Chicago events calendar for August 2016. Best festivals, fun things to do, weekend street fairs, kids activities, and free entertainment in Chicago, Illinois.

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Best events for 12 months
August 2016
August 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.


August 1, 2016 (7:30 p.m.)

1.9 miles west

Chicago Jazz Orchestra plays big band and Great American Songbook classics accompanied by jazz singer Dee Alexander at City Winery, 1200 W. Randolph Street. Discount tickets $9.

Watch football practice

August 1 - 9, 2016 (also July)

59 miles south

It’s free to attend the Chicago Bears Training Camp at Olivet Nazarene University in Bourbonnais.

Millennium Park music

August 1 - 25, 2016 (begins June 6)

0.7 miles SE

Millennium Park Summer Music Series (formerly Downtown Sound) features great music artists Monday and Thursday evenings in Millennium Park. Free.

Evening cruise

August 1 - 30, 2017 (6:30 p.m.)

0.7 miles east

An After Work Cruise on Anita Dee II offers amazing views from the open top deck, dancing, and pricey drinks, departing from 200 N Breakwater Access.


August 1 - 31, 2016 (also July)

multiple locations

Discount prices include all taxes and ticket fees.

Movies in the Parks

August 1 - Sept. 10, 2016 (begins June 11)

Chicago locations

See 250 Movies in the Parks, if weather allows. Free.

Ravinia music festival

August 1 - Sept. 17, 2016 (begins June 2)

23 miles north

See nationally known performers at Ravinia Festival, billed as America’s oldest outdoor music festival at Ravinia Park in Highland Park.

French fair

August 2, 2016

11 miles west

Immerse yourself in French art, food, wine, music, activities, and films at Art dans la Rue in Oak Park.

Singers: Lovato & Jonas

August 2, 2016 (7 p.m.)

18 miles NW

Demi Lovato & Nick Jonas sing alone and together at Allstate Arena in Rosemont. Discount tickets $24.

Disney musical

August 2 - 7, 2016 (begins July 28)

0.7 miles SW

Newsboys take on a ruthless newspaper tycoon to fight for what’s right in the high-energy Broadway hit Newsies at Cadillac Palace Theatre.

Discount tickets $39 to $75.

Classical concerts

August 2 - 10, 2016

25.1 miles north

Hear the Chicago Symphony perform with guest musicians at Ravinia Pavilion in Highland Park.

Book of Mormon musical

August 2 - 14, 2016 (also July)

0.8 miles south

The Book of Mormon is an outrageous comedy in the vein of South Park that has won nine Tony Awards, at The PrivateBank Theatre. Discount tickets $39 to $90.

Classical music festival

August 2 - 20, 2016 (begins June 15)

Chicago locations

Grant Park Music Festival is an outdoor classical music series at Jay Pritzker Pavilion in Millennium Park. The rear seats are free, or bring a blanket or lawn chairs. (Inside Harris Theater on July 30.)

Millennium Park movies

August 2 - 30, 2016 (Tuesdays from June 21)

0.5 miles south

Get a seat or sit on the lawn to see films on a 40-foot screen at Millennium Park Summer Film Series. Free.

Race in show business

August 3 - 14, 2016 (also July)

0.7 miles north

Set in 1908, Thaddeus and Slocum is about two best friends of different races struggling to promote their show filled with slapstick, burlesque, song, and dance at Lookingglass Theatre. Discount tickets $30.

Black hero

August 3 - 14, 2016 (begins July 21)

4.8 miles north

Douglass: An American Drama is a multimedia show about Frederick Douglass, the ex-slave who became a leader of the anti-slavery movement at Theater Wit. Discount tickets $13.

Witty comedy about friends

August 3 - 28, 2016 (also July)

7.5 miles north

An after-dinner game reveals secrets among friends turning 30 in This, “The best new play to open off Broadway” [New York Times 2009] at Windy City Playhouse. Discount tickets $15 to $28.

Dinner cruise

August 3 - 31, 2016

1 mile east

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

Discount tickets $78.

Jazz at the aquarium

August 3 - Sept. 14, 2016 (Wed. from June 22)

2 miles south

Hear musicians and vocalists, see views from the terrace, buy cocktails & food, and visit the aquarium at Jazzin’ at the Shedd at Shedd Aquarium.

Comedy dinner

August 3 - Sept. 14, 2016 (also July)

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 $20 to $40.

Free foreign films

August 3 - Sept. 28, 2016 (Wednesdays from June)

0.4 miles south

See a different comedy film each week at International Screenings Program at Chicago Cultural Center. Free.

Blue Man show

August 3 - Oct. 2, 2016

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.

