CHICAGO — You can spend your weekend sipping wine at Jonquil Park, celebrating fall with a food truck festival in the woods or exploring Liberian culture and cuisine at the inaugural Kobo Fest.
The Historic Pullman House Tour, Drum Talk Book & Literary Fair and Chicago Beer Fest are also on deck.
Here’s a roundup of 48 things to do in Chicago this weekend:
5-10 p.m. Friday, 11 a.m.-10 p.m. Saturday, 11 a.m.-7 p.m. Sunday
Jonquil Park, 1001 W. Wrightwood Ave.
Enjoy wines from around the world and shop vin-related crafts and goods at Wine Fest while DJ Julio spins tunes through the day. There will also be food from Cafe Tola, Las Tablas and Taqueria La Ciudad. Festgoers can sign up for two-hour tasting sessions for $35, which include 12 tasting tickets and a commemorative tasting glass. VIP tickets for $75 offer access to an additional five tastings, private seating area and restrooms. Tickets for $58 will be sold at the door if available. Proceeds benefit the Wrightwood Neighbors Association, which includes care of Jonquil Park.
10 a.m.-6 p.m. Saturday-Sunday
LaBagh Woods, 5275 N. Cicero Ave.
Gourmet food trucks will gather in the woods for the 10th edition of this fall food festival. Attendees can also enjoy fall cocktails, outdoor games like cornhole and music. General admission is free, but online registration is required. Beer, wine, cocktails and T-shirts are available to buy here.
3-7 p.m. Saturday
6200 S. Drexel Ave.
Explore authentic Liberian culture through food, music and storytelling at the inaugural Kobo Fest. More than a dozen dishes will be served, from jollof rice to cassava leaf and palava sauce. General admission tickets are $15 online.
Credit: ProvidedKicks off 11:30 a.m. Saturday-Sunday
Between Begyle Brewing Co. and Dovetail Brewery, at the corner of Ravenswood and Belle Plaine avenues in the Ravenswood Corridor
Begyle Brewing Co. and Dovetail Brewery’s annual Oktoberfest celebration returns this weekend with food trucks, live music on stage and lots of beer. All ages (and dogs) are welcome. There is a $5 suggested donation to benefit local food pantry The Friendship Center. A $20 donation can provide about 150 meals to older people and families in the community.
7-11 p.m. Saturday
The Field Museum, 1400 S. Lake Shore Drive
Experience a night at the museum alongside more than 65 breweries serving seasonal beer samples. This is a 21-and-older event. Tickets are $65 for early admission at 7 p.m. and $50 for general admission at 8 p.m. They are available to buy online.
5 p.m. Saturday-1 a.m. Sunday
Co-Prosperity Sphere, 3219-21 S. Morgan St.
Buy, sell, exchange and enjoy records, CDs and tapes 5-9 p.m Saturday with a variety of local vendors, including Shady Rest Vintage & Vinyl, Shmee Records and Areaman Chicago. Then dance the night away to beats by DJs Material Luv, Leja Hazer, Wolfgang Amadidas, Drasii and more. RSVP for free online.
Credit: Mercury Cruises10 a.m. Saturday-Sunday
Chicago Riverwalk, 112 E. Wacker Drive
Bring your pup in costume (and feel free to dress up yourself) for Mercury Canine Cruises’ special Halloween-themed tours. The 90-minute river and lake cruise features city highlights as well as pumpkin-flavored dog treats and prizes for best costumes. Tickets are $44 for general boarding, $49 for priority boarding for adults, $20 general, $25 priority for kids 5-15 and $10 for dogs.
10 a.m.-noon Saturday
6300 S. Harper Ave.
Take a trolley tour around the South Side, learn about the neighborhood and visit its community gardens. The tour is led by The Chicago Peace Fellows. RSVP for free online.
2-5 p.m. Saturday
Start at Edgebrook Cycle, 6450 N. Central Ave., or New Book Joy, 5512 W. Devon Ave.
Trick or treat and taste local craft beers at 20 stops through Edgebrook. Each business will also hold scratch-off reveals for a chance to win prizes. This is a family-friendly stroll along Central and Devon avenues. Tickets are $40 online.
Starts Oct. 6 and runs through Oct. 20
Various restaurants and food trucks
Dine at Chicago’s rich and diverse Latin American eateries and enjoy a variety of specials during Latin Restaurant Weeks, which kicks off this weekend. Find a list of participating restaurants, food trucks and culinary institutions here.
