Chicago events September 2019. Things to do in Chicago.

Best events for 12 months

Chicago events September 2019

Chicago Jazz Festival

September 1, 2019
0.5 miles south
Chicago Jazz Festival is a free event held in Millennium Park (see a list of what you can bring). Also see the list of neighborhood concerts from Aug. 23 to 29.

Labor Day festival

September 1, 2019
(1 to 10 p.m.)
18.6 miles south
Friends of Labor Festival promises “plenty of food, music, a kids’ activity area, community booths, and more” at Calumet Park. Free.

Festival of Lebanon

September 1, 2019
24 miles west
Enjoy Lebanese food, beer, wine, music, folk dancing, and kids’ activities at the Lebanese Festival at Our Lady of Lebanon Maronite Catholic Church in Lombard. Children younger than age 5 are free.

Music on the lake

September 1 - 2, 2019
(2 to 8 p.m.)
1 mile east
Hear live music at Live on the Lake in the beer garden at Navy Pier. Free for all ages.

African festival

September 1 - 2, 2019
7.9 miles south
African Festival of the Arts celebrates African art, crafts, drumming, food, and entertainment “in a simulated African village” at Washington Park. Cost.

Polish festival

September 1 - 2, 2019
10 miles NW
Taste of Polonia has 35 bands on four stages, food (polska kielbasa, potato pancakes, pierogi, and beer), vendors, and carnival rides in Jefferson Park.

Schaumburg festival

September 1 - 2, 2019
33 miles NW
Septemberfest includes an arts & crafts show, a carnival, lots of live music, a beer & wine tent, the Taste of Schaumburg (Sat. & Sun.), fireworks (Sun. or if rain Mon.), and a parade (Mon. 10 a.m. on Summit Drive) at Robert O. Atcher Municipal Center. No pets. Free.

Naperville festival & parade

September 1 - 2, 2019
34 miles west
Naperville Last Fling is a family event with carnival rides, a children’s area, two stages of entertainment, food vendors, and a Labor Day Parade (Monday 10 a.m.) at Naperville’s Riverwalk Park.

Renaissance fair

September 1 - 2, 2019
49 miles north
Watch knights joust, shop in an artisan market, mingle with costumed minstrels, play games, and attend shows at Bristol Renaissance Faire in 16th century England (also known as Kenosha, WI). Open weekends and Labor Day.

Ravinia music festival

September 1 - 15, 2019
23 miles north
See nationally known performers at Ravinia Festival, billed as America’s oldest outdoor music festival at Ravinia Park in Highland Park.

Circus in the park

September 1 - Oct. 20, 2019
Chicago locations
Midnight Circus in the Parks is a series of shows at nine parks, which is perfect for families.

Free science museum

September 3 - 26, 2019
8 miles south
Show Illinois ID to enter the Museum of Science and Industry free during Free Days in February and September. The museum is not free on Fridays, Saturdays, or Sundays.

Movies in the Parks

September 3 - 27, 2019
Chicago locations
Watch 130 Movies in the Parks, beginning at dusk. Dates may change depending on the weather. Free.

Small-town fair

September 4 - 8, 2019
62 miles SW
Head to the Sandwich Fair for carnival games, fair food, grandstand shows, and farm animals.

Wine tasting

September 5, 2019
(5:30 to 8 p.m.)
1 mile north
Around the World Wine Tasting is a walkabout tasting of 200 international wines with light appetizers at The Drake Hotel for age 21+.

Mexican independence festival

September 6 - 8, 2019
9.6 miles SW
Thousands attend Festival de La Villita for authentic Mexican cuisine, music, artisans, carnival rides, and family entertainment at 26th Street and Kostner Avenue. Free.

Northwest neighborhood festival

September 6 - 8, 2019
11.8 miles NW
Hear retro tunes at Throwback Music Fest, which also offers arts & crafts, kids’ activities, beverage tents, and classic cars on display Sunday in Gladstone Park on Milwaukee Avenue (from Elston to Peterson). Donation $5.

