Chicago events calendar for October 2016. Best festivals, fun things to do, weekend street fairs, kids activities and Halloween haunted houses in Chicago, Illinois.

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Best events for 12 months
October 2016
October 2016

Enjoy the best Chicago events, festivals, and things to do with this calendar of events.

Mileage is from the Wrigley Building in downtown Chicago, Illinois.

Art fair indoors

October 1, 2016 (begins Sept. 30)

2.5 miles west

Enjoy visual art, music, and fashion in restaurants and shops during West Town Art Walk at Chicago Avenue & Ashland Avenue. Free.

Beer festival

October 1, 2016

7 miles NW

Try 50 beers from 20 breweries at Logan Square Beer Festival in Logan Square Auditorium.

Vegan event

October 1, 2016

9 miles north

VeganMania includes samples, speakers, live music, and a food court at the Broadway Armory. (Unlike vegetarians, vegans don’t eat eggs and milk.) Free.

Oktoberfest in Naperville

October 1, 2016 (begins Sept. 30)

32 miles SW

Enjoy live music from classic German to classic rock, German beer and food, and family-friendly activities on Saturday at Oktoberfest.

Woodstock ale festival

October 1, 2016 (1 to 5 p.m.)

61 miles NW

Woodstock Ale Fest features 80 craft beers, bacon, and bluegrass music. Discount tickets $25.

Chili festival

October 1 - 2, 2016

1 mile NW

Chili Fest Chicago has three kinds of tickets (taste chili, or drink craft beer and Mimosas, or both) at 218 West Ohio Street in River North.

Apple festival

October 1 - 2, 2016

7 miles NW

Get some apple pie and cider, listen to local music, or visit the kid zone at Apple Fest at Lincoln & Leland Avenues. Free.

Tasting event

October 1 - 2, 2016 (begins Sept. 30)

7 miles NW

Sample signature dishes made by renowned chefs at 12 grilling stations during Taste Talks All-Star BBQ at Palmer Square Park.

Art, food, and music festival

October 1 - 2, 2016 (begins Sept. 30)

13 miles north

Evanston Art & Big Fork Festival features restaurant food, live music, and an art festival, all beginning Friday at 4 p.m. Free.

Oktoberfest in Roselle

October 1 - 2, 2016

30 miles west

Oktoberfest at Lynfred Winery includes a pig roast, grape stomping, wine tasting, and crowds.

Odd bike show

October 1 - 2, 2016 (begins Sept. 30)

30.3 miles SW

See recumbent, folding, tandem, and even electric bicycles and test ride them (age 16+ with a helmet) at Chicago Unconventional Bicycle Expo, which also includes seminars at Tinley Park Convention Center.

Circus in the park

October 1 - 16, 2016 (begins Aug. 27)

Chicago locations

Midnight Circus in the Parks is a series of daytime shows on the weekends at eight parks, which is perfect for families.

Haunted farm

October 1 - 30, 2016 (starts Sept. 17)

32 miles SW

The Haunted Barn at Bengtson’s Pumpkin Fest in Homer Glen is fine for mature kids. The Fun Barn will entertain even the youngest children. Also visit the corn maze, kids’ rides, and petting zoo.

Pumpkin patches & corn mazes

October 1 - 31, 2016

Chicago area

Visit pumpkin patches at local farms for fun family activities, or romp through the cornfields in corn mazes.

Aurora haunted house

October 1 - 31, 2016 (starts Sept. 24)

38 miles west

Basement of the Dead offers three horrifying attractions in one place. See schedule.

Joliet haunted house

October 1 - 31, 2016 (starts Sept. 29)

38 miles SW

Take a 40-minute trip through 40 terrifying rooms and play Zombie Paintball at Statesville Haunted Prison & City of the Dead [sound] in Crest Hill. Open Thurs. to Sun. plus Oct. 31.