Credit: Maia McDonald/Block Club Chicago11 a.m.-5 p.m. Saturday-Sunday
Pullman Exhibit Hall, 11141 S. Cottage Grove Ave.
The 50th annual Historic Pullman House Tour is back this weekend with live music, food, a Sunday antique car show and more. Visitors will be able to tour iconic homes on the Far South Side and learn about their history and architecture on a self-guided walking tour, co-sponsored by Historic Pullman Foundation and Pullman Civic Organization. Tickets start at $12 online.
10 a.m.-2 p.m. Saturday
Monument Park, 6679 N. Avondale Ave.
The Edison Park Community Council is hosting its second pet fair with pet-focused businesses and organizations, including a pet photographer. The pet blessing starts at 10 a.m.
3-5 p.m. and 6-8 p.m. Friday, 2-4 p.m. and 6-8 p.m. Saturday, 2-4 p.m. and 6-8 p.m. Sunday, 2-4 p.m. Monday
The Northman Beer & Cider Garden, 233 E. Riverwalk
Grab a seat by the river and enjoy a free live music series in celebration of Indigenous Peoples Day. Catch performances by Denise La Grassa, Alpine Thunder, The Rolling Clones and more.
The Northman Beer & Cider Garden, 233 E. Riverwalk
11 a.m.-10:30 p.m. Friday-Sunday
Alongside live music performances, there will be sausage, cider, pretzels, beer and more to celebrate Oktoberfest along the Riverwalk.
Credit: InstagramVarious times and locations Thursday-Saturday
Chicago’s Latina Comedy Festival is back and bigger for its second edition. The fest is now a three-day event across multiple venues featuring more than 35 Latinx comedians. Find the full lineup and tickets here.
7-10 p.m. Friday, 11 a.m.-3 p.m. Saturday-Sunday
Time Out Market Chicago, 916 W. Fulton Market
German band Die Musikmeisters, stein hoisting competitions, a Steins and Sam Adams pop-up bar, music by a live DJ and more are coming to Time Out Market this weekend. There will also be a kids’ story time and Oktoberfest samplings and giveaways. RSVP for free online.
4:30-6:30 p.m. Saturday
Music Box Theatre, 3733 N. Southport Ave.
Six Black and Brown women filmmakers will take the stage in this showcase to share their art and answer film-related questions. Meet with spotlight directors, writers and artists; enjoy a cocktail while browsing artist merchandise; view screenings; enter a raffle and more. General admission tickets are $20 online.
Credit: Simeon Frierson/Provided.2-7 p.m. Saturday
The Arts Lawn, 337 E. Garfield Blvd.
University of Chicago’s Arts + Public Life initiative is launching its Arts Lawn this weekend with performances by Kuumba Lynx and the King High School Marching Band, family-friendly activities and a photo booth. The lawn is a new outdoor venue and “dynamic green space” that will host a variety of arts programs, including film screenings, live theater performances, arts marketplaces and music experiences. It features a performance space, outdoor seating, a lawn, a pavilion and planter seating. Attendees can RSVP online.
7:30 p.m. Thursday and Saturday, 3 p.m. Sunday
The Den Theatre, 1331 N. Milwaukee Ave.
This one-woman show written and produced by its star, Merit Kahn, takes a comedic approach to life’s everyday dramas, from divorce and illness to career and dating mishaps. General admission tickets are $46 and VIP tickets are $56. Get yours online or by calling 773-697-3830.
7:15 p.m. and 9:30 p.m. Friday
The Den Theatre, 1331 N. Milwaukee Ave.
After being named The Reader’s Best Stand-up Comedian in Chicago in 2010, Beth Stelling relocated to Los Angeles, made her late-night TV debut, released two comedy albums and appeared on popular cable comedy network programs. She returns to Chicago this weekend for a night of stand-up in Wicker Park. Tickets start at $19 online or at 773-697-3830. There is a two-drink minimum at this event.
6:30 p.m. Thursday
At Barcocina West Town, 1814 W. Chicago Ave., and Barcocina Lakeview, 2901 N. Sheffield Ave.
Paint pumpkins on the Barcocina patio at this spooky event hosted by artists from Bottle & Bottega. Limited space is available, and kids get in free. Tickets are $40 online, which includes two cocktails, chips and salsa and free swag.
Credit: Colin Boyle/Block Club Chicago11 a.m.-4 p.m.
