The Best festivals and fairs in Chicago & Illinois

by Paul Joseph  |  Published April 8, 2018

Dotted with farmland, forests, rolling hills and wetlands, 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 on the shores of Lake Michigan is unquestionably the most famous, thanks in large part to the skyscrapers that dominate the landscape. ca

A view of Chicago’s Clark Street Bridge over the river (Photo: Peter Miller via Flickr)

A huge number of festivals and fairs take place in Chicago, and indeed across Illinois, throughout the year, many of which pay homage to the region’s rich and diverse cultural heritage. If you’re planning a trip over the remainder of 2018, you may want to see if your dates of travel coincide with one of these memorable events. To help you, we’ve selected some of the best Chicago and Illinois festivals and fairs of 2018. And if you’re looking for events in 2019 instead, be sure to check on the festival websites towards the end of this year, when official dates will start being confirmed.

Chicago Ale Fest

The summer edition of this biannual beer festival takes place in historic Grant Park, 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, there’s also live music and some of the city’s favourite food trucks.

LOCATION Grant Park, Chicago DATES 20 January

Chicago Ale Fest

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

University of Chicago Folk Festival

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

LOCATION University of Chicago, Hyde Park DATES 9-10 February

Frost Fest University of Chicago Folk Festival

Dancers at the University of Chicago Folk Festival (Photo: University of Chicago Folk Festival)

Frost Fest Craft Beer Festival

The fourth annual Frost Fest craft beer festival returns to Chicago’s Boystown, promising yet another winter celebration of craft beer, spirits, and cider, including local brewers and premium vendors sampling their finest seasonal and specialty creations. There’s also live DJ’s, a rainbow light show, ice sculpture carving, sponsor giveaways and more, leave festival-goers feeling positively warm and fuzzy during one of the coldest months of the year in the Windy City.

LOCATION Halsted & Brompton Avenue, Boystown, Chicago DATES 24-25 February

Good Food Festival

The Midwest’s premier annual celebration of the fast-growing Good Food movement brings together regional and national leaders in local, sustainable food — from farmers to chefs, entrepreneurs to policy makers — to discuss the movement that’s transforming the way people eat. The three-day symposium features speakers, panel discussions, cooking demos, DIY workshops, tastings from local food artisan, an interactive kids’ corner, and more.

LOCATION UIC Forum, University of Illinois, Chicago DATES 23-24 March

Frost Fest Craft Beer Festival

A butchering demo at the Good Food Festival (Photo: Megg via Flickr)

Chicago Flamenco Festival

Witness jaw-dropping performances by an array of international stars at this popular annual festival. Held over five full weeks, the programme includes both traditional and contemporary Flamenco music and dance, with a line-up of more than nine flamenco groups spanning the world of music and dance. Among them are some of the art form’s brightest rising stars as well as established and critically acclaimed artists too.

LOCATION Instituto Cervantes Chicago DATES 23 March-21 April

Outside The Box Music Festival

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

LOCATION Southern Illinois University, Carbondale DATES 4-8 April

CarbondALE Brew Fest

Featuring small batch craft brews from all over the Midwest, including home brews from several local breweries, this festival in Downtown Carbondale is a celebration of Illinois’ burgeoning beer-making credentials. As well as plenty of mouth-watering beer tasting opportunities, there’ll also be 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.

LOCATION Carbondale Town Square Pavilion, Carbondale DATES 4 May

CarbondALE Brew Fest

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

Chicago Critics Film Festival

Founded by the Chicago Film Critics Association, this 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 and thought-provoking documentaries. There’s also a couple of programmes of shorts too.

LOCATION Music Box Theatre, Chicago DATES 4 – 10 May MORE INFO

Chicago Critics Film Festival

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

Peoria Wingfest

The perfect combination of food, music, drinks and fun happens on Peoria’s beautiful Riverfront on the first Sunday of May. Enjoy wings from the area’s best restaurants, live entertainment from local bands and a large selection of unique craft beers. And then the real fun starts as crowd voting helps award bragging rights to the best of the best. This rain-or-shine, family- friendly event sells out every year and kicks off a full season of Riverfront activities in Peoria.

LOCATION Festival Park at The Peoria RiverFront, Peoria DATES 6 May

Peoria Wingfest

Festival-goers enjoy the sunshine at Peoria Wingfest (Photo: Peoria Wingfest)

Springfield PrideFest

Free to enter, this family-friendly festival kicks off with a morning Pride Parade followed by a day of fun and celebration that lats late into the evening. There’ll be over 50 vendors selling merchandise, art, food and drinks, plus a hugely popular kid’s and teen area. The Club Station House stage features live music including Fun DMC, Thornhill, and The Shenanigan’s, not to mention a drag show extravaganza.

LOCATION Phoenix Center, Downtown Springfield DATES 19 May

Springfield PrideFest

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 Herrin’s hugely popular Memorial Day weekend, attracting thousands of visitors who come to celebrate the city’s rich Italian heritage. The family-friendly event is held over one day and features mouth-watering Italian food, fine arts and crafts exhibitions, and an array of fun-packed competitions. One of the highlights of the day will once again be the annual ‘Bocce’ tournaments – a traditional Italian sport that combines the precision of horseshoes with a bowling-style play.