Noir film festival

September 6 - 12, 2019
6 miles north
Noir City screens classic films that are stylish, cynical, and melodramatic at the Music Box Theatre.

Charity cocktail party

September 7, 2019
(8 to 11 p.m.)
1.2 miles south
A $115 ticket to Illuminate includes food, an open bar, entertainment, and a silent disco experience at Venue Six10. You are welcome to wear blue cocktail attire and a masquerade mask.

Dance music

September 7, 2019
(3 to 10 p.m.)
3.8 miles north
Birdhouse Festival features Claude VonStroke, Paul Johnson, Walker & Royce, Mason Maynard, Chambray, DJ Deeon, and VNSSA on the shores of Lake Michigan at Lakefront Green, with street fair games and food trucks for age 18+.

Outdoor games for adults

September 7, 2019
(11 a.m. to 4 p.m.)
5.8 miles north
A ticket to Chicago Field Day includes unlimited beer, DJ music, a costume contest, and fun childhood games for your team of 6 to 8 people (tug-o-war, relay races, a scavenger hunt) at Sydney R. Marovitz Golf Course.

Forest Park Ribfest

September 7, 2019
(1 to 10 p.m.)
11 miles west
Hear live music, eat great food, visit the beverage tent, and enjoy children’s activities at Ribfest at 7824 Madison Street in Forest Park. Free admission.

Beer & wine tasting

September 7, 2019
(3 to 6:30 p.m.)
12 miles NW
Taste 50 beers or wines with hors d’oeuvres outdoors, and bid in the silent auction indoors during Stems and Steins at Norwood Park Historical Society for age 21+.

Waukegan air show

September 7, 2019
41 miles north
Bring your own chairs to watch planes on the ground and in the air at Northern Illinois Airshow, with food and non-alcoholic drinks for sale. Wear sunscreen. No pets. Children age 12 and younger are free.

Craft fair

September 7 - 8, 2019
3.5 miles NW
Shop from hundreds of artisans and chefs at the Renegade Craft Fair in Wicker Park on Division Street (from Ashland to Damen). Free.

Ukrainian festival

September 7 - 8, 2019
3.6 miles west
Ukrainian Village Fest offers folk dancers, music, food (potato pancakes, borsch, pierogi, kabobs, blintzes), beer, wine, and a kids’ area on Superior Street (from Oakley to Leavitt).

Caribbean food festival

September 7 - 8, 2019
(noon to 9:30 p.m.)
4.1 miles south
Jerk, Seafood, and Vegan Festival promises live music, dancing, arts & crafts, outdoor games, and food (jerk chicken, vegan, soul, BBQ, and desserts) at Park 540. Free admission for children younger than age 12.

Family festival

September 7 - 8, 2019
11 miles south
The 79th Street Renaissance Festival in Auburn Gresham is a community festival with entertainment, food vendors, a marketplace, and a kids’ corner on 79th Street (from Racine to Loomis). Free.

Oak Brook art fair

September 7 - 8, 2019
19 miles west
The Fine Art Festival features artwork, artists in action, and music in Oak Brook. Repeats in May. Free.

Small art fair

September 7 - 8, 2019
42.3 miles NW
Shop from 40 artists at Deer Park Art Show, with live music, kids’ activities, and food vendors outdoors at Deer Park Town Center. Free admission and parking.

Race at the zoo

September 8, 2019
14 miles SW
ZooRunRun includes a timed 5K and a 1-mile kids’ dash entirely within Brookfield Zoo.

British car show

September 8, 2019
(9 a.m. to 3 p.m.)
29.5 miles NW
See British cars and motorcycles on display at the British Car Festival, with bagpipes, an Irish dance team, and food for sale at Harper College in Palatine. No pets or smoking. Free.

Scandinavian festival

September 8, 2019
46 miles NW
Enjoy food, crafts, and entertainment from Northern Europe at Scandinavian Day Festival at beautiful Vasa Park in South Elgin. Children age 12 and younger free.

