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.

Discount tickets marked green are from trusted sellers (Goldstar, Groupon, and LivingSocial).

Bacon and beer

October 1, 2016

2 miles south

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

Discount tickets are $65 at Groupon and LivingSocial.

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.

Discount tickets $38.

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.

Beer run at Joliet Airport

October 1, 2016

45 miles SW

Run a mile on the runway at 10:30 a.m., or taste beer at noon if you are age 21+, or do both at Run the Runway 1 Mile Run at Joliet Regional Airport.

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.

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.

Neighborhood Oktoberfest

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

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.

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.

Musical: Funny Girl

October 1 - 2, 2016 (also Sept.)

14 miles north

Based on the film starring Barbra Streisand, Funny Girl tells the true story of legendary comedian and vaudeville great Fanny Brice at Skokie Theatre. Discount tickets $24.

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 Chicagoland Unconventional Bicycle Expo, which also includes seminars at Tinley Park Convention Center.

Dinner cruise

October 1, 8, 14, 2016

1 mile east

Enjoy a buffet meal, DJ dance music, and views of the Chicago skyline aboard the Spirit of Chicago Dinner Cruise, which departs from Navy Pier.

Discount tickets $82.

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 weekends at eight parks, which is perfect for families.

Game of Thrones parody

October 1 - 16, 2016 (also Sept.)

3.8 miles north

Described as “darkly humorous and beautifully vulgar,” Thrones! The Musical features hilarious songs about six seasons of the HBO show at Apollo Theater for age 16+. Discount tickets $20.

Dr. Seuss in Des Plaines

October 1 - 16, 2016 (begins Sept. 23)

21 miles NW

See a family-friendly version of Seussical, featuring the Cat in the Hat, Horton the Elephant, the Grinch, the Whos, and Gertrude McFuzz. Discount tickets $15.

Funny musical

October 1 - 16, 2016 (begins Sept. 29)

27.8 miles north

An ambitious window washer learns how to climb the corporate ladder in How To Succeed in Business Without Really Trying, an award-winning musical at Marriott Theatre in Lincolnshire. Discount tickets $20.

Irreverent puppet comedy

October 1 - 23, 2016 (also Sept.)

3.6 miles north

Hand to God is a “flat-out hilarious” [NY Times] sock-puppet comedy with adult language at Victory Gardens. Discount tickets $25.

Diverse circus

October 1 - 23, 2016 (begins Sept. 28)

9 miles south

UniverSoul Circus includes Caribbean dancers, Chinese acrobats, African clowns, and exotic animals in a heated tent in Washington Park. Discount tickets $12 to $23.

Adult variety show

October 1 - 29, 2016 (also Sept.)

7 miles north

Kiss Kiss Cabaret is a fun mix of burlesque, off-color comedy, music, magic, and variety acts at Uptown Underground. Reviews.

Discount tickets $14.

Magic lounge

October 1 - 29, 2016 (also Sept.)

7 miles north

Chicago Magic Lounge is an old-school magic show with close-up magic, bar magic, table-hopping magicians, and main stage acts at Uptown Underground. Discount tickets $14.

Female Sherlock Holmes

October 1 - 30, 2016 (also Sept.)

10.2 miles north

Miss Holmes (private investigator) and Miss Watson (doctor) are unconventional women solving a murder mystery at Lifeline Theatre. Discount tickets $20.

Hitchcock play

October 1 - 30, 2016 (begins Sept. 27)

31 miles north

Based on the thrilling film, The Birds features two strangers holed up in an abandoned house to escape avian attacks at Citadel Theatre in Lake Forest. Discount tickets $9 to $19.

Halloween 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. 23)

38 miles west

A ticket to Basement of the Dead [website has sound] also includes the 3D flashlight haunt. 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 in Crest Hill. See schedule.

Intense haunted house

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

45 miles NW

The Realm of Terror Horror Experience is halfway to Milwaukee in Round Lake Beach. Open Friday, Saturday, and Sunday plus Oct. 20, 27, and 31.

