1. Broken Oar - Port Barrington
📍614 Rawson Bridge Road | Port Barrington | IL
Set right on the scenic Fox River, Broken Oar offers a relaxed yet lively atmosphere perfect for Bears playoff viewing. With plenty of indoor seating, river views, and live music, it's a great place to gather with friends. Expect great drinks, hearty pub fare, and plenty of screens to catch every play.
2. Niko's Red Mill Tavern - Woodstock
📍1040 Lake Ave. | Woodstock | IL
A true McHenry County staple, Niko's blends historic charm with vibrant game-day energy. With classic comfort food, an enormous bar, and TVs throughout the restaurant, it's a go-to place for Bears fans.
Bonus: It's one of the official stops on the McHenry County Bloody Mary Trail, serving their Mega Mary on Sundays!
3. Ortmann's Red Iron Tavern - Woodstock
📍1040 Lake Ave. | Woodstock | IL
Ortmann's delivers serious Cheer's vibes! Its friendly tavern atmosphere makes it a place where locals love to watch big games. With solid drink selections and a regular rotation of local food trucks, it's ideal for catching Bears playoff action. Plus, it's another Bloody Mary Trail location - perfect for fans who love brunch cocktails with a kick!
4. Sideouts Sports Tavern - Island Lake
📍4018 Roberts Rd. | Island Lake | IL
True to its name, Sideouts is built for sports fans. This lively tavern features numerous TVs, a welcoming crowd on game day, and a menu full of classic favorites like wings, burgers, and cold beers - everything you want while watching playoff football. Sideouts also participates in the Bloody Mary Trail Challenge!
5. Sweet Melissa's Pizza & Pub - Lakemoor
📍134 Rand Rd. | Lakemoor | IL
Sweet Melissa's is a cozy, family-friendly pub with a laid-back vibe that heats up during Bears games. Known for its pizza and signature Bloody Mary, it's the perfect place to be for kickoff!
6. The Cottage - Crystal Lake
📍6 E. Crystal Lake Ave. | Crystal Lake | IL
The Cottage combines neighborhood charm with a sports‑friendly setting — perfect for watching Bears playoff games. With TVs throughout and a welcoming bar staff, it’s ideal for groups. Don’t miss their Bloody Mary specials to kick off your game‑day brunch!
7. Tracks in Cary - Cary
📍108 W. Main St. | Cary | IL
Tracks is a classic sports bar crowd‑pleaser with big screens, an energetic atmosphere, and a loyal local fan base. Famous for its burgers, cold brews, and Bloody Mary Trail offerings, it’s a top choice for watching Bears football in Cary.
8. Harts Saloon - Hebron
📍9932 Main St. | Hebron | IL
For a more old‑school, laid‑back saloon feel, Hart’s is a must‑visit during playoff season. Locals pack the bar for Bears games, and its inclusion on the Bloody Mary Trail means great brunch drinks to enjoy before kickoff. Don't forget to grab one of their famous brick oven pizzas for the game!
9. Sew Hop'd Brewery & Taproom - Huntley
📍One Union Special Plaza | Suite 113 | Huntley | IL
Fans of craft beer will love Sew Hop’d Brewery’s welcoming taproom and brewery atmosphere. With rotating brews on tap and TVs ready for every play, you can sip local beer and savor the Bears playoff experience. It’s also a Bloody Mary Trail stop on weekends.
10. Crystal Lake Brewing - Crystal Lake
📍150 N. Main St. | Crystal Lake | IL
Crystal Lake Brewing offers a spacious taproom and a large projection screen for game day. Enjoy local craft beers, food trucks, and fellow Bears fans as you watch every moment of the playoff games. It’s a fantastic spot for both beer lovers and sports enthusiasts.