5 Best Holiday Marketing Strategies for Chicago Businesses

Last-minute holiday shopping is losing its luster. Today, 50% of Chicagoans are snapping up gifts before Halloween decorations come down. And it’s affecting businesses’ holiday marketing in a big way.

Chicagoland companies are feeling the impact. It’s an exciting opportunity — and a challenge with plenty of competition, plus the need for more time to plan effective campaigns.

It can feel overwhelming, but you’re not alone. With our sister company, Chicago Parent, Zoe Marketing & Communications has helped businesses tailor holiday messages to their local markets for nearly 40 years.

Here, we’ll highlight exactly what customers want, from Albany Park to Aurora. Then, we’ll dive into the best strategies to reach them:

• Streaming video and radio 
• Targeted email marketing
• Traditional media (print, TV and radio)
• Social media ads and livestreams
• Daily deals (i.e., discount websites)

You'll learn where to put your local holiday marketing budget for the most significant impact. And you can decide on your next steps.

Deals are on the minds of Chicago holiday shoppers in 2023

Understanding the headspace of your ideal Chicagoland customer is crucial. And, this year, bargains are on their minds, thanks to lingering inflation. A recent survey by Numerator found:

• 67% of shoppers plan to buy holiday gifts on sale
• 48% of shoppers plan to buy fewer gifts
• 47% of shoppers plan to use more coupons

So, what does this mean for you? Discounts and deals are the name of the game. Whether it's a 10% discount or a 40% markdown, make it targeted and time-sensitive. Avoid increasing prices before cutting them; this can risk losing shoppers’ trust in the long run.

Also, deliver these messages starting in October — when many are beginning to shop. Your marketing should be in full swing by November to keep competitive.

5 best holiday marketing strategies to reach Chicagoans

So, let’s detail five impactful holiday marketing strategies. These include streaming media, email, traditional media, social media ads and daily deals.

1. Streaming media hones in on a precise Chicago audience

Streaming video or audio ads connect with customers while they’re enjoying their favorite content. These options include: 

• OTT (over-the-top): Delivers on-demand streaming shows via Apple TV, Amazon Fire, Roku Stick and more.
• Streaming audio: Includes SoundCloud, Spotify and Pandora, to name a few. Beyond audio ads, you’ll find some options for image or video ads.
• CTV (connected TV): Includes smart TVs, gaming consoles and digital media players. They’re used to watch videos via the web.

In all cases, you can tailor your ads to specific Chicago neighborhoods, suburbs or interests. These platforms often allow clickable or scannable calls to action, or CTAs, too. That makes it easier for potential customers to take immediate shopping action.

2. Targeted email campaigns are a direct line to your local shoppers

Next, targeted mail marketing reaches people throughout Chicagoland based on various demographic details. This can get as detailed as “last-minute holiday shoppers” or people who commonly buy higher-end luxury items or experiences.

Plus, if your emails entice people to click to your site, but they don’t purchase anything, you can also retarget them with more emails for even better results.

Ensure your emails contain a straightforward message. Highlight your discounts and focus on time sensitivity.

Plus, don’t forget your in-house enewsletter subscribers. Consider email holiday campaigns for your existing Chicago-area clients, too.

3. Traditional media increases exposure in the city and the suburbs

Chicago's local newspapers, TV stations and radio channels often offer special holiday ad packages. In these cases, you’ll jump on their deals to highlight your deals.

After all, these classic advertising options still hold clout. Their reach is broad and highly local, with loyal readers, viewers and listeners. Your ad in their media is an implied endorsement.

Plus, options like newspaper holiday guides let your ads leverage a larger holiday marketing campaign. This exposes you to a more extensive regional audience.

4. Social media ads and live events engage Chicagoans in real time

Social media ads on platforms like Facebook and Instagram are invaluable when reaching a broad yet targeted audience in Chicago. Entice people with offers like:

• “Celebrate Chicago-Style: Enjoy 15% Off Your Order with Code WINDYCITY”
• “Savor the Season: Claim Your Exclusive Holiday Dinner Package”
• “Deck the Halls, Chicago! Save 10% on All Purchases Today”

Rolling out campaigns over several days is one method worth trying. Think “Festive Fridays,” where you highlight a new exclusive deal each Friday leading up to the holiday. Or try a “12 Days of Christmas in Chicago”-style approach to build excitement and sales. 

Livestreaming is another engaging way to connect. Imagine hosting a 30- to 40-minute live event, akin to a digital holiday market, where you showcase your best holiday offers.

Promote these live events in advance and schedule them consistently to boost your visibility.

5. Daily deals offer enticing bargains for the Chicago market

In a city as bustling as Chicago, people always watch for deals, especially during the holiday season. That's where “daily deal” platforms like Groupon and LivingSocial are powerhouses.

More than just digital coupons, these savvy marketing tools use customer data to promote your offers to the right audience. From location to past purchases, you’ll pinpoint your ideal customers. Then, you’ll determine your deal.

For instance, you could run a limited-time three-day special with exclusive discounts on popular items or services — from a spa day package at half-price to 20% off a local food truck tour.

Finally, these platforms promote your deals on their websites, mobile apps and targeted emails. 

Next steps for holiday marketing in the Windy City and beyond

The festive season is a key time for Chicago businesses to grow and shine. When your holiday marketing strategy includes streaming media, emails, traditional ads, social media and daily deals, you're not just casting a wide net — you're casting the right net.

Still, running these campaigns can seem complex and stressful. If you find yourself in need of guidance, talk to us. Zoe’s team at Chicago Parent can craft a message that speaks to your audience — and deliver it through the best tactics.

And, whether you go full-throttle on holiday marketing or take a more measured approach, ensure you have a comprehensive, year-round strategy. To learn more, discover:

• The different types of social media ads and how they work
• Why multichannel marketing or layering tactics is important