Autumn Decoration

Autumn in the City

You better be-LEAF it: autumn is officially here! From pumpkin spice-filled drag queen performances on Mag Mile and delectable fall-themed vegan dining experiences to mysterious theatre performances, a Fall Harvest Festival pop-up event with Parks and Recreation’s Li’l Sebastian and more, we have rounded up the top fall events, dining options and activities in Chicago for locals and visitors alike to enjoy.

Make Autumn-Themed Pour Decisions at Fun Drag Performances

ENO Wine Room is officially extending its successful Pour Decisions drag brunch series through the end of the year by popular demand! Every Sunday, guests may enjoy bottomless mimosas, an entrée from the new brunch menu created by Executive Chef Craig Couper and appearances by well-known drag entertainers. Hosted by Chicago’s own Fox E. Kim, ENO Wine Room’s Pour Decisions will feature weekly themed performances by Alex Kay and Mikki Miraj, with pop-in performances by several RuPaul’s Drag Race alumni. Autumn themes include: Pumpkin Spiced Ladies, It’s Britney, Witch, Scream Queens, Harry Pocus, Monster Mash Halloween Bash, Canadian Thanksgiving, Hashtag Squash Goals and 50 Shades of Gravy. Doors open at 12 p.m. and the Drag show runs through 2 p.m. Walk-ins are welcome, though guests are encouraged to purchase tickets in advance online for $45.

Take a Wine Tour Through Italy Without Ever Leaving the City

Chicago’s oldest wine bar, Geja’s Café, is welcoming the upcoming fall season with the debut of its three-month wine festival Giro d’Italia, going on now through Saturday, November 30th. Throughout these three months, wine enthusiasts of all calibers will have the opportunity to enjoy selections from the largest boot on Earth, perfectly complemented with Geja’s 3 course Premier Fondue Dinners. Geja’s exclusive wine list will be available by the glass and the bottle at low promotional prices. For more information, visit

Golf in a Kilt, All for a Good Cause

Hole in one! The Chicago Scots, the oldest non-profit organization in Illinois celebrating their 175th anniversary in the upcoming year, is thrilled to announce their 18th Annual Kilted Classic Golf Tournament on Thursday, October 3 from 11 a.m. to 4 p.m. Hosted for the first time at the magnificent Cantigny Golf Course in Wheaton, the tournament will feature multiple golf competitions and Scottish themed challenges throughout the course. There will be an assortment of food and drinks available for participants, plus a raffle, a special dinner service, whisky lounge and an auction benefitting Caledonia Senior Living and Memory Care, the Chicago Scots’ primary beneficiary for over one hundred years that offers a range of outstanding services including Assisted Living, Memory Care, Skilled Nursing and Respite stays. Tickets, registration, and donations can be found and made by clicking here.

Join Leslie Knope and Li’l Sebastian at Replay Lincoln Park’s Harvest Festival and Pop-Up Bar

Replay Lincoln Park, Chicago’s favorite arcade bar, recently transformed into the fun-loving town of Pawnee, Indiana for a Parks and Recreation pop-up experience! Guests are invited to celebrate like a Pawneean at several themed events including The Harvest Festival, a Glitter Factory Breakfast Buffet, a Mouserat Concert, trivia, bingo and more. The Harvest Festival will occur on Friday, October 4 with a special appearance by Li’l Sebastian at 6 p.m.! The pop-up will feature custom artwork and several fun photo opportunities at iconic Pawnee destinations including the Department of Parks and Recreation, Shoe Shine Stand, Li’l Sebastian’s Stable, Eagleton Fence, the Pit and the World’s Smallest Park, plus delicious bites inspired by JJ’s Diner and Sweetums and specialty cocktails like Galentine’s Day, The Ron Swanson and Snake Juice. For more information, visit

Delight in Vegan and Gluten Free Food Heaven in Lincoln Park

Things are about to heat up! Michelin Star Chef Christian Fantoni of Casati’s has challenged Master Pinsa Chef Daniele Papa to fly in from Rome for the ultimate Pinsa Pizza Showdown on October 8 – and guests are invited to witness (and enjoy) what will become the most delicious battle yet. Chef Papa will go head to head with Chef Fantoni to determine whose Pinsa, an inventive, delectable take on traditional pizza which offers 90% less carbs, fat and gluten, reigns supreme. All day, diners may enjoy a four-course meal handcrafted by both pedigreed Chefs, featuring two entrée Pinsas and two dessert Pinsas, for just $24 per person. Each guest will have the chance to vote to determine which Chef takes the crown. For more information, visit

Enjoy a Mysterious Performance at the Historic Mayslake Peabody Estate

To open its 24th season, First Folio Theatre will begin with the literary-inspired production SHERLOCK’S LAST CASE, by Charles Marowitz. A threat hangs over the world’s most famous detective as he faces an opponent he never expected. This thrilling adventure mixes suspense, humor, and breath-stopping surprises. Directed by Janice L. Blixt, SHERLOCK’S LAST CASE previews October 2-4, opens October 5 and runs through November 3, 2019. Tickets are on sale now and may be purchased by calling the box office at 630.986.8067 or online at

