10 Chicago Cocktail Bar Happy Hours

Caché 310 Happy Hour

Caché 310 is a West Loop cocktail lounge inspired by 1920s Paris. The space is intimate and tucked away from the main street, offering a quiet alternative to busier after-work spots. Happy hour details: Monday through Thursday, 6:00 pm to 8:00 pm. Specials: $10 signature cocktails, $5 beers and seltzers. Caché 310 is known for classic cocktails with a modern presentation.

Nine Bar Happy Hour

Nine Bar is an Asian-inspired cocktail bar located in Chinatown. The space combines classic cocktails with a menu of shareable small plates. Happy hour details Sunday through Thursday, 5:00 pm to 6:00 pm. Drink specials: $9 classic cocktails, $5 beer, $5 sake bombs. Food specials: $5 crab rangoon, $6 spring rolls, $7 mapo hot fries. Nine Bar offers an early evening option for after-work gatherings or pre-dinner drinks.

Truce Happy Hour

Truce is a coffee and cocktail bar located in Bucktown. The venue operates as a cafe by day and transitions to a cocktail bar in the evening. Happy hour details Sundays, 4:00 pm to close. Specials: $10 classic cocktails, $5 pizza bagels. Truce offers an extended Sunday happy hour that works well for winding down the weekend.

Scofflaw Happy Hour

Scofflaw is a gin-focused cocktail bar in Logan Square known for its extensive gin selection and craft cocktails. The bar offers a neighborhood-friendly atmosphere with an emphasis on classic and seasonal drinks. Happy hour details: Monday through Thursday, 5:00 pm to 7:00 pm | Friday through Sunday, 3:00 pm to 5:00 pm. Specials: $8 all happy hour cocktails. Scofflaw runs happy hour seven days a week with earlier weekend hours.

Moonflower Bar Happy Hour

Moonflower is a plant-filled cocktail bar in Portage Park. The space features a botanical aesthetic and a menu of approachable classics. Happy hour details: Daily, Until 6:00 pm. Specials: $6 drinks, including red sangria, lemon drop, margarita, gimlet, daiquiri, old fashioned, and Guinness. Moonflower’s daily happy hour offers a consistent early evening option throughout the week.

The Pearl Club Happy Hour

The Pearl Club is a cocktail lounge in West Town that draws inspiration from London’s classic cocktail scene while incorporating modern lounge elements. The space offers a polished setting for after-work gatherings. Happy hour details: Monday through Thursday, 5:00 pm to 7:00 pm. Drink specials: $12 classic cocktails, $10 featured cocktail, $12 wines. Food specials: $12 maple gochujang nuggets + house focaccia. The Pearl Club’s happy hour runs weekdays and pairs traditional cocktail service with a focused food offering.

Arbella Happy Hour

Arbella is a River North cocktail bar with a globally inspired drink menu. The bar focuses on travel-influenced cocktails and a rotating selection of daily specials. Happy hour details: Monday through Friday, 4:00 pm to 6:00 pm. Drink specials: $6 cocktail of the day, $5 beer of the day, $7 glasses of wine, $9 Peruvian Passport, $9 Sangre De Mi Sangre, $11 Traveling Old Fashioned, $10 From the Vault. Food specials: $5 five spiced nuts, $13 chicken tenders Arbella’s weekday happy hour offers a mix of rotating daily deals and signature cocktails.

Dearly Beloved Happy Hour

Dearly Beloved is a River North cocktail lounge known for elevated cocktails and a full dinner and late night menu. The space offers a polished atmosphere suited for both after-work drinks and evening dining. Happy hour details: Wednesday through Sunday, 4:00 pm to 6:00 pm. Drink specials: $10 martinis, $8 wines by the glass. Food specials: $2 oysters, ½ off select shareables. Dearly Beloved’s happy hour runs five days a week with a focus on classic drinks and bar snacks.

Gus’ Sip & Dip Happy Hour

Gus’ Sip & Dip offers a classic tavern experience in River North. The bar keeps things straightforward with a focus on approachable cocktails and a casual setting. Happy hour details: Monday through Friday, 4:00 pm to 5:00 pm. Specials: Rotating $6 cocktail of the day. Gus’ Sip & Dip runs a short weekday happy hour featuring one daily cocktail at a set price.

Storyville Happy Hour

Storyville is a New Orleans-inspired restaurant and cocktail lounge located in River North. The menu features Southern classics and craft cocktails in a casual setting.Happy hour details: Daily, 4:00 pm to 6:00 pm. Drink specials: $12 house cocktails, $6 old fashioned, $8 frozen cocktails, $6 all beer and seltzer cans. Food specials: $12 burger + fries, $25 NOLA sampler platter, $2 beignets, $10 cajun wings + fries, ½ off shareables. Storyville’s daily happy hour includes an extended food menu with New Orleans staples.