October 2019 Chicago Events Guide

Chicago’s crisp, cool October air may entice you to stay in—but know that there are plenty of fun things to do outside this month. This October 2019 Chicago events guide features fall activities for you to do. From delicious fall food festivals to creative content-driven conversations—this October guide spotlights some of the best events in the city. Check out the full guide of Chicago events this month below.



Friday| October 18th | 6:30 p.m. – 9:30 p.m.

Garfield Park Conservatory | 300 North Central Park Ave. | $195

FLEUROTICA |Image by Elly Elite

Experience a bountiful botanical show FLEUROTICA at the Garfield Park Conservatory. The event features 18 botanical looks created by Chicago’s leading floral designers, fashion designers, landscape artists and students as they create breathtaking garments made entirely from plants, flowers, and natural materials. Proceeds benefit the Garfield Park Conservatory Alliance and our mission to change lives through the power of nature. For more details, visit the event page.

FGI Chicago Presents: A Chat With: Past Rising Stars, Where Are They Now?

Thursday | October 3rd| 5:30 p.m. – 8:00 p.m.

The Chicago Fashion Incubator | 111 N State St. | $20 – $35

Image | Fashion Group International of Chicago Inc.

Sit in on a fashion-forward conversation this month. FGI Chicago’s A Chat With (ACW) series was created to offer more intimate events where participants can be closely connected with speakers and have more immersion in the topic. Gather with fellow creatives as you get the inside scoop on some of Chicago’s rising stars within the fashion industry. The event will feature a product showcase of our speakers, networking, drinks and light bites. To purchase tickets, visit the event page.

Runway Latinx

Thursday – Saturday | October 3rd – 5th | Time Varies

Location Varies | Price Varies

Image | Runway Latinx

Experience a global movement of fashion in Chicago this October. Runway Latinx is a fashion week dedicated to local designers, vendors, and those that love the fashion industry. The multi-day branded entertainment environment provides opportunities for fashion designers and sponsors to come face-to-face with celebrities, musical talents, media, and major consumers. To purchase tickets to one or more of the events surrounding Runway Latinx, visit the website here.

Made-To-Measure By Gitman Bros.

Saturday – Sunday | October 5th – 6th | 11:00 a.m.

Independence | 920 W Randolph St. | Free

Image | Gitman Bros.

Fellas, get a made to measure shirt that is perfect for work or play this October. Gitman Bros, a manufacturer creating high-quality shirts and ties since the 1970s in the U.S. along with Independence Chicago, will host a special made-to-measure event. Get professionally measured and choose from dozens of options to design your custom shirting – from collar to cuff. Or choose from one of Gitman Bros.’ classic styles and select your fabric and color. Get creative and custom this fall—for more details, event page.

Food + Drink:

Taste of Logan Square

Tuesday | October 22nd | 6:00 – 9:00 p.m.

Logan Square Chamber of Commerce | 3147 W Logan Blvd. | $0 – $2,015

Check out Taste of Logan Square, a fall food event taking place in Logan Square this October. Stroll the boulevard’s food scene through small bites at some of our favorite eateries, in the West Side neighborhood. For a list of participating restaurants, tickets, menu items, and more visit Logan Chamber.org.

Apple Fest

Saturday – Sunday | October 5th – 6th | 9:00 a.m. – 6:00 p.m.

Lincoln Ave between Lawrence & Eastwood | $5 Donation

Go apple picking—without leaving the city this month. Check out the Annual Apple Fest in Lincoln Square as you peruse over a dozen options of the best apples, fall treats, and more. Pick up fresh apple pie, hot apple cider, or even a whole bushel of apples. For families and solo adventurers alike, this event is the perfect way to spend a weekend afternoon this October. For more details on this event, visit the website here.

Bacon and Beer Classic

Saturday | October 12th | 2:00pm – 5:00pm (VIP Entry at 1:00pm)

Soldier Field | 1410 Museum Campus Dr. | $55 – $99

Image | Bacon and Beer

Warm up this fall with a delicious combination of bacon and beer. This October food event features over 80 craft beers and more than 40 different mouth-watering bacon-themed tasty bites created by local restaurants. Treat yourself this fall by grabbing tickets to this savory event. For more details, visit the website.

Bloody Mary Festival

Sunday| October 20th | 8:30 a.m. – 4:00 p.m.