Haunted house at Rosemont

Oct. 1 - Nov. 5, 2016 (begins Sept. 30)

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

Oct. 1 - Nov. 5, 2016 (begins Sept. 23)

14 miles NW

House of Torment has two themes at 8240 N. Austin Ave. in Morton Grove. (Closed on Oct. 3, 4, 5, 10, 17, and Nov. 1, 2, 3.)

Magic show

October 1 - Nov. 26, 2016 (also Sept.)

0.7 miles south

The Magic Parlour is an evening of close-up magic by an award-winning magician in the beautiful Palmer House Hilton Hotel. Discount tickets $49.

Blue Man show

October 1 - Dec. 24, 2016 (also Sept.)

4.5 miles north

Blue Man Group puts on an exciting show that combines comedy, theater, music, and special effects at Briar Street Theatre. Discount tickets $36.

Tasting event

October 2, 2016 (12 and 2:30 p.m.)

9 miles NW

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

Discount tickets $44.

Dating comedy

October 2 - 30, 2016 (also Sept.)

2.1 miles north

Based on actual online-dating conversations, #DateMe: An OKCupid Experiment is a comic mix of original music, improvisation, and multimedia elements at Up Comedy Club. Discount tickets $17.

Funny racial drama

October 3 - Nov. 27, 2016 (begins Sept. 28)

9.4 miles north

Red Velvet recalls the “shocking” night in 1863 when the first black man appeared on a London theater stage at Raven Theatre East Stage. Discount tickets $16 to $23.

Comedy dinner

October 5 - Nov. 12, 2016 (also Sept.)

5.8 miles north

We Gotta Bingo delivers corny, bawdy, slapstick humor, lasagna, bread, and salad, as you participate in a bingo game between rival parishes at Chicago Theater Works. Discount tickets $35.

Wine at the conservatory

October 6, 2016 (6 to 9 p.m.)

5 miles west

Enjoy artisan wine paired with local, sustainably grown food at Wine under Glass, and explore the Garfield Park Conservatory. This event is for age 21+.

Comedy: Scooby-Doo

October 6 - Nov. 4, 2016 (7:30 p.m.)

8 miles north

Skooby Don’t is a send-up of the Hanna-Barbera cartoon classic Scooby-Doo in quaint Hamburger Mary’s theater. Discount tickets $14.

Beer & music event

October 7, 2016 (5:30 p.m., VIP 4:30)

0.5 miles west

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

Discount tickets $6.

Beer tasting

October 7, 2016 (5 to 8 p.m.)

0.5 miles south

A ticket to Harvest Hopdown includes unlimited seasonal beer tastings from 23 local breweries, passed beer bites, and live music at 11 N Michigan Avenue. Discount tickets $30.

Contemporary ballet

October 7 - 8, 2016 (7:30 p.m.)

1.2 miles north

Ballet 5:8 performs five works by two choreographers at Ruth Page Center for the Arts. Discount tickets $13.

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.

Adventure day at Northerly Island

October 8, 2016 (12 to 4 p.m.)

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.

Farm festival

October 8, 2016 (rain date Oct. 22)

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.

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.

Drink beer for the beasts

October 10, 2016 (6 to 8 p.m.)

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+.

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.

Soccer

October 13 & 16, 2016

15 miles SW

Watch Chicago Fire play a home game at Toyota Park.

Discount tickets $14 to $52.

Cinderella ballet

October 13 - 23, 2016

1 mile south

Joffrey Ballet presents a bold contemporary version of Romeo & Juliet, the timeless story of star-crossed lovers at Auditorium Theatre. Discount tickets $60.

Film festival

October 13 - 27, 2016

0.5 mile east

The Chicago International Film Festival [website may be slow] features 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., VIP 6)

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.

