Chicago's most romantic drinking rooms are the ones locals use for first dates. The date night bars on this list span every neighbourhood worth a trip — the central districts all show up — and every price tier from a $5 local pour to a $25 hotel-bar tasting. Each bar earns its spot for a different reason. We have visited every one.

What unites the ten? The bartenders care. The rooms feel right at the time of night they are designed for. The drinks list reads clearly without showing off. We rate wine flights and quietly precise cocktails and the small things that turn a one-and-done visit into a regular's habit: an unhurried welcome, a warm room temperature in winter, a cool one in summer, and a bartender who remembers your name on the second visit.

Use this guide either as a single curated route through Chicago or as a checklist to revisit over a long weekend. Reservations are flagged where they matter. Otherwise, walk in. Below: the ten date night bars that any serious drinker in Chicago would tell you to put on the list.

The list

01

Andy's Jazz Club

RIVER NORTH · $$$ · COCKTAIL BARS

Andy's Jazz Club draws a steady local crowd in River North. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. Order: the bar's house signature. Best time: Tuesday and Wednesday before 9pm, when the regulars haven't filled the room yet. Best for cocktail-curious drinkers who want technique without theatre. Saturday after 10pm gets crowded — book ahead or arrive early.

Full review →
02

The Aviary

WEST LOOP · $$$$ · COCKTAIL BARS

The Aviary draws a steady local crowd in West Loop. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. Order: the bar's house signature. Best time: any weeknight between 7pm and 9pm, when the bar settles into its rhythm and the bartender has time to talk. Best for cocktail-curious drinkers who want technique without theatre. Friday from 8pm fills up; reserve a counter seat or a high table.

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03

Bar Pastoral

LAKEVIEW · $$$ · COCKTAIL BARS

Bar Pastoral draws a steady local crowd in Lakeview. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. Order: the bar's house signature. Best time: Sunday from 6pm, when it's the room's quietest premium night and the kitchen is unhurried. Best for cocktail-curious drinkers who want technique without theatre. Avoid post-match nights if the local team is playing — the upstairs gets loud.

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04

Bavette's Bar

RIVER NORTH · $$$$ · COCKTAIL BARS

Bavette's Bar draws a steady local crowd in River North. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. Order: the bar's house signature. Best time: Thursday late or Friday early, when you'll catch the room building toward its weekend tempo. Best for cocktail-curious drinkers who want technique without theatre. First-Friday traffic in the district can mean a 20-minute wait at the door.

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05

Billy Sunday Chicago

THE CENTRE · $$ · COCKTAIL BARS

Billy Sunday opened on Logan Boulevard in 2013 and is named after the early-20th-century evangelist who campaigned for Prohibition. The bar's response is to sto. Order: the bar's house signature. Best time: Tuesday and Wednesday before 9pm, when the regulars haven't filled the room yet. Best for cocktail-curious drinkers who want technique without theatre. Saturday after 10pm gets crowded — book ahead or arrive early.

Full review →
06

Buddy Guy's Legends

SOUTH LOOP · $$ · COCKTAIL BARS

Buddy Guy's Legends draws a steady local crowd in South Loop. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. Order: the bar's house signature. Best time: any weeknight between 7pm and 9pm, when the bar settles into its rhythm and the bartender has time to talk. Best for cocktail-curious drinkers who want technique without theatre. Friday from 8pm fills up; reserve a counter seat or a high table.

Full review →
07

The Celtic Knot Public House

EVANSTON · $$ · COCKTAIL BARS

The Celtic Knot Public House draws a steady local crowd in Evanston. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. Order: the bar's house signature. Best time: Sunday from 6pm, when it's the room's quietest premium night and the kitchen is unhurried. Best for cocktail-curious drinkers who want technique without theatre. Avoid post-match nights if the local team is playing — the upstairs gets loud.

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08

Delilah's

THE CENTRE · $ · COCKTAIL BARS

Open since 1993, Delilah's proves that a dive bar doesn't need to reinvent itself to stay relevant. The whiskey list runs to over 800 bottles and includes serio. Order: the bar's house signature. Best time: Thursday late or Friday early, when you'll catch the room building toward its weekend tempo. Best for cocktail-curious drinkers who want technique without theatre. First-Friday traffic in the district can mean a 20-minute wait at the door.

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09

Drumbar Chicago

THE CENTRE · $$$ · COCKTAIL BARS

Drumbar occupies the 18th floor of the Raffaello Hotel in Streeterville. The rooftop terrace and indoor lounge offer views of the Magnificent Mile and Lake Mich. Order: the bar's house signature. Best time: Tuesday and Wednesday before 9pm, when the regulars haven't filled the room yet. Best for cocktail-curious drinkers who want technique without theatre. Saturday after 10pm gets crowded — book ahead or arrive early.

Full review →
10

Emporium Arcade Bar Logan

LOGAN SQUARE · $$ · COCKTAIL BARS

Emporium Arcade Bar Logan draws a steady local crowd in Logan Square. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. Order: the bar's house signature. Best time: any weeknight between 7pm and 9pm, when the bar settles into its rhythm and the bartender has time to talk. Best for cocktail-curious drinkers who want technique without theatre. Friday from 8pm fills up; reserve a counter seat or a high table.

Full review →

By neighbourhood at a glance

Centre: Billy Sunday Chicago, Delilah's, Drumbar Chicago. Evanston: The Celtic Knot Public House. Lakeview: Bar Pastoral. Logan Square: Emporium Arcade Bar Logan. River North: Andy's Jazz Club, Bavette's Bar. South Loop: Buddy Guy's Legends. West Loop: The Aviary. Most of these bars sit walking distance from each other within their districts. Chicago's drinking neighbourhoods are compact — plan two or three bars in a single evening rather than racing across town.

Before you go

Reservations are recommended on Friday and Saturday evenings at any of the higher-priced rooms above. Mid-week before 8pm, walk-ins are usually fine. Tipping in Chicago is appreciated; check our city guide for local norms. Cards are accepted everywhere on this list except where the bar specifies cash only — usually the older heritage rooms. Chicago's last-call laws vary by district; plan your route from the strictest to the most relaxed.

"You'll know which of these ten date night bars matches your night within the first sip."

Want more Chicago? Our full Chicago bar guide covers every neighbourhood and every category. For the broader category index, see all date night bars worldwide. And if you have a recommendation we missed, tell us — our editors review every reader submission.