December 2017
Chicago Architecture Biennial
The largest international survey of contemporary architecture in North America, the Chicago Architecture Biennial draws more than half-a-million visitors who come to admire the cutting-edge ideas of 120 architects and firms from more than 30 countries.
Winter WonderFest
This annual indoor winter carnival features a whole host of family-friendly, fun-packed activities including a toboggan tunnel, ice-skating rink, winter mini golf, 15-foot “snow tubing” hill and various carnival rides.
Caroling at Cloud Gate
Large numbers of singers from choral groups across Chicago take part in this annual holiday tradition. After the singing of classic carols, visitors don their skates and hit the ice at the Millennium Park McCormick Tribune Ice Rink.
Music Box Christmas Show
Celebrate the festive cheer by catching some classic Xmas movies at the Music Box Christmas Show. Don’t miss the singing of Christmas carols with your fellow patrons during the intermission.
Renegade Craft Fair
Arts and crafts lovers can pick up an eclectic mix of handmade trinkets at this mega annual fair. It’s the perfect place to find Christmas gifts and maybe a little something for your mantelpiece at home as well.
January 2017
The Chicago Sketch Comedy Festival
Said to be the largest sketch comedy festival in the country, this mirth-filled event presents a packed line-up of hilarious performers that will make you forget about those icy temperatures outside.
Cubs Convention
Dedicated fans off the Chicago Cubs baseball team can interact with players, coaches and alumni, while attending Q&A sessions and checking out interactive exhibits at this annual Convention.
Donut Fest
Fans of the humble, but oh-so-tasty donut will want to head to Chicago’s famous Chop Shop multi-purpose venue for a day of celebrating everyone’s favourite circular, sugar-coated pastry. Be sure to bring your appetite.
Handmade Market Chicago
Held across five months, this much-loved market makes for a great, atmospheric New Year activity, featuring more than 30 venders selling their homemade wares in a celebration of the local and the artisanal.
Chicago Ale Fest
Fans of craft beer can sample up to 150 variations at this fun-filled Ale Fest that takes place at Navy Pier’s Grand Ballroom. There’s also food trucks and DJ music among the entertainment.
February 2018
BeadQuest
At this annual Mardi Gras pub crawl participants bounce between over 20 bars, partaking in a number of drink and food specials while collecting beads and posing for snaps along the way.
Chicago Restaurant Week
Chicago’s finest restaurants, delicatessens and cafes offer special deals and even more special dishes during this vibrant restaurant festival that celebrates the very best the city’s culinary scene has to offer.
Folk Music Festival
Music lovers come to celebrate traditional music from around the world with a wide programme of concerts and workshops staged at the prestigious venue of Mandel Hall, which forms part of the University of Chicago.
Cider Summit Chicago
Revellers can sample up to 150 artisanal ciders from throughout the world at this bustling cider summit held at Naval Pier. Fear not, there’s also plenty of food samples to line the stomach.
March 2018
St. Patrick’s Day
Chicago’s huge Irish-American population come out to celebrate the anniversary of Saint Patrick, the foremost patron saint of Ireland. Look out for bagpipers, Irish dancers and even the Chicago river being turned green.
One Earth Film Festival
The preservation of the planet is the noble focus of this well attended film festival which screens an array of movies exploring eco-themes such as climate change, sustainability and environmental activism.
Chicago Flower & Garden Show
Green-fingered types flock to this vast show each year, featuring 24 gardens, 90 vendors, cooking demonstrations, seminars, a kids’ activity garden, and plenty more.
Whisky Festival
Master distillers from Chicago and across the US gather at the luxurious Hyatt Regency hotel. Visitors can sample up to 300 whiskeys as well as learn about the craft behind this enduringly popular fine spirit.
Chicago Tattoo Arts Convention
Fans of body ink can head to the Chicago Tattoo Arts Convention, featuring live tattooing, sideshows, and a whole range of other activities and events themed around the decorative art of tattoos.
May 2018
Chicago Critics Film Festival
Now in its sixth year, this annual film fest offers the public a chance to view some of the hottest unreleased films. Check out this year’s most eagerly awaited flicks before anyone else.
