Laney Luvs Adventure: Chicago Edition
When You Have a Spare Weekend, Head to Chicago
I chose Chicago to adventure in because it’s a sister city to Toronto. Aesthetically, there are similarities between the two cities, but Chicago is more grand. Most of my favourite Mericans are from Chicago and the city has a very big Art Expo that I wanted to attend. When I was younger, the first international film festival that showed my work was in Chicago. It will forever have a place in my heart.
Imagine what kind of person I would’ve turned out to be if I lived in Chi Town. I think it’s a city that has a foundation for black excellence and understands that excellence needs a place to be fostered. It’s not like NYC, which has out priced everyone for no reason. It’s a city of possibilities. It’s a city where Michelle O. lives and I intend to meet her one day.

Let the adventure begin
So, I found a cheap flight leaving from the island airport, which was fabulous. I was able to take a quick bike ride along the water to make it to my flight. Easy peasy check-in and the forecast said the weather in Chicago was hot!
When I arrived in Chicago, I was able to take the subway to my hotel, The Viceroy Chicago . Door-to-door it was a total of 5 hours. Not bad. And they weren’t joking when they said the weather was HOT. It was at least 15ºC warmer than Toronto. It felt like summer… and I was wearing all black – wool sweater and long work pants. I booked a supposed 5-star hotel, but honestly it felt more like a strong 3.75-star. It was fine because the location was prime and it was a safe clean space.
But surprise surprise! I got my period so I had to be preserve my energy levels to enjoy my weekend plans. I was definitely having an Endo flare-up (intense bloating), so I didn’t feel as cute as I wanted to. I can’t let things like that bother me because I went to Chicago with a mission: to buy some art and to find Michelle O. I showered and headed to the hotel’s rooftop before heading to Soho House to meet a friend.
My social anxiety was up but with reason. It was the first time I had been anywhere in months and traveling to the States as a single Black woman can be daunting. But I wasn’t going to spot Michelle in my hotel, so that gave me the motivation to get out and live life.
The roof top of the hotel was a bop. I chatted with people and we headed to Soho together. Soho was a bop too and I had a blast with my buddies. On my Lyft ride home, some runt-of-the-litter troll tried to start something, while I was filming in the back of my ride. Saying, ‘You people think you’re…’ and giving me the finger.
He was a racist. No sugarcoating it.
He was annoyed that I was living my best life and he had thoughts that he clearly expressed. My young Russian driver, looked in the mirror, rolled his eyes and took a smooth quick left, leaving that loser with his thoughts. Non-white racists are a mystery to me. Doing Massa’s work but also looking real dumb because it always backfires. Anyway, I arrived at the hotel safely and happy before heading to bed.

Chicago Walks and Lunch at RL’s
Next day, I felt fresh and excited for a nice, fancy lunch with my pal Andre. Yes, we saw each other only a few hours before, but he’s good people and I love hanging out with him whenever I can. I took my time to walk there and explored the city before our lunch at RL Restaurant.
Chicago is amazing. It’s a perfect blend of old and new. It didn’t tear down everything older than 100 years (like Toronto did) and preserved something iconic from each decade. I LOVE IT! Architecturally, I get why the greats started in Chicago (Frank Lloyd Wright, Jeanne Gang, Mies van der Rohe, and Beverly Loraine Greene).
Lunch was Amerciana-coded: Burgers and fries. We had a long kiki, filled with giggles, while enjoying the snobbery on display at Ralph’s. It was the pick-me up I needed for my afternoon of art. I went to MCA and grabbed a Warhol Brillo tote for myself before heading to the Art Expo.

The Art Expo
Okay, but did you know Chicago has beaches?!? Gworl, nobody told me nothing about these cute beaches close to the Art Expo/ Convention Center. I would have worn something short to tan my pale legs.
Gosh, this city has everything.

When I finally arrived at the Art Expo, I thought I was gonna die of heat exhaustion though. I was SO parched and needed fluids ASAP. I quickly downed a litre of H2O before starting my art hunt. When I saw the size of the expo, my heart stopped. This place was enormous. Each gallery stall had so much wall space. Most works were full size items for larger homes, few pieces were for cozy apartments like mine. I did manage to find a gallery I adored and… it was Canadian LOL. I travelled all that way to find Canadian artists (and one of them happened to be my neighbor!).


The day ended with me having dinner at a steak house patio, struggling to get through these American portions but leaving satisfied. The people watching was top tier and I loved that families were out together enjoying this pre-summer night.

Until Next Time
When morning came I didn’t want to leave.. but alas, duties call at home. I gave myself a long time to get to the airport so I could enjoy the last sites in Chicago.
I’ll definitely be back 🙂
VLOG CHAPTERS
0:00 Thursday – Toronto departure
1:03 Chicago arrival
2:01 The Viceroy Chicago mini tour
2:27 Greetings kiki
4:43 Night out in ChiTown looking for Michelle O., Viceroy Rooftop, Soho House Chicago
7:27 TRIGGER WARNING – verbal violence from pocket sized troll
9:01 Friday – Glossier opening, Ralph Lauren Cafe, & walk to the Navy Pier
12:35 Art Expo Chicago
15:01 Dinner
16:14 Saturday – one last ride through the city
*List of music used in video*:
♫ Lights – TrackTribe
♫ Robots and Aliens – Joel Cummins
♫ Sound of Aging – Max McFerren
♫ Cover Charge – TrackTribe
♫ City Blocks – TrackTribe
*psst… Don’t forget to like and subscribe to my channel.
Chat soon Luvlies!
xoxo Luv Laney Luv

