September 19th – 22nd Chicago: EXPO Chicago, Midwest Flair Fest and more things to check out this weekend

This weekend, experience a weekend full of unique arts and culture from around the world, and right here at home. Shop local goods in the West Loop or find some new flair in Pilsen. Experience Chicago in the most unique way this weekend. Check out the full details of things to do below.


Midwest Flair Fest

Sunday | September 22nd | 11:00 a.m. – 4:00 p.m.

Thalia Hall | 1807 S Allport St. | Free

Image | Midwest Flair Fest

Midwest Flair Fest is a gathering of all things flair. The market features over 40 vendors from all over the US. The flair includes pins, patches, apparel and more. The event is free for all ages. Arrive early and receive a free tote bag filled with swag from the various vendors participating in the event. For more details on this event, visit the event page here.

Chicago Artisan Market

Sunday | September 22nd | 10:00 a.m. – 4:00 p.m.

Morgan MFG| 401 North Morgan St. | $0 – $25

This weekend, check out the Chicago Artisan Market in the West Loop. The market will showcase over 100 local artisans, crafters, and designers. Peruse one-of-a-kind designs, home goods, fashion, art, food, and more. The family-friendly event offers a kids zone as well as a VIP experience—the ultimate shopping experience for your fall refresh takes place this weekend. Grab a pair of free or discounted tickets here.

Food + Drink: 

The Original Rainbow Cone Comes to Stan’s

Saturday – Sunday | September 21st – 22nd | 1:00 p.m. – 9:00 p.m.

Stan’s Donuts and Coffee Chicago | 1560 N Damen Ave. | Free

Check out the sweetest collaboration of the year in Wicker Park this weekend. The Original Rainbow Cone, located on the South Side of Chicago, will host a pop-up experience with Stan’s Donuts at their Wicker Park location. Enjoy the last days of summer with an iconic cake cone and donut this weekend in Chicago.

Chicago Japanese Matsuri

Saturday – Sunday | September 20th – 22nd | 3:00 p.m. – 5:00 p.m.

New City | 1457 N Halsted St. | Free

Sample and savor Japanese food and culture this weekend in Chicago. Chicago Japanese Matsuri hosted by Kizuki Ramen & Izakaya and Japanese Culture Center – 日本文化会館will host a traditional Japanese summer festival in the heart of Chicago this summer. All festival foods will be prepared by chef Kevin Yu and his team from Kizuki Ramen & Izakaya which means true Japanese culinary authenticity and deliciousness. For more event details, be sure to visit the festival event page.


Soap Box Ball 2019: City’s Bureau’s Biggest Party of the Year

Thursday | September 19th | 6:00 p.m. – 10:00 p.m.

Glessner House | 1800 S Prairie Ave. | $100 – $125

Hop on your soapbox this weekend in Chicago. Join City Bureau for their 2019 Soap Box Ball. This year’s derby takes place at the historic Glessner House and features poetry, music, spoken word, and a live DJ throughout the evening. Of course, there will be food and libations to enjoy throughout. Support local journalism at this annual celebration. For tickets, visit the event page.

Arts + Culture:

EXPO Chicago

Thursday – Sunday | September 19th – 22nd | 6:00 p.m. – 7:00 p.m.

Navy Pier | 600 E Grand Ave. | $30 – $45

Observe modern and contemporary art with fellow art lovers at this weekend’s EXPO Chicago. The annual exposition hosts more than 135 leading International exhibitors, alongside one of the highest quality platforms for global contemporary art and culture. In addition to the show, there are talks, conversations, and workshops taking place across the city in celebration of the major art event. For tickets and more details, visit the EXPO

The Chicago Pancakes & Booze Art Show

Saturday | September 21st | 8:00 p.m. – 2:00 a.m.

Reggies | 2105 S State St. | $10 – $15

Pancakes, art, and booze—sounds like the perfect Saturday to me! Experience this annual pop-up show this weekend. Check out provides art from more than 100+ local Chicagoland artists. Find your next collector’s item in the South Loop this weekend. For tickets and details, visit the event page.

The Weekend Seekers Guide shares some of the best things to do in the city over the weekend, but there are even more events that make some of our other major lists. For more events, be sure to check out the fall guide as well as the best things to do in September.

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