FALL FESTIVAL GUIDE 2025
AUGUST
August 29, September 5, 12, 19, 26, October 3
CHI FOOD TRUCK FESTIVAL
Daley Plaza, 50 W. Washington 11 am-3 pm
Every Friday starting May 16, the Chicago Department of Business Affairs and Consumer Protection (BACP) hosts a rotating selection of food trucks from around the city to support small businesses and bring diverse lunch options to the Loop. Enjoy comforting classics, tasty treats and fusion cuisine, all in one location. Follow BACP on Twitter, FB and Instagram.
SEPTEMBER
September 5-7
RETRO ON ROSCOE
Roscoe, from Damen to Leavitt Fri 5-10 pm, Sat Noon-10 pm, Sun Noon-8 pm
Stroll down Roscoe Street and soak up the nostalgic vibes, from decades-spanning hits on multiple stages to rows of rare and restored classic cars gleaming in the sun. Indulge in delicious eats from top local vendors, sip on craft beer, taste wine & spirits, let the kids enjoy the family-friendly games and activities in the dedicated children’s area. Tribute bands TBA. Beneficiary is Roscoe Village Neighbors. chicagoevents. com/event/retro-on-roscoe/
September 5-7
EDGEWATER MUSIC FEST
Broadway & Thorndale, steps from the CTA Red Line
Ric Wilson, Foxy Shazam, Sludgeworth and 25+ more artists TBA; 80 vendors; food; drinks; kids zone. $10 suggested donation benefits the Edgewater Chamber of Commerce, producers of the fest. www.edgewater.org/
September 5-7
TASTE OF CHICAGO
Grant Park, security entrances Jackson/Columbus, Ida B. Wells/Michigan, Columbus/Balbo Noon-9 p.m.
Over 60 restaurants and food trucks, from every cuisine throughout Chicago. All food and beverage vendors take credit cards, few take cash. Unlike in previous years, no Taste tickets will be sold.
September
5-7
THROWBACK
MUSIC FEST
6030 N. Milwaukee Ave. Fri 4-10:30 pm, Sat 10 am-10:30 pm, Sun 11 am-8 pm
A blast from the past comes to Gladstone Park, with live tribute bands, a classic car show, food vendors, a carnival, an 11:30 a.m. Sunday First Responders Heroes celebration, and more. Music lineup includes LP Vinyl (Journey Tribute), The PriSSillas, 7th Heaven, Northside, The Stray Dogs Band, The You Know Who Band, Bon Journeyed, The St. Patrick’s High School band, and more. Other highlights include a 10 a.m. Saturday pet parade and costume contest and an 11 a.m. Sunday "Miss Throwback" contest with styles of the 1940s-60s open to those 21+ (no burlesque). $5 donation; proceeds to Gladstone Park Chamber Scholarship Fund. throwbackmusicfest.com
September
6
FESTIVAL DE LA MONARCA
Kosciuszko Park, 800 W. 151st St., East Chicago, IN Sat 11 am-5 pm
Each fall as temperatures begin to drop in North America, orange-andblack monarch butterflies fill the skies. They travel up to 100 miles daily as they make their way south to the Oyamel fir forests of Mexico, journeying up to 3,000 miles, connecting Canadian, U.S. and Mexican communities, and inspiring us with their endurance. Enjoy music, art and food with the Nature Conservancy, Audubon Great Lakes, The Field Museum, Save the Dunes and oth ers. FREE. www.nature.org/en-us/ get-involved/how-to-help/events/ indiana-monarch-festival-2025/
September
6-7
PRINTERS ROW LIT FEST
On Dearborn from Polk St. to Ida B Wells St. Sat-Sun 10 am-6 pm
Largest free literary festival in the Midwest returns to Printers’ Row, headlined by poet, short story writer, novelist, and essayist Sandra Cisneros (“The House on Mango Street”) whose “Woman Without Shame” is her first new collection of poetry in 28 years.