Rubber duck race

August 4, 2016

0 miles

Send a rubber duck downstream for charity and enjoy family fun at Windy City Rubber Ducky Derby.

Meditation festival

August 4, 2016 (7 to 9 p.m.)

0.5 miles south

Festival of Inner Peace promises uplifting, soothing, and life-affirming music, art, and dance at Harris Theater in Millennium Park. Free tickets online.

Dark comedy

August 4 - 7, 2016

5 miles north

Based on the cult-classic movie with Winona Ryder, Heathers: The Musical is about three high-school divas and a girl who dares to put them in their place, at Stage 773. Discount tickets $23.

Game of Thrones parody

August 4 - 21, 2016 (also July)

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 $15 to $35.

Shakespeare comedy

August 4 - 27, 2016 (begins July 21)

11.3 miles west

Hilarious antics and a battle-of-the-sexes ensue when a suitor woos a wealthy maid in The Taming of the Shrew at Oak Park Festival Theatre.

Discount tickets $15.

Baseball & fireworks

August 5, 2016 (7:10 p.m.)

5.5 miles south

Watch the White Sox play a game followed by fireworks at U.S. Cellular Field. Discount tickets $11.
  • August 5 - Baltimore Orioles
  • August 19 - Oakland Athletics
  • August 26 - Seattle Mariners

Rap festival

August 5, 2016 (5:30 p.m.)

32.4 miles south

Hear a dozen rap music artists at Art of Rap Festival at Hollywood Casino Amphitheatre in Tinley Park.

Hot dog festival

August 5 - 7, 2016

2.3 miles north

Chicago Hot Dog Fest features hot dog vendors, beer, music, and entertainment in Lincoln Park at Clark Street and W LaSalle Drive. Free entry. Discount admission and food deal $25.

Horror convention

August 5 - 7, 2016

16 miles NW

Flashback Weekend offers celebrity guests, vendors, and evening events at Crowne Plaza Chicago O’Hare.

Adult variety show

August 5 - 27, 2016 (also July)

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 $13.

Johnny Cash show

August 5 - 28, 2016

26 miles NW

Ring of Fire features the story and music of legendary musician Johnny Cash at Metropolis Performing Arts Centre in Arlington Heights. Discount tickets $19.

Black film festival

August 5 - Sept. 1, 2016

0.5 miles SW

Black Harvest Film Festival celebrates the stories, images, heritage, and history of the black experience with dozens of films at Gene Siskel Film Center.

Family football festival

August 6, 2016

2 miles south

Chicago Bears Family Fest includes activities and live music outside Soldier Field from 9 to 11:30 a.m. and 2 to 3:30 p.m., plus a 12:30 p.m. team introduction and practice inside the stadium.

Urban international festival

August 6, 2016

12 miles SW

Takin’ it to the Streets promises music, dance, family activities, inspirational talks, multi-ethnic food, and an international bazaar in Marquette Park. Donation.

Beer festival

August 6, 2016

27 miles west

Taste 80 micro brews, sample food, and hear live music at Wheaton Brew Fest in Wheaton.

Dogs at the park

August 6, 2016

27 miles west

Dog Days offers a pet play area, high-flying disc-catching dogs, agility demonstrations, and vendors at Cantigny Park in Wheaton. Free except parking.

Corn festival

August 6, 2016

28 miles NW

A ticket to Corn Fest gets you a hamburger, brat, or hot dog; pop, watermelon, and all the fresh-picked corn you can eat. Also see the arts & craft fair and bazaar at Community Church in Rolling Meadows.

Taste of Lincoln Avenue

August 6 - 7, 2016 (12 to 10 p.m.)

3.5 miles north

Hear 20 music acts on two stages, see juried art, shop vendors, and take the kids to an afternoon carnival on Altgeld Street with games, pony rides and petting zoo at Taste of Lincoln Avenue from Fullerton to Wrightwood. Donation. Wine tasting discount tickets.

Wrigleyville summer festival

August 6 - 7, 2016

5 miles north

Wrigleyville Summerfest has a kids’ zone, food, drinks, and music at 3300 N Seminary Ave. Donation.

Edgewater festival

August 6 - 7, 2016

8 miles north

Edge Fest offers North Side cuisine, local bands, karaoke, costumed dogs, and art on North Broadway from Thorndale to Ardmore. Donation.

Evanston arts festival

August 6 - 7, 2016

13 miles north

Lakeshore Arts Festival showcases 80 artists, live music (jazz, blues, folk, bluegrass, rock, baroque, and indie pop), a silent art auction, a children’s craft tent, and food vendors at Dawes Park in Evanston. Free.

