Chicago Festival Guide
[ Special Events & Festivals ]

Chicago Festival Guide: What’s Happening in the Windy City

The wonderful thing about traveling to a big city such as Chicago is the abundance of events and festivals happening throughout the year. When planning your trip to the Windy City, use our Chicago Festival Guide to find out which popular festivals are scheduled during your vacation.

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Rely on our Chicago Festival Guide to help plan your trip.
Image via The Chicago Sketch Comedy Festival / Facebook


If you’re planning to visit Chicago during January, bring layers! Although, these hot festivals will warm you up:

Chicago Sketch Comedy Festival
January 10-20, 2019
As the largest sketch comedy festival in the world, 35 comedy groups gather in Chicago annually.

Chicago Restaurant Week
January 25 – February 7, 2019
A foodie’s dream come true, Chicago Restaurant Week showcases top restaurants throughout the city.

Chicago Ale Fest
February 2, 2019
Set at the iconic Navy Pier, the Chicago Ale Fest features more than 150 craft beers, popular city food trucks, and a DJ.

The Chicago Auto Show should not be missed. Check out more events in the Chicago Festival Guide.
Image via The Chicago Auto Show / Facebook


Visiting Chicago during the frigid month of February? Grab your coat and our Chicago Festival Guide, before you head out to these events.

Chicago Auto Show
February 9-18, 2019
Operating since 1901, the Chicago Auto Show is the biggest auto show in all of North America.

Cupid’s Undie Run
February 16, 2019
Don’t be surprised if you see citizens running around Chicago in their underwear in February. Cupid’s Undie Run is an annual fundraiser and race for The Children’s Tumor Foundation and neurofibromatosis research.

Chicago Chinese New Year Celebration
February 4-17, 2019
Celebrate the Chinese New Year in one of the largest Chinatowns in the nation.

Use the Chicago Festival Guide to organize your St. Patrick's Day fun.
Celebrate St. Patrick’s Day in Chicago at one of the many parades and festivals.


From holidays to the arts, there’s always something happening in Chicago during the month of March.

Celebrating St. Patrick’s Day in Chicago
If you know the Windy City, you know that St. Patrick’s Day is a big deal. Don’t miss these exciting events and remember, wear green!

Chicago Flower & Garden Show
March 20-24, 2019
Tracing all the way back to 1847, this renowned show is held annually at Navy Pier and draws in over 40,000 gardening enthusiasts.

Macy’s Flower Show and Carnival
March 24 – April 7, 2019
If the flower and garden show at Navy Pier wasn’t enough for you, continue the green fun at Macy’s annual festival.

International Quilt Festival
March 28-30, 2019
This 3-day event includes hundreds of vendors, hands-on learning classes, and a chance to speak with artisans from around the country.

WhiskyFest Chicago
March 29, 2019
Do you take your whisky neat or on the rocks? Either way, you’ll sample more than 300 whiskeys from across the globe at this boozy festival.

You bet the Holi Festival is in our Chicago Festival Guide!
Have you ever participated in the Holi Festival?


Welcome the spring season with these intriguing Chicago festivals:

Baconfest Chicago
April 5-6, 2019
With ‘bacon’ in the title, need I say more? Chicago chefs gather each year to create works of culinary art using the world’s best ingredient: bacon.

Holi – Festival of Colors
April 6, 2019
The celebration of Holi welcomes the arrival of spring and culture through vibrant colors, captivating performances, and delicious food for a life-changing experience.

Tinley Park Brew & Vine
April 13, 2019
Come enjoy the only indoor beer, wine, and food festival of its kind in the Chicagoland area. Featuring more than 200 vendors and beverages, this is the perfect way to spend an afternoon in Chicago.

Heroes & Villains FanFest
April 19-21, 2019
Hosted at the Donald E. Stephens Convention Center, fans of superheroes and super villains alike come together for this festival of epic proportions.

Walker Stalker Con Chicago
April 19-21, 2019
In combination with the Heroes & Villains festival, Walker Stalker celebrates the award-winning television series, The Walking Dead, with actor meet and greets, exhibits, and more.