Intense haunted house

October 1 - 31, 2016 (starts Sept. 30)

45 miles NW

The Realm of Terror Horror Experience is halfway to Milwaukee in Round Lake Beach. See hours.

Sample 12 plays

October 7 - 8, 2016

17.5 miles south

See a scene from six different plays per day for $20 at A Taste of Theater at Gwendolyn Brooks College Preparatory Academy.

Marathon & fitness expo

October 7 - 9, 2016

Chicago locations

The free Chicago Marathon Health & Fitness Expo is Friday and Saturday at McCormick Place. The Chicago Marathon begins and ends Sunday in Grant Park, with a post-race party in Butler Field.

Beer festival

October 7 - 9, 2016

2.2 miles west

Rocktober Beerfest offers beers, bratwurst, and live music under a heated tent at Randolph and Ogden.

Pumpkin festival

October 7 - 9, 2016

28 miles north

The Great Highwood Pumpkin Festival has a parade, pet costumes, 5K races, hayrides, vendors, pumpkin carving and lighting in Highwood. See schedule.

Scarecrow festival

October 7 - 9, 2016

37 miles west

Vote for your favorite handmade scarecrow at Scarecrow Fest, which includes live entertainment, arts and crafts, food, a carnival, and a petting zoo in St. Charles. Free.

Flower bulb festival

October 8 - 9, 2016

24 miles north

Find more than 200 varieties of bulbs, gourmet foods, gardening demonstrations, live music, and kids’ activities at the Fall Bulb Festival at the Chicago Botanic Garden in Glencoe. Free except parking.

Columbus Day Parade

October 10, 2016 (12:30 p.m.)

1.3 miles south

The Columbus Day Parade celebrates the historic voyage of Christopher Columbus to America and Italian-American culture on State Street from Wacker to Van Buren. Free.

Pinball Expo

October 12 - 16, 2016

32 miles north

Pinball Expo has a game hall, tournament, vendors, speakers, and a banquet at the Westin in Wheeling.

Beer tasting in the garden

October 13, 2016 (6 to 8 p.m.)

24 miles north

Sample seasonally selected beers, and then purchase them by the bottle at Autumn Brews at Chicago Botanic Garden in Glencoe.

Film festival

October 13 - 27, 2016

0.5 mile east

The Chicago International Film Festival features more than 100 short and full-length films from 50 countries, free panel discussions, and an opening night gala. Films show at the AMC River East 21.

Beer festival

October 14, 2016 (7 p.m.)

1.9 miles west

Festiv-Ale offers fine Midwest beers, excellent food, music, and a silent auction for charity at Revel Fulton Market.

Culinary events

October 14 - 15, 2016

Chicago downtown

Taste Chicago features a cocktail reception and dinner by celebrity chefs at LondonHouse on Friday, plus cooking demonstrations on Saturday.

Wine tasting

October 14 - 15, 2016

1.7 miles west

Choose from 250 wines to taste at Wine Riot at Venue One, and track your favorites on the free mobile app. Repeats March.

Andersonville Arts Weekend

October 14 - 16, 2016

8 miles north

Andersonville Arts Weekend starts Fri. night with receptions in galleries and shops, followed by scheduled exhibits, readings, shows, and art walks.

Family Halloween

October 14 - 16, 2016

36 miles SW

Halloween Hollow has carnival rides, hayrides, pony rides, laser tag, contests, treats, entertainment, and food at 10925 W La Porte Road in Mokena.

Home Movie Day

October 15, 2016 (11 a.m. to 3 p.m.)

1.8 miles north

See home movies and bring your own to be shown at Home Movie Day at Chicago History Museum. Free.

Spirits tasting at the zoo

October 15, 2016 (6 to 10 p.m.)

2.5 miles north

Taste 12 samples of 50 spirits in animal houses at Wild Spirits in Lincoln Park Zoo.

