1/5

CHICAGO EVENTS & FESTIVALS: 2014 CALENDAR HIGHLIGHTS

From favorite food festivals and can't-miss music concerts to annual events and holiday celebrations, check the 2014 calendar for Chicago before planning your next trip.

Back to Previous Page

Dyeing the Chicago River emerald green. Devouring 75,000 slices of cheesecake. Parading the streets with gay pride flags. Biking Lake Shore Drive, flying kites and racing Chinese dragon boats. Chicago knows how to have fun and everyone is invited! 

What makes Chicago’s festival season so great is that many of the biggest events are completely FREE – including the Chicago Blues Festival, Grant Park Music Festival, Chicago Jazz Festival and Chicago World Music Festival.

But it’s also the sheer variety of festivals, fairs and events that fill the calendar that makes for a one-of-a-kind itinerary for every visitor. The city celebrates everything from fine art to the fringe movement, craft beer to cultural heritage, and everything in between — be it film, fashion, literature, etc. Mixed in are huge holiday gatherings, and during the warm weather months, neighborhood street festivals every weekend across the city.

No doubt though that food and music are some of the biggest draws — from summer’s mega music spectacle Lollapalooza and the 5-day, belt-busting Taste of Chicago to the epicurean crowd-pleaser in the fall, Chicago Gourmet. There’s no better place to eat your heart out and to catch the best musical acts.

In 2014, a few new events make their debut: the inaugural Chicago International Art, Antique and Jewelry Show in April and the Great Chicago Fire Festival, a celebration 100 years in the making. The year will also mark some incredibly momentous occasions:

This is your guide to the biggest and best of 2014. Get out your schedule and start planning your trip to Chicago now!

JanFebMarchAprilMayJuneJulyAugSepOctNovDec


JANUARY 2014


 

Chicago Sketch Comedy Festival
January 9 – 19

Tomorrow Never Knows Festival
January 15 – 19

Chicago Boat, Sports & RV Show
January 16 – 20

Strictly Sail Chicago
January 23 – 26

Chicago Restaurant Week
January 24 – February 6

Chicago Chinese New Year Celebration
January 31 – February 14

 

FEBRUARY 2014


 

Chicago Restaurant Week
Through February 6

Chicago Chinese New Year Celebration
Through February 14

Snow Days Chicago at Navy Pier
February 8 – 9

Chicago Auto Show
February 8 – 17

Chicago Theatre Week
February 11 – 16

University of Chicago Folk Festival
February 14 – 16

 

MARCH 2014


 

St. Patrick's Day Parade & River Dyeing
March 15

Chicago Flower & Garden Show at Navy Pier
March 15 – 23

Randolph Street Market Festival
March 29 – 30

Chicago Improv Festival
March 31 - April 6

 

APRIL 2014


 

Chicago Improv Festival
Through April 6

Chicago International Art, Antique and Jewelry Show
April 24 – 28

C2E2: Chicago Comic and Entertainment Expo
April 25 - 27

Randolph Street Market Festival
April 26 – 27 

 

MAY 2014


 

CIMMfest: The Chicago International Movies & Music Festival
May 1 – 4

Cinco de Mayo Festival in Little Village
May 2 – 4   

Chicago Humanities Festival: Stages, Sights & Sounds
May 5 – 24

Mayfest
May 16 – 18

Riverfront Mayfest
May 16 – 18

Chicago Memorial Day Parade                                                          
May 24

Randolph Street Market Festival
May 24 – 25

Bike the Drive
May 25

Pivot Arts Festival
May 28 – June 14 

Loops and Variations in Millennium Park
May 29 – July 3: Thursdays

Maifest
May 29 – June 1

Festival del Taco
May 30 - June 1

Millennium Art Festival
May 30 – June 1

Do Division Street Fest & Sidewalk Sale
May 30 – June 1

 

JUNE 2014


 

Festival del Taco
Through June 1

Millennium Art Festival
Through June 1

Do Division Street Fest & Sidewalk Sale
Through June 1

Loops and Variations in Millennium Park
Through July 3: Thursdays

Pivot Arts Festival
Through June 14  

Downtown Sound in Millennium Park          
June 2 – August 4: Mondays

Chicago In-Water Boat Show
June 5 – 8

Andersonville Midsommarfest
June 6 – 8

RibFest Chicago
June 6 – 8

Millennium Park Workouts                                                    
June 7 – August 30: Saturdays

