Chicago's skyline drinks better than its postcards. The rooftop 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 sunset cocktails with a view 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 rooftop bars that any serious drinker in Chicago would tell you to put on the list.

The list

01

Cindy's Rooftop

LOOP · $$$ · ROOFTOP BARS

Cindy's Rooftop draws a steady local crowd in Loop. 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 sunset drinks or a slow first date. Saturday after 10pm gets crowded — book ahead or arrive early.

Full review →
02

I|O Godfrey Rooftop

RIVER NORTH · $$$ · ROOFTOP BARS

I|O Godfrey Rooftop 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: any weeknight between 7pm and 9pm, when the bar settles into its rhythm and the bartender has time to talk. Best for sunset drinks or a slow first date. Friday from 8pm fills up; reserve a counter seat or a high table.

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03

LH Rooftop

LOOP · $$$$ · ROOFTOP BARS

LH Rooftop draws a steady local crowd in Loop. 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 sunset drinks or a slow first date. Avoid post-match nights if the local team is playing — the upstairs gets loud.

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04

VOL. 39

LOOP · $$$ · ROOFTOP BARS

VOL. 39 draws a steady local crowd in Loop. 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 sunset drinks or a slow first date. First-Friday traffic in the district can mean a 20-minute wait at the door.

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05

Vu Rooftop

SOUTH LOOP · $$ · ROOFTOP BARS

Vu Rooftop 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: Tuesday and Wednesday before 9pm, when the regulars haven't filled the room yet. Best for sunset drinks or a slow first date. Saturday after 10pm gets crowded — book ahead or arrive early.

Full review →
06

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: 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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07

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: 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

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: 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

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: 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.

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10

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: 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. Lakeview: Bar Pastoral. Loop: Cindy's Rooftop, LH Rooftop, VOL. 39. River North: I|O Godfrey Rooftop, Andy's Jazz Club, Bavette's Bar. South Loop: Vu Rooftop. 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 rooftop 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 rooftop bars worldwide. And if you have a recommendation we missed, tell us — our editors review every reader submission.