Bach Week Festival
April 26 – May 3, 2019
Is classical music your thing? If so, take advantage of the myriad of concerts happening for Bach Week in Chicago.

Chicago Rum Festival
April 27, 2019
When Captain Jack Sparrow keeps asking “Where has all the rum gone?”, the answer is to Chicago! This festival includes tastings, educational opportunities, and entertainment.

Looking for wine festivals? Check the Chicago Festival Guide for your answer.
Image via Lincoln Park Wine Festival / Facebook


As the summer season approaches, Chicago ramps up its festival lineup. Keep our Chicago Festival Guide handy as you venture into the city for these summertime festivals.

20th Chicago Kids and Kites Festival
May 4, 2019
An ongoing tradition on Cricket Hill in Lincoln Park, this festival is perfect for families looking for fun in the Windy City. You don’t want to miss the main event: the Big Kite Candy Drop.

Chicago Beer Classic
May 4, 2019
If you love Chicago and beer, head over to Soldier Field for brewing experts, world-class brews, games, and activities.

The Chicago Nerd Comedy Festival
May 8-11, 2019
Looking for hilarious comedy this May? The Chicago Nerd Comedy Festival might just be for you!

May 17-19, 2019
Mayfest serves as the kick-off to “festival season” in Chicago. For more than 20 years, Mayfest has celebrated Chicago’s festivals with exceptional local food, entertainment, music, and vendors.

Lincoln Park Wine Festival
May 17-19, 2019
At the Lincoln Park Wine Festival, guests enjoy fine art, wine from across the nation, and speak with wine connoisseurs.

Mole de Mayo
May 24-26, 2019
Want to know who makes the best mole in all of Chicago? You’ll have to visit the Mole de Mayo festival at Ashland and 18th Street to find out.

Chicago Gaelic Park Irish Fest
May 24-26, 2019
Featuring riveting Irish music, delicious food, and ongoing entertainment, this cultural festival in Chicago should not be missed.

Chicago Gospel Music Festival
May 31-June 1, 2019
Each year, the Chicago Gospel Music Festival lights up Millennium Park with world-class choirs, performers, and artists.

Plan out your concert festivals with our Chicago Festival Guide.
Music in Millennium Park by Connie Ma / flickr


June marks the beginning of the summer festival season. You do not want to miss Chicago’s top summer events.

Millennium Park Summer Music Series
June through August each year.
Throughout the summer, Millennium Park hosts a free music festival on Monday and Thursday nights. Bring a blanket, a picnic, and enjoy the show!

Grant Park Music Festival
June through August each year.
The Grant Park Music Festival is a free weekly concert series featuring renowned classical musicians, performers, and orchestras.

57th Street Art Fair
June 1-2, 2019
This two-day celebration of the arts features more than 200 exhibitors, from paintings to sculptures.

Millennium Park Summer Film Series
June 4-August 20, 2019
Watch your favorite films and new movies all summer long under the stars every Tuesday night during the summer at Millennium Park.

ago Blues Festival
June 7-9, 2019
If there’s one thing you learn from this Chicago Festival Guide, it’s that Millennium Park is the place to be for amazing concerts in Chicago. With performances by top blues artists, this annual festival is not to be missed.

Ribfest Chicago
June 14-16, 2019
Consistently ranked as “Best Food Festival” in Reader’s Choice, Ribfest features delectable ribs, a great band lineup, and activities for all.

Craft Brews at the Zoo
June 14-15, 2019
Discover zoo animals, local and regional beers, and fantastic entertainment at the Lincoln Park Zoo this summer.

June 26 – August 24, 2019
Dust off your dancing shoes and head to Grant Park for SummerDance. Listen to live music, enjoy dance lessons, and boogie the night away each week.

Taste of Chicago should not be missed!
Image via Taste of Chicago / Facebook


Clearly, Chicago is the place to be each summer. Much like the month of June, July boasts a wide range of exciting festivals to choose from.

African/Caribbean International Festival of Life
July 4-7, 2019
Hosted at Union Park, this festival celebrates the unity of nations and cultures through music.

