Cutest Coffee Shops in Chicago

When I visit a new city, I want to visit the cutest coffee shops, and my new home in Chicago is no exception. Since we’ve moved here, I’ve been looking for the cutest coffee shops in Chicago to enjoy a quiet cup, or sometimes I want a louder spot with music to get some work done. Often, I look for a space that feels cozy to invite a friend or one of my students.

I love my coffee nice and hot, so fall and winter are the best times to check out new coffee shops for me. I wanted to share my top version of the cutest coffee shops in Chicago. I chose these locations because they are either great for people watching, offer a quiet corner, or they have the best blends when you want to try something new.

“L” Cafecito/ Jumping Bean

My first pick is Jumping Bean, especially the “L” Cafecito location on the pink line. Let me explain, the “L” train is Chicago’s public transportation train that runs mostly above ground.

The Pink Line covers a route that stretches from its eastern terminus at the Loop, Chicago’s downtown business and cultural hub, to its western terminus in the historic neighborhood of Cicero. Along its journey, the Pink Line makes stops at several key destinations, including the bustling West Loop, the iconic United Center (home to the Chicago Bulls and Blackhawks), the culturally rich neighborhoods of Pilsen and Little Village, and the suburban community of Cicero.

“L” Cafecito has 2 locations, one in Pilsen along 18th street, as well as one on the L Train Pink Line Damen stop. I love both locations, but the one right at the Damen stop is especially great because of the convenience (the 18th street location is notoriously difficult to park at), and the people watching outside an L station can’t be beat.

There are cute drinks, with lots of nods to Mexican roots, like chocolate, horchata, etc.

October Café

Located in the Avondale neighborhood of Chicago, October Café is new this month, but I’ve already visited! The reason I wanted to give it a try is the theme.

The clue is the name. October Café is all about fall, so imagine the décor inside! The café is loaded with fall leaves, pumpkins, gold, orange, and brown colors.

They have plenty of harvest inspired flavors on the menu, and honestly, their pumpkin spice latte is one of the best I’ve ever had. It tastes natural and subtle without any overly sweet or artificial-tasting kicks.

There are also sandwiches and snacks. But the best part I found was the greenery outside the windows. Located in Avondale means that there were more trees and grass, which was something that made the mood extra special when you want to get a break from city views.

Hearts and Flour Bakery & Café

Hearts and Flour Bakery & Café is one of my favorites because of the drive-through option and the selection. If you’re staying in, the large windows let in lots of natural light, and the streets are great for people watching.

Passing through Ravenswood neighborhood of Chicago can mean narrow streets, limited parking, and fast stop-and-go lights, with limited options to pull over for a quick coffee, but Hearts and Flour is a respite for me on my drive to work! It has a great drive-thru option, breakfast and coffee choices that are always yummy. They also have pre-packed options on their shelves, and I’ve picked up goodies from here plenty for my graduate students.

Best of all, this café is run by Misericordia, which is a Catholic Charity of the Archdiocese of Chicago with the mission of providing a quality of life for their residents, who have a wide variety of developmental and intellectual disabilities.

Dulce de Leche Cafecito

Dulce de Leche Cafecito is my youngest daughter’s favorite café in Chicago. We would visit here way too much back in the winter. This is the smaller of the two locations, in the North Center neighborhood.

This is a very cozy café in an older building. There are not many seats or tables, which adds to the special feeling you get sitting inside, especially by this cute window with views of the beautiful homes across the street.

The menu options are amazing, with lattes like horchata, rose, dulce de leche (my daughter’s favorite), and even a beautiful blue matcha. There are many, many drink options, and food as well.

I love the walkable neighborhood setting, and there are plenty of dogs to see having a stroll outside the windows while you sip your coffee inside.

What are your favorite coffee shops like where you live? Let me know in the comments!