Chicago Festivals 2020, 2021

The Shops at Roosevelt Collection Pumpkins on the Plaza 2020

The Shops at Roosevelt Collection Pumpkins on the Plaza

October, 2020

The Shops at Roosevelt Collection, 150 W Roosevelt Rd Chicago, IL, Chicago, Illinois

Parade 2020

Parade

October, 2020

Theatre Wit, Chicago, Illinois

The Whisky Extravaganza 2020

The Whisky Extravaganza

October, 2020

Union League Club, 65 W Jackson Blvd Chicago, IL, Chicago, Illinois

Freaky Deaky Halloween Costume Party 2020

Freaky Deaky Halloween Costume Party

October, 2020

Toyota Park, 7000 Harlem Ave Chicago, IL, Chicago, Illinois

LaughingStock 2020

LaughingStock

October, 2020

Elbo Room, 2871 N Lincoln Ave Chicago, IL, Chicago, Illinois

Chicago International REEL Shorts Film Fest 2020

Chicago International REEL Shorts Film Fest

October, 2020

Hokin Screening Room - Columbia College Chicago, 623 S Wabash Ave Chicago, IL, Chicago, Illinois

Chicago International Social Change Film Festival 2020

Chicago International Social Change Film Festival

October, 2020

Showplace ICON Theater, 1011 South Delano Court Chicago, Chicago, Illinois

St. Viator Haunted House - Stairway to Insanity 2020

St. Viator Haunted House - Stairway to Insanity

October, 2020

St. Viator School, Chicago, Illinois

Showcase your play at A Taste Of Theatre 2020

Showcase your play at A Taste Of Theatre

October, 2020

Carver Military Academy, Chicago, Illinois

CoffeeCon 2020

CoffeeCon

October, 2020

Revel Space, 1402 N Western Ave Chicago, Chicago, Illinois

Chicago Dessert Fest 2020

Chicago Dessert Fest

October, 2020

Moe's Cantina River North, Chicago, Illinois

Chicago Marathon 2020

Chicago Marathon

October, 2020

Chicago, Illinois

Rocktober Beerfest 2020

Rocktober Beerfest

October, 2020

West Loop at W Randolph St & Ada St, 1361 West Randolph Street Chicago, IL, Chicago, Illinois

Andersonville Arts Weekend 2020

Andersonville Arts Weekend

October, 2020

Multiple Locations around Clark & Berwyn, 5300 North Clark Street Chicago, IL, Chicago, Illinois

Andersonville Dessert Crawl 2020

Andersonville Dessert Crawl

October, 2020

Multiple Locations in Andersonville along Clark St, 5211 N Clark St Chicago, IL, Chicago, Illinois

River North Halloween Crawl 2020

River North Halloween Crawl

October, 2020

Moe's Cantina River North, Chicago, Illinois

Chicago ArtOberfest 2020

Chicago ArtOberfest

October, 2020

The Shops at Roosevelt Collection, 150 W Roosevelt Rd Chicago, IL, Chicago, Illinois

Spooky Zoo Spectacular 2020

Spooky Zoo Spectacular

October, 2020

Lincoln Park Zoo, Chicago, Illinois

Kaskade 2020

Kaskade

October, 2020

Skyline Stage At Navy Pier, Chicago, Illinois

Chicago Food Truck Festival 2020

Chicago Food Truck Festival

October, 2020

Lacuna Artist Lofts and Studios, Chicago, Illinois

Clark Street Spooktacular 2020

Clark Street Spooktacular

October, 2020

Clark Street in Lincoln Park, N Clark St & W Montrose Ave Chicago, IL, Chicago, Illinois

Haunted Booze Cruise on Halloween 2020

Haunted Booze Cruise on Halloween

October, 2020

Anita Dee II, Chicago, Illinois

A Taste of Theatre 2020

A Taste of Theatre

October, 2020

Gwendolyn Brooks College Prep , Chicago, Illinois

Chicago Book Expo 2020

Chicago Book Expo

October, 2020

Columbia College Chicago, 1104 S. Wabash Ave. Chicago, Chicago, Illinois

A Taste Of Theater 2020

A Taste Of Theater

October, 2020

Gwendolyn Brooks College Preparatory Academy, 250 E 111th St Chicago, Chicago, Illinois

About Festivals in Chicago

The Windy City of Chicago offers a broad selection of attractions for travellers of all types and ages, from beautiful architecture, lip-smacking offerings of food and drink and loads of sports events. Every year, it also holds a number of exciting festivals to celebrate food, drink, music, films and more.

Perhaps Chicago’s most famous festival is Lollapalooza, a massive music event which spans the genres of alt-rock, heavy metal, rock, hip hop, punk and more, and hosts more than 150,000 people every year. If you’re a music fan of any description, it’ll have something tuneful to fill your ears, and previous artists have included the likes of Eminem, Muse, The Smashing Pumpkins, The Cure, Arcade Fire, Pearl Jam, The Killers, The National and a whole lot more. If they’re a big name, you’ll find them here. It’s one of the biggest and most prestigious music festivals in the whole of the states and it comes with good vibes and a chilled-out atmosphere.

Chicago Underground Film Festival is a rather more leftfield affair, and showcases a range of alternative cinema, including short films, independent films, documentaries, foreign cinema and more. The event also screens shocking and controversial films for those who like something provocative. If you’re keen to discover strange, unusual and interesting cinema, this is the event for you, with a firm focus on celebrating the artistic and aesthetic aspects of filmmaking and screening radical and challenging content.

Chicago also plays host to loads of big parades throughout the year, including the St Patrick’s Day Parade, Chicago Gay Pride Parade, and the Chinese New Year Parade. All of these offer floats, bands, entertainment, food and drinks, with a variety of themed happenings depending on the particular event.

Chicago’s biggest festival is Taste of Chicago, a tastebud-tingling smorgasbord of foods and drinks from around the world. In what is probably the biggest outdoor food festival in the whole of the states, you can get your lips around plenty of tasty morsels and meals, from gourmet banquets to street food and everything in between. There are also cookery demonstrations, top chefs, samples, restaurants and food booths, with music and other entertainment for those looking to give their bellies a break.