Lakeview: This year is the 15th Anniversary of the Lakeview East Festival of the Arts! On Saturday September 14 and Sunday September 15, this incredible festival showcases over 150 juried artists featuring paintings, sculpture, photography, furniture, jewelry, and more. There are also live demonstrations, entertainment stages with live music, family activities, and a garden oasis. The festival is presented by the Lakeview East Chamber of Commerce and is located along Broadway between Belmont and Hawthorne. There is a $5 suggested donation upon entrance. Hours are Saturday from 10 am to 7 pm (with additional hours for music, food, and drink tents until 10 pm) and Sunday from 11 am to 7 pm. Find more information here.
Lincoln Park: Mark your calendars for Lincoln Park Uncorked: A Lincoln Avenue Wine Stroll! On September 26 from 6 to 9 pm, gather your group and stroll Lincoln Avenue between Diversey and Fullerton. Businesses will be transformed into pop-up tasting rooms with curated selections from Vin Chicago! You’ll taste some of the season’s best wines, paired with delicious small bites from a selection of Lincoln Park’s best restaurants. Get your tickets early- because this event is expected to sell out! Early Bird admission tickets are on sale now through August 25 for just $30. General admission tickets are $40 and go on sale on August 26. Find more information here!
Bucktown and Wicker Park: The Wicker Park Bucktown Chamber of Commerce presents its annual Fall Dinner Crawl! On Tuesday September 17 from 6 to 9 pm, foodies around Chicagoland will taste small bites and signature appetizers from participating restaurants while exploring Wicker Park and Bucktown. The crawl is divided into two routes: Fork and Knife. The Fork route is comprised of Amaru, Dorian’s, Kizuki Ramen, Urbanbelly, Knead Pizza, Tricycle, and Club Lucky. The Knife route includes Caspian Kabab Fine Persian Cuisine, Ina Mae Tavern & Packaged Goods, Antique Taco, Tous Les Jours, Smoke Daddy, Fatpour Tap Works, Pub Royale, and Caffe Gelato. Tickets are $35 a piece and can be purchased here.
Chicago Loop: For ONE DAY ONLY, connect the history of Chicago’s food and drink with the story of Bridgeport- a historically working class neighborhood. Big Shoulders is offering a Historic Bar and Food Bus Tour in Bridgeport on the 15th of September. This tour is normally only offered for private groups! It’s a 2.5 hour tour and you’ll visit three historic bars that are quintessential to Bridgeport history. You’ll try a variety of food, including an authentic Chinese bao, Lithuanian beer, a Polish cookie, and the “mother-in-law” sandwich–a South Side Chicago specialty. Highlights include the White Sox stadium, seeing the Chicago Stock Yard Gates, classic Chicago homes, street art and murals, a historic bakery, and much more. Tickets are $58 per person, plus an optional drink package. Advance reservations are required and can be made here.
Lincoln Square: Fall into Damen at Night: The Fall Edition! On Friday September 20 between 6 and 9 pm, the businesses along Damen between Leland and Ainslie will be open late! Enjoy exclusive specials, in-store designers, pop-up sidewalk vendors, live music, and much more. Find more information here!
Oak Park: Downtown Oak Park presents Oaktoberfest! This fantastic event is from 4 to 10 pm on Friday September 20 and from noon to 10 pm on Saturday September 21. Admission is free! You’ll enjoy a premier music lineup, delicious fall foods from local restaurants, specialty craft beers, and a Kids Root Beer Garden. On Friday, the live music line-up includes Emily Blue, The O’My’s, and !ESSO! Afrobeat. On Saturday, you’ll see The Rico Band, Sarah Borges & The Broken Singles, Patrick Sweany, Alanna Royale, and Black Joe Lewis & The Honeybears. Come celebrate the changing of the seasons at this fun fall event! Click here for more info.
RACHEL HOOVLER & DEAN’S TEAM CHICAGO