The Best Drinks Date Spots in Chicago
Choose between the downtown riverfront and a neighborhood plan. The map helps separate a central-city meeting from a longer trip north or west; there is no need to cross the whole city for a first introduction.
Start with one place for a drink and leave the rest of the evening open. These five bars and lounges offer different settings for that first conversation. Check the current menu, music schedule and any reservation or entry requirements on the venue website, especially if you want a quieter evening.
This selection includes Gus' Sip & Dip, Three Dots and a Dash, Arbella Cocktail Bar, Lazy Bird and Ghost Donkey. Use the map and practical details below to pick the one that fits your date.
Gus' Sip & Dip
A River North tavern that welcomes walk-ins. Start with one drink together and decide on the rest of the evening as you go. Check the bar website for current opening times and entry arrangements.
Three Dots and a Dash
A tropical cocktail bar with a strong rum focus. A useful choice when a drinks-first plan sounds more comfortable than a full dinner. Check the bar website for current opening times and entry arrangements.
Arbella Cocktail Bar
A Chicago cocktail bar pairing drinks with music. Make this your first stop rather than committing to a whole night of venue-hopping. Check the bar website for current opening times and entry arrangements.
Lazy Bird
A Fulton Market lounge pairing cocktails with live music. Check the current drinks list together, especially if one of you wants an alcohol-free option. Check the bar website for current opening times and entry arrangements.
Ghost Donkey
A Dearborn Street bar with a mezcal program. Pick a meeting time that gives you room to settle in and talk. Check the bar website for current opening times and entry arrangements.
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