Belmont-Sheffield Music Festival *30th annual*
June 7 – 8

57th Street Art Fair
June 7 - 8

Printers Row Lit Fest *30th annual*
June 7 – 8

Grant Park Music Festival *80th annual*
June 11 – August 16

Fiestas Puertorriqueñas: Puerto Rican People’s Day Parade & Festival
June 12 – 15

Chicago Blues Festival *31st annual*
June 13 – 15

Taste of Randolph
June 13 – 15

Spring Awakening Music Festival
June 13 – 15

Wells Street Art Festival *40th annual*
June 14 – 15

Six Corners BBQ Fest
June 14 – 15

Chicago Pride Fest
June 21 – 22

Gold Coast Art Fair
June 21 – 22

Green Music Fest
June 21 – 22

Millennium Park Film Series
June 24 – August 26

Chicago Gospel Music Festival *29th annual*
June 27 – 29

Chicago SummerDance *18th annual*
June 27 – September 14

ITU World Triathlon Series
June 27 – 29  

Old St. Pat’s World’s Largest Block Party *30th annual*
June 27 – 28

Milwaukee Avenue Arts Festival
June 27 – 29

Chinatown Dragon Boat Races
June 28

Randolph Street Market Festival
June 28 – 29 

Chicago Pride Parade
June 29

 

JULY 2014


 

Loops and Variations in Millennium Park
Through July 3: Thursdays

Downtown Sound in Millennium Park
Through August 4: Mondays (no concert 7/28)

Grant Park Music Festival *80th annual*
Through August 16

Millennium Park Film Series
Through August 26: Tuesdays

Millennium Park Workouts
Through August 30: Saturdays

Chicago SummerDance *18th annual*
Through September 14

African/Caribbean International Festival of Life
July 3 – 6

Fourth of July Fireworks at Navy Pier
July 4

Windy City RibFest in Uptown
July 4 – 6

Riverwest Music Festival
July 4 – 6 

Taste of Lakeview
July 5 – 6

Taste of Chicago *34th annual*                                
July 9 – 13

Square Roots Festival
July 11 – 13

Tour de Fat
July 12

Roscoe Village Burger Fest
July 12 – 13  

Summer on Southport
July 12 – 13

Windy City Smokeout
July 12 – 14

West Fest
July 12 – 13

Green City Market Chef BBQ
July 17 

Pitchfork Music Festival
July 18 – 20

Taste of River North
July 18 – 20

Chicago Yacht Club Race to Mackinac
July 19

Sheffield Garden Walk
July 19 –20

Chicago Craft Beer Festival
July 19 – 20

Celebrate Clark Street
July 19 – 20

Chinatown Summer Fair
July 20

Dearborn Garden Walk
July 20

Made in Chicago: World Class Jazz at Millennium Park
July 24 – August 28

Jeff Fest! Arts & Music Festival
July 25 – 27

Wicker Park Fest
July 26 – 27

Taste of Lincoln Avenue
July 26 – 27

Randolph Street Market Festival
July 26 – 27 

Fiesta del Sol
July 31 – August 3


AUGUST 2014



Fiesta del Sol
Through – August 3

Downtown Sound in Millennium Park
Through August 4: Mondays

Grant Park Music Festival *80th annual*
Through August 16

Millennium Park Film Series
Through August 26: Tuesdays

Millennium Park Workouts
Through August 30: Saturdays

Chicago SummerDance *18th annual*
Through September 14

Taste of Latin America
August 2 – 3

Edge Fest
August 3 – 4

Wrigleyville SummerFest
August 3 – 4

Ginza Festival Chicago
August 8 – 10

Bud Billiken Parade
August 9

Northalsted Market Days
August 9 – 10

Chicago Hot Dog Fest
August 9 – 10

Retro on Roscoe
August 10 – 11

Festa Italiana
August 14 – 17

Glenwood Avenue Arts Fest
August 15 – 17

South Shore Summer Festival
August 16

Chicago Air and Water Show *56th annual*
August 16 – 17

Great American Lobster Fest *new event*
August 16 – 17 

Albany Park World Fest *new event*
August 16 – 17

Chicago Dancing Festival
August 20 – 23

The Magnificent Mile Shopping Festival
August 22 – September 1 

The Boulevard
August 22 – 24

SausageFest Chicago
August 23 – 24

Taste of Greektown *25th annual*
August 23 – 24

Bucktown Arts Festival
August 23 – 24

Chicago Food Social
August 23 – 24

Chicago Fashoin Fest
August 23 – 24

Chicago New Orleans Fest *new event*
August 23 – 24

Bash on Wabash
August 23 – 24

Chicago Fringe Festival
August 28 – September 7

Chicago Jazz Festival *36th annual*
August 28 – 31

African Festival of the Arts
August 29 – September 1

North Coast Music Festival
August 29 – 31

Remix Chicago: Chicago’s Recycled Art Fair
August 30 – 31

Randolph Street Market Festival
August 30 – 31


SEPTEMBER 2014


 