Kite festival

September 8, 2019
(11 a.m. to 4 p.m.)
68 miles west
Bring sunscreen and a chair or blanket to DeKalb Kite Fest to watch giant inflatable kites, dancing kites, and fighting kites, with free kite making and a candy drop for kids, plus kites for sale at Lucinda Avenue and Kishwaukee Drive in DeKalb. Free except parking.

Mexican parades

September 8 - 15, 2019
Chicago locations
Celebrate Mexico’s separation from Spain at these Mexican Independence Day parades, with colorful floats, mariachi bands, and street dancing. Free.

Oktoberfest in Glendale Heights

September 12 - 22, 2019
32 miles west
Glendale Heights Oktoberfest promises good music, a great beer selection, authentic German food, and friendly service at Camera Park in Glendale Heights.

Beer tasting on the river

September 13, 2019
(5:30 to 8:30 p.m.)
0.4 miles east
A $20 ticket to Chicago Friday Night Flights includes 10 tastes (3 ounces) from among 20 breweries, with live music and food for sale at 305 Chicago Riverwalk.

Whisky tasting

September 13, 2019
1.9 miles west
The Whisky Extravaganza includes unlimited tastes of more than 100 whiskies, culinary pairings, and master classes at Revel Fulton Market for age 21+.

Rock festival

September 13 - 15, 2019
7 miles SW
Riot Fest is a huge outdoor punk, rock, and alternative music festival on multiple stages at Douglas Park for all ages. It has food vendors, bars, and carnival rides. Gates open at 11 a.m. Read the section on this page called Is it allowed at Riot Fest?

World Music Festival

September 13 - 29, 2019
Chicago locations
World Music Festival Chicago features artists and ensembles from all over the world. No shows on Monday & Tuesday. Free.

Aurora haunted house

September 13 - Nov. 2, 2019
38 miles west
Basement of the Dead has creative special effects and entertaining characters. Recommended for age 13+. Expect lines. See schedule.

Halloween farm

September 13 - Nov. 3, 2019
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 enjoy kids’ rides, pig races, a pumpkin chucker, and a petting zoo.

Free talent show

September 14, 2019
(11 a.m. to 2 p.m.)
1.1 miles east
Watch “amazing music, dance, magic, comedy, and more by some of the city’s most talented performers with and without disabilities” at Center Stage for Access and Inclusion south of the ferris wheel on Navy Pier. Free.

Wine tasting

September 14, 2019
1.7 miles west
A ticket to Wine Riot includes unlimited tastes of hundreds of wines at Revel Fulton Market for age 21+.

Dessert festival

September 14, 2019
(6:30 to 11 p.m.)
2.5 miles north
A ticket to Dessert Fest includes dessert tastings, interactive games, entertainment, and access to some of the animal areas at Lincoln Park Zoo for all ages. Champagne, beer, and wine will be sold.

White Sox beer festival

September 14, 2019
(1 p.m., VIP noon)
5.2 miles south
Sample beers from 40 local breweries in the outfield concourse during ChiSox Craft Beer Fest, with food concessions, games, and live entertainment at Guaranteed Rate Field for age 21+. Free parking. No pets.

Beer festival

September 14, 2019
(1 p.m., VIP noon)
20 miles west
A $50 ticket to Elmhurst Craft Beer Fest includes 18 samples from among 100 beers and ciders, with live music and snacks on the grounds of Elmhurst History Museum for age 21+. No pets.

Art fair

September 14 - 15, 2019
1.5 miles south
Printer’s Row Art Fest features “juried artists, live music, and great food” near Printer’s Row Park, on Dearborn Street (from Polk to Harrison). Free.

Lakeview East art festival

September 14 - 15, 2019
5 miles north
Meet 150 juried artists selling paintings, sculpture, photography, furniture, and jewelry at Lakeview East Festival of the Arts, which has a children’s area and music on two stages along N. Broadway (from Belmont to Roscoe). Donation.

