Monk’s Pub is a cozy, monastery-inspired bar in the Loop serving a wide variety of beers and hearty pub fare — an unexpected escape from the downtown rush.

Orso’s in Old Town is a cozy, old-world Italian gem with house-made pasta, live piano, and a charming patio—perfect for date nights or celebrations.

I am always stunned by Middlebrow's appetizers, including "the big salad," which includes seasonal vegetables topped with plenty of pepper and shredded cheese.

Tavern-style pizza takes the crown at PIZZ'AMICI — thin, crispy crust, cozy vibes, and big local love since they moved from apartment to restaurant in 2024.

Vito & Nick's doesn't make typical Chicago pizza: it's the thin crust that reigns supreme here. I drive out of my way to get there, but it's worth it.

Reggies Chicago is a grunge bar, concert venue, and shuttle hub with great eats, Sox game packages, a beach bar and unique events like a pancake art show.

The 606 (aka the Bloomingdale Trail) in Chicago is a repurposed walking trail on a disused piece of L train track. In my opinion, it's a piece of art.

Luft Balloons in Chicago isn't just a balloon shop – it's a female-operated & owned business that makes balloon sculptures specifically for marches...

Little Madrid in Chicago feels so European, it's surprising — trust me, I've spent some time in Madrid myself. Great place for a date or coworker night.

Rice'N Bread in Chicago is a special spot for dinner or even pre-gaming a baseball game, a Korean restaurant that always makes my day. Try the bibimbap!

I'm not vegan but I do think that "Vegan Plate" in Lincoln Park is one of the best bang-for-your-buck restaurants in Chicago. Try the curry combo plate!

"Argyle Street" is Chicago's first shared street. The concept allows cafes to extend outside their doors and provide spaces for the summer night market...