African Festival of the Arts
Through September 1

Chicago Fringe Festival
Through September 7

Chicago SummerDance *18th annual*
Through September 14

Shock Top Oyster Fest
September 6

Venetian Night at Navy Pier
September 6

Renegade Craft Fair: September Market
September 6 – 7

The Berghoff Oktoberfest
September 10 – 12

World Music Festival Chicago *16th annual*           
September 11 – 21

Festival de La Villita *25th anniversary*
September 12 – 14

Crush in Old Town
September 13 – 14                  

Lakeview East Festival of the Arts *10th anniversary*
September 13 – 14

EXPO Chicago
September 18 – 21

Gallery Weekend Chicago
September 18 – 21

Design Harvest Festival
September 20 – 21

Food Network In Concert at Ravinia
September 20

Sam Adams' Lakeview Taco Fest
September 20 – 21 

AAHH! Fest by Common
September 21

Chicago Gourmet
September 26 – 28

Oktoberfest Chicago
September 26 – 28

Hyde Park Jazz Festival
September 27 – 28

Randolph Street Market Festival
September 27 – 28 

 

OCTOBER 2014


 

Chicago Artists Month *19th annual*                              
October 1 – 31

Great Chicago Fire Festival presented by Redmoon             
October 3 – 4

Chicago International Film Festival *50th annual*
October 9 – 23 

Chicago Marathon
October 12

Italian Food & Wine Festival at Eataly
October 14 – 16

Randolph Street Market Festival
October 17 – 19 

Open House Chicago presented by Chicago Architecture Foundation
October 18 – 19

Happy Hauntings at the Chicago Cultural Center
October 23 – 26

Chicago International Children's Film Festival
October 24 – November 2 

 

NOVEMBER 2014


 

SOFA Art + Design Fair
November 7 – 9

Macy's Great Tree Lighting & Holiday Window Display Unveiling
November 8 

McCormick Tribune Ice Skating Rink in Millennium Park
November 14 – March 7, 2015 

Christkindlmarket
November 21 – December 24

Randolph Street Market Festival
November 21 – 23

The Magnificent Mile Lights Festival
November 22

Christmas Tree Lighting Ceremony at Daley Plaza
November 25

Santa House at Daley Plaza                                                   
November 25 – December 24

McDonald’s Thanksgiving Parade
November 27

Caroling at Cloud Gate in Millennium Park
November 28 - December 19 

ZooLights at Lincoln Park Zoo
November 28 – January 4, 2015

Wreathing of the Lions at the Art Institute of Chicago
November 28 

 

DECEMBER 2014


 

Caroling at Cloud Gate in Millennium Park
Through December 19

Santa House at Daley Plaza
Through December 24  

Christkindlmarket
Through December 24  

McCormick Tribune Ice Skating Rink in Millennium Park
Through March 7, 2015  

ZooLights at Lincoln Park Zoo
Through January 4, 2015

Winter WonderFest at Navy Pier
December 5 – January 11, 2015

One of A Kind Show and Sale
December 4 – 7

Renegade Craft Fair: December Market
December 6 – 7

Julmarknad at Swedish American Museum
December 6 - 7 

Do Division Holiday Fest
December 7 - 8 

Randolph Street Market Festival
December 12 – 14

Lucia Celebration at Swedish American Museum
December 12 

HoliDose Market
December 14 

Kwanzaa Candle Lighting Celebration at the Dusable Museum
December 26 – December 31 

New Year's Eve Fireworks at Navy Pier
December 31

Please note that dates are subject to change. Visit individual event websites for details and the latest updates.

Featured Partners
Book a Trip
Find Hotels In
Check In
Check Out
Rooms
Travelers
From
To
Depart
Return
Travelers
Flying From
Find Packages In
Check In
Check Out
Rooms
Travelers
From
To