West Fest
July 5-7, 2019
Located in the West Town Community, this festival puts a distinct emphasis on local vendors, entertainment, and food.

Taste of Chicago
July 10-14, 2019
Hosted at Grant Park each summer since 1980, this premier food festival showcases the best of Chicago’s culinary scene.

Southport Art Fest
July 13-14, 2019
Located a few steps from Wrigley Field, this street festival showcases all styles and forms of fine art.

Dearborn Garden Walk
July 21, 2019
Get a glimpse of Chicago’s natural beauty during the annual Dearborn Garden Walk.

Chicago Margarita Fest
July 27-28, 2019
This festival is exactly what it sounds like. On top of the refreshing margaritas, food trucks and games are onsite.

Fiesta del Sol
July 25-28, 2019
As the largest Latino festival in the Midwest, Fiesta del Sol includes a 5k race, food vendors, a jam-packed music lineup, and activities for the whole family.

Wicker Park Fest
July 26-28, 2019
Focusing on the neighborhood’s rich heritage, Wicker Park Fest has been called “Chicago’s Best Street Festival of the Summer” by Chicago Tribune.

Interested in the Chicago Air and Water Show? Check out the Chicago Festival Guide for details.
Image via Chicago Air and Water Show / Facebook


When scrolling through our Chicago Festival Guide, you’ll notice that the summer months are packed with festivals and August is no exception!

August 1-4, 2019
As Grant Park’s iconic music festival, Lollapalooza features top artists such as Radiohead, Future, and the Red Hot Chili Peppers each year.

Chicago Hot Dog Fest
August 9-11, 2019
Depending on where you’re from, there’s a right way and a wrong way to eat a hot dog. Discover the Chicago way at this festival benefiting the Chicago History Museum.

Ginza Festival Chicago
August 9-11, 2019
Learn more about the Japanese culture and heritage at the Ginza Festival featuring cultural performances, exhibits, shopping, and Japanese cuisine.

Edison Park Fest
August 16-18, 2019
What was once a small sidewalk sale has transformed into a 3-day event with music, food, and vendors to benefit the neighborhood.

Glenwood Avenue Arts Fest (GAAF)
August 16-18, 2019
Celebrated in Rogers Park, this weekend-long, free festival celebrates music, art, theater, cuisine, and more with over 120 vendors and live entertainment.

Chicago Air & Water Show
August 17-19, 2019
This free air and water show is the largest of its kind in the nation.

Chicago Jazz Festival
August 23 – September 1, 2019
In search of more world-class music? Head back to Millennium Park for a top-notch, weekend-long jazz festival in Chicago.

Great American Lobster Fest
August 30 – September 1, 2018
An entire festival dedicated to lobster and seafood? I’m in. Visit Navy Pier during Labor Day Weekend for this tasty festival.

North Coast Music Festival
August 30-31, 2019
From hip hop to indie rock, this concert festival boasts a wide variety of musical genres for visitors to enjoy.

You can't pass up the opportunity to devour lobster in Chicago! The Chicago Festival Guide will tell you when and where you can.
Image via Great American Lobster Fest / Facebook


While September signifies the end of summer, that doesn’t mean the festival season slows down in Chicago. Check the Chicago Festival Guide for top events before you visit the city in September.

August 31-September 2, 2019
With a carnival, arts and crafts show, endless entertainment, a parade, and fireworks, there’s never-ending fun available at the Schaumburg Septemberfest each year.

Chicago German-American Oktoberfest
September 6-8, 2019
Celebrate Oktoberfest with authentic German traditions, food, music, and more on Lincoln Avenue.

Renegade Craft Fair
September 7-8, 2019
Boasting more than 250 artists and makers, this craft fair is packed with beautiful works of art.

World Music Festival
September 13-29, 2019
This month long and city-wide festival celebrates the music of our world. With multiple events at various venues around Chicago, you’re bound to find time to experience this noteworthy festival.

Lakeview East Festival of the Arts
September 14-15, 2019
Showcases more than 150 juried artists along with performances, demonstrations, family activities, and much more.

