Named for Time Out founder Tony Elliott, Tony’s is the crown jewel of Time Out Market Chicago. The cozy all-season rooftop bar is decorated in vintage Time Out London covers, twinkling lights and handsome wood beams that stretch the length of the room. The space is anchored by a sprawling bar that serves a curated selection of wines, beers and signature cocktails. If the sun is shining, wander outside to take in skyline views (you can easily peep some architectural gems from here).