Ina Mae

Nestled in the luxurious St. Regis Chicago, Tre Dita is a stunning Italian haven by chef Evan Funke, dishing out heavenly Tuscan pastas and glorious river views.

A cozy Thai gem featuring a vast menu of favorites like pad thai and curries, plus a BYOB option for the perfect casual dining experience.

Boleo, perched atop the Kimpton Gray Hotel, is a lively South American rooftop restaurant with a retractable glass roof, offering vibrant cocktails and a festive atmosphere perfect for both casual hangouts and special occasions.

Reclaimed is a laid-back eatery blending Southern-inspired comfort food with craft cocktails, all set against a cozy backdrop of reclaimed materials and good vibes.

Moody Tongue blends inventive, seasonally driven dishes with bold, house-crafted beers in a sleek, moody South Loop brewery.

Cozy Lincoln Square Italian spot with housemade pasta, a lush patio, and a seasonal wine list perfect for date nights and chill vibes.

Cozy family-run bookstore meets café in Wicker Park, offering curated reads, espresso, wine, and snug nooks to unwind.

Kumiko is a sleek West Loop spot blending creative Japanese cocktails and refined bites, with omakase-style drink tastings in a cozy, artful setting.

The Walnut Room at Macy's, a Chicago holiday icon, offers cozy American classics like pot pie under a festive 45-foot Christmas tree.

Superdawg is Chicago’s iconic 1948 drive-in serving snappy all-beef hot dogs with a pickled green tomato and crinkle fries, carhop-style.