The call: Go to The Well Monday at 4–6 PM—the $20 Flamingo burger + Old Fashioned is the strongest actual dinner-and-drink value downtown, and Monday adds $1 off select bourbon and whiskey starting at 4 PM.

Real-time local factors

• For Monday, September 14, downtown’s official Deals page lists The Well’s food-and-cocktail combo 4–6 PM, valid through Dec. 30.
• The Well: $1 off select bourbons/whiskeys on Bourbon Mondays, beginning 4 PM.
• Restaurant Iron: half-off classic cocktails, wine by the glass, and beer 2–5 PM daily—best if you can eat early. Official listing
• The Wine Bar on Palafox: half-price glasses of wine 11 AM–6 PM daily; good for a wine-first early dinner. Official listing
• These specials are listed as current, but can change without notice—confirm before heading over.

Runners-up

• Restaurant Iron — go here instead if you can arrive by 5 PM and want the best cocktail savings with a more polished dinner.
• The Wine Bar on Palafox — go here instead if you want wine rather than bourbon; its half-price-by-the-glass window lasts until 6 PM.
• Cabaret — go here instead if you want your night to roll into 9 PM karaoke; happy hour runs 3–8 PM daily, though the official listing does not specify the discounted items.

What flips this — If you can’t make it by 6 PM, skip the deal-chasing and choose Cabaret for the longest listed Monday happy-hour window and karaoke afterward.

👉 Are you looking for an actual dinner special, or mainly the cheapest drinks Monday night?