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The Best Festivals and Fairs in Chicago & Illinois

by Paul Joseph  |  Updated January 12, 2023

A huge number of festivals and fairs take place in Chicago and across Illinois throughout the year, many of which pay homage to the region’s rich and diverse cultural heritage.

Chicago Ale Fest

Revellers line up at a drinks stand at the Chicago Ale Fest (Photo: Chicago Ale Fest)

Dotted with farmland, forests, and rolling hills, the Midwestern state of Illinois is a nature lover’s paradise. But the so-called Prairie State – a nickname that dates back to a time when it was covered with prairie grasses – is also home to some of the country’s most vibrant metropolises. Among them, the city of Chicago is unquestionably the most famous, thanks in large part to the skyscrapers that dominate the landscape.If you’re planning a trip to Chicago or wider Illinois, you may want to see if your dates of travel coincide with one of the state’s fantastic festivals and fairs.

Chicago Ale Fest

The winter edition of this popular biannual beer festival takes place at the lakefront treasure of Navy Pier, set against the imposing backdrop of the Chicago skyline. Infact, a few beers in, it may well look as if some of those skyscrapers are beginning to sway, so you may want to go easy on the more than 200 American craft beers on offer here. But not too easy, of course. As well as the array of amber nectar on offer, there’s also live music and some of the city’s favourite food trucks.

Navy Pier, Chicago / January each year (winter edition)

Groundhog Days

In 1992, something ground-breaking happened in the city of Woodstock. People came to town and roped off the picturesque city square, moved all sorts of equipment into the park and started playing the Pennsylvania Polka, over and over again. They were filming a movie that has become a favourite of young and old, and the city gathers each year to celebrate the cult move classic and the special community that Woodstock has always been. A great way to shake off the gloom of Winter, the event has attracted visitors from as far away as Australia, as well as actors from the movie keen to be involved in this unique occasion.

Venues across Woodstock / February each year

University of Chicago Folk Festival

Each year, the University of Chicago Folk Festival brings together folk musicians from all over the world for a weekend jam-packed full of concerts, workshops, and dances. From bluegrass to Cajun to traditional Irish music, the event celebrates folk music in all its myriad forms. A production of the University of Chicago Folklore Society, this has been an annual University event since way back in 1961 and remains one of the most popular extra-curricular events on the instutition’s calendar.

University of Chicago, Hyde Park, Chicago / February each year

(Photo: Matt Dinerstein / Courtesy University of Chicago Folk Festival)

Outside The Box Music Festival

A staple on the Illinois cultural calendar, this acclaimed music festival in the city of Carbondale sees performers of international repute join forces with Southern Illinois’ finest musicians and composers to create a weeklong occasion of engaging, contemporary concert music. Daily seminars, discussions and presentations culminate in nightly performances in front of crowds of music lovers. Many of the festival’s concerts and events are free to attend.

Southern Illinois University, Carbondale / March each year

CarbondALE Brew Fest

Featuring small batch craft brews from all across the Midwest, including home brews from several local breweries, this festival in Downtown Carbondale is a celebration of the region’s burgeoning beer-making credentials. As well as plenty of mouth-watering beer tasting opportunities, there’s also an array of live music and food stalls. Ticket prices vary and include a certain number of samples, as well as a premium tasting glass to take home with you as a cherished souvenir.

Carbondale Town Square Pavilion, Carbondale / May each year

Stall holder at the CarbondALE Brew Fest (Photo: CarbondALE Brew Fest)

Chicago Critics Film Festival

Founded by the Chicago Film Critics Association, this prestigious festival gives movie lovers the chance to catch the year’s hottest flicks before they’re put on general release. An eclectic selection of films ranging from recent festival favourites to as-yet-undistributed works are screened during the event, spanning genres including rip-roaring comedies, foreign-made dramas, thought-provoking documentaries, and plenty more. There’s also a couple of programmes of shorts, too.

Music Box Theatre, Chicago / May each year

An audience at a movie screening during the Chicago Critics Film Festival (Photo: Chicago Critics Film Festival)

Springfield PrideFest

Free to enter for all, this family-friendly festival in Illinoi’s capital of of Springfield aims to promote and celebrate inclusivity, and kicks off with a morning Pride Parade followed by a day of fun and revelry that lasts late into the evening. There are over 50 vendors selling merchandise, art, food and drinks, plus a hugely popular kid’s and teen area. Meanwhile the Club Station House stage features live music including Fun DMC, Thornhill, and The Shenanigan’s, not to mention a drag show extravaganza (not for kids).

Phoenix Center, Downtown Springfield / May each year

Crowds gather in front of a stage at Springfield PrideFest (Photo: Springfield PrideFest)

HerrinFesta Italiana

Now in its 27th year, this volunteer-run festival forms part of the city of Herrin’s hugely popular Memorial Day weekend, attracting thousands of visitors who come to celebrate the city’s rich Italian heritage. The event is held over one day and features mouth-watering Italian food, fine arts and crafts exhibitions, and an assortment of fun-packed competitions. One of the highlights is the annual ‘Bocce’ tournaments – a traditional Italian sport in which contestants roll a ball as close as possible to a smaller target ball.