DuSable Black History Museum and Education Center, 740 E. 56th Place
Explore a variety of books and meet with authors at the third annual Drum Talk Book & Literary Fair. There will be a Professional Writer’s Workshop 1-2 p.m. and two rounds of Spoken Word Open Mics noon-1 p.m. and 2-3 p.m.
4-6 p.m. Saturday
DuSable Black History Museum and Education Center, 740 E. 56th Place
Right after Drum Talk, the DuSable Museum is partnering with Chicago’s own Dilla the Urban Historian for a bus tour exploring famous historical areas in Black literature. Pickup and dropoff will be at the museum. Tickets are $45 online. There is a 20 percent discount for museum members and people 60 and older.
1-10 p.m. Saturday
Howard Street Brewing Company, 1617 Howard St.
Indulge in German cuisine, sample 12 beers on tap and play trivia at Howard Street Brewing Company’s Oktoberfest celebration. General admission tickets are $35 online.
2-5 p.m. Saturday
Uptown Taproom, 1265 W. Wilson Ave.
Lederhosen is optional at this Oktoberfest celebration. Tickets are $15 online and include a drink ticket and raffle ticket for prizes like Uptown Taproom gear and an Egg Harbor Cafe gift card. Attendees can also learn about Holy Family Ministries Fellowship Alliance Board and how to get involved.
7-11 p.m. Friday
Hairpin Arts Center, 2810 N. Milwaukee Ave.
Artists William Baker III and Ronise Doss will display their work in Avondale this weekend, reimagining the traditional American family home “as a space that fosters healing, understanding, hope and community.” Drawing inspiration from pop art and prison culture and using artwork disguised as home decor, the collection explores the experiences of Black individuals navigating the justice system. It opens Friday at nonprofit arts organization Hairpin Arts Center. Tickets to the exhibit are $20 online.
Credit: Facebook/Uptown Church11 a.m.-3 p.m. Saturday
Uplift Community High School, 900 W. Wilson Ave.
Enjoy pony rides, a petting zoo, carnival rides, free lunch, live music, raffles, games and more at this free community block party. The fest attracted more than 1,700 people in 2021. Sign up to be a volunteer here.
4:30-7 p.m. Saturday, soccer game at 7:30 p.m.
Soldier Field, 1410 Special Olympics Drive
Meet with employers from the Bulls, Cubs, Blackhawks and a dozen other Chicago sports organizations at this career fair hosted by the Chicago Fire — and potentially land a mini interview. Attendees will also receive tickets for the Chicago Fire vs. Charlotte FC game at 7:30 p.m. Register for $35-$55 online.
7 p.m. Thursday
The Epiphany Center, 201 S. Ashland Ave.
Composer David T. Little’s “Soldier Songs” is a highly charged monodrama that follows the life of a solider through youth, combat and old age, drawing from recorded conversations with veterans. Described as a “theatrical cantata,” it combines classical music and heavy metal while exploring the psychological impact of war. General admission tickets are $60. VIP cabaret tickets with table seating and an artist reception are also available for $175. Buy them online.
2-6 p.m. Saturday
South Asia Institute, 1925 S. Michigan Ave.
“Shades of Blue” is a South Asia Institute open house hosted in conjunction with its current art exhibit by Shelly Jyoti, “Indigo: The Blue Gold.” This program will also celebrate the Chicago blues and jazz scene and South Asian arts with a variety of music and dance performances. Admission is free with online registration.
Credit: Eric Allix Rogers/Open House Chicago4-8 p.m. Saturday
Working Bikes, 2434 S. Western Ave.
Gather with Working Bikes staff, partners, friends and community to celebrate its 24th anniversary in the city. Swing by for a free block party and enjoy warehouse tours, a silent auction, a family-friendly drag show, games and music. There will also be bites and beverages provided by local vendors. Get tickets for $40 online.
Doors open 7:30 p.m., show starts 8 p.m. Friday
Color Club, 4146 N. Elston Ave.
Denver-based comedian, writer and improvisor Hannah Jones is bringing her cheeky, satirical takes on sex, dating and gender politics to Chicago this weekend. She is the creator of retired satire publication Westish, has been invited to a variety of comedy festivals, is a regular at Denver Comedy Works and her videos have been viewed online over 20 million times. Tickets are $20 online.
11 a.m.-noon Saturday
The Salud, 3039 E. 91st St.