Dumplings & hip hop

October 15, 2016 (7 p.m., VIP 6)

2.7 miles SW

A ticket to Dumpling Fest presents Wrappers Delight gets you dumplings from around the world, drinks, and ‘90s hip hop music at UIC Forum for age 21+.

Green Halloween

October 15, 2016

11 miles west

The Green Pumpkin Trail begins at Oak Park Visitors Bureau and includes healthy snacks and activities in local shops for kids 3 to 8. Costume optional. Free.

Beer tasting

October 15, 2016

17 miles SW

Taste 150 craft and import beers with food and live entertainment at indoor Brew Moon Fest in McCook.

Architectural open house

October 15 - 16, 2016

Chicago locations

Get a rare behind-the-scenes look at 200 of the city’s finest buildings during Open House Chicago. Free.

Ideas Week

October 17 - 23, 2016

Chicago locations

Attend talks, labs, and dinners with inspirational thought leaders (artists, scientists, musicians, inventors, explorers) during Chicago Ideas Week.

Whisky tasting

October 20, 2016

1 mile south

The Whisky Extravaganza includes unlimited tastes from distillers and a buffet at the Union League Club. The dress code requires a jacket.

Halloween festival

October 20 - 23, 2016 (6 to 10 p.m.)

24 miles north

Chicago Botanic Garden in Glencoe is full of spooky sights and fun activities for children and adults during HallowFest. Buy tickets early.

Halloween festival & parade

October 22, 2016 (2 to 8 p.m.)

Downtown Chicago

Halloween Gathering includes a daytime festival at Millennium Park and Sir George Solti Garden 2 to 5 p.m., and a parade on Columbus Drive from Balbo to Monroe 6 to 8 p.m. Free.

Latin opera singers

October 22, 2016 (8 p.m.)

16 miles NW

Il Divo is three tenors and a baritone singing sultry music from Spain, Cuba, and Central and South America at Rosemont Theatre. Discount tickets $35 to $75.

Halloween flea market

October 22, 2016

31 miles west

Come in costume to the Wheaton Haunted Halloween Flea Market, which features a zombie crawl and dance with live music, plus antiques & collectibles for sale at DuPage County Fairgrounds.

Street party in Elgin

October 22, 2016

37 miles NW

Nightmare on Chicago Street is a zombie-theme party with two stages of entertainment, bands, food, booze, food vendors, a costume contest, and graffiti artists on Chicago Street between Douglas & Villa.

Boo at the Zoo

October 22-23 and 29-30, 2016

14 miles SW

Boo at the Zoo has games and activities for kids, a hayride, and a costume parade at 1 p.m. at the Brookfield Zoo.

Wearable art show

October 23, 2016

47 miles west

Uncommon Threads is a luncheon and juried fashion show of fine textile works at Q Center in St. Charles.

BatFest for families

October 24, 2016

44 miles west

BatFest has a parade, pumpkin roll, entertainment, trick-or-treating, hayrides, games, and a farmers’ market in Batavia. Free.

Halloween party - opera house

October 28, 2016 (8 p.m.)

1 mile SW

A Night at the Opera House includes DJ music, an open bar, and appetizers at the Civic Opera House. Costumes welcome.

Halloween dance class

October 28, 2016

6.4 miles NW

Halloween Tango Dance Party has a new theme every year, a dance class with guided practice, a costume contest, and BYOB at Duet Dance Studio for age 21+.

Halloween pub crawls

October 28 - 31, 2016

Multiple locations

Get drink specials at bars (costume optional).

Children’s film festival

October 28 - Nov. 6, 2016

Chicago locations

Billed as North America’s largest film festival for children, the Chicago International Children’s Film Festival (CICFF) showcases the best in culturally diverse, non-violent, value-affirming new cinema for children and offers interactive workshops.

Halloween cruise

October 29, 2016

1 mile east

Put on a costume and arrive early for a cruise on Lake Michigan with DJ music and a cash bar for age 21+.