Family musical

August 6 - 7, 2016 (also July)

13.6 miles north

Based on a popular children’s book, Elephant & Piggie’s “We Are in a Play!” is an imaginative musical romp about the importance and true meaning of friendship in Evanston. Discount tickets $11.

Glenview art festival

August 6 - 7, 2016

22 miles NW

Art at the Glen Town Center features 185 artists, live music, food, and kids’ activities in Glenview. Free.

Fairy festival

August 6 - 7, 2016

38 miles west

The World of Faeries Festival welcomes you with or without costume for dance, music, games, shopping, and tea parties at Vasa Park in South Elgin.

Magic lounge

August 6 - 27, 2016 (also July)

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 beautiful Uptown Underground. Discount tickets $14.

Renaissance fair

August 6 - Sept. 5, 2016 (weekends from July 9)

49 miles north

Watch knights joust, shop an artisan market, mingle with costumed minstrels, play games, and attend shows at Bristol Renaissance Faire in 16th century England (i.e. Kenosha, WI).

Cabaret variety show

August 6 - Dec. 16, 2016 (also July)

5 miles north

Vaudezilla! promises one-of-a-kind burlesque, drag, aerial acts, and cutting-edge performance artists who change weekly at Stage 773. Discount tickets $13.

Country music

August 7 - 20, 2016

31.8 miles south

Hear country superstars perform live at Hollywood Casino Amphitheatre in Tinley Park.

Taste of Andersonville

August 10, 2016 (6 to 9 p.m.)

9 miles north

A ticket to Taste of Andersonville Dinner Crawl gets you samples from 11 local restaurants.

Magic show

August 10 - Sept. 14, 2016 (Wednesdays)

3.3 miles north

The Magic Cabaret entertains with mind-boggling sleight of hand and audience participation in small Greenhouse Theater Center. Discount tickets $10.

Nerdy comedy

August 11 - 14, 2016

5 miles north

If you love comedy about nerdy subjects like the Twilight Zone, Buffy the Vampire Slayer, Jane Austen, and Star Trek, NerdFest will get you laughing at Stage 773.


August 11 & 27, 2016

2 miles south

Watch the Chicago Bears play Denver on Aug. 11 or Kansas City on Aug. 27 in a pre-season game at Soldier Field. Discount tickets $56 to $161.

Free concert

August 12, 2016 (7 p.m.)

3.9 miles SW

Hear indie hero Mikal Cronin and Chicago natives Varsity at Thalia Hall, with beer for sale. Free tickets.

Naperville Wine Festival

August 12 - 13, 2016

33 miles west

Sample fine wines, buy restaurant appetizers, and hear music at Naperville Wine Festival.

Discount tickets for two people: $50.

Japanese festival

August 12 - 14, 2016

3 miles north

Ginza Holiday offers Japanese dance, martial arts, drumming, bonsai, craftsmen at work, sushi, and teriyaki at Midwest Buddhist Temple. Donation.

Retro on Roscoe

August 12 - 14, 2016

7 miles NW

Watch top entertainment on 3 stages, shop 6 blocks of art and antique vendors, and see 50 classic cars at Retro on Roscoe in Roscoe Village. Donation.

Cuban festival

August 12 - 14, 2016

12 miles NW

Festival Cubano [sound] promises Cuban music, Latin American food, vendors, and a kids’ area in Riis Park at Narragansett Avenue & Fullerton Avenue. Discount tickets $20 for two.

Beatles festival

August 12 - 14, 2016

16 miles NW

The Fest for Beatles Fans [sound] has a Beatles marketplace, guest speakers, a dance party, look-alike contest, games, and exhibits at Hyatt Regency O’Hare.

Rock and roll icon

August 13, 2016 (8 p.m.)

0.4 miles SW

Aerosmith frontman Steven Tyler performs with the Nashville-based band Loving Mary and shares career stories at The Chicago Theatre. Discount tickets $56.

Overnight bike ride

August 13, 2016

1 mile south

L.A.T.E. Ride begins late Saturday night at Buckingham Fountain and continues 15 or 25 miles into Sunday morning, followed by optional breakfast. Awards for the best “glowing” bicycle decorations.

Beer festival

August 13, 2016 (5 p.m.)

2.5 miles west

Beer Mansion promises “an immersive room-by-room journey through the world of beer, complete with food, live music, games, prizes, and a handful of surprises” in West Town.

Pokemon pub crawl

August 13, 2016 (2 to 8 p.m.)

3.7 miles NW

Pokemon Go Pub Crawl Chicago includes a photo hunt with prizes and drink specials at four bars in Wicker Park for age 21+. Discount tickets $11.

