Chicago’s smallest bar, with the biggest charm.

For 75 years and counting, The Matchbox has been a beloved and iconic neighborhood bar. Known for its small size and big charm, one of Chicago’s most intimate bars has changed hands without changing what makes it so special. Step off the busy avenues into an intimate space where you can enjoy some hand-crafted premium cocktails, bring a friend, bring a date, let us show you why this tiny bar has made such a big impression.

75 years of serving up premium cocktails in one of Chicago’s most intimate bars.

Check Out Our Newly Renovated Patio!

Open Daily 3pm-2am

Bring your Pups!

Outside Food Welcome!

Book Your Party At matchboxmatchbox2020@gmail.com

Chicago’s Smallest Bar.
A Neighborhood Favorite.

For over 75 years, The Matchbox has been a neighborhood favorite and one of Chicago’s most iconic small bars. Known for its tiny footprint and undeniable charm, it has changed hands without losing what makes it special. Step off the busy avenue into an intimate space for thoughtfully crafted cocktails. Bring a friend, a date, or your dog and see why this little bar continues to leave a lasting impression.

Outside Food Welcome

Great drinks, great food, your way. Order takeout or delivery from nearby spots and enjoy it here. Pie Eyed Pizzeria is just around the corner and a local favorite. Grab something good and stay awhile.
Year Round Patio

Our patio is built for year round hangs. Open air in the summer, enclosed and heated in the winter, it’s the perfect spot to kick back and stay awhile.
Dog Friendly

Dogs are always welcome here. Inside or on the patio, bring your pup along. We’re big dog people and wouldn’t have it any other way.
Signature Margarita

Our egg white margarita is our signature for a reason. Made with premium ingredients and fresh juice, it’s smooth, balanced, and easily our most popular cocktail.
Our History

Founded in 1945, The Matchbox is a true Chicago legend. Small in size but big in impact, it has long been a place to share drinks in an intimate setting. Through multiple ownership changes, one thing has stayed the same: preserving the charm that made it special. Today, after thoughtful updates, Matchbox remains just as it’s always been, welcoming new neighbors, longtime regulars, and anyone looking for a little nostalgia.
Private Parties

Description goes hereHost your next event at Matchbox. From start to finish, we’ll work with you to make it easy, seamless, and exactly what you’re looking for. Call or email us to get started.
75 Years of Matchbox

For over 75 years, we’ve been serving premium cocktails in one of Chicago’s most intimate bars. It’s a legacy we’re proud of and one we carry forward every day.