Re tro On Roscoe
Indoor and outdoor stages with discussions and readings by prominent authors, alongside 100+ booksellers and a literary programs for adults and children. printersrowlitfest.org
September 6-7
MIRACLE IN MUNDELEIN
RISE Mundelein, 1255 Armor Blvd, Mundelein
This 21+ only concert allows cannabis consumption on the grounds. Headliners include Damien & Stephen Marley, Umphrey’s McGee, De la Soul, Dark Star Orchestra. Tickets $64+ at themiracleconcert.com
September 6-7
RENEGADE CRAFT FAIR
On Division St. between Damen and Ashland Aves. Sat-Sun 11 am-7 pm
Renegade offers an answer for conscious consumerism, sustainability, and an accessible creative economy with 400+ craft designers and makers of clothing, furniture, jewelry, ceramics, beauty and food products. Entry is a $5 suggested donation. renegadecraft.com
September
7
GROWING HOPE
CONCERT
Gallagher Way, 3635 N. Clark St. Sun 7-8:30 pm
3rd annual concert featuring singer/ songwriter and founding member of the Grammy Award-winning band Wilco, Jeff Tweedy. JCC Chicago’s Growing Hope is a call to action, a mindset, and movement designed to combat a growing crisis of hopelessness, anxiety, and fear by engaging our community, and youth in particular, as upstanders in their communities. It’s rooted in the Jewish spirit of Tikkun Olam (repairing our world). FREE, but registration required at www.gallagherway.com/ events/jcc-chicago-growing-hopeconcert-2025/2025-09-07
September 11 & 13-14
OAK PARK IL FILM FESTIVAL
Lake Theater, 1022 Lake St.; & Madison Street Theater, 1010 Madison St., Oak Park “Snap out of it!” with a special screening of “Moonstruck” and tribute to John Mahoney opening night at the Lake Theater (1022 Lake St.) and then two more nights at the Madison Theater (1010 Madison St.). Second-year fest showcases films with a unique Oak Park connection—through content, cast, crew, or setting. www.opliff.org
September 12-13
NORWOOD PARK FALL FEST
On Northwest Hwy bet. Raven & Newark, and Centennial Park Fri 4-10 pm, Sat Noon-10 pm Rock, country and blues music from all eras; selection of beers, wines and seltzers; kids zone; local merchandise at Norwood Park Chamber fundraiser. $5 donation goes toward local beautification. npfallfest.org
September
13
FAR SOUTH FOOD TRUCK FEST
Maple Park Marketplace, 821 W. 115th St. Sat 1-5 pm
Eight featured food trucks including Whadda Jerk, Harold’s Chicken 55 and Tacos 606, plus dessert from Rainbow Cone, with more TBA. Live music provided by J.ARTiz and Mo’ Soul. Food is included with free registration at farsouthcdc.org/festivals Far South Community Development Corporation is redeveloping this shopping plaza as part of its initiative to repurpose nearly 1 million square feet of blighted community areas into thriving community anchors.
September
13
BLACK WALL STREET CHICAGO FESTIVAL
63rd Street Commercial Corridor (63rd & Cottage Grove) 11 am-7 pm
A vibrant celebration of culture, commerce, creativity, and community. This year’s theme, "A Tribute to Our Youth," honors the next generation of leaders and entrepreneurs by providing spaces for inspiration, learning, and empowerment. Activities include an art and history walk celebrating the legacy of Black Wall Street in Tulsa, as well as a Black-owned business marketplace, food court, youth entrepreneur zone and university row to help youth plan their futures.
September 13-14
RAVENSWOOD ART WALK
Ravenswood Industrial Corridor, Irving to Lawrence Sat-Sun, 11 am-6 pm
Open studios and galleries, pop-up performances and activations, and an outdoor arts market featuring 60+ local makers, two stages of live music, a pop-up beer garden, kids activities, food trucks (at Berteau), and more. ravenswoodchicago. org/signature-events/ravenswoodartwalk/
Lakeview East Festival of the Arts
September 13-14
LAKEVIEW EAST
FESTIVAL OF THE ARTS
Broadway, Belmont to Hawthorne 11 am-7 pm both days, music until 10 pm Sat
120+ juried artists, featuring paintings, sculpture, photography, furniture, jewelry and more, for sale in a wide range of prices. Live demonstrations, live music on 2 stages, (charlie otto + his gear, Simple Remedy, Nelson Street Revival, Shadowfields, Todd Allison & The Kind Force, Mr. Blotto, Fox Crossing Stringband, Redbud Park, Robert Rolfe Fedderson), local cuisine, family activities and a garden oasis. $5 donation to Lakeview East Chamber, producers of the fest. lakevieweastfestivalofthearts.com
September 13-14
EL GRITO AT GRANT PARK
Butler Field, Grant Park (LSD @ Monroe)
Sat-Sun 2-10 pm
“El Grito” was the 1810 cry for independence, which will be repeated in an official ceremony led by the Consul General of Mexico. Celebration of Mexican Independence Day features live music, authentic Mexican food, culture, art and an artisan mercado. Tickets $40+ at elgritochicago.com
September 14
RUN FOR THE PARKS 5K RUN, WALK, OR ROLL
3100 S. Lake Shore Drive
Sun 9 am-Noon
In support of the Chicago Parks Foundation, Run in the Parks presents a timed 5K run along the Lakefront Trail, 1-mile guided walk in Burnham Park, Kids’ Dash, post-race pancake party. Entry is $40 for the 5K; $25 for nature walk; $10 for Kids’ Dash. www.chicagoparksfoundation. org/run
September
14
ANNUAL 26TH
STREET MEXICAN INDEPENDENCE DAY PARADE
26th Street., from Albany to Kostner Aves. Sun Noon-3 pm
The 54th annual parade highlights Mexican cultural traditions, from Quinceañeras to the captivating rhythms of Mexican folkloric dancing and the skillful artistry of Charrería equestrians, on the 1.6-mile course up 26th Street. Presented by the Little Village Chamber of Commerce.
