What I Love About My City | Chicago

Jacqueline Howard tells us how she made the Windy City her home

Welcome back to What I Love About My City—a series in which our favorite single girls dish on everything from the best places for a single girls weekend to the secret spots only the locals know about. If you’re thinking about moving or just planning your next trip, we’ll fill you in with all the essential details on the cities our crew knows best.

Jacqueline Howard is an editor at Huffington Post and a host of Talk Nerdy to Me who holds a Master’s degree in Journalism from the University of Southern California. Originally from Cincinnati, Jacqueline attended the University of Michigan, studied abroad in Melbourne, Australia, and lived in Los Angeles for a few years before heading back to the Midwest. It was as fellow interns at C Magazine that I got to know Jacqueline as one of the smartest and most insightful peers I’ve ever met. We became fast friends when I realized I could talk to her about anything (career choices, reality TV, boys, women’s issues in the media) and get sound advice or an interesting conversation. I still miss her in L.A., but I can’t wait to visit her in her new home.

Jacqueline Howard at Chicago Fashion Week

C: You’ve wanted to move to Chicago for a while. How did you come to your final decision?

I was actually inspired after reading Arianna Huffington’s On Becoming Fearless, in which she encourages to be fearless in going after what you want. So I finally became fearless in moving to a new city that I wanted to call home.


C: What makes the city appealing for a Single Girl*? (*definition = young, ambitious, go-getter girl)

Chicago gives a go-getter girl all of the qualities of a big city without the hassle. It’s easy to navigate, it’s clean, there are parks galore, it’s populated with other young people who have ambitions, and you get the beach and the seasons! You can also easily travel anywhere as the O’Hare is an international hub, and the city is centrally located in the country. Plus, my favorite, the restaurant and shopping scene is à mourir pour!


C: How have you made it your “home”?

It’s home now because I have a great group of friends here that I’ve known previously and just met. What makes a city a home is your network of friends and family, in my opinion.


C: What are your favorite things about the city?

That I can spend my summers on the beach (because of the lake) and my holidays in a winter wonderland!


C: What has surprised you most about living there?

It’s not called the windy city for nothing!! It really is windy here, and the wind is not cute. Heavy winds caused my car door to slam on my arm once, and I was jogging on Lake Shore Drive when the wind pushed me over.


C: Best spot for a first date?

I just recently visited City Winery and absolutely would recommend it for a first date. Along with the restaurant and bar, the venue includes an acoustic concert space.


C: How have you made new friends in this city?

I learned to become comfortable attending events solo and, honestly, it has been a gem. I’ve met so many wonderful people at charity events and various showcases simply because I would go by myself. I also learned a lot about Chicago as well as made new friends through volunteer work. Around the same time I moved to the Windy City, I heard about a nonprofit organization called Hashtag Lunchbag, which originated in Los Angeles. The group gathers together volunteers to pack lunches for the homeless and then hands out these lunches to people living on the streets. I thought it would be fun to do the same thing in Chicago, which was a great way to make new friends as well as was a truly fulfilling experience.


C: Girls Night Out: where do you go?

Pops for Champagne


C: If you have girlfriends coming to visit. Where do you take them?

The Signature Room at the top of the John Hancock Tower for a round of cocktails because of the amazing view.


C: You miraculously have a free Saturday. How do you take advantage?

A jog in the park, a quick stop by a nearby farmer’s market, shopping on Michigan Avenue, and dinner at the Terrace rooftop at Trump Tower.


3 words I’d use to describe Chicago: Soulful, Unapologetic, Home

The one thing I miss about L.A.: The style!

The tourist spot I secretly love: Willis Tower (or Sears Tower)

I absolutely can’t resist eating: Deep dish pizza from Giordano’s

When I’m hunting down a good sale I head straight to: Akira

You know you belong in Chicago when: you stand up against the wind! 😉


Want to see more from Jacqueline? Follow her on Twitter.

Love your city? Want to share all that’s great about it with our readers? Email us at leadingladies@toastmeetsjam.com for the chance to be featured in our next series post!


Catherine Abalos is founder and editor of The Single Diaries.

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