21+ Events in Chicago
345 events in Chicago
Ravenswood Costume Crawl
21+ Halloween treats and drinks crawl along Montrose and Ravenswood Avenues.
360 Oak Park - "Stage and Screen"
FITZGERALDS NIGHTCLUB PRESENTS:360 Oak Park Stage and ScreenFREE / RSVP FOR GUARANTEED SEATING360 Oak Park is a free storytelling event...
Mike Wheeler and Mzz Reese
Blues show at Blue Chicago in River North.
Comedy Night at The Charleston
A free comedy show featuring Chicago’s BEST stand-up comedian and touring comedians.
Giulio Brouzet - Chromatic Harmonica meets Chicago blues - Acoustic Series
Seating locations are determined based on special needs, party size, specific requests, and are subject to Rosa's Lounge’s discretion...
Jimmy Burns - Host The Jam
Blues show at Buddy Guy's Legends in South Loop.
Scary-oke
Stay for the screams.
Nate Manos Band - Pro-Jam
Shared-table and bar seating are available as space permits.
Nicholas Alexander Blues Band/Joanna Connor Blues Band
World famous Kingston Mines features the best Blues music from 2 bands on 2 stages.
Chicago Comedy Club
Doors open at 630PM.
Hex and the City: Market and Party
A little shopping, a little sipping & a whole lot of witchy behavior.
Spooky Night Market
Halloween festival at The Alley Cat Bar in Wicker Park.
The Fright Crawl | Chicago Halloween Bar Crawl 2026 | Thursday, October 29
Kickoff night of Chicago's Halloween weekend.
Premonitions Inc. at Kermess
Guests arrive as clients, only to find themselves caught in a night of outrageous fortunes, horoscope roasts, audience games, and...
Laretha Weathersby and Mike Wheeler
Blues show at Blue Chicago in River North.
The Rocky Horror Picture Show Sing Along at Replay Lakeview
Sing along to your favorites, quote every line and embrace the strange with host Margo.
Iris Marlowe
Her latest album Dead By Dawn is a collective of spaghetti western tunes inspired by 80s horror movies that will chill you to the bone.
Rock & Rye
Event features a General Admission Dance Pit in front of the stage.
Dead Sullivan’s Retro Rock & Roll Halloween Bash!
Halloween surf rock show at Fitzgeralds Nightclub in Berwyn.
Joey J. Saye - Traditional Blues Hour
Seating locations are determined based on special needs, party size, specific requests, and are subject to Rosa's Lounge’s discretion...
Nigel Mack
Blues show at Buddy Guy's Legends in South Loop.
Thursday Night Live Blues: Feat. Lil’ Ed Williams w/ Sumito Ariyoshi
Shared-table and bar seating are available as space permits.
Old Town Halloween Bar Crawl 2026
Halloween in Old Town.
Lincoln Park Halloween Bar Crawl 2026
Halloween on Halsted and Armitage.