The Best Happy Hours in South Loop, Chicago

South Loop has 14 happy hour spots on Spotd right now — from dive-bar well drinks to half-price oysters.

Standouts include Brando's Speakeasy, Buddy Guy's Legends, Half Sour, Jazz Showcase and 10 more. Recent deals: Nightly karaoke at Brando's Speakeasy; Blues performances every night open; cover charge $15 weeknights, $25 Fri-Sat; 21+ after 8pm at Buddy Guy's Legends.

Tap any spot below for its full deal list, hours, reviews and map. Happy hour times change often, so always verify directly with the venue before you head out.

All days Monday Tuesday Wednesday Thursday Friday Saturday Sunday

14 spots in South Loop, Chicago

Brando's Speakeasy Karaoke Lounge · Daily, evenings 🍹 Nightly karaoke ✓ Verified Sep 2026
Buddy Guy's Legends Blues Club · Wed-Thu 5pm-12am, Fri-Sat 5pm-1:30am, Sun 5pm-12am, Mon-Tue closed 🍹 Blues performances every night open; cover charge $15 weeknights, $25 Fri-Sat… ✓ Verified Jun 2026
Half Sour All-day bar and Jewish deli-inspired American · Mon-Fri 12pm-2am, Sat 10am-2am, Sun 10am-12am 🍹 House-fermented half sour pickles ✓ Verified Aug 2026
Jazz Showcase Jazz and blues club · Mon-Sat 7pm-11:30pm, Sun 3:30pm-10pm, sets nightly 8pm and 10pm, Sunday matinee 4pm 🍹 Nightly 8pm and 10pm sets from touring and local jazz greats ✓ Verified Aug 2026
Kasey's Tavern Tavern · Sun-Fri 11am-2am; Sat 11am-3am 🍹 Over 130 beers on tap and bottled ✓ Verified Jul 2026
Kroll's South Loop American · Daily 11am, dining room to 10pm, late-night bar menu after 🍹 Neighborhood bar and grill with daily drink specials ✓ Verified Sep 2026
M Lounge Martini lounge · Mon-Thu 4pm-12am, Fri-Sat 4pm-3am 🍹 Live jazz Tuesday & Wednesday 7-10pm, no cover charge ✓ Verified Aug 2026
Printers Row Wine Shop Wine Bar · Mon-Thu 12pm-10pm · Fri-Sat 12pm-12am · Sun 12pm-8pm 🍹 Natural wines from around the world ✓ Verified Sep 2026
Reggie's Music Joint Music Venue · Mon-Fri 11am-2am, Sat 11am-3am, Sun 11am-2am 🍹 Happy hour Mon-Fri 11am-7pm: $4 cans, $5 well drinks; free show nights rotate… ✓ Verified Jun 2026
Roots Handmade Pizza South Loop Quad Cities-style pizzeria and bar · Closed Mon-Tue, Wed-Thu 11am-10pm, Fri-Sat 11am-11pm, Sun 11am-10pm 🍹 Trivia Thursdays at 7:30pm with prizes ✓ Verified Aug 2026
Signature Bar + Restaurant Elevated sports bar · Mon-Wed closed, Thu 5pm-12am, Fri 11:30am-12am, Sat 10am-12am, Sun 10am-12am 🍹 Signature smashburger, double patty with caramelized onions and yuzu pickles ✓ Verified Aug 2026
The Chicago Firehouse Restaurant Steakhouse · Mon-Thu 4pm-10pm; Fri-Sat 3pm-10pm; Sun 4pm-9pm 🍹 Weekday happy hour Mon-Fri 4pm-5pm at the bar ✓ Verified Jul 2026
Vitalogy on Dearborn Cocktail Bar · Tue-Thu 4pm-10pm, Fri-Sat 4pm-12am 🍹 Craft cocktails $13-16; small plates; happy hour Tue-Thu 4pm-6pm ✓ Verified Jun 2026
Weather Mark Tavern Bar · Mon-Wed 4pm-12am, Thu-Fri 11am-12am, Sat 10am-1am, Sun 10am-12am 🍹 Daily 4-6pm happy hour; bottomless mimosas Sat-Sun $25 with food purchase ✓ Verified Jun 2026

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Frequently Asked Questions

How many happy hour spots are in South Loop, Chicago?

Spotd lists 14 happy hour spots in South Loop, Chicago right now, each with up-to-date deals and hours.

What time does happy hour start in South Loop, Chicago?

Most happy hours in South Loop, Chicago start around 11am, with some kicking off as early as 11am. Each spot's exact window is listed on its page.

Which South Loop spots have happy hour on Tuesday?

4 South Loop spots run a Tuesday happy hour on Spotd, including Brando's Speakeasy, Kroll's South Loop, Printers Row Wine Shop. See the full list on the Tuesday filter.

What are the best happy hour deals in South Loop, Chicago?

Popular picks include Nightly karaoke at Brando's Speakeasy; Blues performances every night open; cover charge $15 weeknights, $25 Fri-Sat; 21+ after 8pm at Buddy Guy's Legends; House-fermented half sour pickles at Half Sour. Browse every deal on the spots below.