The Allis
Its rich ambiance and easy exiting make this candlelit lounge at the trendy club Soho House an ideal prelude to dinner on Restaurant Row. Expect a crowd (old and young, some dressed up but just as many not). Intimate seating suits both conversation and good drink. To that end, the Vaquero Sour, made with Ancho Reyes liqueur, might be the best winter cocktail in town. West Loop, 113–125 N. Green St., sohohousechicago.com
Lone Wolf
The moody craft beer and cocktail haven—all black leather booths and dark hardwood—makes for an unpretentious precursor to a night out in its sometimes pretentious neighborhood. Opt for a sgroppino, a not-too-filling bubbly concoction designed specifically for the predinner drinker, and you’ll still have an appetite for that Au Cheval burger. West Loop, 806 W. Randolph St., lonewolftavern.com
Maude’s Liquor Bar
Loungey, cozy, and warm, the downstairs bar at this French charmer has a carefree aura that might make you forget about your rumbling stomach. You could easily lose an hour or two chasing the maraschinos at the bottom of the Aviation (Sipsmith gin, lemon, crème de violette). West Loop, 840 W. Randolph St., maudesliquorbar.com