TOP 30 Beer and live music in Waukegan, Illinois

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Win Win Restaurant & Bar is a vibrant and welcoming establishment located in the heart of Waukegan, Illinois. Our cozy restaurant offers a diverse menu of delicious dishes, from mouthwatering burgers and sandwiches to savory pasta and seafood options. Our fully stocked bar serves up a variety of craft cocktails, beers, and wines to complement your meal. With friendly service and a relaxed atmosphere, Win Win Restaurant & Bar is the perfect spot to enjoy a satisfying meal with friends and family. Come visit us at 30 North Genesee Street for a dining experience that's a win-win for everyone!

The Toadstool Pub, located in Highwood, Illinois, is a popular bar known for its award-winning Bloody Marys and wide selection of beer, wine, and cocktails. The knowledgeable and enthusiastic staff are ready to serve you in a 21st century environment with "Old World" undertones. The name "The Toadstool" is inspired by the amazing characteristics of toadstools, symbolizing rapid growth, longevity, medicinal properties, and a touch of magic. Whether you're looking for a fun night out with friends or a relaxing drink after work, The Toadstool Pub is the perfect spot to enjoy good company and great drinks. Visit us at 327 Waukegan Avenue or call 847-748-8658 for more information. Cheers to good times at The Toadstool Pub!

Jesters is a lively bar located at 1500 North Lewis Avenue in Waukegan, Illinois. Known for its fun and welcoming atmosphere, Jesters is a popular spot for locals and visitors alike to enjoy a cold drink and good company. With a wide selection of beers, cocktails, and spirits, as well as a menu of tasty bar snacks, Jesters is the perfect place to unwind after a long day or catch up with friends. Whether you're looking to watch the game on one of their big screen TVs or dance the night away to live music, Jesters has something for everyone. Come on down and see why Jesters is the go-to spot for a great night out in Waukegan.