Promontory
5311 S. Lake Park Ave.
Promontory’s trendy style is unlike anything you’ll find in Evanston. One of Hyde Park’s newest additions, it’s a great venue to discover an unknown DJ or soul singer. Tickets can cost up to $40, but most of the underground techno you’ll hear will be $10 to $20.
The concert venue is upstairs while the restaurant is downstairs, so dinner and the show come separate. The chefs put mouthwatering twists on American classics (lamb burger with chickpea fries, anyone?). An entree and appetizer will be $20 to $40, but it’s worth it. Since it’s farther away, Promontory provides a more upscale night out, especially for the 21-and-up crowd who can try their artisan cocktails.
Smoke Daddy
1804 W. Division St.
Smoke Daddy in Wicker Park is not only home to some of the most amazing BBQ ribs in Chicago; it’s also a place to kick back and listen to (free) live blues. If you’ve ever wanted to witness the true Amercican spirit in a restaurant, Smoke Daddy is the place, in a more metropolitan, less “rev up the pickup” way. BBQ isn’t always cheap, but considering how much meat you get, Smoke Daddy is a good deal. Under $20 for a full order of rib tips and two sides isn’t half bad.
The live music can be a little loud for comfortable conversation, but your mouth will be so full of meat smothered in delicious gluten-free BBQ sauces that it might not matter.
Bandera
535 N. Michigan Ave.
Always be wary of music venues downtown where super-expensive tourist traps abound. Fortunately, Bandera restaurant is not one of them. At around $30 per person – fairly reasonable for dinner and music on the Magnificent Mile – Bandera offers a slightly fancier atmosphere than your average gritty jazz-and-blues bar, with a nice view of the most bustling section of the shopping area to boot.
A bit of a hidden jewel on Michigan Avenue, Bandera is the perfect location for those too lazy to trek to River North for a break from shopping or sightseeing to enjoy some tunes and food.
Martyrs’
3855 N. Lincoln Ave.
Martyrs’, just west of Lakeview, is a golden opportunity to immerse yourself in hipster culture. A cozy venue to hear anything from local bands to slam poetry to Pecha Kucha Nights (fast paced presentations on art and architecture), Martyrs’ has an amazing sound system for its size. Covers for shows are very reasonable, ranging from $7 to $20, and there’s even room to dance.
They have a limited menu of new takes on cheap, American bar food, such as fairly tasty $12 smoked ham andf fig pizza. Still, go for an interesting show, an artsy dim-lit atmosphere and friendly, bespectacled, flannel-wearing clientele.