Chicago Holiday Events

Red, White & Cruise | Chicago July 4th Weekend Yacht Party

Spirit of Chicago Yacht 3 Jul 2026

Windy City Food & Craft Festival

337 E Randolph St 3 Jul 2026

Chicago Memorial Day Weekend Cruise | All White Attire Party

Spirit of Chicago Yacht 24 May 2026

Chicago Labor Day Weekend All White Attire Party Cruise

Spirit of Chicago Yacht 6 Sep 2026

Colombian Fest Chicago 2026

Humboldt Park 17 Jul 2026

Fourth of July at IO Godfrey Rooftop

IO Godfrey Rooftop Lounge 4 Jul 2026

Randolph Street Market

1341 W Randolph St, Chicago, IL 60607-1523, United States 23 May 2026

Chicago Halloween Bar Crawl

Kaiser Tiger 24 Oct 2026

Chicago Pride Bar Crawl

PB&J: Pizza Beer and Jukebox 20 Jun 2026

Chicago Pride Bar Crawl Party 2026 | Saturday, June 27th

TBA 27 Jun 2026

Chicago Halloween Bar Crawl 2026

PB&J: Pizza Beer and Jukebox 31 Oct 2026

Chicago Memorial Day Bar Crawl Party 2026 | Saturday, May 23

TBA 23 May 2026

MEMORIAL MAYHEM WEEKEND BAR CRAWL (10+ BAR/CLUBS INCLUDED) 2 DAYS OF PARTY!

Bandit 23 May 2026

Memorial Day at ROOF on theWit | All White Attire | 5.25.26

ROOF on theWit 25 May 2026

Afrobeats Saturdayz: 4TH OF JULY WEEKEND

Masada 4 Jul 2026

DESIPALOOZA 2026: Chicago's Premier South Asian Nightlife Festival

ROCBAR 22 May 2026

AFROBEATS SUNDAY - One Night Only (MDW)

Masada 24 May 2026

4th of July Chicago Bar Crawl 2026 | Saturday, July 4th

TBA 4 Jul 2026

Just Because 2026 Chicago Summer Holiday Bar Crawl

Lincoln Park, River North, Wicker Park Bars All Access 20 Jun 2026

Chicago Christmas in July Bar Crawl 2026

PB&J: Pizza Beer and Jukebox 25 Jul 2026

Monday Afrobeats on the beach with DJ Diesel @ Pier 31 (Free event)

Pier 31 restaurant & bar 25 May 2026

May 24th! Rooftop Sunday Funday Series Downtown!

Reserv 24 May 2026

Daily Stoic Live | Onstage with Ryan Holiday

Gateway Theater at Copernicus Center 19 Aug 2026

REFRESH

Point & Feather 24 May 2026

SwervCup Events Presents: Beach Prom - The 4th of July Holiday Formal Coed Doubles Tournament

Montrose Beach 4 Jul 2026

Memorial Day Fireworks Booze Cruise!

Chicago Lakefront Cruises 23 May 2026

J Holiday - Nahum Thorton Grymes at City Winery - Chicago

City Winery - Chicago 14 Aug 2026

Jared Freid "Walking Red Flag" Book Launch and Signing

Everybody's Coffee 12 Jun 2026

T!TS the Season: Int Wh*re’s Day Pole Show

The Newport Theater 29 May 2026

GAY Soul Food (Chicago)

Definition Theatre 14 Aug 2026

Wild Fork Lincoln Park | Kick off summer this Memorial Day Weekend

1001 W North Ave 16 May 2026

Memorial Day 1M 5K 10K 13.1 26.2

Chicago 25 May 2026

Daddy Disco Party

3349 N Halsted St, Chicago, IL, United States, Illinois 60657 23 May 2026

Memorial Day Weekend at Mac’s Wood Grilled

Mac's Wood Grilled 22 May 2026

July Book Club w/ Three Avenues Bookshop: Upward Bound

Beermiscuous 19 Jul 2026

Funny Funny Fashion Comedy Show

The Lincoln Lodge 16 May 2024

2026 BATES HALL FAMILY REUNION (CHICAGO, IL)

__ 25 Jun 2026

Register Early_8am Mondays I & II Quarter "FREE" Line-Dance @ Museum_Maddy!

Griffin Museum of Science and Industry (G-MSI) 13 Jan 2025

VIRGOS TAKE ANTIGUA 🇦🇬

The Loop 4 Sep 2026

Workplace Diversity & Inclusion – Empower Teams in Chicago, IL

For venue details reach us at: [email protected] 19 Nov 2025