Cheese tasting

October 15, 2016 (2 sessions)

3 miles SW

Taste cheesy foods like pizza, grilled cheese, poutine, and macaroni & cheese from restaurants and cheese vendors during Say Cheese at Chicago Marriott at Medical District/UIC.

Discount tickets $11.

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.

Party cruise

October 15 & 22, 2016

0.7 miles east

A Booze Cruise aboard the Anita Dee II offers amazing views from the open top deck, dancing, and a cash bar, departing from 200 N Breakwater Access. Discount tickets $25.

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

Oct. 20 - 23, 2016 (6:30 to 10:30 p.m.)

24 miles north

Chicago Botanic Garden in Glencoe is full of spooky sights and fun activities for children and adults during Night of 1,000 Jack-o’-Lanterns (formerly 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-themed party with two stages of entertainment, bands, food, booze, food vendors, a costume contest, and graffiti artists on Chicago Street between Douglas & Villa.

Chili festival

October 22 - 23, 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.

Halloween pub crawls

October 22 - 29, 2016

Multiple locations

Get drink specials at bars (costume optional).

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.

Journey to Mars

October 24 - 25, 2016 (7 p.m.)

0.5 miles SW

Hear a columnist with National Geographic describe the thrilling first flight to the planet Mars in Mankind to Mars, and see stunning feature-film quality visuals at Goodman Theatre. Discount tickets $28 (Oct. 25).

Halloween movies

October 24 - 31, 2016

10 miles north

Scarefest shows a different scary movie every night, with $3 cocktails available at The New 400 Theaters.

Halloween party - opera house

October 28, 2016 (8 p.m.)

1 mile SW

Halloween Masquerade 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+.

Alternative dance party

October 28, 2016 (11 p.m.)

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.

Halloween party - O’Hare

October 28, 2016 (8 p.m.)

18.3 miles NW

The Halloween Costume Party has a DJ, dance floor, cash bar, food for sale, and prizes at Galaxy Banquet for age 21+. Pay at the door.

Ghost stories

October 28, 2016

41 miles north

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

Trick or treat in Crystal Lake

October 28, 2016 (6:30 to 8:30 p.m.)

49 miles NW

Bring kids in costume to Trunk or Treat, where they get candy from 25 decorated car trunks, with hayrides, face-painting, an outdoor movie, and Halloween games at St. Paul’s United Church of Christ. Free.

Addams Family musical

October 28 - 30, 2016

15.3 miles NW

In this “lost” episode of The Addams Family TV show, the daughter falls in love and invites a “normal” boy and his parents to dinner, live onstage in River Forest. Discount tickets $12.

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.

All-American musical

October 28 - Nov. 6, 2016

27.8 miles north

Singin’ in the Rain is a song and dance classic about actors in the early days of Hollywood at Marriott Theatre in Lincolnshire. Discount tickets $40.

Halloween party - Congress Plaza

October 29, 2016 (9 p.m.)

1 mile south

Haunted Halloween Ball is a giant costume party with “celebrity DJs playing house & top 40 hits” at the Congress Plaza Hotel for age 21+.

Halloween party - Navy Pier

October 29, 2016 (8 p.m.)

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. Discount tickets $11.

Halloween at the zoo

October 29, 2016

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 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.

Halloween cruise

October 29 - 31, 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+.

Young Frankenstein the musical

October 29 - Nov. 6, 2016 (begins Sept. 28)

26 miles NW

Young Frankenstein is a live musical by Mel Brooks that spoofs the horror-film genre at Metropolis Performing Arts Centre in Arlington Heights. Discount tickets $19 (Sept. 28, Oct. 29, Nov. 3-4).

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 (1 to 4 p.m.)

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 (1 to 4 p.m.)

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 (6 to 9 p.m.)

32 miles NW

Kids will enjoy hayrides, crafts, carnival games, entertainment, and trick-or-treating at Halloween Boonanza in Schaumburg.
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© October 2016 calendar of events in Chicago, IL: Halloween haunted houses, parties, festivals, best things to do in Chicago, Illinois. ord-10