September 2018 Guide

South Side I Do, Hyde Park Jazz Festival, Fulton Market Harvest Fest, Windy City Ball, plus more exciting events to check out this September in Chicago. Make this ninth month of the year, the best month yet!


South Side I Do

Sunday | September 9th | 12:00 p.m. – 4:00 p.m.

Harper Court | 5235 S. Harper Court | $8 – $24

If you are seeking wedding inspiration or helping plan the big day for a friend, then the “South Side I Do” Hyde Park Wedding Stroll is the perfect event for you. The exclusively South Side-based wedding event is the first of its kind that spotlights the Hyde Park neighborhood and the businesses that offer couples options when planning their special day. Guest will start the stroll at Harper Court to pick up a complimentary tote bag – making stops at Jojayden, The Silver Room, Hyatt Place Chicago, and Vanille Patisserie, before ending at The Promontory. The event will also feature 35+ other participating vendors. Tickets are $15 per person or $25 per couple. Proceeds from the event will be donated to Wish Upon A Wedding, a non-profit group granting wedding wishes to couples dealing with serious illness or a life-altering circumstance. Want to win free tickets to South Side I Do for you and your boo/bae? Be sure to visit my Instagram for more details!

Covet Market September 2018

Sunday | September 23rd | 10:00 a.m. – 5:00 p.m.

Revel Fulton Market| 1215 West Fulton Market. | $8 – $24


The curators and editors of Chicago Woman magazine bring together a locally-made goods to independent boutiques and designers all together under one roof at Revel Fulton Market. Refresh your home, your style for the fall with options from more than 80 vendors. Between shopping, sip on included Sunday cocktails at the Mimosa and Bloody Mary Bar and stop by the beauty bar for a braid or mini mani. Plus, you can explore a food hall featuring budding culinary brands and makers, in partnership with the incubator The Hatchery Chicago. Get ready for a new season as you shop locally. Be sure to follow my link for free tickets to the market.

Chicago Men’s Fashion Awards 2018

Wednesday | September 12th | 5:00 p.m. – 8:00 p.m.

Room & Board | 55 E Ohio St. | $75 – $250


Join the Costume Council of the Chicago History Museum for the third annual Chicago Men’s Fashion Awards. As the premier men’s fashion event in the city, this year’s affair will feature a sultry, deco-inspired theme sure to entertain all fashion enthusiasts. Hosted by celebrity stylist Eric Himel, and award-winning journalist Darlene Hill, the awards are to formally recognize the most stylish men in Chicago for their dedication to fashion and individual style. Guaranteed to be one of the most fabulous and fashionably enthusiastic crowds in Chicago complete with fall fashion highlights from Saks Fifth Avenue Men’s Collection, cocktails from Rhine Hall Distillery, hors-d’oeuvres from DineAmic Group, music by Bonzai, and stylish home décor vignettes from Room & Board. Purchase your tickets for the fashion-forward event here.

Clothing Swap + Fair Trade Pop-up Shop

Saturday | September 22nd | 4:00 p.m. – 8:00 p.m.

Mata Traders | 5112 N Ravenswood Ave. | Free

Sustainable shoppers! Help save your favorite threads from going into the landfill. This September, bring in your lightly used clothing and swap for some new to you threads or fair trade fall fashions. Items are exchanged on a one for one trading system. All pieces must be clean and in excellent condition. The event is hosted by Chicago Fair Trade + Mata Traders. For more details on fair trading and ethical fashion, check out the event website.


Oktoberfest at St. Alphonsus

Friday – Sunday | September 28th – 30th | Time Varies

1429 W Wellington Ave. | Free


Bring on autumn and pull out the lederhosen! One of Chicago’s most popular celebrations of fall and all things Bavarian — Oktoberfest Chicago at St. Alphonsus — returns for its 17th year of seasonal entertainment. Oktoberfest at St. Alphonsus has grown tremendously since its inception, expanding from a parking lot in West Lakeview into Southport into three days of beer, brats, bands, and all things Bavarian. The ever-popular Craft Beer Night takes place Friday and Saturday evenings in the parish’s festive German Beer Hall, and two stages host some of Chicago’s favorite festival bands including 16 Candles, Polkaholics, and American English. Learn more about the favorite fall event here.

Loft Golightly

Thursday – Sunday | September 20th – 23rd | 8:00 p.m. – 1:00 a.m.

The Chop Shop & 1st Ward | 2033 West North Avenue | $50 – $60

Loft Golightly is an immersive theatrical event based on the party Holly Golightly throws in the iconic movie, Breakfast at Tiffany’s. Tickets to the event include an open bar for the duration of each “party” with a surprise ending. Mingle with characters from the movie, dance to our DJ with sounds from the mid-century, and enjoy replica fixtures from the film. Cocktails and beer are included with your ticket (excluding premium liquor, shots, and specialty drinks). Mid-century (50’s-60’s) attire is highly encouraged, be a part of the fun! Get more information on the event by visiting Loft

JSVFest – Jerk, Seafood & Vegan Festival

Saturday – Sunday| September 8th – 9th | 6:00 p.m. – 9:00 p.m.