Herrin / May each year

A young girl carries a toddler on her back at HerrinFesta Italiana (Photo: HerrinFesta Italiana)

Southern Illinois Music Festival

Musicians from across the globe perform a dazzling collection of orchestral and chamber music, opera, patriotic music, and jazz at this annual festival that takes place at venues all over the state. Among the highlights over the years have been Mozart’s Magic Flute and Rossini’s Messa di Gloria, a Double Concerto for Violin and Cello by Jacob Tews, and Wind and String Octets by Beethoven and Mendelssohn. Other notable acts on the festival programme each year include a virtuoso organ recital.

Venues across Southern Illinois / May-June each year

A performance at the Southern Illinois Music Festival (Photo: Southern Illinois Music Festival)

Old Town Art Fair

Thi s fine art fair takes place in the heart of the charming Old Town Triangle Historic District in Chicago and has been voted #1 Art Fair in America.  There are 200+ nationally acclaimed artists, an estimated 30,000 art lovers, a Garden Walk, Live Music, Food Court and Children’s Corner. It ncludes Mixed Media, Drawings, Paintings, Photography, Printmaking, Ceramics, Glass, Fibre, Jewellery and works in Metal, Stone and Wood. Each year, every artist is selected by an independent jury of art professionals from the Chicago area. There are returning favorites along with many fresh things to explore — with nearly half of the exhibiting artists new to the Fair.

The Old Town Triangle Historic District on Chicago’s North Side Center of the Fair: 1763 N North Park Avenue / June each year

Crowds at the Old Town Art Fair (Photo: Old Town Art Fair)

Gebhard Woods Dulcimer and Traditional Music Festival

This outdoor festival features the mountain dulcimer and hammered dulcimer along with other traditional instruments. Talented national and regional musicians play continuously on the main stage from 10am until 6pm on both days of the festival, performing music of many genres for young and old alike. Visitors can come and enjoy the simple pleasures of a music-filled day in the park, including supervised children’s activities, festival food, friendly and knowledgeable music vendors, and hands-on opportunities for all ages.  And if you already play an instrument, you can even join in the open jams and instructional workshops. www.GebhardDulcimer.org.

Goold Park, Morris, Illinois / June each year

A live stage performance at the Gebhard Woods Dulcimer and Traditional Music Festival (Photo: Gebhard Woods Dulcimer and Traditional Music Festival)

Woodstock Pride

Created to celebrate Lesbian, Gay, Bisexual, and Transgender Pride Month, Woodstock Pride is a fun-packed multiday event featuring a parade, festival, live music, vendors, a drag show and children’s’ activities, all taking place on and around Woodstock’s historic Square. The event often attracts notable speakers too, with U.S. Rep Lauren Underwood, D-Naperville among those to appear in recent years, delivering a speech intended to further promote and celebrate the advancement in LGBT rights.

Historic Woodstock Square, Woodstock / June each year

Legacy of Giving Music Festival

Billed as the largest party of the year, the Legacy of Giving Music Festival in Springfield is not just a musical extravaganza – it’s also an event with a truly altruistic side, raising tens of thousands of dollars each year for local charities. Visitors can look forward to more than 60 musical acts across 5 stages, plus a vendor fair, arts & crafts, mouth-watering food, and a dedicated children’s area featuring inflatables, face painting, kid’s games, and more. Affiliated citywide activities include bocce ball and disc golf tournaments, as well as 5K and 10K races.

Downtown Springfield / June each year

A raucous crowd at the Legacy of Giving Music Festival (Photo: Legacy of Giving Music Festival)

57th Street Art Fair

Taking place on the streets of the city’s historic Hyde Park neighbourhood, the Midwest’s oldest juried art fair dates back over three-quarters of a century and kicks off summer in Chicago in style. A family-friendly affair, it features 200-plus artists, live music presented by Buddy Guy’s Legends, kids’ activities and a food court. The event also offers a fantastic opportunity to view and purchase works of art from around the country, spanning glass, jewellery, leather, photography, printmaking, painting, sculpture, wood, ceramics and fiber, as well as a chance to speak with artists about their work.

56th, 57th and Kimbark Streets between Kenwood and Woodlawn Avenues, Hyde Park, Chicago / June each year

isitors pass along stalls at the 57th Street Art Fair (Photo: 57th Street Art Fair)

The Edwardsville Route 66 Festival

Classic cars, live music, great food and oodles of family fun are on the agenda each year at the Edwardsville Route 66 Festival in the city of Edwardsville, which attract nearly 10,000 visitors each year. The most eagerly awaited segment of the event is the legendary Car Cruise, which sees vast numbers of beautiful classic cars lead a procession through town. Other notable features include local artists, children’s activities, arts and crafts vendors, trolley rides, and a 10k run.

