The Cubby Bear Chicago in Chicago, IL

What Sets This Bar Apart

What makes The Cubby Bear stand out isn’t just its history—it’s how it brings together die-hard Cubs fans, music lovers, and party people under one roof. Its location right across from Wrigley Field means you’re in the thick of the action, especially when the Cubs are playing. On game days, the energy is off the charts: the crowd spills out onto the sidewalk, the air is full of excitement (and the smell of stadium food), and you’ll hear everything from live bands to classic sports anthems blasting over the speakers. Even when there’s no game, the live music scene draws big-name and up-and-coming acts, making it a nightlife staple in Wrigleyville.

The Offering

• Signature drinks & atmosphere: Expect a classic bar lineup—domestic and craft beers (starting at $5), cocktails, and plenty of shots for celebrating a win. People rave about the energy here as much as the drinks: it’s all about that “everyone’s a friend” vibe, especially at the bar or packed tables on game days.
• Drink quality & service: Drinks are poured strong and served quick, but service can slow down when the place is packed (which is often during big events). Bartenders know their stuff and keep the lines moving, but patience is key on those high-traffic nights.
• Drink menu & entertainment options: The Cubby Bear is as much about entertainment as it is about the bar—live concerts, DJ nights, and event watch parties are regular features. The event calendar is always changing, so there’s usually something going on whether you’re into sports or music. Food-wise, you’ll find classic bar fare: wings, burgers, nachos, and other crowd-pleasers, with most dishes priced between $10 and $20.
• Special events & seasonal cocktails: Look out for themed nights, big-name concerts, and special events during baseball season. Drink specials and limited-edition cocktails pop up during Cubs games and holidays, making it worth checking their website or social media for what’s new.

The Experience

The lively, high-energy atmosphere means you’ll be surrounded by fans, music, and more than a little noise. This is not the spot for a quiet drink or a work meeting—think cheering crowds, packed dance floors, and the kind of camaraderie you only get in a true Chicago sports bar. The lighting is dim, the music is loud, and there’s always a buzz of excitement, especially when the Cubs are at home or a big band is playing. Expect to stand, shout, and maybe even dance a little.

Service experience: Staff are friendly and know how to handle a crowd, but things can get hectic on busy nights. If you want faster service, grab a seat at the bar or arrive early—otherwise, be ready to wait a bit when the place is hopping.

Detailed Experience Breakdown

• Arrival process: On non-event days, you can usually walk right in. On game days or for concerts, expect a line out the door and security checking IDs. Reservations are a smart move for groups or during peak times.
• Space & layout: The Cubby Bear is sprawling, with multiple bars, a big dance floor, plenty of high-top tables, and standing-room areas. Navigating the crowd can be tricky when it’s packed, but there’s usually room to squeeze in somewhere.
• Interaction style: It’s a social scene—don’t be surprised if you end up chatting with Cubs fans, concert-goers, or out-of-towners at the next table. Staff keep things moving, but the crowd is the real star of the show here.