Independent Book Stores, Unique Chicago Restaurants, Community Activists to Know with Amanda Elliott

In this week’s Seek Like a Local, Amanda Elliott shares how she remains active, optimistic, and engaged in Chicago’s food, fashion, and networking scene—in-person and online.


Explore Chicago Like Amanda Elliott

Amanda Elliott is an award-winning content creator, writer, and speaker. She believes that meeting people in person is important and creates content to help people have better cocktails and connections with one another. With a cheeky look at dating, career, and friendships, she also spotlights restaurant openings, events, and networking.

Amanda Elliot of Windy City Cosmo  in Chicago featured on The Haute Seeker

In 2015, Amanda launched Windy City Cosmo, to help people make connections in the city as they build their businesses, start and end relationships, and see and be seen through dynamic interviews on her celebrated platform.


What do you love about the food scene in Chicago?

Every place kind of has its specialty, ya know? You have to figure out why you’re going to the place you’re going to and what kind of experience you want to have. I’m personally an ambiance girl and a happy hour girl. If I’m out, I stay out till I’m home, and then it’s just too hard to go out.

If I want a vibe, like sit and feel like you’ve been taken to another world—Beatnik West Town makes me feel like I’m in a jungle. Three Dots and a Dash makes me feel like I got off a cruise ship at night. BLVD makes me feel so sophisticated—like I found a hidden gem. They have cake and milk on the menu and yes, you should get it. And honestly, there’s something about Navy Pier. Offshore Rooftop and Bar, it’s seriously a perfect summer vibe and makes Navy Pier feeling classy. Pueblito Viejo is kind of out of nowhere but you go in and there’s a ton of pennies glued to the walls. There’s a dance floor and margaritas with Coronas right in the center. It’s the type of place that brings all types of people together (last time I went we ended up on the dance floor with moms who were having a night out). Whiskey Business has a great rooftop and is always having a party and finding a new way to entertain. Labriola is a perfect date night spot and is great for burrata & basil deep dish pizza and an Aperol Spritz. The vibe was right, too. The Dawson has a great patio, plus the cheese curds and oysters are magic.

Interior of Pueblito Viejo Columbian restaurant in Chicago featured on The Haute Seeker Seek Like a Local
Interior of Pueblito Viejo // Image via Facebook

Finally, If you want good cocktails—like really good cocktails, go to ROOH, Scofflaw, Casati’s.

What are your favorite neighborhood shops?

While I wish there were more stores to have everything that I need (my go-to shop was Macy’s at Water Tower), I will say that my favorite bookstore is Volume’s Book Cafe. My favorite Chicago author, Emily Belden, had a book reading there. I’ve met there for trivia night and date nights. They have good lattes and great books supporting local authors. I think it’s one of the best parts of Wicker Park. 

What’s your ideal way to spend a day in Chicago?

I love to explore. I am happiest in the sunshine and a sundress, getting a late start to the morning. Once I am ready, I enjoy meeting up with a friend or boy for brunch and letting the day unfold. This recently happened when my friend and I went to Beatnik in West Town and sat at the bar. The bartender gave everyone a shot of champagne and said, “you could be spending your morning anywhere, and you’re spending it with us.” I love the energy of Chicago restaurants. We then took a walk and wandered into a plant store. I had never been in one and it was surreal. What I love most about Chicago are all the possibilities to meet new people, discover a shop or restaurant I’ve never been to, and see art.

When everything was shut down in quarantine, I took a virtual vacation to “Rome.” I found a church nearby and called it the “Spanish Steps.” I also found a Dark Matter Coffee shop in my neighborhood, that I had never been to and also discovered Shit’s Fountain.

Two hands holding cocktails on the Kennedy Rooftop in Chicago featured on The Haute Seeker Seek Like a Local
Drinks at Kennedy Rooftop // Image via Facebook

Even after eating out at all the patios this past summer, I still have places that blow me away. When I went to the Kennedy Rooftop, I felt like I was in Aladdin. Chicago just felt like a “whole new world.”

Tell us about a few Chicago artists whose work you are loving right now?

Laura Bean, I first noticed her work when I walked into Evolve Her coworking space. I was blown away by the wall of portraits dedicated to women that she painted. You should definitely support her! Luvvie Jones is a great writer and she’s amazing at building a presence online. I first heard of her from her commentary on the show, Scandal. I’ve since admired her blog posts and voice on Twitter and Instagram. 

What type of community organizations in Chicago do you support and admire?

It’s been a bit difficult to volunteer in Chicago, but I’ve tried several different ways to stay better connected. I was a Girl Scout leader and that was a lot of fun. I really saw how much the girls loved being creative and learning and how it was important for them to have people they could look up to. The other Girl Scout leader and I took the troop to Art Institute and to the Chicago Architecture Foundation and we had so much fun. We were late to the cookie game but got enough in donations to get all the girl’s uniforms and the badges they earned. It was really fulfilling. 

I also went through volunteer training with 826CHI. An organization that collaborates with after-school programs and community-based organizations to offer creative writing workshops to students in neighborhoods across Chicago. It’s located right in Wicker Park and I love the idea of helping kids write and tell their stories. 

Students in 826CHI Chicago Teen Writers Studio featured on The Haute Seeker  Seek Like a Local
Students in 826CHI Teen Writers Studio // Image via Facebook

I also support my friend and fellow blogger, Sany from Sany.Delight. She is a fearless leader and motivator. She does everything from setting up running challenges with Nike to most recently founding Celebrate Argyle. It is a community initiative that aims to shine a spotlight on immigrant-owned restaurants and businesses in the West Argyle Historic District, as a unique culinary destination, while also connecting community members to critical resources to meet pressing needs through the pandemic and beyond. Sany is always seeing the needs in her community and helping. She organized a drop-off with businesses to give toys and clothes to shelters and community centers throughout Chicago. She inspires me to be a better person and to give back to my community. 


Seek Like A Local, and discover things to do, places to dine, and more of what the city of Chicago has to offer this week. Check out previous guides from influential Chicago locals here.


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In this week’s Seek Like a Local, Tanya Taylor shares travel tips for locals and tourists visiting Chicago, where you can find the best pizza in Chicago (down to the exact location), and where to shop if you are frugal and fashionable in Chicago.



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