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How to Escape The $20 Cocktail

Skip to main content Current eater city: Chicago A guide to Chicago's best happy hour drink deals Jun 30, 2025, 4:20 PM UTC Lisa Shames has been a regular contributor to Eater Chicago since 2021. Although Chicago's embracing of happy hour was late to the easy-on-the-wallet party — it only became legal in 2015 — it's made up for lost time ever since. It's at the point where not offering some sort of special seems strange. With that abundance in mind, we opted to do two separate guides. This one highlights places where specially priced happy hour drinks are the focus, and the other spotlights places where you'll find terrific food and drinks. If bottomless brunches are more your thing, we've got you covered here. For a breakdown of 14 can't-miss drink-focused happy hours from Andersonville to Hyde Park, explore the map below. Schedules, prices, and menus can vary significantly with little notice, so patrons would be wise to check out a venue's website before making plans. We've added plenty of newcomers from the West Loop's Bisous and Logan Square's Spilt Milk to Ceres Cafe in the Loop. — Additional reporting by Sam Nelson A guide to Chicago's best happy hour drink deals Jun 30, 2025, 4:20 PM UTC Lisa Shames has been a regular contributor to Eater Chicago since 2021. Although Chicago's embracing of happy hour was late to the easy-on-the-wallet party — it only became legal in 2015 — it's made up for lost time ever since. It's at the point where not offering some sort of special seems strange. With that abundance in mind, we opted to do two separate guides. This one highlights places where specially priced happy hour drinks are the focus, and the other spotlights places where you'll find terrific food and drinks. If bottomless brunches are more your thing, we've got you covered here. For a breakdown of 14 can't-miss drink-focused happy hours from Andersonville to Hyde Park, explore the map below. Schedules, prices, and menus can vary significantly with little notice, so patrons would be wise to check out a venue's website before making plans. We've added plenty of newcomers from the West Loop's Bisous and Logan Square's Spilt Milk to Ceres Cafe in the Loop. — Additional reporting by Sam Nelson The team behind Logan Square's Whistler unveiled this come-as-you-are Avondale haunt in 2018 and rapidly attracted a cadre of loyal fans with a sizable lineup of cider and sour beers, as well as a wide variety of live music acts. Happy hour specials run from 6 to 8 p.m., with $2 off all beer and cider drafts (except PBR) Monday and Tuesday, $5 well drinks Wednesday, and $8 draft cocktails Thursday. Additionally, from 6 to 8 p.m. Monday through Thursday, there's a $5 rotating shot. 3734 W Belmont Ave (Ridgeway), Chicago, IL 60618 (773) 654-3971 (773) 654-3971 Visit Website One of the city's best bars is tucked behind Rush and Division and Mariano Park on the bottom floor of a 1927 Art Deco apartment building. Sparrow is a charmingly moody spot inspired by the rum bars of Havana from years ago. Find $5 drafts and $10 glasses of wine from 4 to 7 p.m. Monday through Friday. 12 West Elm Street, Chicago, Illinois 60610, United States Visit Website With a name that celebrates the little wins in life, Little Victories is one of those neighborhood bars everyone wants to call their own, no matter where they live. A square bar in the middle of the room encourages conversations, while the dart board and pool table are there for the competitive types. It's all-day happy hour specials (4 p.m.-midnight Sunday through Wednesday, 4 p.m. to 1 a.m. Thursday, noon to 2 a.m. Saturday) add to that neighborly attitude. Belly up for specially priced beer ($4 to $5), wine ($8), a house vermouth-infused shot ($5), and a daily cocktail special ($9 to $10). 1725 W Division St, Chicago, IL 60622 (312) 248-3484 (312) 248-3484 Visit Website Perhaps you'd like to combine your weekday imbibing with some high-tech shuffleboard? At the Loop's Electric Shuffle (from the same folks as nearby dart-focused Fight Club), happy hour 3 to 5 p.m. Monday through Friday features $10 margaritas, espresso martinis, and house pizzas along with $5 beer, wine, seltzers, and fries.