Bourbon & BBQ

September 14 - 15 2019
6.6 miles NW
Chicago Bourbon & Barbecue Fest has live music, barbecue kitchens, a bourbon tasting pavilion, and vendor booths filling the streets at Damen Avenue & Roscoe Street. Donation $5.

Ravenswood Art Walk

September 14 - 15, 2019
7 miles north
Visit 300 artists in tents and shops along Ravenswood Avenue during Ravenswood ArtWalk and RAW Street Fest, which has music stages, food trucks, a beer garden, artists, and kids’ activities. Donation.

Butterfly festival

September 15, 2019
(11 a.m. to 4:30 p.m.)
22 miles SW
The Monarch Butterfly Festival has a butterfly tent, live animals, an arts & crafts fair, children’s activities, and food vendors at Lake Katherine Nature Center in Palos Heights. Free for age 2 and younger.

Fall Dinner Crawl

September 17, 2019
(6 to 9 p.m.)
4 miles NW
Buy tickets for one of the routes, and then get samples from restaurants along the way during Fall Dinner Crawl in Wicker Park and Bucktown.

Art for seniors

September 18, 2019
(9:30 a.m. to 2 p.m.)
1 mile south
Reflections offers lectures, demonstrations, and free entry for seniors and adult chaperones at Art Institute of Chicago, 159 E. Monroe Street. Buy optional lunch reservations online.

Dog fashion show

September 19, 2019
(6:30 to 9:30 p.m.)
0.7 miles north
A $200 ticket to Haute Dog includes cocktails, hors d’oeuvres, a fall fashion show featuring dogs and their owners, a silent auction, a speaker, and a look at canine companion puppies at The Peninsula. No pets.

Art in Andersonville

September 19 - 22, 2019
8 miles north
Andersonville Arts Week includes three major events.

Gay film festival

September 19 - 29, 2019
Chicago locations
Reeling is Chicago’s LGBTQ international film festival.

Oak Park “Oaktoberfest”

September 20 - 21, 2019
9 miles west
Enjoy live music, craft beer, wine, local restaurant food, and a kids’ root beer garden (Sat. noon to 5 p.m.) at Oaktoberfest in Oak Park. Bring cash. Free.

Japanese festival in Lincoln Park

September 20 - 22, 2019
2.9 miles NW
Experience authentic Japanese festival food, beverages (tea, beer, sake), and cultural performances (Taiko drumming, calligraphy, martial arts, ink painting) at Chicago Japanese Matsuri in the plaza of NewCity at 1457 N. Halsted Street.

Vampire festival

September 20 - 22, 2019
16.1 miles NW
VampCon has celebrity guests, vendors, a vampire ball, an escape room, movies, and a costume contest at Hyatt Regency O’Hare in Rosemont.

Craft expo

September 20 - 22, 2019
24 miles north
Shop from 140 artisans exhibiting one-of-a-kind “museum quality artwork” at American Craft Exposition at Chicago Botanic Garden.

Free museum day

September 21, 2019
Get a free ticket that allows two people to visit one of the many museums participating in Museum Day Live.

Festival of young artists

September 21, 2019
0.5 miles south
YAS Fest (Youth Arts Showcase) offers a wide range of dance performances, live and DJ music, theater shows, and visual art at Millennium Park. Free.

Underground art show

September 21, 2019
(8 p.m.)
3 miles south
The Chicago Pancakes & Booze Art Show is a traveling exhibition by 100 artists, with free pancakes, DJ music, live body painting, and a bar at Reggie’s Chicago for age 21+. Pay cash at the door or buy a line-jumper ticket online.

Small art fair

September 21, 2019
16 miles NW
Fall Arts & Crafts Adventure is a friendly juried show at Hodges Park in Park Ridge. Repeats in May. Free.

Lisle Ale Fest

September 21, 2019
(4 to 8 p.m.)
27 miles west
Lisle Ale Fest has 80 American craft beers (including Oktoberfest and pumpkin), live music, and local food for age 21+. No pets.

