Celebrate Hellenic pride with authentic dishes, music and entertainment at the Taste of Greektown. Fill up at a competitive gyro-eating contest (6 p.m. Saturday) that includes a chance to win a $250 Visa gift card. (Psst! The runner-up gets a $100 gift card – all the more reason to chow down.) Catch performances by Greek dancers throughout the weekend and see the Jesse White Tumblers perform at 5 p.m. Saturday and Sunday.
Details: 4-11 p.m. Friday; noon-11 p.m. Saturday and Sunday at Halsted and Van Buren Streets. $5 suggested donation / MAP
Get ready to laugh as the annual Women’s Funny Festival returns with more than 70 shows, from “relatable” stand-up to “highbrow” musical improv to character-driven sketch and everything in between. Expect to see veteran Chicago groups, like the Off Off Broadzway, and newcomers like Sarah Squirm Sherman. Other highlights: Shows featuring Mary Kennedy, who plays the “New Fiona” in Season 7 of “Shameless,” and Jen Murray, a Los Angeles-based comedian and winner of the IO West Comedy Festival’s “Best Comedian” Award in 2015.
Details: 8-10 p.m. Thursday; 8-11 p.m. Friday; 4:30-11 p.m. Saturday; 2-7 p.m. Sunday at Stage 773, 1225 W. Belmont Ave. $15 for individual tickets; $150 all-festival pass / MAP
Community organizers, volunteers, artists and educators band together for the music-centric fest Villapalooza. Founded in 2011, the fest is dedicated to promoting nonviolent spaces for arts, culture and community engagement. See more than 30 local artists and 40 musical acts showcase their talents.
Details: Noon-10 p.m. Saturday at Central Park Avenue and 26th Street. Free / MAP
Mark the 50th anniversary of the 1968 Chicago Democratic National Convention at Logan Monument ReAssembly, an interactive reinterpretation of Peter Bullock’s iconic photograph of protesters swarming the Gen. John Logan Monument in Grant Park. Using puzzle-piece like signs of the original photo, participants will be moved into place using dance and performance by Move Me Soul. Audience participation is highly encouraged.
Details: Noon-2 p.m. Sunday at Michigan Avenue and 9th Street. Free / MAP
5. Pick up
No need to cook this weekend or argue of which brunch spot to hit up. At the Logan Square Food Truck Social you can nosh on bites from more than a dozen eateries serving up everything from lobster rolls to donuts to pierogi. Enjoy musical performances programmed by iconic music lounge Empty Bottle. Retail vendors and artists showcase their wares while the Shedd Aquarium sets up shop with a pop-up gallery featuring live art making (11 a.m.-3 p.m. Saturday).
Details: 5-10 p.m. Friday; 11 a.m.-10 p.m. Saturday; 11 a.m.-8 p.m. Sunday along Humboldt Boulevard between Armitage and Bloomingdale Avenues. $5 suggested donation / MAP
Indulge your taste buds with a sweet treat (or several) at Gelato Festival America. Enjoy artisanal Italian gelato from international and national makers, including mouth-watering flavors like Eli’s strawberry cheesecake and dark chocolate infused with Jack Daniel’s whiskey and topped with hickory-smoked bacon. (Yum!) Attend gelato school to learn what it takes to be a gelato chef, vote for your favorite flavors and participate in a gelato-eating contest in which the winner takes a gallon of the stuff home.
Details: Noon-8 p.m. Saturday; noon-7 p.m. Sunday at Chicago Premium Outlets, 1650 Premium Outlet Blvd., Aurora. $30; $25 for kids and seniors / MAP
Raise a glass to fermented grapes at Naperville Wine Fest, where you can sample more than 250 global wines. Attend wine seminars and cooking demonstrations while you sip. Live music and vendors from area restaurants round it out.
Details: 5-10 p.m. Friday; 3-8 p.m. Saturday at Naper Settlement, 523 S. Webster St., Naperville. $40-$55 / MAP
Support local merchants while shopping al fresco at the Wicker Park Bucktown Summer Sidewalk Sale, featuring special promotions throughout the weekend. (See a map of participating vendors.) Enjoy circus performers, live music and a fashion show (4:30 p.m. Saturday at Boombox Plaza, 1262 N. Milwaukee Ave.).
Details: 11 a.m.-6 p.m. Saturday and Sunday along Milwaukee Avenue from North Avenue to Division Street. Free / MAP
Music, beer and carnival rides are among the highlights of Skokie’s Backlot Bash. See performances by Sister Hazel (Friday), Foghat (Saturday) and Tributosaurus becomes AC/DC (Sunday). Play bingo, try your luck at a dunk tank and browse wares from local merchants, artisans and crafters along Lincoln Avenue. Carnival rides and crafts keep kids entertained. Check out a classic car show Sunday (noon-5 p.m.).
Details: 6-10 p.m. Friday; 11 a.m.-1o p.m. Saturday; noon-8 p.m. Sunday at Oakton Street and Floral Avenue, Skokie. Free / MAP
Discover the talents of more than 300 international artists at the Port Clinton Art Festival. Young artists shine at the fest, with their own dedicated youth art division. Extras: live music, interactive art demos and vendors from neighborhood restaurants.
Details: 10 a.m.-6 p.m. Saturday and Sunday at 600 Central Ave., Highland Park. $5 suggested donation / MAP
Events listed are subject to change. We recommend double-checking times and locations before you head out the door. Want to share your upcoming events with us for consideration in a future roundup? Send us an email.