Theater on the Lake | 2401 N Lake Shore Dr. | $35 – $80

Image | Bloody Mary Fest

Looking for the best Bloody Mary in Chicago? Look no further than the Bloody Mary Fest this October. Bloody Mary Fest is an all day celebration of brunch and Bloody Mary’s taking place in Chicago. The festival features a Bloody Mary competition, artisan market, specialty brunch-themed cocktails, craft beer, brunch bites, yoga, a fun run, lawn games and much more. For tickets to this event, visit Bloody Mary Chi.com.


8th Annual I Am Your Neighbor

Friday | October 4th | 7:00 p.m. – 11:00 p.m.

Artifact Events | 4325 North Ravenswood Ave. | $125 – $1000

Image | Common Pantry

Come together with neighbors, friends, and the community for Common Pantry’s 8th annual I Am Your Neighbor fundraising event. The North Side organization will bring together their large community together for a celebration of their good work and local services of providing emergency food and social services to our neighbors in need. Enjoy live music, food and drink from our favorite local restaurants and craft beverage all night long with proceeds to benefit Common Pantry. For tickets, visit the event page here.

3rd Annual Gather Gala

Thursday | October 17th | 7:00 p.m. – 10:00 p.m.

Salvage One | 1840 West Hubbard St. | $80 – $200

Image | I Grow Chicago

Join I Grow as they continue their mission to help over 3000 people move from trauma to transformation this October in Chicago. The local organization will host their 3rd Annual Gala in the West Loop this month. The I Grow Chicago Gala 2019 will feature delectable bites from various Chicago restaurants and drinks from local beverage markers. Spend the evening socializing with fellow supporters and community members, dancing the night away, and bidding on an array of unique silent auction items. For tickets to the event or to learn how you can volunteer for this organization, visit the event page.

Find Your Cause with Chicago Cares

Thursday | October 21st | 5:30 p.m. – 7:30 p.m.

Chicago Cultural Center | 2033 West North Ave. | $15 – $20

Image | Chicago Cares

Find the perfect match and ways to give back through Chicago Cares this October. Find Your Cause is the city’s top matching event for passionate professionals looking to use their skills for good. Find Your Cause is a unique networking opportunity that connects your employees to 50 cutting-edge social impact organizations with hands-on, skills-based, and auxiliary board service opportunities. Held over drinks and appetizers at the beautiful Chicago Cultural Center. To register for this event, visit the event page here.

Arts + Culture:

Open House Chicago

Saturday – Sunday | October 19th – 20th | 10:00 a.m.

Location Varies | Free

Beverly Unitarian Church | Image by Taylor Justin

Open House Chicago is the city’s annual celebration of architecture around the Chicagoland area. One of my favorite fall events, Open House Chicago allows visitors to explore historic neighborhoods and undisclosed buildings over the course of two days this fall. To learn more about the 2019 sites, visit Open House Chicago.org.

Chicago Ideas Week

Saturday – Thursday | October 12th – 17th | Time Varies

Location Varies | $15 – $40

You Are Beautiful | Image by Taylor Justin

Chicago Ideas is a week-long series of events inspiring people from every single part of Chicago to take action. From world class speakers and influencers to groundbreaking accessible events this grassroots initiative is all about thought-provoking content and inspires attendees to create the change that they want to see in the world. For tickets and a full schedule of events activities visit Chicago Ideas.

FPC Block Party – Logan Square

Sunday | October 6th | 1:00 p.m. – 5:00 p.m.

Logan Square | 2650 N. Drake Ave. | Free

Image | Front Porch Concerts

Front Porch Concerts is a pop-up concert series taking place on front porches throughout Chicago. Enjoy free live music from local bands across three front porches in Logan Square this October. Food trucks and local snack vendors will also be on hand. Don’t forget to BYO(bring your own) chair for this outdoor concert series. Register to attend this event by visiting the event by visiting the Facebook page.

Celebrating Day of the Dead: Workshop Series

Saturdays | October 5th & 19th | 12:00 p.m. & 2:00 p.m.

Casa Michoacán | 1638 S. Blue Island Ave. | $10

Image | Casa Michoacán

Join Inherit Chicago as they continue their month-long festival of intercultural art. This October, the organization will host a two-part series surrounding the celebration of the Day of the Dead. Lead by a Mexican artisan, guests will learn about why Mexicans commemorate death in this way. Part 1 consists of decorating sugar skulls, and part 2 consists of decorating Catrinas, a female representation of Death. To learn more about this unique cultural event and how you get involved, visit Inherit Chicago.org.

This list contains only a few of the great events happening in Chicago. Find other great events by checking out the ultimate fall guide.


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