September 14-21
CHICAGO SOUTH ASIAN FILM FESTIVAL
AMC River East, 322 E. Illinois St. & The Matrix Club, 808 IL Rt. 59, Naperville CSAFF has highlighted the richness of South Asian cinema and its impact on the global film industry for 16 years. www.csaff.org
September
17-21
CHICAGO
UNDERGROUND FILM FESTIVAL
CUFF seeks films that break rules, take risks, and confront audiences. The world’s longest-running underground film festival, CUFF extends beyond screenings. It includes latenight events, music performances, and meaningful conversations. Most films screen at The Harper Theater and The Gene Siskel Film Center. cuff.org
September 18-20
ENGLEWOOD JAZZ FESTIVAL
513 W. 72nd St.
Starts 6 pm Thursday and Friday indoors; Noon-6 pm Saturday outdoors
The 26th annual festival in Hamilton Park is partially supported by a CityArts grant from the Chicago Department of Cultural Affairs and Special Events. This year, it celebrates the 60th anniversary of the Association
for the Advancement of Creative Musicians, featuring Ernest Dawkins, Adegoke Steve Colson, Renee Baker, The Young Masters, Jovia Armstrong, Isaiah Spencer, Dee Alexander and the Alexander McLean Project. englewoodjazzfestival.org
September 19
80S VS. 90S NIGHT
Lincoln Park Zoo, 2400 N. Cannon Drive 6:30-10 pm
After-hours access for age 21+ lets you sip ’n stroll while visiting 200 species, listening to live music and DJ or singing karaoke. Pop-up bars for beer, wine, canned cocktails and seltzer; food concessions. Dress in period clothing, if you like. $20+ at lpzoo.org/calendar-events. Events at Lincoln Park Zoo help it remain the nation’s only privately-managed, FREE-admission zoo in the U.S. Tickets $20+ on Eventbrite.
September 19-21
RIOT FEST & CARNIVAL
Douglass Park, 1401 S. Sacramento Drive 11:30 am-10 pm
The best of punk, rock 'n' roll, hiphop, metal and alternative. Headliners this year include blink-182, Weird Al Yankovic, Rilo Kiley, Weezer, Jack White, Dropkick Murphys, Green Day, Idles, Jawbreaker, Bad Religion. One-day passes $125+; 2-day $230+, 3-day $340+ at riotfest.org
September 19 –28
REELING:
THE
CHICAGO LGBTQ+ INTERNATIONAL FILM FESTIVAL
Landmark Century Centre Cinema, 2828 N. Clark St. & Chicago Filmmakers, 1326 W. Hollywood Ave. Marking its 43rd year, Reeling is the second longest-running fest of its kind. It prides itself on showing a diversity of genres to illustrate LGBTQ+ contributions to culture, sensitizing the public to issues and counteracting stereotypes with valid portrayals. reelingfilmfest.org
September 19 – early December
DIA DE MUERTOS: WHERE THE PAST IS PRESENT
National Museum of Mexican Art, 1852 W. 19th St.
Tuesday – Sunday 10 am-5 pm; Closed Mondays and Major Holidays Life and death intertwine at this annual exhibit presented by the National Museum of Mexican Art. Popular artworks from the museum’s collection reveal the importance of death in connection, memory, and family. Admission is free, with donations encouraged to support the museum’s mission of sharing culture and art. On Day of the Dead Xicago October 25, members of the public can bring their own photos and family mementos to participate in , or family altars, outside the museum. nationalmuseumofmexicanart.org
September
20
LAKEVIEW EAST OKTOBERFEST
Murphy’s Bleachers, 3655 N. Sheffield Ave. 3:30-7:30 pm
East Lakeview Neighbors organizes a pig roast, $20,000 in silent auction items, traditional German food, beer and wine, $500 door prize with proceeds to benefit local charities. Tickets are $40 on Eventbrite.
September 20-21
HALFWAY TO ST. PATRICK’S CORNED BEEF FESTIVAL
On Jefferson St., Roosevelt to Grenshaw Sat 11 am-10 pm, Sun 11 am-6 pm Irish tradition at Manny’s Deli! Besides corned beef, slow-cooked to perfection and served with all the classic fixings, savor potato pancakes, cabbage slaw, and more; enjoy Irish music and dancers; games for little leprechauns; green drinks and desserts. Entertainers TBA. chicagoevents.com/event/st-patricks-corned-beef-festival/
September
21
SENSORY-FRIENDLY ZOO
Lincoln Park Zoo, 2400 N. Cannon Drive Sun 8-10 am
Before the zoo opens to the public, guests of all ages, disabilities or chronic illness can experience the grounds in a comfortable, inclusive environment. Modifications include limited capacity and muted attractions such as the Endangered Species Carousel and Lionel Train Adventure. Not all animal buildings may be open. Free event requires advance registration at tickets.lpzoo. org/events
September
21
CLINK WINE & SPIRITS FESTIVAL
Morgan Manufacturing, 401 N. Morgan St. Sun 3-8 pm
Created by the nonprofit Sip & Empower Foundation to address the lack of BIPOC (Black, Indigenous, and People of Color) entrepreneurs. Less than 1% of négociants (wine merchants) are Black women. The barriers to entry are significant: lack of access to capital, limited industry knowledge, systemic exclusion from distribution networks, and few mentorship opportunities. $125 on Eventbrite.
