Five Guys N. Sheridan (x)

Hidden behind a graffiti-covered wall, this cozy cocktail lounge offers expertly crafted drinks, small bites, and a relaxed speakeasy vibe perfect for any night out.

Tropic Island in Chatham serves up generously portioned Caribbean and soul food, featuring must-try jerk dishes and a laid-back vibe.

Empanada Mama is a cozy, family-run Puerto Rican joint in West Town, serving vibrant empanadas and culinary delights in a lively tropical setting.

This cozy Edgewater eatery serves delicious Ethiopian stews and boasts a welcoming vibe, making it a favorite for families and food lovers alike.

Tucked at the end of a Bucktown street, the Leavitt Street Inn & Tavern serves up smash burgers and local brews in a cozy, community-focused setting with a charming patio and three guest rooms above.

Nestled in the Thompson Hotel, Nico Osteria serves up sleek Italian seafood with a fresh twist, perfect for any meal from breakfast to a festive dinner.

Tandoor Char House is a vibrant Lincoln Park spot known for its fusion of Indian and Pakistani flavors, offering everything from traditional tandoori dishes to creative takes like empanadas and burgers, all served in a cozy atmosphere.

Beatnik on the River dazzles with its bohemian flair, global cuisine, and tropical cocktails, perfect for lounging riverside amid a lush, vibrant setting.

Nestled near the bustling McCormick Place, Il Culaccino offers a chic Italian escape complete with a retractable rooftop, generous pasta portions, and a cozy patio for laid-back dining.

Nancy's Pizza in the West Loop is a must-visit for its iconic Chicago-style stuffed pizza and thin-crust creations, all served in a cozy, friendly atmosphere.