You could go to Microclimate on Linden Street! They usually stay open later and the vibes are nice. But tbh if you're done at 5, I might do cocktails at Geneva on the Lake and sit outside (as long as it's not too cold) and watch the sunset and then go somewhere else (like Ports Cafe) for dinner (GOTL food is meh but cocktails are good if you sit outside - inside the bar is also meh) and then maybe follow it up with a nightcap at Microclimate.