Conversation-friendly. Easy to leave. Drinks under $20. Ten bars our editors keep recommending when readers ask where to take a first date.
First dates are the highest-stakes hospitality test in the city. The room has to be quiet enough to hear each other but full enough that a long silence does not feel cavernous. The drink list has to give a reader who does not drink a graceful out. The exit has to be easy. Our editors have spent the past year vetting Chicago's cocktail rooms specifically for this question — where do you take someone you might not see again, but might see for the next twenty years?
Where the editors take a first date in Chicago
The first six picks below are the editors' default — the rooms we send a friend to first when they ask. Each is followed by a recommendation we have ordered ourselves at least three times. Click any bar name to read the full review, signature drink notes, neighbourhood guide and how to book.
Lost Lake, in Logan Square, the door is unmarked enough to feel discovered and known enough to be reliable. Pick a corner two-top and order across the menu — the staff are unfussed, the room is dim enough that you can read each other but bright enough that you can read the menu. Editors' rating in our database: 4.7 of 5.
Sportsman's Club sits in Ukrainian Village and the sportsman highball is on the menu year-round for a reason and the bartenders pour with intent. Easy to leave gracefully if it is not working. Easy to extend if it is. The exit has a quiet street, not a queue. Editors' rating in our database: 4.6 of 5.
At Scofflaw in Logan Square, the scofflaw cocktail is on the menu year-round for a reason and the bartenders pour with intent. Conversation here travels well. The acoustics are tuned for two people leaning in, not eight people leaning out, which is exactly what a first date needs. Editors' rating in our database: 4.6 of 5.
The Matchbox, in West Town, the gimlet arrives in a coupe and the bar staff move at the right pace. Conversation here travels well. The acoustics are tuned for two people leaning in, not eight people leaning out, which is exactly what a first date needs. Editors' rating in our database: 4.5 of 5.
Three Dots and a Dash, in River North, the three dots mai tai is on the menu year-round for a reason and the bartenders pour with intent. Pick a corner two-top and order across the menu — the staff are unfussed, the room is dim enough that you can read each other but bright enough that you can read the menu. Editors' rating in our database: 4.7 of 5.
In Logan Square, Billy Sunday the room is what it should be — quiet without being precious, busy without being a queue. Easy to leave gracefully if it is not working. Easy to extend if it is. The exit has a quiet street, not a queue. Editors' rating in our database: 4.7 of 5.
Order: Sunday Punch
The full Chicago guideEvery bar category, every neighbourhood. Our complete Chicago guide covers cocktail bars, rooftops, hidden gems and more across the city.
These last four are the editors' deeper-cut picks. Smaller rooms, more specific energy. If the first six feel obvious to you — meaning you have already been — start here.
At The Violet Hour in Wicker Park, the door is unmarked enough to feel discovered and known enough to be reliable. Pick a corner two-top and order across the menu — the staff are unfussed, the room is dim enough that you can read each other but bright enough that you can read the menu. Editors' rating in our database: 4.7 of 5.
Sparrow, in Gold Coast, the door is unmarked enough to feel discovered and known enough to be reliable. Easy to leave gracefully if it is not working. Easy to extend if it is. The exit has a quiet street, not a queue. Editors' rating in our database: 4.7 of 5.
The Whip sits in Lincoln Park and the whip punch arrives in a coupe and the bar staff move at the right pace. Conversation here travels well. The acoustics are tuned for two people leaning in, not eight people leaning out, which is exactly what a first date needs. Editors' rating in our database: 4.4 of 5.
At Lazy Bird in West Loop, the room is what it should be — quiet without being precious, busy without being a queue. Easy to leave gracefully if it is not working. Easy to extend if it is. The exit has a quiet street, not a queue. Editors' rating in our database: 4.6 of 5.
Order: Bird's Word
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More Cocktail Bars in ChicagoThe full editor-curated list of Cocktail Bars in Chicago, with neighbourhood notes and signature-drink picks.
If you are reading this article, you are probably between the booking confirmation and the actual date. Three rules. Book the table — walking in with a reservation says you put thought in. Pick the bar nearest to public transport, not the one with the best view. And keep dinner reservations elsewhere; if the conversation works, you are going to want a second venue.
If you are between stages: our companion Chicago guidesFrom first-date picks to anniversary rooms - every occasion in Chicago our editors cover, cross-linked.
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