African American parade

August 13, 2016 (10 a.m.)

5 miles south

Bud Billiken Parade is billed as the oldest and largest African American parade in America. It goes south down MLK Drive from Oakwood Blvd. to a picnic with food vendors in Washington Park. Free.

Arlington horse race

August 13, 2016

27 miles NW

Watch jockeys compete for $1 million in the prestigious Arlington Million horse race in Arlington Heights.

Journey & The Doobie Brothers

August 13, 2016 (7 p.m.)

31.8 miles south

See two popular bands live when Journey (Don't Stop Believin’) and The Doobie Brothers (Listen to the Music) perform at Hollywood Casino Amphitheatre in Tinley Park. Discount tickets $20 to $55.

Farm festival

August 13, 2016

37 miles SW

Farm & Barn Fest has sheep shearing, blacksmithing, horse riding, a petting zoo, a flea market, restaurant food, music, and contests at Main Park in Mokena.

Northalsted Market Days

August 13 - 14, 2016

5 miles north

Northalsted Market Days is a popular gay-friendly street fair and music festival with 300 food, art, and craft vendors plus musical acts on 4 blocks of North Halsted Street from Belmont to Addison. Donation.

Kite festival

August 13 - 14, 2016

24 miles north

Make a kite in a workshop and fly it, watch stunt kites perform to music, and buy lunch at the Kite Festival in the meadow at Chicago Botanic Garden in Glencoe. See schedule of events.

Art fair in Lincolnshire

August 13 - 14, 2016

33 miles north

Lincolnshire Arts & Eats features 100 juried artists, live music, food, and children’s art activities. Free.

French day in the park

August 14, 2016

27 miles west

French Connection Day features a French open-air market, wine tasting, French food, music, street performers, and children’s activities at Cantigny Park in Wheaton. Free except parking.

Show about magic

August 14 - 21, 2016 (also July)

2.8 miles NW

Death and Harry Houdini is the story of America’s greatest magician, in a show that includes original music, dance, film, and magic acts at Chopin Theatre. Discount tickets $42.


August 14 & 24, 2016

15 miles SW

Watch Chicago Fire play a home game at Toyota Park.

Military block party

August 18, 2016

1 mile NW

Celebrate America’s military service members and their families with live music, games, military vehicles, and refreshments at USO Clark After Dark in River North. Donation.

Italian festival

August 18 - 21, 2016

3.5 miles SW

Festa Italiana features Italian food, music, folk dance, a meatball-eating contest, and a Sunday procession on W Taylor Street at Ashland. Donation.

Comic book convention

August 18 - 21, 2016

17 mile NW

Wizard World Chicago Comic Con is about comic books, wrestling, science fiction, fantasy, film, horror, animation, anime, manga, and card games, at the convention center in Rosemont. Discount tickets for Thursday $23.

Scrapbook Expo

August 19 - 20, 2016

27 miles NW

Scrapbookers will find classes, vendors, and crop parties at the Scrapbook Expo at Renaissance Schaumburg Convention Center.

Art on Glenwood Ave.

August 19 - 21, 2016

9 miles north

Glenwood Avenue Arts Fest (GAAF) is a Friday night Cobblestone Jam plus a weekend artists’ market with 3 stages of music in Rogers Park. Free.

Edison Park festival

August 19 - 21, 2016

14 miles NW

Edison Park Fest offers food, beer, live music, an 11 a.m. Saturday parade, a family stage, and a ticketed amusement area at 6730 N Olmsted Avenue. Free.

Noir film festival

August 19 - 25, 2016

6 miles north

Noir City screens classic films that are stylish, cynical, and melodramatic at the Music Box Theatre.

Oak Park beer tasting

August 20, 2016 (3 p.m., VIP 12:30)

11 miles west

Oak Park Micro Brew Review features tastings of 200 craft beers from 70 Midwest microbreweries and local restaurant food at 100 N Marion St. in Oak Park.

Air and water show

August 20 - 21, 2016 (10 a.m. to 3 p.m.)

2 miles north

The Chicago Air & Water Show features daredevil pilots, parachute teams, and jets flying in formation, plus water-skiing and boat jumping. See it from the waterfront near North Avenue Beach. Free.

Albany Park festival

August 20 - 21, 2016

8.7 miles NW

Albany Park World Fest offers diverse music, eclectic cuisine, global arts and crafts, and a family activity area at W. Lawrence Ave. and N. Kimball Ave. Donation.

Oak Park art festival

August 20 - 21, 2016

9.1 miles west

The Arts & Crafts Show at Oak Park Ave. & Lake St. features 125 artists in Scoville Park. Free.

