The 316 Club in Chicago

Co-owners Greg Savarese and Tony Montemurro were going for Rat Pack–era 1960s Las Vegas when they opened the 316 Club in downtown Chicago, so they loaded the place with leather lounge chairs, red felt billiards table, fireplaces, and flat screens playing classic gangster movies. If you're fenced about committing to an annual membership fee of $620 – which includes unlimited hot towels treatments, haircuts and shoe shines – the club offers a more approachable six-month membership for $335. [312-880-0316, 316barberspa.com]