Chicago Beer Classic
Enjoy the finest beer the city has to offer while sampling brews from more than 80 participating breweries. Festival-goes receive 48 two-ounce samples, as well as access to exclusive beers, activities and interactive beer-making workshops.
Kids and Kites Festival
Celebrate the arrival of spring at this free, outdoor family-friendly festival where kids can fly a kite or watch expert demonstrations. Free paper kites are provided, but families can also purchase more intricate contractions on-site.
Chicago Zine Fest
Makers of DIY publications gather for two days of sharing knowledge, stories and enthusiasm for handmade art. There are panels and talks, while participants can also show off their wares in a giant marketplace.
Mayfest
This German-inspired neighbourhood tradition kicks off the street festival season, featuring food and music under a giant tent. Get in the spirit by munching on pretzels, grabbing a brew from the outdoor beer garden and taking in the live music.
Food Truck Social at Lincoln Park Zoo
Tuck into tacos, grilled cheese, doughnuts, pierogis and plenty more at this annual foodie gathering. Guests can enjoy access to dozens of Chicago’s best food trucks as well as live DJs and admission to the zoo.
Lincoln Park Wine Fest
Sample more than 100 wines from across the globe while listening to classical music at one of Chicago’s newest festivals, now in its second year after a successful inaugural event.
June 2018
Chicago Gospel Music Festival
The city’s annual celebration of gospel music welcomes a diverse line-up of national touring acts and up-and-coming local talent for two days of uplifting songs and hymns.
57th Street Art Fair
This juried craft fair features paintings, sculptures, jewellery and ceramics from more than 200 artists. There are pop-up artist talks as well as an artist-at-work area, where attendees can observe the process of creation.
CAKE: Chicago Alternative Comics Expo
Each year this hugely popular convention brings together creators and fans of independent comics and small press publications for two action-packed days of panels, workshops and shopping.
Spring Awakening Music Festival
Chicago’s largest EDM festival returns armed with some of the world’s best DJs and electronic acts for three days of bass drops, pyrotechnics and high-tech light shows.
Chicago Blues Festival
The largest free blues festival in the world brings together a heady mix of living legends and local 12-bar players. As well as the headlining sets, local acts perform on side stages.
Ribfest Chicago
Dig into more than 50,000 pounds of ribs and BBQ at this annual celebration of saucy pork. Among the highlights, amateur and professionals alike compete for a coveted rib-eating prize.
Chicago Tribune Printers Row Lit Fest
Publishers, booksellers, literacy and cultural organisations advocate books and related merchandise across a variety of literary genres, while authors participate in panels and discussion.
Country LakeShake Festival
One of the region’s biggest country music events, this festival draws revellers from far and wide. Headliners for 2018 include The Voice judge Blake Shelton and singer-songwriter Dierks Bentley.
July 2018
African Caribbean International Festival of Life
Designed to promote cultural awareness, this festival offers a weekend full of reggae, dancing, soccer, art and mouth-watering Afro-Caribbean food.
West Fest
This annual street festival focuses on local offerings and local talent, featuring neighbourhood retailers and restaurants, fine artists and crafters, plus live cutting-edge music.
Taste of Chicago
This granddaddy of food festivals gives visitors the chance to sample some of the city’s best culinary offerings. You can also listen to live music as you tuck into your treats.
Windy City Smokeout
Grilled meats and country music are the order of the day at this annual festival. Attendees can sample smokey culinary creations from local barbecue restaurants while tapping their feet to the tunes.
Roscoe Village Burger Fest
If you love succulent, beef patties then loosen your belt and head to Roscoe Village, where you can taste grilled creations from local restaurants while enjoying live music.
Southport Art Festival
This two-day festival, brings together a variety of artists and local vendors. Guests can peruse pieces, shop at Southport Avenue stores or get up early on the Sunday to enjoy the annual Gospel Brunch.
Pitchfork Music Festival
This laid-back weekend of musical discovery showcases rising bands, underground legends and mainstream performers with strong independent roots, This year’s line-up includes Aussie psych-rockers Tame Impala and rapper/singer DRAM.