Things to Do in Chicago, IL

Family activities, museums, markets, and outdoor events in Chicago.

Sat, Dec 19 · 11:00 AM

The Shops - Holiday Edition #2 - Final 2026 Pop-up!

Water Tower Place (Level 3 Next to JJill and White House Black Market)

See listing

Sat, Dec 19 · 4:00 PM

Chicago SantaCon Bar Crawl 2026

PB&J: Pizza Beer and Jukebox

$0 +

Sat, Dec 19 · 4:00 PM

The Christmas Bar Crawl - Chicago

SPIN

$7.14 +

Sat, Dec 19 · 6:30 PM

Soulful Holiday Lights Trolley Celebrating Motown, R& B & House

230 W North Ave

$78.50 +

Wed, Dec 30 · 6:00 PM

Best Offer - Chicago 3 Day All Access New Years Eve (NYE) Bar Crawl - Dec 30-Jan 1

Pour Decisions, DSTRKT + Many More Down Town Chicago

$0 +

Wed, Dec 30 · 8:00 PM

Eve of the Eve Lake Cocktail Cruise on Wednesday, December 30th

Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below)

$20 +

Thu, Dec 31 · 4:30 PM

New Year's Eve Sunset Cocktail Cruise on Thursday, December 31st

Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below)

$20 +

Thu, Dec 31 · 7:00 PM

Chicago NYE 2027 Bar Crawl - Wrigleyville's New Year's Eve Party | 10+ Bars

Wrigleyville's Best Bars TBA

$10 +

Thu, Dec 31 · 9:45 PM

All Inclusive New Year's Eve 2027 Fireworks Cruise aboard Anita Dee II

Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below)

$99 +

Sat, Jan 23 · 11:00 AM

Mac & Cheese Crawl - Chicago's Cheesiest Bar Crawl! Mac & Cheese Included!

Wrigleyville's BEST Bars TBA

$10 +

Sat, Jan 23 · 2:30 PM

Best Offer - Chicago Winter Whiskey Tasting Festival - Jan 23

King's

$0 +

Sat, Feb 20 · 12:00 PM

National Redhead Fest in Chicago | Fireball Shots, Live Music & More!

The Cubby Bear Chicago

$10 +

Sat, Feb 20 · 2:30 PM

Intro Price - Chicago Winter Tequila Tasting Festival - Feb 20

King's

$0 +

Fri, Mar 12 · 6:00 PM

3 Day All Access Chicago St Patrick's Day Bar Crawl

Downtown Chicago

$0 +

Sat, Apr 17 · 10:00 AM

Chicago Donut Fest: Donut Tastings, Live DJ, Donut Photo Ops & More!

Old Crow

$14.99 +

Sat, Apr 24 · 2:30 PM

Chicago - Spring 2 Summer Cocktail Tasting Festival - April 24

Venue TBA - Chicago

$0 +

Sat, May 15 · 12:00 PM

Chicago Pickle Fest: Live Bands, Beer and Everything Pickle!

Wrigleyville's BEST Bars TBA

$10 +

Fri, Jun 25 · 6:00 PM

Best Offer - Chicago 2 Day Wig Out For Summer Holiday Bar Crawl - Jun 25-26

DSTRKT Bar & Grill

$0 +

Thu, Jul 22 · 2:00 PM

LimeLife Palooza - July 22nd-24th, 2027

Chicago

$212.61 +