Riot Fest
September 21
BRYN MAWR BLOCK PARTY
Bryn Mawr, Kimball to Sawyer 10 am-6 pm
Stamp your “passport” with food from around the world ’til 5:30 pm; wander the community market; play in the inflatables or bubble balls; get your face painted. Entertainers include Robby Celestin Project, Korean Performing Arts Institute, Soul Daddy, School of Rock Andersonville, NCP Varsity Dance Team and more. Raffle for gift cards to local restaurants. Free entry, donations encouraged. Sponsor is the HollywoodNorth Park Community Association hnpca.org/blockparty
September
21 – 29
CHICAGO GOURMET
Various venues & times
From Tacos and Tequila to a North Side/South Side Hamburger showdown and brunch favorites, fest offers world-class food and beverages from renowned chefs including Art Smith, Joe Flamm, Sarah Grueneberg, Rick Bayless, Lorena Garcia, Marcos Carbajal, Stephanie Izard and Karen Akunowicz. Tickets at chicagogourmet.org
September 26-28
OKTOBERFEST CHICAGO
1429 W. Wellington Ave. Fri 5-10 pm, Sat Noon-10 pm, Sun Noon-7 pm
The iconic St. Alphonsus Church brings a slice of Bavaria to the city: live music, frothy German brews, brats and pretzels. Live Bands TBA. Admission is a $10 suggested donation Fri/Sat, $5 Sun. chicagoevents. com/event/oktoberfest-chicago
September 26-October 5
WORLD MUSIC FESTIVAL CHICAGO
78 E. Washington St., Various Venues & Times
A week of music from across the world comes to Chicago, centered at the Chicago Cultural Center. Seating is first come, first served. www.chicago.gov/city/en/depts/dca/ supp_info/wmf.html
September-October
JACK’S PUMPKIN POP-UP
1265 W. Le Moyne St.
An all-out Halloween celebration returns to Goose Island for its 7th year. Features include a real corn maze, a pumpkin patch with 10,000+ pumpkins, axe throwing, carnival games, live music, and food and drink vendors. Waitlist, timed tickets at jackspumpkinpopup.com.
September 26 – October 26
LINCOLN PARK ZOO FALL FEST
2400 N. Cannon Drive
10 a.m.-5 p.m.
FREE all-ages fest returns with live music, a pumpkin patch, s’mores, photo ops, animal enrichment and learning chats, penguin encounters. Special events include Haunted History lectures on Lincoln Park’s beginnings as a cemetery Tuesdays and Wednesdays by Adam Selzer; Sound Meditation Saturday, October 4 and Nature’s
Playground Monday, October 13.
Ticketed attractions include Endangered Species Carousel, Zoo Train Adventure, and Gorilla Trek VR Experience; $4.50 per person per ride. Pop-up food and drink vendors. www.lpzoo.org/event/fall-fest
