The Best Date Night Bars in Chicago

Grant Achatz and Nick Kokonas's cocktail bar in the West Loop is one of the most ambitious drinking establishments in the United States. The cocktail menu is a menu in the same sense that Alinea's food menu is a menu — a sequence of experiences rather than a list of drinks — and the team executes it with the same rigour applied to the three-Michelin-starred restaurant in the same building. A date at The Aviary is an occasion, not just an evening. Reserve weeks in advance for prime time slots and consider the prix-fixe cocktail experience for a complete version of what the bar can do.

Order: The current prix-fixe cocktail sequence — the editors' definitive Chicago date night recommendation

Drumbar on the 18th floor of the Raffaello Hotel in Streeterville has been Chicago's best rooftop date bar since it opened, and it has not been surpassed. The panoramic view of the city and Lake Michigan at night is the kind of backdrop that turns a first date into a second date before the first drink is finished. The cocktail programme is serious and draws on classic American templates with a seasonal update that keeps regulars returning. Live jazz several nights a week adds the exact right kind of ambient noise — present but not overwhelming.

Order: The house Old Fashioned — rye-based, properly made, with a generous piece of expressed orange peel

The Pump Room has been Chicago's most storied bar since the 1930s — Bogart, Sinatra, Judy Garland all drank in Booth One. The current incarnation at the Public Chicago hotel has preserved the mythology while updating the cocktail programme to match. The room is Art Deco and impossibly glamorous; the bar staff make drinks with the confidence that comes from operating in a room that has been doing this for ninety years. For an occasion-level date, the Pump Room makes the case that Chicago knows how to do this better than New York, which is not something to say lightly.

Order: A dry Martini — this is a Martini room and it has been since before you were born

The Violet Hour on Damen Avenue is one of the best bars in the country and has been since it opened in 2007. The entrance is unmarked — look for the mural — and the house rules (no phones at the bar, no standing at the table) enforce exactly the kind of focused presence that makes a date bar work. The cocktail programme is serious and changes seasonally; the room is long, dimly lit, and divided by curtains into sections that create a degree of privacy unusual in a bar this popular. Our top pick in Chicago for a second date or a significant evening.

Order: The current seasonal cocktail — the programme rotates and each version is worth ordering

Billy Sunday on Milwaukee Avenue in Logan Square has one of the most serious spirits collections in Chicago — hundreds of expressions of whisky, rum, and other aged spirits organised on shelves that go to the ceiling — and a cocktail programme that uses them intelligently rather than just as a collection to admire. The bar is warm and neighbourhood-feeling in a way that The Violet Hour is not, which makes it better for a first date where you want the environment to be encouraging rather than imposing. The bartenders are genuinely knowledgeable and happy to guide the selection.

Order: A whisky recommendation from the bartender — tell them your preference and budget and let them pick

Scofflaw on Milwaukee Avenue is a gin bar in the technical sense — the menu organises the world's gin styles into a coherent taxonomy — but it functions as a neighbourhood bar that happens to make excellent drinks. The room is comfortable without being studied; the prices are honest for the quality; the crowd is local. For a date in Logan Square where you want the drinks to be the best in the neighbourhood without the evening feeling like a field trip to a serious institution, Scofflaw is the correct answer. Reserve for Thursday through Saturday.

Order: The Scofflaw cocktail — the house namesake, rye, dry vermouth, grenadine, orange bitters, lemon

The Coq d'Or opened the day after Prohibition ended in 1933 and has not closed since. The room is original — wood panelling, leather booths, a long bar that curves at the end — and the drinks list has been making proper Old Fashioneds, Martinis, and Manhattans for ninety years. The cocktail programme has been updated to include contemporary options without losing the character of a bar that understands its own history. For a date where you want to drink in a room that has absorbed ninety years of significant evenings, the Coq d'Or is the choice.

Order: Manhattan — rye, sweet vermouth, Angostura, house-stirred for exactly the right dilution

Cindy's on the rooftop of the Chicago Athletic Association hotel looks directly at Millennium Park, the Cloud Gate, and the lake beyond. On a clear evening the view from the terrace is one of the best in the city and makes the case for the Midwest's largest urban park as one of the world's great public spaces. The cocktail programme is competent without being exceptional — the view is the programme here, and the bar knows it. For a summer date where the setting is the primary consideration, Cindy's is the correct call.

Order: The house Chicago Sling — a long, refreshing cocktail designed for the terrace and the view

The Long Room on Irving Park Road is a neighbourhood bar that does everything right: good beer selection, well-made classic cocktails, a room long enough that you can always find a quiet corner, and a crowd of Irving Park and Ravenswood locals who chose it because it is the best bar in the neighbourhood by a significant margin. For a date in the North Side neighbourhoods where you want the evening to feel like you live there — the best kind of date — The Long Room is the answer. No reservations, first come first served, worth arriving before 7pm on weekends.

Order: Old Fashioned or a local craft beer — the bar does both with equal commitment