Dearborn at 24th St & State St.| $5 – $10

The Jerk, Seafood, and Vegan(JSV Fest) food festival with drinks, music, arts, crafts and fun for the entire family. In celebration of Ephraim Martin’s International 35th Anniversary, the JSV Fest will help celebrate the success of the well-known festival planner. For more information, check out the event page.

Fulton Market Harvest Fest

Friday – Sunday | September 14th – 16th | Time Varies

Fulton Market & Halsted| $30 -$200


Fulton Market Harvest Fest brings together the country’s best chefs, craft beer, live music, and Chicago’s best restaurants for a weekend of culinary fun. The variety of activities includes cooking demonstrations, dinners, and a brunch featuring some of Chicago’s tops chefs( Stephanie Izard, Rick Bayless, Fabio Viviani, and more), plus food and beverage classes and a neighborhood street fest featuring Chicago artists and vendors. General admission tickets are $30(entry and $20 worth of food/drink tickets) classes and other special events will be sold separately. Get more details on the event by visiting Fulton Market Harvest



Friday | September 28th| 6:00 p.m. – 9:30 p.m.

National Museum of Mexican Art |1852 West 19th St. | $25 – $500


Make your way to Pilsen for Globalfest 2018 – the fair trade party of the year. Tickets to the annual event will include an open bar featuring fair trade wine and local craft beer, a globally inspired buffet, live music, plus a private viewing of the highly acclaimed exhibition Day of the Dead. Early bird tickets to the event are now on sale. Be sure to save on admission by visit the event page.

MS Summer Social 2018

Friday | September 14th| 8:00 p.m. – 11:00 p.m.

The Chop Shop & 1st Ward |2033 West North Ave. | $80 – $450

MS Summer Social is a cocktail party fundraiser hosted by Multiple Solutions, the local Chicago Junior Board and Auxiliary for the National Multiple Sclerosis Society. The event will feature an open bar, appetizers, desserts, live music, and a luxury raffle drawing. Learn more about this event and the awareness it builds surrounding the disabling disease by visiting the event page.

Windy City Ball

Saturday | September 29th | 9:00 p.m. – 1:00 a.m.

Venue West | 221 N Paulina St.| $100 – $150


The 4th annual Windy City Ball(WCB) blows its way into Chicago this September. The charity gala for young professionals will be held at Venue West with all proceeds benefiting the Rice Child & Family Center, an organization which provides a temporary home and therapeutic setting for local children in Illinois’ foster care system who face severe mental and behavioral challenges. The WCB supports a different cause each year, and more info on past beneficiaries can be found on their website here. Included in the tickets, which are on sale now, is a 4-hour premium bar, passed appetizers, live music, and a silent auction. Join this organization for a great cause by purchasing tickets to the event here.

Arts + Culture:

Hyde Park Jazz Festival

Saturday – Sunday | September 29th – 30th | Time Varies

Location Varies | $0 – $50


The Hyde Park Jazz Festival is a collaborative platform dedicated to supporting the presentation and ongoing development of jazz, particularly on the South Side of Chicago. The free two-day festival features the finest in local jazz and national and international jazz artists; diverse performance venues; outdoor dance floor; food/beverage vendors and picnic areas; artisan vendors; and family-friendly programming. Learn more about the talented acts taking the stage by visiting Hyde Park Jazz

The Other Art Fair Chicago: Curated Gallery Show

Friday – Sunday | September 28th – 30th | 10:00 a.m. – 5:00 p.m.

Mana Contemporary | 2233 S Throop St. | $0 – $15


Based in the U.K. and making its appearance during Chicago’s famous Art Week, The Other Art Fair lands in a new city, offering a curated selection of works from more than 130 emerging artists, hand-picked by a select committee of experts. With pieces starting at $75, this show from Saatchi Art spans mediums and styles and allows you direct contact with the makers. The event will feature an artist panel, interactive installations, and a kids’ corner. Get discounted tickets to this unique event here.

Sunday | September 2nd | 7:00 p.m.

The Chicago Theater | 175 S State St. | $10 – $45


Hannibal Buress, the mildly popular comedian, writer, and actor will make his way home to Chicago this September for a special one night show. The Austin neighborhood native will be joined by Chicagoans fellow comedian and actor Lil Rel(“Get Out,” “Rel”) as well as artist and activist Vic Mensa ( the artist recently hosted an “Anti-bait Truck” giveaway). The show will benefit Melvina Masterminds. Grab your tickets today by visiting the website.

29th Annual African Festival of the Arts

Friday – Monday | August 31st – September 3rd | Time Varies

Washington Park | 5100 S. Cottage Grove Ave. | $5 – $40


The annual African Festival of the Arts takes place in September during Labor Day Weekend. The festival grounds of Chicago’s Washington Park come alive in a simulated African village. Attendees are transported across the Diaspora with interactive engagements, vibrant drumming, museum quality and collectible artifacts, colorful and rich hand-woven fabric and textile, and other program spaces. Interactive spaces during the event will include Drum & Afro-folk Village, Children and Family, African Heritage, African Spirituality, Wellness (Health) Village, Books and Authors, Fine Art, Film and Video, Food Court, Seniors and Quilting, and the African Marketplace. Tickets are $15 online, and $20 at the gate. Grab your tickets for a one day experience or a weekend pass by visiting the website here.

Have an event to share this fall? Be sure to submit it by completing the contact form.


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