Taco festival

September 21 - 22, 2019
5 miles north
Try tacos from a dozen restaurants and vote for the best, drink beer, hear live music on two stages, visit the kids’ area, and watch Mexican wrestlers at Lakeview Taco Fest on Southport Avenue (from Addison to Roscoe). Donation $10.

Food truck festival

September 21 - 22, 2019
10.3 miles NW
Chicago Food Truck Fest brings “up to 40” food trucks, beer, wine, sangria, and live music to LaBagh Woods.

Englewood Jazz Festival

September 21 - 22, 2019
(12 to 6 p.m.)
11 miles south
Englewood Jazz Festival features a dozen performances over two days in Hamilton Park (in the auditorium if it rains). Free.

Food truck festival

September 21 - 22, 2019
15.8 miles NW
Chicago Food Truck Fall Festival promises 40 food trucks, live bands, DJs, beer, wine, and sangria at Saint Paul’s Woods in Morton Grove. General admission tickets are free on their website.

North Shore art festival

September 21 - 22, 2019
17 miles north
Northshore Affordable Art Sale features juried artists, live music, art projects for kids, and food outdoors at Westfield Old Orchard Mall in Skokie. Free.

Naperville art fair

September 21 - 22, 2019
32 miles west
Riverwalk Fine Art Fair is a juried fair with 140 artists at a scenic park in downtown Naperville. Free.

Pow wow in Naperville

September 21 - 22, 2019
33 miles west
Experience Native American culture through dance, drumming, art, and storytelling at the Harvest Pow Wow, which also has archery, birds of prey, food booths, crafts for sale, and a kids’ corner at Naper Settlement.

Artisan market

September 22, 2019
1.9 miles west
Shop from 100 independent vendors of food, fashion, art, and home goods at the Chicago Artisan Market at Morgan Manufacturing, including a kids’ zone. Children age 11 and younger are free. Held in multiple months.

World peace ceremony

September 23, 2019
(12 to 1 p.m.)
0.7 miles SW
Gather in Daley Plaza to hear live music, see performances, listen to speakers, and watch a ceremony calling out the name of every country with its flag on Peace Day. Free.

Chicago Gourmet

September 24 - 29, 2019
0.5 mile south
Chicago Gourmet offers premium food and wine events, with the main events on Saturday and Sunday showcasing hundreds of restaurant chefs, vintners, and breweries in Millennium Park.

Spirits tasting

September 25, 2019
(6:30 p.m., VIP 5 p.m.)
1.2 miles south
Sample handcrafted spirits and meet the distillers at Chicago Independent Spirits Expo at Hilton Chicago for age 21+.

Arts festival

September 25 - 29, 2019
8.7 miles NW
Mosaic Arts Fest “​is a weekend-long exploration of arts & culture of the Northwest Side” including a party, a film, exhibitions, storytelling, talks, music, dance, and theater. Many of the events are free.

Small-town Oktoberfest

September 26 - 29, 2019
51 miles south
Manteno Oktoberfest has a beer tent, food, a kids’ carnival, live music, a garage sale (Fri. to Sun.), a pet parade (Fri. 6 p.m.), and a lighted parade (Sat. 6:30 p.m.). Schedule. Free.

Hamburger party

September 27, 2019
0.5 miles south
Eat gourmet burgers with beer, wine, and spirits when top chefs compete at the $145 Hamburger Hop on the rooftop of Harris Theater, followed at 9 p.m. by a $59 Late Night Gourmet after party at 59 W. Hubbard Street. Both events age 21+.

A taste of Korea

September 27, 2019
(6 p.m.)
7.5 miles north
A ticket to Eat, Drink, Korea gets you “an evening of phenomenal food [made by acclaimed chefs], adult beverages, and music” at Ravenswood Event Center to support North Korean refugees living in China.

Art fair indoors

September 27 - 28, 2019
3.2 miles NW
West Town Art Walk includes visual art, music, and fashion in restaurants and shops along W. Chicago Avenue (from N. Milwaukee Ave. to N. Western Ave.). Free.

