Windy City Wine Festival, Sept 5–6
Daley Bicentennial Plaza, 337 E Randolph St at Columbus Dr. Fri 4–10pm; Sat 3–10pm; $30, advance $25, advance designated driver $10, under 21 with paid adult free.
* FREE German–American Festival, Sept 5–7
4700 N Lincoln Ave at Leland Ave. Fri 5–11pm; Sat noon–11pm; Sun noon–10pm. Parade Sat 2pm.
Oktoberfest revelers pack the heart of Lincoln Square each year for this German-American celebration that includes generous mugs of beer, brass bands for dancing and juicy sausages.
Guinness Oyster Fest, Sept 6
2000 W Roscoe St at Damen Ave. Noon–11pm, $5.
Fresh-shucked oysters and perfect pints are doled out to the sounds of a Wicker Park–appropriate band lineup.
Italian Village Ferrari Fest, Sept 7
Monroe St between Clark and Dearborn Sts. Times and prices TBA.
Get an up-close view of more than 50 Ferraris at this luxury-car event. Balloon makers, face painters and street performers are available to entertain those who can’t quite reach the wheel yet.
Naperville Wine Fest, Sept 12–13
Naper Settlement, 523 S Webster St, Naperville. Fri 4–10pm; Sat 2–9pm; $30, advance $25, designated driver $10, under 21 free with adult.
FREE Little Village Festival, Sept 12–14
26th St and Kostner Ave. Fri 3–10pm (carnival and food); Sat 11am–10pm, Sun noon–10pm.
People will be celebrating Mexican Independence Day all over the city, but you’ll be at the heart of it all at this family-friendly fiesta in the Little Village neighborhood.
FREE Celtic Fest Chicago, Sept 13–14
Grant Park, Jackson Blvd at Columbus Dr. 11am–9:30pm.
Discover Celtic music and culture beyond the borders of Irish stout and St. Pat’s Day revelry. The fest features handmade crafts, a kids’ area, a Scottish heavy athletic competition and sheep herding.
Chicago’s Taste of Romania, Sept 13–14
Continental Cafe, 3661 N Elston Ave between Addison and California Sts. 11am–10pm, $10.
Forget the standard festival vendor-booth; this hands-on fest does more than reheat food, it features delicacies prepared before your very eyes, including juice from grape stomping and meat roasted on a spit.
FREE Lakeview East Fine Art Fair, Sept 13–14
Broadway between Belmont Ave and Roscoe St. Sat 10am–6pm; Sun 10am–5pm.
* FREE Renegade Craft Fair, Sept 13–14
Division St between Damen Ave and Wood St. 11am–7pm.
Browse crafty creations from dozens of DIY vendors. Local and national indie designers showcase everything from homemade clothing and handbags to poster art and jewelry.
The Wine Crush in Old Town, Sept 13
Wells St between North Ave and Schiller St. 11am–10pm, wine tasting 1–6pm; $6, wine tasting fees $20–30.
FREE Pioneer Day, Sept 14
Farmhouse Museum, 399 Biesterfield Rd, Elk Grove Village. Noon–4pm.
Locals look back on simpler times with parlor entertainment, Civil War reenactments, President Lincoln impersonations, scarecrow stuffing and pioneer crafts demonstrations.
Winefest Chicago, Sept 19–21
Northcenter, 3840 N Lincoln at Berenice Ave. Fri 5–10pm; Sat 2–10pm; Sun 2–8pm; $25.
World Music Festival: Chicago 2008, Sept 19–25
Several venues including Millennium Park, Michigan Ave between Monroe and Randolph Sts. 6pm, free–$15.
More than 50 concerts—several are free—feature contemporary music from around the world, ranging from pop to traditional tunes. A performance by Calexico and Mariachi Luz de Luna closes out the fest.
FREE Eli’s Cheesecake Festival, Sept 20–21
Eli’s Cheesecake Company, 6701 W Forest Preserve Dr. Sat 10am–5pm, Sun 11am–5pm.
Live music, a culinary tent and local performances accompany platters of creamy cheesecake.
* Hideout Block Party, Sept 20–21
1354 W Wabansia Ave at Throop St. Noon–10pm, prices TBD.
The bar and music venue throws one family-friendly weekend of concerts a year.
* Decibelle Music & Culture Festival, Sept 23–27
Various venues around Chicago.
The gal-friendly Estrojam fest returns under a new moniker. A performance by synth-laden NYC outfit Plushgun kicks off the fest tonight, followed by four more days of live sets, workshops, readings, screenings and more. See event web site for venue, performance and schedule details.
Oktoberfest, Sept 26–28
St. Alphonsus Church, 3000 N Lincoln Ave at Southport Ave. Fri 5–10pm; Sat noon–10pm; Sun noon–8pm; $5.
The church—founded in 1882 to serve the neighborhood’s German immigrants—tips a feathered hat to its heritage with this sixth annual festival of beer, brats, dancing, kids’ activities and live music.
FREE Hyde Park Jazz Festival, Sept 27
Multiple venues including Midway Plaisance Park, 59th St and Woodlawn Ave. 11am–2am.
Watch local jazz artists play a music marathon around Hyde Park. Performers include Nicole Mitchell, Willie Pickens, Orbert Davis, Reginald R. Robinson and several others.
FREE Lynfred Winery Oktoberfest, Sept 27–28
Lynfred Winery, 15 S Roselle Rd, Roselle. Sat 3–9pm; Sun noon–7pm.
Discover a little bit of Napa Valley in the Northwest Suburbs at this Oktoberfest. Expect German sing-alongs, kids’ grape spitting contests, cork tossing, grape stomps and barrels of Lynfred’s special Oktoberfest wine.
FREE 57th Street Children’s Book Fair, Sept 28
57th St from Kimbark to Kenwood Aves. 1–6pm.
Stoke your kid’s interest in reading beyond the Harry Potter series at this fest featuring music and dance performances, author readings, appearances by popular book characters and new and used children’s titles.