September
27
OUT OF THE DARKNESS CHICAGOLAND WALK
601 W. Montrose Ave.
Event starts 9 am, walk begins 11 am
The American Foundation for Suicide Prevention presents a 3-mile walk to raise funding for life-saving research, education, advocacy, and support for those impacted by suicide. Virtual walk available. afsp.chicagowalk.org/ details
September
27
AIDS RUN/ WALK
1410 Special Olympics Drive
Since its inception in 2001, annual walk has raised awareness and funds for AIDS Foundation Chicago and 25+ Community Direct programs to improve the lives of Chicagoans living with and vulnerable to HIV or chronic conditions. aidschicago.org
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September 27
ELIM DUTCH FESTIVAL
13020 S. Central Ave., Crestwood Pancake Breakfast 7:30-10 am; Farmer’s Market and Dutch Village 8 am-4 pm; Main Stage Entertainment 9 am-4 pm
Traditional Dutch celebration is a fundraiser for Elim's mission of assisting children and adults with disabiilties. Dutch treats like pancakes, hutspot (beef and potatoes), ban-
Chicago Gourmet
ket (pastry with almond filling), and oliebollen (Dutch pastry) are cooked alongside American favorites. Clog dancers, live reptiles, a petting zoo, and a train ride keep the kids entertained. www.elimcs.org/dutch-festival
September 27-28
HYDE PARK JAZZ FESTIVAL
Various Venues & Times
19th annual event features everything from solo improvisation to big band ensembles at venues throughout the neighborhood. Performers this year include 2 Brown Sisters: Africa and Maggie Brown, Billy Branch and The Sons of Blues, Fay Victor’s Herbie Nichols SUNG, Hamid Drake Quartet
70th birthday celebration, Kenwood Academy Jazz Band, Trio Imagination (David Virelles, Reggie Workman, Andrew Cyrille), and more. hydeparkjazzfestival. org
Late SeptemberNovember DESTINOS
LATINO THEATER FESTIVAL
Various venues & times
Theatrical works celebrating Latino culture in all its dimensions are presented across the city. clata.org
October 3-5
LINCOLN PARK WINE FEST
Jonquil Park, 1001 W. Wrightwood Ave. Fri 5-10 pm, Sat 11 am-10 pm, Sun 11 am-7 pm
Jonquil Park transforms into an open wine pavilion, with tastings. General admission starts at $40, covering
one session of 12 tastings. chicagoevents.com/event/ lincoln-park-wine-fest
October 3-5
WEST TOWN ART WALK
Fri 5-8 pm, Sat-Sun 10 am-6 pm
Self-guided art tours are free in this Chicago Avenue cultural hub for businesses, visitors and residents. westtownchamber.org/west-town-art-walk
October 3-5
ANDERSONVILLE ARTS WEEKEND
Explore art openings, pop-up exhib its, live performances, and special programming throughout the Clark/ Foster district. This year’s event is dedicated to the memory of Todd Mack, beloved artist and founder of Foursided, whose visionary spirit and commitment to uplifting fellow creatives helped shape Andersonville’s artistic identity. andersonville.org/ events/arts-weekend
October 3-5
LINCOLN SQUARE APPLE FEST
October 4
WALK TO END ALZHEIMER’S
Lincoln Park Grove 2, 1735 N. Stockton Drive Sat 8 am opening, 10 am ceremony, then start
The Alzheimer’s Association hosts a choice of 1.5 or 3-mile walks to support patient care and research. Free registration required at act.alz.org, and seach Chicago.
Lincoln Ave., between Lawrence and Sunnyside Fri 3-7 pm, Sat/Sun 9 am-6 pm
Apple Fest returns to Lincoln Square for its 38th year. Local food vendors provide apple fritters, cider, pies, and tamales, along with specialty items from farms throughout the Great Lakes. Live music and a Kids’ Zone run all day on dedicated stages. Admission by $5 suggested donation. lincolnsquare.org/apple-fest
October 4
CHICAGO BEER FESTIVAL
Field Museum, 1400 S. Lake Shore Drive 7-11 pm
Over 65 breweries offer craft beers alongside exclusive access to some of the Museum’s most popular exhibits. Early admission (7-11 p.m.) is $70, while general admission (8-11 p.m.) is $55. Food sold separately. Advance tickets only at thechicagobeerfestival.com
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October 4-25
JOURNEY CHICAGO
Various venues & times From "Zoo Fiesta" (below) to "Asian Dance, Folk Music and Crafts” hosted by the Chinese American Museum and the Field Museum on October 4, to the Homerathon, multilingual readings on October 24 and 25 by the National Hellenic Museum and the University of Illinois/Chicago, Polish Museum of America, DANK Haus, Instituto Cervantes and T.G. Masaryk Czech School, the Chicago Cultural Alliance offers a series of programs that show commonality in food, fashion, art, dance, music, embroidery and more. www.chicagoculturalalliance.org/ about-journey-chicago
October 8-12, 15-29, 22-26
CHICAGO BOTANIC GARDEN’S NIGHT OF 1000 JACK-O'-LANTERNS
1000 Lake Cook Road, Glencoe 6:30-10:30 pm
Dare to walk an eerie path, aglow with artist-carved pumpkins featuring tributes to Chicago sports teams, famous vampires, pets in Halloween costumes, and more. Among them, 75 giant pumpkins tip the scales at 150 pounds each. Watch live carving in action, meet costumed characters, and enjoy playful frights around every corner. Food and drinks available. Costumes encouraged. Tickets are $22-27 for adults; $15-$18 for children; parking $15-$25 at chicagobotanic.org/halloween
October 11
LINCOLN BRUNCH FEST
On Lincoln, Diversey to Wellington 10 am-2 pm
Free brunch samples, live music, FREE admission sponsored by Special Service Area 27. www.lakeviewssa27.com/brunch-fest
October 11
ZOO FIESTA
Lincoln Park Zoo, 2400 N. Cannon Drive 6-10 pm
A play on “su fiesta,” Zoo Fiesta is a 21+ event celebrating Latinx and Afro-Latino cultures and communities with after-hours access and Spanish-language animal chats focused on wildlife native to Central and South America, plus free rides on the Giant Fun Slide, Ferris Wheel, and Endangered Species Carousel; live band, DJ; indoor and outdoor food and drink concessions. $20 at lpzoo.org/event/zoo-fiesta
October 11-12
HISTORIC PULLMAN HOUSE TOUR
11141 S. Cottage Grove Ave. 11 am-5 pm
Since 1973, Historic Pullman Foundation and Pullman Civic Organization have co-sponsored this annual self-guided tour of homes, a crosssection of those built in the 1880s for the planned industrial community that made passenger cars for transcontinental railroad travel. Tour beautiful homes, select public buildings, live music, food, antique cars (Sunday only) a video history, and more. Pullman is a City of Chicago, State of Illinois, and U.S. Department of the Interior-designated landmark district. On Feb. 19, 2015, Pullman was designated as a National Monu ment, and on Dec. 29, 2022, Pullman was elevated to a National Histori cal Park. Advance tickets $24+ on Eventbrite.
