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Holiday Events and Things to do in Chicago, IL

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Intro Price - Chicago 2 Day Wig Out For Summer Holiday Bar Crawl - Jun 25-26
Fri, Jun 25, 6:00 PM
Wicker Park · DSTRKT Bar & Grill
Intro Price - Chicago 2 Day Wig Out For Summer Holiday Bar Crawl - Jun 25-26
Fri, Jun 25, 6:00 PM
Wicker Park · DSTRKT Bar & Grill
3 Day All Access Chicago St Patrick's Day Bar Crawl
Fri, Mar 12, 6:00 PM
Lincoln Park · Downtown Chicago
3 Day All Access Chicago St Patrick's Day Bar Crawl
Fri, Mar 12, 6:00 PM
Lincoln Park · Downtown Chicago
Local Edition Fall Night Market
Thu, Oct 8, 4:00 PM
West Town · Walden
Local Edition Fall Night Market
Thu, Oct 8, 4:00 PM
West Town · Walden
Denim Festival & Bear Down Patch Up Tailgate
Sat, Sep 12, 1:00 PM
Chicago Lawn · Thrift LLC
Denim Festival & Bear Down Patch Up Tailgate
Sat, Sep 12, 1:00 PM
Chicago Lawn · Thrift LLC
Fall Equinox Ceremony
Thu, Sep 24, 6:15 PM
Goose Island · We The People Fitness Studio
Fall Equinox Ceremony
Thu, Sep 24, 6:15 PM
Goose Island · We The People Fitness Studio
Haunted Museum
Sat, Oct 24, 4:00 PM
Hyde Park · 1155 E 58th St
Haunted Museum
Sat, Oct 24, 4:00 PM
Hyde Park · 1155 E 58th St
IPH's Fall Fest on The Riverwalk w/ Hayrides on the River & More in Chicago
Sat, Sep 19, 12:00 PM + 6 more
New Eastside · Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk)
IPH's Fall Fest on The Riverwalk w/ Hayrides on the River & More in Chicago
Sat, Sep 19, 12:00 PM + 6 more
New Eastside · Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk)
This is life Trunk or Treat & Halloween Costume Contest
Sat, Oct 24, 12:00 PM
Englewood · Hamilton Park
This is life Trunk or Treat & Halloween Costume Contest
Sat, Oct 24, 12:00 PM
Englewood · Hamilton Park
Monster Mall Chicago: Boo's and Brews
Sun, Sep 20, 12:00 PM
West Town · Midwest Coast Brewing Company
Monster Mall Chicago: Boo's and Brews
Sun, Sep 20, 12:00 PM
West Town · Midwest Coast Brewing Company
Halloween Event
Sat, Oct 31, 12:00 PM
The Loop · 111 N State St
Halloween Event
Sat, Oct 31, 12:00 PM
The Loop · 111 N State St
The Balzekas Museum Guild Holiday Craft Fair
Sat, Nov 21, 11:00 AM
West Lawn · Balzekas Museum Of Lithuanian Culture, South Pulaski Road, Chicago, IL, USA
The Balzekas Museum Guild Holiday Craft Fair
Sat, Nov 21, 11:00 AM
West Lawn · Balzekas Museum Of Lithuanian Culture, South Pulaski Road, Chicago, IL, USA
Fall Fashion Celebration Saturday | September 26, 2026 (State Street)
Sat, Sep 26, 1:00 PM
The Loop · Macy's State Street
Fall Fashion Celebration Saturday | September 26, 2026 (State Street)
Sat, Sep 26, 1:00 PM
The Loop · Macy's State Street
The Holiday Market at Palmhouse
Sat, Dec 12, 11:00 AM + 1 more
Clyde Avenue · PALMHOUSE
The Holiday Market at Palmhouse
Sat, Dec 12, 11:00 AM + 1 more
Clyde Avenue · PALMHOUSE
Luxury Delight Candle Company 1st Annual Fall Festival
Sun, Oct 4, 12:00 PM
Franklin Park · Villa Bella Banquets
Luxury Delight Candle Company 1st Annual Fall Festival
Sun, Oct 4, 12:00 PM
Franklin Park · Villa Bella Banquets
OKTOBERFEST TO SUPPORT ENGER SCHOOL
Sat, Sep 19, 6:00 PM
Riverview · 4501 25th Ave
OKTOBERFEST TO SUPPORT ENGER SCHOOL
Sat, Sep 19, 6:00 PM
Riverview · 4501 25th Ave
Elk Grove Village Oktoberfest 2026
Schnells Corner · Rotary Green
Elk Grove Village Oktoberfest 2026
Schnells Corner · Rotary Green
Save The Date: Harvest Fest 2026
Sat, Oct 10, 11:00 AM
South Chicago · South Chicago Farm
Save The Date: Harvest Fest 2026
Sat, Oct 10, 11:00 AM
South Chicago · South Chicago Farm
SPOOKEASY 3: THE SAM-HAIN CIRCUS
Thu, Oct 29, 6:30 PM
Fay's Point · The Lyric Theater Blue Island
SPOOKEASY 3: THE SAM-HAIN CIRCUS
Thu, Oct 29, 6:30 PM
Fay's Point · The Lyric Theater Blue Island
Lux IS Love ... OUTSIDE
Fri, Sep 25, 5:00 PM
Lake Calumet Industrial District · Big Marsh Park
Lux IS Love ... OUTSIDE
Fri, Sep 25, 5:00 PM
Lake Calumet Industrial District · Big Marsh Park
Scream or Cream Nightmare on Cottage Grove Ave.
Sat, Oct 31, 9:00 PM
Berger · 14733 Drexel Ave
Scream or Cream Nightmare on Cottage Grove Ave.
Sat, Oct 31, 9:00 PM
Berger · 14733 Drexel Ave

Trends in Chicago

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Frequently asked questions about Chicago

What are the best festival events to attend?

According to Eventbrite, the best festival events are:

Intro Price - Chicago 2 Day Wig Out For Summer Holiday Bar Crawl - Jun 25-26

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

Local Edition Fall Night Market

Fall Equinox Ceremony

Which events are currently trending in Chicago?

The trending searches this month in Chicago are:

memorial day weekend

Which festival events are coming up?

Discover the best festival events happening soon – you don't want to miss them:

Denim Festival & Bear Down Patch Up Tailgate

IPH's Fall Fest on The Riverwalk w/ Hayrides on the River & More in Chicago

OKTOBERFEST TO SUPPORT ENGER SCHOOL

Monster Mall Chicago: Boo's and Brews