the store I’m horrified to see this sign on the door:

Todd told me about the No Guns signs that he’s seen on business trips, but in person they’re so much worse and the horror of a country that needs them is so shocking I just stand there by the door with my mouth hanging open. (If I ran a store in America my door would be NOTHING BUT those stickers.)

I walk back to the Roosevelt train station:

And grab (slurgy) enchiladas before performing non-musical improv at a variety show. The best part of the show is, by far, this trumpet-playing skeleton talking about what separates art from crass commercialism – the piece is daring and strange and bold, and I corner the artist afterwards and rave for a long time about how much I love her ideas.

When I get back to the AirBnB house after midnight, my key doesn’t work. I try it a hundred different times. No luck. I don’t own a smartphone, so once again I need to figure this out all by myself. “A hotel,” I think, “I’ll stay in a hotel tonight. Get it sorted out tomorrow.” I walk towards Damen Avenue in the hopes of grabbing a taxi, but then I see two men and a woman standing in front of Danny’s Tavern, a tiny dark bar. Because it’s after midnight but there’s a woman there, I walk over and explain my situation. (The woman, hilariously, immediately leaves. Bye!) But one of the two men quickly takes out his phone and gives it to me. I call the host, who thankfully is just down the street at a friend’s house, and the host says she’ll meet me at the house.

I thank the two men profusely, and when I turn to leave one of them says, “Wait – are you all right? Do you have a place to stay?”

And I’m so touched. That guy could have been opening a massive can of worms. I could have said, “No, I have nowhere to stay,” and THEN what? He didn’t have to ask, but he did, and though I am grateful every single day that I live in Canada – moments like these remind me that sometimes Americans have a heart that truly is the size of Texas.

I reassure them both that I’ve sorted it out, and meet the host at the house. The problem turns out to be a same-key deadbolt that gets turned after midnight that I didn’t know about.

In the morning I walk to a new breakfast restaurant just after dawn. No one else is walking in this industrial neighbourhood. It doesn’t seem to matter what time it is, any walk in Chicago unearths spectacular beauty.

(But don’t fall in the water, guys. I’m pretty sure that life preserver is older than ME.)

When I go to take a photo of this ancient car’s dashboard, I see a man lying full length in the back under a blanket checking his mobile phone. Blushing, I walk away as fast as I can.

I sit down and order coffee. The server brings cream and I pour it in. It looks curdled. (I know this post is making me sound like a massive fusspot when it comes to restaurants but I’m really not.) I point it out to the waitress and she says that it’s WHIPPING CREAM and always looks like that. And listen, I’m a person who would happily eat a bowl of whipping cream for dessert, and EVEN I am horrified. I ask for milk instead. Slurgy pancakes over, I take a long walk to the train station. On the way my eye is caught by very green trees off to the left. I go over to investigate and find a sign that says “NO TRESPASSING UNION TRAIN COMPANY” but can’t resist the opportunity to take a photo of the (ground level) train tracks and sidestep the sign. As I’m taking the photo a little cat comes out of nowhere.

She scowls at me, then zooms off into the underbrush. She’s sleek and well-fed, and when I check out a nearby abandoned golf cart I see why:

The entire back is filled with empty cat food cans.

Adventures!

When I get to the train station, I go downtown. Before I left Toronto, a friend mentioned “architecture boat tours”. I secretly rolled my eyes. But when I get off the train I stand for a good ten minutes gawping at the beauty from this bridge. No WONDER there are architecture boat tours.

(I know, sorry about the Trump building.)

As I walk downtown I’m slayed by this man’s sense of style and ask permission to take his photo. He is game at first, but suspicious when I tell him I’m in the city to perform in an improv show, and says, “WAIT, are you taking a photo of me to make fun of for your show?” and I reassure him, wondering internally, “WHAT KIND OF MONSTER WOULD DO THAT?”

At the Navy Pier I find amusement park rides and a food court. It’s a humid and overcast Friday, so there are only two people on the rides.

I go inside and buy a giant pretzel (cooked dough with salt on top, mustard on the side for dipping), and I SWEAR I am not a fusspot, but it’s disappointingly dry and flavourless. Chicago! You are so dazzling to look at but everything I eat is so slurgy!

On my way back to the train station, I see a sign for Ohio Street Beach and make a sharp right to investigate. I am rewarded with a stunning vista:

I wander over to the cement steps that overlook Lake Michigan and spend a delightful two hours reading in the shade about the women who inspired the musical Chicago.