LOCATION 1 North Park Avenue, Herrin, Illinois DATES 24 May

HerrinFesta Italiana

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

Southern Illinois Music Festival

More than 30 performances by members of the New Chicago Chamber Orchestra along with musicians from across the globe perform orchestral and chamber music, opera, patriotic music, and jazz at this annual festival. For 2018, the event will be titled ‘Twos By Tews’ and will feature music in pairs. Among the highlights will be 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 include a virtuoso organ recital.

LOCATION Venues across Southern Illinois DATES 25 May – 10 June

Southern Illinois Music Festival

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

Legacy of Giving Music Festival

Billed as the largest party of the year, the Legacy of Giving Music Festival 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.

LOCATION Downtown Springfield, Illinois DATES 1 – 2 June

Legacy of Giving Music Festival

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

Chicago Southland Dragon Boat Festival

Celebrating the camaraderie and competitive spirit produced by the high-octane sport of Dragon Boat racing, this festival brings together friends, neighbours and total strangers who go head to head in their efforts to achieve the ultimate accolade: the title of Dragon Boat Festival Champions. Hosted by the Blue Island Park District, the event features practice runs and competitive races, plus live music, food and craft beer stalls, an awards ceremony, and a famously raucous after party. Both teams and individual can compete in the racing.

LOCATION Chatham St. & Fulton St., Blue Island DATES 2 June

Chicago Southland Dragon Boat Festival

A festival goer plays air guitar with an oar at the Chicago Southland Dragon Boat Festival (Photo: Chicago Southland Dragon Boat Festival)

57th Street Art Fair

Taking place on the streets of the historic Hyde Park neighborhood, the Midwest’s oldest juried art fair features 200-plus artists, live music presented by Buddy Guy’s Legends, kids’ activities and a food court. The event offers a fantastic opportunity to view and purchase works of art from around the country, as well as a chance to speak with artists about their work, enjoy top quality live music and plenty more.

LOCATION 56th, 57th and Kimbark Streets between Kenwood and Woodlawn Avenues, Hyde Park, Chicago DATES 2-3 June

57th Street Art Fair

Visitors 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 once again on the agenda at the 2018 edition of the Edwardsville Route 66 Festival, 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.

LOCATION City Park, Downtown Edwardsville DATES 8-9 June

The Edwardsville Route 66 Festival

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

African Caribbean International Festival of Life

Designed to promote cultural awareness, this annual 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’s also an array of activities and products for visitors to enjoy including dancing, soccer, arts and crafts, jewellery, literature, and mouth-watering Afro-Caribbean food. Confirmed entertainers for 2018 include Capleton, Sweet Micky (former President of Haiti) and Yellowman – King of Dancehall.

LOCATION Union Park, Chicago DATES 6-8 July

Festival of Life

A stage performance at the African Caribbean International Festival of Life (Photo: Martin International)

West Fest

Since 2004, Chicago’s annual street festival of West Fest has stood out thanks to its emphasis on local offerings and 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 family-themed stage show. More than anything, this festival reflects the eclectic and hip West Town community.

LOCATION Chicago Avenue between Damen and Wood DATES 6-8 July

West Fest

Crowds gathered at West Fest (Photo: Vital Kopy)

Southport Art & Music Fest

Hosted by the Southport Neighbor’s Association, this 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.

LOCATION The Southport Corridor, Chicago DATES 14-15 July

Southport Art & Music Fest

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


Established more than 20 years ago, this yearly music festival is one of the biggest in America, drawing more than 150,000 revellers to historic Grant Park. Among the notable names to have appeared in previous years are Kanye West, The Smashing Pumpkins, Red Hot Chili Peppers, Arctic Monkeys and Radiohead. The event also attracts groups who use the festival to convey political messages to the assembled masses.

LOCATION Grant Park, Chicago DATES 2-5 August

Chicago Jazz Festival

Now in its 40th year, Chicago’s annual Jazz Festival has grown into something of Labor Day tradition over the past four decades – and for good reason. The action-packed, lakeside event in Chicago’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.

LOCATION Grant Park, Chicago DATES 30 August-2 September

Alton Jazz and Wine Festival

Taking place on the banks of the Mississippi River, the Alton Jazz and Wine Festival combines two universally popular categories of entertainment for one day. Thousands descend on the show to hear groovy beats and sip fresh drinks, all set against the backdrop of the Mississippi. 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.

LOCATION Liberty Bank Alton Amphitheater, Alton DATES 8 September

Alton Jazz and Wine Festival

A performer plays a trumpet at the Alton Jazz and Wine Festival (Photo: Alton Jazz and Wine Festival)

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 100 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.

LOCATION Downtown Sycamore DATES 24-28 October

Sycamore Pumpkin Festival

Creatively decorated pumpkins at the Sycamore Pumpkin Festival (Photo: EarlRShumaker via Flickr)

Magnificent Mile Lights Festival

Mickey and Minnie Mouse are the grand marshals of this annual 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 1 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.

LOCATION Michigan Avenue between Wacker Drive and Oak Street, Chicago DATES 16-17 November

Magnificent Mile Lights Festival

Festival-goers gathered at the Magnificent Mile Lights Festival (Photo: Ceyhun (Jay) Isik via Flickr)

Midwest Museum of Natural History’s Festival of Trees

Throughout December, the Midwest Museum of Natural History 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.

LOCATION Midwest Museum of Natural History, Sycamore DATES 1-31 December