City Park, Downtown Edwardsville / June each year

Classic cars at the Edwardsville Route 66 Festival (Photo: Edwardsville Route 66 Festival)

African Caribbean International Festival of Life

This annual Chicago event celebrates African and Caribbean culture in an exciting and fun-packed way that grabs all of your senses and gives them a serious shake. More than 70 reggae, world music, R&B, gospel, latin, rock, blues, jazz and other bands strut their stuff across three live stages and there are also numerous activities and product stalls for visitors to enjoy including dancing, soccer, arts and crafts, jewellery, literature, and mouth-watering Afro-Caribbean food. Notable entertainers down the years have included Capleton, Sweet Micky (former President of Haiti) and Yellowman – King of Dancehall.

Union Park, Chicago / July each year

West Fest

Since 2004, Chicago’s annual street festival has stood out thanks to its emphasis on local talent. Planned and managed by the West Town Chamber of Commerce, the event features cutting edge live music, neighborhood retailers and restaurants, fine artists, crafters, and more. There’s quite simply something for everyone here – even a Pet Fest area with pet vendors and dog activities for charity, plus a Kid Fest zone where family friendly vendors offer children’s activities and age appropriate stage show. More than anything, this festival reflects the eclectic and hip nature of the West Town community.

Chicago Avenue between Damen and Wood, Chicago / July each year

Crowds gathered at West Fest (Photo: Vital Kopy)

Southport Art & Music Fest

Hosted by the Southport Neighbor’s Association, this Chicago festival benefits important local causes by showcasing the work of more than 75 local artists, photographers and abstract painters whose work spans a variety of mediums, including oil, acrylic, watercolour, jewellery, sculpture, glass and mixed media. In addition to supporting the arts and viewing incredible artwork that’s available for purchase, guests also have the chance to meet and engage with the artists themselves through live art demonstrations.

The Southport Corridor, Chicago / July each year

An artist paints a portrait during the Southport Art & Music Fest (Photo: Amdur Productions)




Established more than two decades ago, this world-renowned yearly music festival is one of the biggest in America, drawing more than 150,000 revellers to the vast green expanse of historic Grant Park. Among the prestigious musical names to have performed in previous years have been the likes of Kanye West, The Smashing Pumpkins, Red Hot Chili Peppers, Arctic Monkeys and Radiohead. The event is also known for attracting groups who use the festival to convey political messages to the assembled masses.

Grant Park, Chicago / August each year

Chicago Jazz Festival

Now in its 40th year, Chicago’s annual Jazz Festival has grown into something of a Labor Day tradition over the past four decades – and for good reason. The action-packed, lakeside event in the city’s beautiful Millennium Park showcases free live performances by some of the best and most talented names from the world of Jazz, including several jazz legends and lesser known contemporary voices too. As well as the outdoor sets, some performances also take place inside the nearby Chicago Cultural Center.

Millennium Park, Grant Park, Chicago / August-September each year

Alton Jazz and Wine Festival

Taking place in the city of Alton on the banks of the Mississippi River, the Alton Jazz and Wine Festival combines two universally popular categories of entertainment for one day only. Thousands descend on the show to hear groovy beats and sample wine, all set against the backdrop of the river. Distinguished figures from the Jazz world such as Ptah Williams Quartet, Funky Butt Brass Band, and Keyon Harrold provide the sounds, leaving festival-goers with the enviable task of relaxing, tapping their feet to to the beats and soaking up the atmosphere – and of course the wine.

Liberty Bank Alton Amphitheater, Alton / September each year

Sycamore Pumpkin Festival

What began as a simple idea to encourage creativity among local students in the city of Sycamore has blossomed into a neighbourhood-wide event. Over 1,000 entries vie for the prize of best pumpkin, while visitors are also treated to two carnivals, two large indoor craft shows, historic home tours and a wide number of vendors helping to raise money for local causes by selling their creative wares. A 10k Pumpkin Run and a fun-packed Sunday parade round off proceedings.

Downtown Sycamore / October each year

Creatively decorated pumpkins at the Sycamore Pumpkin Festival (A Syn via Flickr / CC BY-SA 2.0)

Magnificent Mile Lights Festival

Mickey and Minnie Mouse are the grand marshals of this fun-filled festival parade, featuring more than 40 floats, helium-filled balloons, marching bands and performers on a route that extends along the upscale section of Chicago’s Michigan Avenue. But the highlight of the event is the more than one-million lights that are turned on, creating a magical visual spectacle. Adding to the optics is a spectacular fireworks display to bring the festival to a grand conclusion.

Michigan Avenue between Wacker Drive and Oak Street, Chicago / November each year

Dazzling illuminations at the Magnificent Mile Lights Festival (Photo: Rachel Kramer via Flickr / CC BY 2.0)

Midwest Museum of Natural History’s Festival of Trees

Throughout December, the Midwest Museum of Natural History in the city of Sycamore becomes the stage for an eye-catching display of Christmas trees to mark the holiday season. Dotted throughout the museum’s main galleries, the trees in question are sponsored by local organisations, businesses and non-profits who lend it their own personal touch with decorations. Members of the public are invited to vote for their favourite by making a donation in jars placed in the lobby.

Midwest Museum of Natural History, Sycamore / December each year