October 11-12
NATIVE AMERICAN HARVEST POW WOW
2015 Manchester Road, Wheaton, IL
A full troupe of Native American dancers in regalia open each day inside the DuPage County Fairgrounds, led by the Midwest SOARRING Foundation (Save Our Ancestors Remains and Resources Indigenous Network). Also find Native American drumming, foods, arts and crafts, children’s activities, cultural demonstrations
and musicians. Adults $17, Seniors 62+ $12, Children 3-12 $7. Kids under 3 free. Weekend Adult pass $30; discounts before October 4 at harvestpowwow.com
October 12
BANK OF AMERICA CHICAGO MARATHON
Starting in Grant Park, Columbus & Monroe Drives
Sunday event is one of the six World Marathon Majors (alongside Boston, New York, London, Berlin, and Tokyo) and traverses Chicago. Over 45,000 runners from 100+ countries race through 29 neighborhoods, each with special cheering sections. The nearly flat course has led to six world records over 46 previous years. chicagomarathon.com
October 15-26
CHICAGO
INTERNATIONAL FILM FESTIVAL
Various venues
North America’s longest-running competitive film festival celebrates its 61st year. chicagofilmfestival.com
October 18
ARTS IN THE DARK PARADE
State St., from Lake to Van Buren 6-8 pm
Magical evening procession celebrates Halloween as the “artist’s holiday” with representation of Chicago film, photography, museums, visual arts, theatre, architecture, drag performance, fashion, dance, circus arts, creative youth, hip-hop, jazz, rock, opera, street arts, fire arts, drumlines, puppeteers and so much more. Additionally, the parade will feature a diverse mix of Irish, Columbian, Polynesian, Brazilian, South Asia, Korean, Puerto Rican, Caribbean, Chinese, Indonesian, Peruvian, and LGTBQ+ organizations and groups. Named “one of the best Halloween celebrations in the world” by UK-based Wanderlust Magazine, Arts in the Dark is presented by LUMA8 and the City of Chicago with Major Support from the Chicago Loop Alliance and Goodwill Greater Milwaukee & Chicago. It is produced in partnership with the Chicago Department of Cultural Affairs and Special Events (DCASE). artsinthedark.com
ROSEHILL CEMETERY
CRYPT 5K RUN & WALK
5800 N. Ravenswood Ave.
Sat. 7 pm Timed Run; 7:15 pm Fun Run/ Walk
Should you be afraid when Chicago’s largest, Victorianera cemetery opens its gates? Entire course is illuminated by candlelight, which casts eerie glows on monuments, intricate headstones, and the final
resting places of some of Chicago’s most notable figures. Rosehill’s eternal residents include 10 Chicago mayors, Oscar Mayer, John G. Shedd, legendary Cubs announcer Jack Brickhouse, advertising icon Leo Burnett, Sears founder Julius Rosenwald, and scores of Civil War veterans. Spirited post-run celebration across the street at the Fireside Inn. Registration starts at $43 at runsignup.com/Race/IL/Chicago/ Crypt5KRunWalk
October 18-19
OPEN HOUSE CHICAGO
Various venues & times
Hosted by the Chicago Architecture Center, this free public festival offers behind-the-scenes access to buildings of architectural, historical and cultural significance, to instill civic pride and highlight businesses, organizations and creative leaders making positive impact in Chicago’s diverse neighborhoods. Past locations include the Walt Disney House & Birthplace, Buddhist Temple of Chicago, Board of Trade Building, Willis Tower, and dozens of other locations. Full list TBA at www.architecture.org/openhouse-chicago/about
October 24
HOWL-O-WEEN
Lincoln Park Zoo, 2400 N. Cannon Drive
Fri 6:30-10 pm
21+/w ID Halloween party includes a haunted trail to test your bravery as you walk among specters, Halloween-themed animal chats, free face-painting, a live DJ, and seasonal pop-up bars, indoor and outdoor concessions. Costumes are encouraged, WITHOUT full-face covering, fur or tentacles/extensions. Tickets $20 at tickets.lpzoo.org/events; (members 20% off).