Holistic expo

August 20 - 21, 2016

16 miles NW

Body Mind Spirit Expo has 110 exhibitors and 72 presentations about alternative health and psychic powers at North Shore Center for the Performing Arts in Skokie.

Oak Brook art fair

August 20 - 21, 2016

19 miles west

The Fine Art Festival features art, artists in action, and music in Oak Brook. Repeats in May. Free.

Japanese garden festival

August 20 - 21, 2016 (10 a.m. to 2 p.m.)

24 miles north

Malott Japanese Garden Summer Festival has a tea ceremony, stories, drumming, and harp playing at Chicago Botanic Garden in Glencoe. Free except parking.

Dance festival

August 23 - 27, 2016

Downtown Chicago

See ballet, dance, and dance films in multiple venues at Chicago Dancing Festival. Free.

Concert: Counting Crows

August 24, 2016 (6:45 p.m.)

2.4 miles SE

Counting Crows (Mr. Jones) and Rob Thomas (Lonely No More) perform at FirstMerit Bank Pavilion at Northerly Island. Discount tickets $34.

Turkish fest

August 24 - 27, 2016

0.7 miles SW

Experience the art, music, dance, and cuisine of Turkey at the free Chicago Turkish Festival at Daley Plaza, 50 W Washington St. Free entry.

Funny musical

August 24 - Oct. 16, 2016

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 $30.

Beer at the zoo

August 26 - 27, 2016

14 miles SW

Enjoy 60 craft beers, live music, a silent auction, and animals at Zoo Brew at Brookfield Zoo for age 21+.

Taste of Greece

August 26 - 28, 2016 (12 to 11 p.m.)

2 miles SW

Enjoy Greek restaurant food, traditional music and dance, handcrafts, and family games at Taste of Greektown at 400 S Halsted Street. Free.

Skokie festival

August 26 - 28, 2016

14 miles NW

Skokie’s Backlot Bash has 15 hours of live music, a carnival, classic car show, free classic movies, kids’ run & 5K, and food and beer vendors. Free.

Street fair in DeKalb

August 26 - 28, 2016

65 miles west

Corn Fest has vendors, a carnival, a family-friendly beer garden and concert area (adults $5), a Saturday car show, and kids’ art activities on the weekend. Free.

Beverage tasting

August 27 - 28, 2016 (1 to 10 p.m.)

2.1 miles south

Get 15 tastes of beer and wine (2 to 6 p.m.) and purchase cocktails at Motor Row Craft Beer & Wine Festival, with crafts, vintage cars, and live music on Michigan Avenue at Cermak. Donation.

Bucktown arts festival

August 27 - 28, 2016

5 miles NW

Bucktown Arts Fest is an arts celebration that showcases 190 artists, musicians, dancers, poets, and performers at N Oakley and Lyndale. Free.

Art & food festivals

August 27 - 28, 2016

27 miles north

Top-rated Port Clinton Art Festival has 260 artists, a youth division, and kids’ art activities on Sat. & Sun. Nearby Taste of Highland Park is 5 p.m. Fri. to 6 p.m. Sun. Free.

Glen Ellyn art festival

August 27 - 28, 2016

28.7 miles west

Glen Ellyn Festival of the Arts features 80 juried artists, 12 musical acts, children’s activities, and food at Lake Ellyn Park.

Circus in the park

August 27 - Oct. 16, 2016

Chicago locations

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


August 28, 2016

1.5 miles south

The Chicago Triathlon follows a picturesque course along Lake Michigan, beginning at Monroe Harbor.

Art fair

August 28, 2016

26 miles NW

See original works from 100 juried artists at A Walk in the Park - Summer Art Fair at North School Park in Arlington Heights. Free.

Feel-good musical

August 30 - Sept. 4, 2016

0.5 miles SW

The Broadway show Kinky Boots, based on a true story about a shoe factory owner and a drag queen, features an inspiring and joyful score by Cyndi Lauper at Oriental Theatre. Discount tickets $34 to $64.

Pop superstars

August 31, 2016 (7 p.m.)

2.4 miles SE

Hear five famous females from the X Factor when Fifth Harmony performs with JoJo at FirstMerit Bank Pavilion at Northerly Island. Discount tickets $20.

Fringe theater festival

August 31 - Sept. 11, 2016

10 miles NW

See 50 weird and wonderful shows by local theater groups at Chicago Fringe Festival in Jefferson Park.
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© August 2016 calendar of events in Chicago, IL. Best events, fairs, festivals, and things to do in Chicago, Illinois.