St. Alphonsus Oktoberfest

September 27 - 29, 2019
5.5 miles NW
Enjoy beer, bratwurst, pretzels, live music, and arts & crafts at Oktoberfest Chicago at St. Alphonsus Church for $10 donation ($5 Sunday).
  • Kinderfest for kids: Sat. & Sun. (12 - 4 p.m.)
  • Ticketed craft beer tasting in the church Fri. & Sat.

Monster trucks

September 27 - 29, 2019
18 mile NW
Big trucks with big wheels create big noise and excitement at Monster Jam in Rosemont’s Allstate Arena.

Beer tasting

September 28, 2019
(4 p.m., VIP 3 p.m.)
5 miles SW
A ticket to BeerHoptacular gets you 20 tickets to taste 3 ounces from among 100 American craft beers, with live music and food trucks in the helicopter hanger at Vertiport Chicago for age 21+. No pets.

Short films

September 28, 2019
6.5 miles NW
A ticket to Shortcut 100 International Film Festival includes a 5 p.m. reception followed by a dozen “quality independent short films” from 6 to 9 p.m. at The Logan Theatre.

Beer in the Woods

September 28, 2019
(2 p.m., VIP 1 p.m.)
10.3 miles NW
A ticket to Beer in the Woods includes tastings from dozens of breweries and cideries, live animal presentations, DJ music, bird walks, home brewing demos, local food trucks, and activities for both beer and nature enthusiasts at LaBagh Woods. Children age 4 and younger are free. No dogs.

Riverside beer festival & house tour

September 28, 2019
14.9 miles SW
Sample offerings from local craft breweries, cideries, and distilleries at HopStop Craft Beer Festival, which also has children’s art activities, live music, and food trucks at Riverside Train Station from 4 to 7 p.m. With a ticket to House Walk: Masterworks, you can visit houses by famous architects from 12 to 4 p.m.

Beer festival

September 28, 2019
22 miles west
Villa Park Brewfest offers “exceptional beers from local & regional craft breweries as well as tasty food truck cuisine” at Cortesi Veterans Memorial Park, age 21+.

Dutch festival

September 28, 2019
24 miles SW
Elim Dutch Festival features Dutch food, dance, music, and vendors, plus a kids’ carnival, petting zoo, and train rides at Elim Christian Services in Palos Heights. Free admission.

Edgewater art fair

September 28 - 29, 2019
8 miles north
Edgewater Arts Festival features 100 local artists, 28 bands, food vendors, and a beer garden on Granville Avenue. Donation.

Hyde Park jazz

September 28 - 29, 2019
8 miles south
Hear jazz performances by 38 top artists indoors and outdoors at the Hyde Park Jazz Festival. Donation.

Oktoberfest in Roselle

September 28 - 29, 2019
30 miles west
Oktoberfest at Lynfred Winery includes grape stomping, cork tossing, a lederhosen contest, wine for sale, roasted pork on the menu, and crowds. Free for children age 13 and younger.

Intense haunted house

September 28 - Nov. 2, 2019
45 miles NW
Realm of Terror Haunted House promises “the craziest, most intense, extreme Halloween experience” located halfway to Milwaukee in Round Lake Beach. Beverages for sale at the bar. See schedule.

Dumpling tasting

September 29, 2019
(12 to 7 p.m.)
0.5 miles south
World Dumpling Fest features “delicious dumplings from ethnic restaurants in and around Chicago, interactive craft tables, cultural art vendors, and exciting global music acts” in Polk Brothers Park at Navy Pier. Free admission, with tasting tickets for sale.

Half marathon & 5K

September 29, 2019
9 miles south
The Chicago Half Marathon begins in Jackson Park and goes along scenic Lake Shore Drive. Free to watch.

Tour historic homes

September 29, 2019
(12 to 5 p.m.)
11.2 miles west
Walk, bike, or drive between houses on the Historic Berwyn’s Bungalow Tour to see how older houses were preserved and adapted for modern living, beginning at Berwyn Historical Society.

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