To Chicago, With Love

February 10, 2019

With love in the air and the die hard romantics making their plans for Valentine’s Day,  it seemed like the perfect time for Curious City to answer a question from Saya Hillman.

Saya wants to know what transplants love about Chicago but maybe didn’t expect to love before they got here.

“It is so nice to hear somebody being appreciative of this amazing city we live in, and too often, we just talk about the bad things or just hear about the bad things,” she says.

So we put Saya’s question to Chicago transplants. From bird watching to architecture, here’s what they say keeps the romance going.

These submissions have been edited for brevity and clarity.

Dear Chicago,

I love how old school and badass people are in Chicago — they’re practical and earnest but a lot of fun, too. I love seeing people decked out in hats and suits like it’s the 1950s, vendors selling food on the street, people out walking in 30-below conditions, having festivals in parking lots, meeting in public places to show their support for an array of causes, and tanning themselves by the sun peeking out from a high rise. Chicagoans don't have something to prove … they're already out there, doing it.

— Kathy O’Neill, moved from West Orange, New Jersey

More about our questioner

Saya Hillman was raised in Evanston, went away for college to Boston, and then returned to the city she loves. Her question grew out of a desire to think more positively about Chicago. And in her full-time job, she essentially helps people do the same — just about themselves.

“I have been blissfully self-employed running a business called Mac & Cheese Productions, which is a lifestyle business that helps people live a more joyful life. I do that through connecting people to people, people to opportunities and jobs, and also people to themselves … the gist is that when we have community and feel like we belong, we feel good about ourselves and we lead the most fulfilled lives.”

When Saya is not helping people connect with themselves and community, she likes to foster puppies and do something called “travel hacking.”

“I love being fake Oprah, which means flying first class and staying in luxury hotels even though I don’t have the budget for that,” she says. “My husband and I play the travel hacking game pretty well.”

And what was something about Chicago that she was surprised to love so much?

“My husband and I love biking for pleasure as opposed to biking for exercise,” she says. “ I know a lot of people talk about the flatness in a negative sense, but I love the flatness here because you can really go anywhere on bike. And the biking community here is wonderful.”