Chicago Bourbon & BBQ Festival
September 14-15, 2019
Bourbon. BBQ. Music. What more could you ask for from a Chicago festival?

Fulton Market Oktoberfest
September 14-16, 2019
Couldn’t attend the Chicago German-American Oktoberfest event? Be sure to go to the Fulton Market Oktoberfest for traditional German cuisine, fun, and more.

EXPO Chicago
September 19-22, 2019
Marvel at contemporary and modern art at Navy Pier during this fall art festival.

Hyde Park Jazz Festival
September 28-29, 2019
Come listen to renowned and local jazz musicians across 12 venues in the Hyde Park neighborhood.

Use the Chicago Festival Guide to plan your vacation.
Chicago Botanic Garden / Facebook


The year may be winding down, but the Chicago Festival Guide isn’t. Spend the fall season visiting these Chicago festivals.

West Town Food Truck Social
2019 Dates TBD
Get your fill of Chicago’s finest food truck cuisine at this one-of-a-kind festival. The Food Truck social also runs in conjunction with the West Town Art Walk.

Apple Fest
October 5-6, 2019
Apple-themed everything is offered at Chicago’s Apple Fest. From pie and candied apples to arts and crafts and entertainment, this fall festival is dedicated to celebrating the apple.

Boo! at the Zoo
October 12 – 27, 2019
This not-so-scary, family-friendly Halloween event at the Brookfield Zoo is the place to be this October. With ample fun for the little ones, they’ll never want to leave!

Chicago International Film Festival
October 16-27, 2019
Are you a movie buff? If so, head to the Chicago International Film Festival. This iconic film festival has been an annual event in Chicago since 1965 and has featured top names in the industry.

Night of 1,000 Jack-o’-Lanterns
October 16-27, 2019 (Select Nights)
The Chicago Botanic Garden gets in the Halloween spirit with 1,000+ hand-carved, glowing Jack-o’-Lanterns placed throughout the gardens. This is a ticketed event.

CoffeeCon Chicago
October 27-28, 2019
Calling all coffee experts, fans, and addicts, CoffeeCon returns to Chicago for the 2019 season. Take classes, visit exhibitors, and mingle with the industries top professionals and brands.

Image via Christkindlmarket / Facebook
Image via Christkindlmarket / Facebook


Finish out the fall season with these entertaining festivals throughout Chicago:

JASC Holiday Delight
November 9, 2019
This Japanese festival includes traditional holiday celebrations, visits from Santa, taiko drumming, and more for all ages.

Christkindlmarket Chicago
November 15-24, 2019
This festival brings the German tradition of Christkindlesmarkt to Chicago with endless vendors, food and beverage packages, and more.

Magnificent Mile Lights Festival
November 22-23, 2019
Watch Magnificent Mile light up with holiday decorations and activities including a parade, tree lighting, and performances.

ZooLights at Lincoln Park Zoo
November 29, 2019, – January 5, 2020
This winter festival features family-friendly activities, twinkling lights, light shows, interactive exhibits, and of course, the Lincoln Park Zoo animals.

Image via Navy Pier / Facebook
Image via Navy Pier / Facebook


As the year comes to an end, so does our Chicago Festival Guide. Finish up the year with these awesome festivals.

Winter WonderFest at Navy Pier
November 29-December 24, 2019
From ice skating to family-friendly activities, it’s impossible to be a Scrooge at this winter wonderland festival.

One of a Kind Show and Sale
December 5-8, 2019
As Chicago’s premier shopping event, this festival features 600+ makers, artists, and vendors.

Caroling at Cloud Gate
December 6, 13, 20, 2019
Participate in one of Chicago’s top holiday traditions by going caroling at Cloud Gate in Millennium Park.

Randolph Street Holiday Market
December 14-15, 2019
Last but certainly not least on the Chicago Festival Guide is the Randolph Street Holiday Market. Pick up the perfect holiday gift for friends and family at this annual holiday market.

Chicago Festival Guide: The Top Events in the Windy City

Now that you know about the top festivals in Chicago, it’s time to start planning your trip. Remember to check Tripster for affordable hotels, exclusive ticket savings, and travel advice!