And now it’s time to perform with my musical improv troupe at the Chicago Musical Improv Festival. Running late, I grab a prepared meal at the nearby Whole Foods – (which now features glasses of wine that the parents are guzzling as they wheel the carts and their toddlers around, prepatory to DRIVING THE HELL HOME, Jesus Christ – the next day at another restaurant a waitress says, “…or we have beer, no shame in beer!” and I really want to say, “IT’S NOT EVEN NINE O’CLOCK IN THE MORNING, WHAT DO YOU MEAN NO SHAME”) – near the theatre and then go into the rehearsal room.

I knew an online friend would be at the show, and I deliberately didn’t tell him I’d be there too so it would be a surprise, so when I walk in the door of the rehearsal he’s singing a song he says, “La la l – HOLY FUCK IT’S SAGE TYRTLE!” and runs over and gives me a hug. It’s very funny and I’m glad I kept my arrival a secret.

My troupe shows up, we warm up, and we perform our show, “America’s Next Top Blank”. I get to play a character called Miss Evil and it’s our best show ever, hands down.

(That’s me, on the far left.)

It’s after midnight again when I arrive at the AirBnB, but I’m prepared this time and I unlock the deadbolt without any trouble. My host has left for the weekend, and when I turn on the Chromebook to talk to Todd, the WiFi no longer works. The last time Todd heard from me, it was 6 AM. I know my online friend probably posted online about seeing me at the show, so Todd will know I was fine at 8 PM. But when one of us is out of town, we ALWAYS check in before going to sleep. Todd’s smart and logical and will be able to figure out that it’s a problem with the WiFi, but I know he’ll be worried anyway. I pass a fitful night.

By 6 AM I’m walking to the train station on the lookout for a Starbucks, where I can get free WiFi. I find one right by the train station and immediately get in touch with Todd, who’s also slept very little. As expected, he knew it was probably the WiFi but was scared too. I tell him I don’t want to stay in an AirBnB by myself ever again, and he laughs and says he would feel the same way.

On my last day in Chicago, I take a meandering walk towards Bang Bang Pie and Biscuits, which is reputed to sell the best pie in the city. When I arrive, eager for a slice of pumpkin pie, there’s a line stretching an entire block, so I turn around and head for a farmer’s market instead which is supposed to be around the corner. I don’t have any luck finding it. I try to head back to the AirBnB room and go the wrong way for fifteen minutes, then have to retrace my steps.

I stand undecided on the sidewalk. The rest of my trip felt charmed. All I had to do was pick a destination and the city threw beauty and adventures at me all the way there. But now I’m hot, overwhelmed, and I have to pee like crazy. I walk past an all but abandoned Chicago Tribune newspaper building:

And remember the days when the newspaper had investigative reporters instead of updates on Angelina Jolie’s vacation plans and sigh. I walk and walk.

Really hungry now and desperate for a restroom, I am scouring every building for a restaurant. When I see a McDonald’s, I scowl and think, “FINE, I’ll pee and have a filet of fish and then a NAP,” and am about to cross the street when a sign for Arturo’s Tacos catches my eye.

And even though I am not a fusspot when it comes to food, every single meal I’ve eaten in Chicago has been vile. I don’t think that’s Chicago’s fault, I think it’s me who’s changed since I left for Canada. I wonder if McDonald’s is the better idea (at least I know it will be mediocre) and then I think “no, no, take advantage of possible adventures” and then my bladder is like I DON’T GIVE A DAMN WHERE WE GO AS LONG AS THERE’S A BATHROOM and so I go to Arturo’s Tacos.

The restaurant is not fancy, which is exactly what I want. It’s still the late 70s inside and Jimmy Carter is still president. I run to the restroom, then sit at a burnt orange booth and order my childhood comfort food, enchiladas, beans, and rice. When the plate arrives I fall on it like a ravening wolf. It is EXACTLY the American food you can’t get in Toronto, Tex-Mex, cheesy, spicy, and delectable. Halfway through my meal two men begin playing guitars, singing in Spanish. I smile to myself and remember whining on the couch about not wanting to go to Chicago.

And even though there were hard moments, even though I am very shy and have trouble talking to strangers and without a smartphone I had to do it all the time, I am so glad I only had my paper maps. If I’d spent my time taking taxis everywhere and knowing exactly where I was and where I was going all the time, I’d have missed every adventure!

I’d have missed all of those kind people, the ones who didn’t vote for Trump, who are big and bold and American enough to ask – “Wait, are you all right? Do you have a place to stay?”