October 25
UPSIDE DOWN HALLOWEEN PARADE
Noon-2 pm
Washington Park
Chicago children and their families will BECOME the parade when they
don their costumes and join the procession down tree-lined Russell Drive (near King Drive and 60th Street). Dance teams, musicians, acrobats, sports mascots will dazzle them on the route – and the first 5,000 kids will receive a complimentary candy bag and other goodies at the closing arches! Part of Mayor Brandon Johnson’s Fall Fest 2025. FREE. artsinthedark.com/upside-downparade
October 27
TRICK OR TREAT ON SOUTHPORT
Roscoe to Grace 4-7 pm lakeviewroscoevillage.org
October 31
HAUNTED HALLOWEEN BALL AT THE CONGRESS PLAZA HOTEL
520 S. Michigan Ave. Fri 9 pm-2 am
The moment you enter, you will be directed to massive 20,000 square foot ballrooms of the 122-year-old hotel, which has been transformed into an abandoned hotel run by zombies. Dance to the dark and dirty beats of world-renowned DJs and recording artists. Encounter vampire bellmen, zombie cocktail servers dressed as French maids and theatrical performances by costumed go-go dancers. $2000 cash prize costume contest. Tickets $20+ at hauntedhalloweenball.com
October 31
28TH ANNUAL HAUNTED HALSTED HALLOWEEN PARADE
Halsted Street, from Belmont to Brompton 6:30-10 pm
Devils, drinks, and drag artists convene on Halsted Street for a free Halloween parade, ranked among Top Ten in U.S. by Fodor’s. Free-toenter costume contest offers $4,000 in cash prizes for Character, Creative, Scary, Youth and Group. northalsted. com/events/halloween-parade
November 2
SKYRISE CHICAGO
233 S. Wacker Drive – or anywhere!
Step up in support of Shirley Ryan
AbilityLab at this 17th annual event – in person or virtually. Shirley Ryan
AbilityLab is a 501(c)(3) and the global leader in physical medicine and rehabilitation for adults and children with the most severe, complex conditions — from traumatic brain and spinal cord injury to stroke, amputation and cancer-related impairment – whose care may not be covered by insurance. You can climb all 2,149 stairs up 105 flights of the Willis Tower. Or, participate at home by running or walking 6,327 steps, stepping up 105 times, or cycling 3.2 miles. skyrisechicago.org/2025
November
2
HOT CHOCOLATE RUN
Grant Park, 301 S. Columbus Dr. 7:30 a.m. start; 9 am for 2-mile run America’s sweetest run offers 5K, 10K, 15K and 2-mile courses past the Art Institute, Buckingham Fountain, the Field Museum, Soldier Field and the River Walk, with a post-run party that will make you go “cocoa crazy.” Registration includes exclusive Hot Chocolate Run jacket, commemorative finisher’s medal, the Run’s famous Hot Chocolate, Chocolate Fondue Finisher’s mug and access to party. $44+ at hotchocolate15k.com/city/chicago
November 4-9
312 COMEDY FESTIVAL
Various venues & times
Up-and-coming and established comedians from across the U.S. Headliners this year include Fortune Feimster, Pete Holmes, Dusty Slay, Earthquake, Jared Freid, Patrick Warburton, Marie Faustin, Joe Machi at Zanies downtown and Rosemont, the Riviera, Vic and Chicago Theaters and Park West. Tickets, dates and times at 312comedyfestival.com
November 7-8
FESTIVAL OF WOOD AND BARREL-AGED BEER
Barrel-aging brewing masters from coast to coast submit their original wood and barrel-aged beer, cider, mead and perry for judging across 13 unique style categories, from porter and stout to barley wine, fruit beer, dark beer, lager and more. fobab.com
November 7-16
BLACK HARVEST FILM FESTIVAL
Gene Siskel Film Center, 164 N. State St. Various times
Celebrating its 31st year as Chicago’s annual showcase for Black film across the diaspora. Born from an urgent need to celebrate the Black experience, the festival highlights emerging and established talents and historical narratives, both short and feature-length films. https://web. saic.edu/blackharvestfest
November 8-9
CHICAGO TOY AND GAME FAIR
Donald E. Stephens Center, 5555 N. River Rd., Rosemont Sat 10 am-6 pm, Sun 10 am-5 pm Kids get to try out the latest new toys and meet their inventors at North America’s largest consumer toy and game fair. Prospective inventors seek feedback too. A past year featured Jedi knights and soldiers of the 501st Legion - “Vader’s Fist.” chitag.com
November
15
CARINO FESTIVAL DE CINE
The Fire Station, 2358 S. Whipple Fest provides a platform for emerging filmmakers age 13-26 to share their unique perspectives on themselves, their communities, and the world. Its namesake is Zedrick “Carino” Alfredo Aurelio, who died at age 26 from cancer, but who dedicated his life to bringing people together. filmfreeway. com/CarinoFestivaldeCine
Mid-November 2025
-First weekend of January 2026
CHRISTMAS AROUND THE WORLD AND HOLIDAYS OF LIGHT
Griffin Museum of Science and Industry, 5700 S. DuSable Lake Shore Drive
This Chicago tradition started with a single tree in 1942, which was decorated every 12 days to represent nations fighting alongside the U.S. in World War II. Today, the annual celebration features a four-story, floorto-dome Grand Tree, surrounded by 50 trees decorated by volunteers to celebrate holiday traditions from
around the globe: not just Christmas, but Hanukkah, Kwanzaa, Diwali, Ramadan, Visakha Puja Day, St. Lucia Day and more. Free with regular museum entry. msichicago.org
November 21
MILLENNIUM PARK CHRISTMAS TREE LIGHTING
Michigan Ave. and Washington St. 6 pm
The City of Chicago’s 112th annual Christmas Tree will remain illuminated through Thursday, Jan. 8, 2026. www.choosechicago.com/event/cityof-chicago-christmas-tree-lightingceremony-2
November 21-23
MILLENNIUM PARK HOLIDAY MARKET
Chase Promenade North, Millennium Park, 201 E. Randolph St. Enjoy shopping, entertainment and concessions. The opening of the market aligns with the lighting of Chicago’s 112th Christmas tree and continues all weekend.