Celebrate the Earth’s Natural Change of Season and Ponder the Future of Our Planet

The nation’s most diverse orchestra, Chicago Sinfonietta is thrilled to present the standout 2019-2020 season opening concert, Forces + Fates: The Beauty and Volatility of Planet Earth, a performance centered on awe, imperfection and disorder found on Earth and how the future may rest in the hands of the human race. Featuring Beethoven’s Symphony No. 5, the “fate” symphony plus a world premiere work commissioned by Sinfonietta, listeners will experience a musical journey that celebrates the beauty that surrounds us while posing the question of what do we need to do to protect the planet. Chicago Sinfonietta’s performances will occur Saturday, October 5, 2019 at 8 p.m. at Wentz Concert Hall, 171 E. Chicago Ave., Naperville, and on Monday, October 7 at 7:30 p.m. at Symphony Center, 220 S. Michigan Ave., Chicago. Tickets range from $10 to $62 when purchased in advance online.

Bring the Family to a New Fall Festival Complete with Petting Zoo

Lincoln Common, the new crossroads of Chicago’s Lincoln Park neighborhood, will host a Fall Family Festival on Saturday, October 12 from 10 a.m. to 12 p.m. in the Plaza. Adults and kids of all ages are welcome to celebrate the beginning of autumn with a petting zoo, fall-themed crafts, sweet treats from Lincoln Park neighbors, Lincoln Common retail tenants and more. This event is free and family-friendly. For more information, visit

Enjoy Twelve Rounds of Non-stop Action at One of the Most Anticipated Boxing Moments of 2019

Cruiserweight boxing champion Oleksandr Usyk is joining the big guns with his Heavyweight Debut and first fight in a multi-fight deal with Eddie Hearn’s Matchroom Boxing USA at the Wintrust Arena on October 12. Usyk will face his competitor Tyrone Spong, who leaves a stellar kickboxing career behind, winning 91 of his 100 bouts in a 13-year career littered with accolades and titles before officially retiring from kickboxing in April 2016 after his last bout in December 2014, turning pro in the boxing ring in March 2015. Tickets start at $40 plus booking fees. Groups of 10 or more will also receive 10% off at the $40 and $60 ticket prices, and can be purchased by clicking here.

Taste Traditional Diwali Favorites with a Modern Twist

ROOH Chicago is celebrating Diwali with a four-course tasting menu available Sunday, October 27. This special menu has been crafted for guests to have a truly unique Diwali experience, courtesy of Executive Chef Sujan Sarkar and Chef de Cuisine Sahil Sethi, and features dishes like Dahi Puri, Tuna Tostada, Tandoori Chicken, Chocolate Rum Ball and so many more. The ticketed experience is $85 per person, including taxes and gratuity. For more information or to make a reservation, visit ROOH Chicago’s website.

Participate in One of Chicago’s Most Epicurean Culinary Events

Kouzina, one of the most highly-anticipated culinary experiences of the season, will be hosted by and held at The National Hellenic Museum on November 7 at 6:30 p.m. Chicago’s top chefs and restaurants will come together to create dishes that feature “a twist on the classics,” highlighting each restaurant’s cuisine, with a hint of Greek inspiration. Over 700 guests will attend to eat, drink and celebrate. Proceeds from Kouzina benefit the museum’s vast efforts to offer rich and diverse programming including new exhibits, educational classes, activities and programs. Tickets to Kouzina can be purchased for $100 in advance by visiting their website or for $125 at the door.

Dine at Chicago’s Newest South Loop Hot Spot

A new American cuisine dining destination, Harbor, is sailing into the heart of the South Loop, opening Fall 2019. Located in the former Gioco space at 1312 South Wabash, Harbor reinvents traditional American fare with a locally sourced menu and unique beverage program, both influenced by the Great Lakes and the founders’ personal passion for sailing. The menu will feature savory dishes prepared on a rotisserie, grill and hearth oven in an open view kitchen for guests to enjoy and watch as chefs prepare their plates. Harbor will be open Tuesday through Thursday from 4 p.m. – 11 p.m. and Saturday through Sunday from 4 p.m. – 12 a.m. with lunch and brunch hours being added soon. For more information or to make a reservation, visit their website.

Plan Your Holiday Shopping Spree

Returning to theMart just in time for holiday gifting, the 19th Annual One of a Kind Holiday Show will bring over 600 artists and makers from across the nation together for a weekend of shopping, food and fun. Offering a range of products from home goods and accessories to fine art and gourmet foods, the show has something for every taste. Guests will be treated to entertainment including creative workshops and gourmet cafes while shopping a variety of handmade, artisan goods. Running from December 5 through December 8, the One of a Kind show will be open on Thursday and Friday from 11 a.m. – 8 p.m., Saturday from 10 a.m. – 7 p.m. and Sunday from 10 a.m. – 5 p.m. Tickets to the show are $12 and can be purchased online.