The South Chicago Neighborhood Network and Yoga Care are hosting free chair yoga sessions Saturdays through Nov. 4. The classes focus on restorative poses, guided meditation, stress reduction and bonding.
11 a.m. Sunday
Three Avenues Bookshop, 3009 N. Southport Ave.
Chicago authors Tanja Babich and Molly Pinta will be at local bookshop Three Avenues this weekend for a signing of their latest “Dear Rebel” book, in which 145 women share advice, experiences and secrets to success through poems, essays, self-portraits and more. Readers can learn about how “Ms. Marvel” actor Iman Vellani connected with her roots through her character, how March For Our Lives co-founder Jaclyn Corin found her voice as an activist and how Carla Pérez made her way to the top of Mount Everest. RSVP for free here.
Credit: Provided1-6 p.m. Sunday
The Hidden Gem, 6330 S. Racine Ave.
Shop record vendors, sample food and spirits from local businesses and listen to DJs spin vinyl all afternoon at this year’s final Vinyl & Vittles record fair and market, held monthly June-October. It will be at a new indoor venue this weekend.
11 a.m.-5 p.m. Saturday
Various neighborhoods around Chicago
South Rhodes and Vinyl & Vittles are hosting an Epic Vinyl Record Hunt, with 10 hidden music packages across the city. Follow @southrhodes and @vinylandvittleschi to discover clues and keep up with discoveries, which they’ll post on Instagram stories throughout the day. Sign up for the hunt online.
5-10 p.m. Friday
DuSable Black History Museum and Education Center, 740 E. 56th Place
The Black Women Professionals League is hosting its seventh annual 40 Under 40 Awards Ceremony, celebrating Black women and trailblazers under 40 who have made “remarkable contributions to their respective fields.” General admission tickets are $75 online.
10 a.m.-noon Saturday
American Islamic College, 640 W. Irving Park Road
The American Islamic College and Chicago History Museum have partnered for a morning of storytelling, recounting how the lives of Shakeela Hassan and Elijah Muhammad became intertwined after summer in Chicago in 1956. Speakers include Hassan, college President Timothy Gianotti, Chicago History Museum President Donald Lassere, museum historians and more. There will be a ceremonial procession and light refreshments afterwards. Register for free online.
Credit: Colin Boyle/Block Club Chicago8 a.m. Sunday
On Adams between Loomis and Laflin on the south side of the street. See map here.
Support runners as they take on the streets of Chicago for this weekend’s major road race. Enjoy light refreshments and celebrate in a blue tent on Adams for the entire marathon or stop by while following a runner around the course. RSVP here.
9 p.m. Sunday-1 a.m. Monday
City Hall, 838 W. Kinzie St.
Chicago running collective Three Run Two has booked City Hall for a post-marathon fiesta featuring DJs Intel, Iggy and Charlie Dark. Athletes can also take advantage of an on-site “recovery oasis” in partnership with Lululemon. Tickets are $25 online.
11 a.m.-5 p.m. Sunday
The Silver Room, 1506 E. 53rd St.
Dig into pre-loved and vintage goods at an outdoor sidewalk sale organized by DJ Tess, with special guest Valentine Vintage.
11:30 a.m.-3:30 p.m. Saturday
Jackson Park, 5700 E. Hayes Drive
The National Alliance on Mental Illness Chicago is hosting a health fest to raise awareness and funds for mental health wellness for Chicago youth. RSVP online.
PLUS: Six Picks From Our Partners At
7:30 p.m. Friday
United Center, 1901 W. Madison St.
Enjoy a comedy-filled night with Dave Chappelle at the United Center.
10 p.m. Friday
TAO Chicago, 632 N. Dearborn St.
Don’t miss the “satisfaction” of seeing Benny Benassi live in Chicago.
8 p.m. Saturday
The Chicago Theatre, 175 N. State St.
“Parks and Rec” star Ben Schwartz is bringing the laughs to The Chicago Theatre this Saturday.
Noon-8 p.m. Saturday
Island Party Hut, 355 Chicago Riverwalk
Celebrate fall on the riverwalk with a Fall Fest at Island Party hut featuring hayrides, a pumpkin patch and more.
6 p.m. Sunday
Metro, 3730 N. Clark St.
Rock out with Arkells and Robert DeLong at Metro this Sunday.
5-10 p.m. Sunday-Monday
Chop Shop, 2033 W. North Ave.
Head to Chop Shop for the fifth annual Indigenous Peoples Day Art and Music festival.
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