Halloween party - Navy Pier

October 29, 2016

1 mile east

Join 3,000 revelers age 21+ at The Haunted Halloween Ball in the Grand Ballroom at Navy Pier, which also includes access to the Saints & Sinners Halloween at Lakeview Terrace.

Halloween parade for dogs

October 29, 2016 (11 a.m. to 1 p.m.)

24 miles north

Dogs in costume are allowed to enter the Chicago Botanic Garden for two hours each year during Spooky Pooch Parade and costume contest.

Freaky Halloween party

October 29, 2016 (8 p.m.)

40.3 miles west

Midwest Freakfest is a multi-stage music and entertainment show with food and drinks for sale in McCook for age 17+ with ID. Video.

Expand your mind

October 29 - Nov. 12, 2016

Chicago locations

Chicago Humanities Festival is a series of talks and events that explore the human condition and feature exciting thinkers, artists, and performers.

Clark Street Spooktacular

October 30, 2016

3 miles north

Clark Street Spooktacular has family-friendly games, trick-or-treating, street magicians, jugglers, balloon artists, and a costume contest. Free.

Andersonville Dessert Crawl

October 30, 2016 (2 to 5 p.m.)

8 miles north

A ticket gets you sweet treats at 11 local restaurants on Andersonville Dessert Crawl.

Halloween for kids

October 30, 2016 (uncertain)

32 miles west

Kids 10 and under will enjoy fun activities, games, fairytales, and treats at Halloween Happening at Naperville Riverwalk’s Grand Pavilion.

Halloween parade

October 31, 2016 (4 p.m.)

4 miles north

Register and wear a Halloween costume to join the Northalsted Halloween Parade, or watch from the sidewalk on Halsted Street from Belmont to Addison. Free. Schedule.

Halloween carnival

October 31, 2016

32 miles NW

Kids will enjoy hayrides, crafts, carnival games, entertainment, and trick-or-treating at Halloween Boonanza in Schaumburg.

Artists Month

October 2016 (undated)

Chicago area

Enjoy performances, exhibitions, films, open studios, demonstrations, and neighborhood art walks during Chicago Artists Month.

Fashion shows

October 2016 (undated)

Chicago locations

Fashion Focus is a week-long celebration of Chicago’s fashion industry that includes designer shows in a tent at Millennium Park.

Beer & music event

October 2016 (undated)

0.5 miles west

Enjoy craft beer, food pairings, and live music at Local Brews Local Grooves at House of Blues.

Beer festival

October 2016 (undated)

1.5 miles SW

Buy tickets online for beer tasting and snacks during an afternoon or evening session at The Chicago Beer Festival in Union Station. Repeats March.

Bacon and beer

October 2016 (undated)

2 miles south

Enjoy craft beer, bacon-inspired tastes from local restaurants, music, and interactive games at Bacon and Beer Classic at Soldier Field.

Adventure day at Northerly Island

October 2016 (undated)

3 miles south

Enjoy arts and crafts, storytelling, a nature hike, and kayaking at Fall Adventure Day, which has outdoor education on the lakefront at Northerly Island. Free.

Drink beer for the beasts

October 2016 (undated)

5 miles NW

Enjoy unlimited appetizers and five house beers during Pints for Pets to protect animals at Revolution Brewing on Milwaukee Avenue for age 21+.

Horror shows

October 2016 (undated)

5 miles north

See murderous and macabre sketch comedy, cabaret, dance, burlesque, and plays at Chicago Horror Theatre Festival at Stage 773.

Pumpkin carving for grown ups

October 2016 (undated)

5.8 miles north

The Pumpkin Carving Party includes everything you need to carve a jack-o-lantern masterpiece, plus food and drinks specials at Matilda for age 23+.

Neighborhood Oktoberfest

October 2016 (undated)

8 miles NW

St. Benedict’s Oktoberfest features German food, beer, and party bands under tents in St. Benedict’s Courtyard, plus a kids’ carnival. Free entry.