November 21-December 24
CHRISTKINDLMARKET
Daley Plaza, 50 W. Washington St. Sun-Thurs 11 a.m.-8 p.m., Fri-Sat-11 a.m.-9 p.m.
Special hours: November 27 (Thanksgiving) & December 24 (Christmas Eve) 11 am-4 pm RiverEdge Park, 360 N. Broadway, Aurora Thurs & Sun, 11 am-6 pm, Fri & Sat, 11 am-9 pm
Special hours: November 27 (Thanksgiving) & December 24 (Christmas Eve) 11 am-4 pm, Mon & Tues, December 22 & 23, 11 am-7 pm
November 21-December 31
Gallagher Way, 3635 N. Clark St. Mon-Thu 3-9 pm, Fri-Sat, 11 am-10 pm, Sun, 11 am-7 pm
Special hours November 27 (Thanksgiving), December 24 (Christmas Eve) & December 31 (New Year’s Eve) 11 am-4 pm; Mon & Tues, December 29 & 30, 11 am-9 pm
Inspired by the 16th century market at Nuremberg, Germany, this is the most traditional holiday market of its kind outside Europe. Enjoy authentic vendors and food, family-friendly events, live entertainment. FREE admission. christkindlmarket.com
November 22
WINTRUST MAGNIFICENT MILE ARTS FESTIVAL
Michigan Ave. from Oak to Illinois Mickey and Minnie Mouse lead the holiday season with marching bands, helium balloons, and 1 million lights on Michigan Avenue’s 200 trees. Sitting right at the end is Santa Claus, ready to cap the festivities with a Fireworks Spectacular. themagnificentmile.com/lights-festival
November 27
CHICAGO THANKSGIVING PARADE
State St., from Ida B. Wells to Randolph Streets 8-11 am
Chicago’s own Thanksgiving show returns for its 90th year. Marching bands, equestrian acts, cultural performances, floats, and plenty of gigantic helium balloons. chicagothanksgivingparade.com
November 27
LIFE-TIME TURKEY TROT 5K & 8K
2601 N. Cannon Drive
Get some exercise before Thanksgiving dinner with this 5K and 8K runs through Lincoln Park, a benefit for the Greater Chicago Food Depository. Kids race in their own Plymouth Rock Ramble. Gather afterwards in the Turkey Trot Tailgate area for games, arts and crafts, and other family activities. Registration at turkeytrotchicago.com
December 5, 12, 19
MILLENNIUM PARK SING-ALONG
Grainger Plaza (Cloud Gate)
Fridays, 6 pm
Part concert, part sing along, as local choral groups lead the audience in holiday favorites with “The Bean” as a backdrop. FREE. www.chicago.gov/city/en/depts/dca/ supp_info/millennium_park13.html
December 11
ADULTS NIGHT OUT: HOLIDAZE
Lincoln Park Zoo, 2400 N. Cannon Drive 6:30-10 pm
Don we now an ugly sweater for the jolly-est night of the year at Lincoln Park Zoo! Exclusive after-hours holiday party for those 21+ without kids and strollers. Bask in the glow of 3 million lights. Enjoy festive music, warm food and drinks, games, holiday characters, and a variety of photo ops. $20 at www.lpzoo.org/event/adults-night-outholidaze
December 20-21
RENEGADE CRAFT FAIR
Morgan Manufacturing, 401 N. Morgan Sat-Sun, 11 am-5 pm
Shop from 170 curated makers of handmade gifts from around the U.S. www.renegadecraft.com/event/chicago-winter
