Small business events in Chicago: 8 ways to grow and market your business in 2021

In this 5-minute read:

  • 8 Chicago events to add to your 2021 business calendar

Wherever your business is located, you can and should take advantage of local events. Whether that is a 2-day business conference to help your team members grow and develop in their roles or a fun family fair in the next town over, these are opportunities to grow your business. 

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We’ve highlighted several Chicago area events that you should consider adding to your calendar. Check them out and see which ones you can actively participate in. Even large, regional events can benefit smaller local businesses if you know how to benefit from the hype and the extra visitors. 

PLEASE NOTE: We have made every attempt to be accurate in our information but as you can imagine during the COVID-19 pandemic, everything is still in flux. Please consult the websites for the individual events and confirm the status of the events you wish to attend.

Chicago Auto Show

When: Spring 2021

Check back at for more specific times and dates as we get closer to the event.

The Chicago Auto Show is the nation’s largest auto show, featuring vehicles all across the board to show consumers the newest and greatest automobiles to date as well as the classics that will never go out of style. 

Whether your business is in the auto industry or not, this is a valuable opportunity to gain some traction with your customers. If you are in the auto industry, see what it takes to participate in the show and bring in more customers that way. 

And if you’re not, then take advantage of this national event by creating fun discounts and deals related to the show. Share that on your social media channels, website, and storefront to bring in more customers throughout the week of the show. 

Maxwell Street Market

When: Sundays, March-December

The Maxwell Street Market starts March 1 and generally goes through the Sunday before Christmas. Every Sunday, Maxwell Street is open to vendors across multiple industries to sell their goods. Become a vendor at the Maxwell Street Market this year or during the market, offer some fun deals at your business to bring in more customers while they are out browsing through the market. 

Learn more about becoming a vendor at

Modern Business Experience

When: TBA

(The 2020 event went “virtual” and we have found no info about a 2021 event as of yet.)

The Modern Business Experience is a conference focused on helping your business learn more about improving customer experience, finance, HR, and supply chain management. Throughout this conference, you’ll gain valuable insights from experienced business professionals and have the opportunity to network with other Chicago businesses with industry breakout sessions and “experience hubs.”

Learn more or sign up now at


When: June 9-10, 2021

DigiMarCon is one of the largest digital marketing conferences in the world. At this conference you will learn the best ways to keep up with your competition through digital marketing strategies and which methods will be most valuable for your business. 

You’ll have the opportunity to learn from the industry’s best, including speakers from Microsoft, Adobe, SEMRush, NBC Sports, Amazon, Paypal, Hubspot, Pizza Hut, and many, many more. 

Sign your marketing team up for this conference now at

Chicago Small Business Expo

When: August 25, 2021

Don’t miss out on the Small Business Expo. This national expo is perfect for entrepreneurs in every industry. Hear from speakers on ways to enhance your business strategies, participate in workshops, and network with other local businesses. 

The best part is your team can attend the event for free! Sign up now at

Illinois State Fair

When: August 12-22, 2021

Located in Springfield, just three hours south of Chicago is the Illinois State Fair. Businesses can gain new customers by setting up a booth at the fair. People from all over the state gather at the fair to have fun, and as they escape the heat to check out the exhibits, they may just find what they have been looking for at your booth. 

Whether you are a service or product-based business, you can benefit from having a booth at the fair. Learn more about becoming a vendor at

Annual Jazz Music Festival

When: TBA

The 2020 event was cancelled, and there are no definite dates for a 2021 even yet. Check for updates at

Chicago is a hub for culture. Throughout the year music festivals of all sorts take place at the Chicago Cultural Center. One of the largest events is the Annual Jazz Music Festival. Bring your team to the event to improve morale and have some fun, but also get your customers excited about the fun through sweet deals and themed discounts at your business. 

Be sure to check out the other annual music festivals that are taking place at the Chicago Cultural Center to see if these events can provide even more opportunities for your business to gain awareness. 

outdoor chicago jazz festival for small business events

Winter Wonderfest

When: (may resume in December 2021)

Important update: Navy Pier has been temporarily closed to the public until Spring 2021, so the 2020-2021 Winterfest did not take place. It may resume in December 2021.

Winter Wonderfest has become a huge annual festivity at Navy Pier during the holidays. Fifth Third Bank hosts this year-end event by setting up the city’s largest indoor winter playground. With carnival rides, an ice-skating rink, holiday-themed activities, a giant slide, vendors, and much more, families gather from all over the state to join in on the fun.

Participate in the fun by taking your team to enjoy the festivities and offering themed discounts and offerings throughout the festival. Stay up to date on this year’s activities by checking back on the event at

Enhance your marketing strategy with reputation management software

As you participate in these local events, be sure to have a plan in place to enhance your marketing even further through the new customers that you gain. 

Capitalize on your customer growth by reminding new customers that you value their online feedback review after their interaction with you. Solutions like Womply’s reputation management software make this process seamless and simple, and you can manage all your online reviews on multiple platforms from one dashboard with one login. 

Learn more, plus get free reputation monitoring and customer insights when you sign up for Womply Free!


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