Irish Oktoberfest

October 2016 (undated)

9.2 miles NW

McToberfest features live German and Irish music, dance, food, and drink at the Irish American Heritage Center.

Farm festival

October 2016 (undated)

22 miles west

Heritage Day celebrates fall with arts and crafts, a bluegrass band, demonstrations (spinning, weaving, candle making), and colonial soldiers who fire a cannon on the hour at Fischer Farm in Bensenville. Free except pony rides, petting zoo, and food items.

Lake Zurich beer fest

October 2016 (undated)

39 miles NW

Taste 45 craft beers, hear live music, and browse arts & crafts in the park at Lake Zurich Craft Beer Festival.

Ghost stories

October 2016 (undated)

41 miles north

The award-winning Ray Bradbury Storytelling Festival features ghost stories, macabre fables, and creepy tales at Genesee Theatre in Waukegan.

Halloween party - Lucky Strike

October 2016 (undated)

0.6 miles NE

Saints & Sinners is a costume ball with open bowling, a cash bar, and all-night dancing at Lucky Strike.

Vintage Halloween bash

October 2016 (undated)

0.6 miles east

MasquArcade features DJ music (swing, house, and alternative), and cabaret performers in a “steampunk circus” style arcade room at FTW for age 21+. Free.

Halloween Segway tour

October 2016 (undated)

0.7 miles south

Step onto a Segway and follow your guide in ghoulish costume on a Haunted Halloween Tour of Chicago’s haunted hotels and sites of gruesome disasters.

Halloween at Navy Pier

October 2016 (undated)

1 mile east

Halloween at Navy Pier includes trick-or-treating, a costume contest, fireworks, and spooky movies. Free.

Halloween party - Congress Plaza

October 2016 (undated)

1 mile south

The Haunted Halloween Ball is a giant costume party at the Congress Plaza Hotel for age 21+, and a pre-party.

Halloween at the zoo

October 2016 (undated)

2.5 miles north

Kids can wear costumes, trick-or-treat, hear music, make crafts, and see a haunted house at Spooky Zoo Spectacular at Lincoln Park Zoo. Free.

Halloween Party - Chop Shop

October 2016 (undated)

4.1 miles NW

The Black Market Ball includes a haunting show with 20 performers, beer and wine until midnight, DJs, and a costume contest at the Chop Shop for age 21+.

Halloween dance party

October 2016 (undated)

7.2 miles north

Nocturna All Hallow’s Eve Ball by American Gothic Productions has DJ dance music (goth, industrial, post-punk, deathrock, ethereal, ebm, new wave, darkwave, dark indie), performances, and a costume contest for age 18+ at Metro Chicago on N. Clark.

Free Halloween movies

October 2016 (undated)

10 miles north

Scare Fest shows scary movies at 9:30 p.m. (with cocktails for sale) plus family-friendly movies Halloween Day at The New 400 Theaters. Free.

Haunted house at Rosemont

October 2016 (undated)

14 miles NW

Disturbia: Screams in the Park is a 35-room nightmare at MB Financial Park at Rosemont. See hours.

Morton Grove haunted house

October 2016 (undated)

14 miles NW

House of Torment has two themes at 8240 N. Austin Ave. in Morton Grove.

Villa Park nightmare

October 2016 (undated)

21 miles west

Great American Nightmare [sound] is 3 high-tech haunted houses based on Rob Zombie’s horror films for age 13+ in the Odeum Expo Center. See hours.

Kids’ haunted house

October 2016 (undated)

40 miles NW

Psychosis Haunted House in Elgin does a low-scare Kids’ Matinee (website has sound on some devices) with candy from 1 to 3 p.m.
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© October 2016 calendar of events in Chicago, IL: Halloween haunted houses, parties, festivals, best things to do in Chicago, Illinois.