The Most Iconic Ads Ever Seen in Chicago (And Why They Worked)

Chicago isn’t just a media market. It’s a stage. When brands get it right here, they don’t just show up, they show up with purpose. From the Dan Ryan to 500 W. Madison to the arrivals hall at O’Hare, Out-of-Home (OOH) campaigns in Chicago have the power to reach audiences in the right place, at the right moment, with messaging that feels like it belongs.

These are some of the OOH billboard moments, past and present, that didn’t just work in Chicago. These billboard campaigns worked because the brands behind them understood the city.

Local Flavor, Served Big

In Chicago, food is more than fuel. It’s identity. And when restaurant and delivery brands show up with the right creative in the right location, OOH drives real decisions.

Take Portillo’s x Uber Eats at 500 W. Madison, a downtown commuter hub. This campaign delivered the message right where thousands of workers pass through daily. Hungry, moving fast, and in the mindset to order on the go. The clean creative and sharp placement proved that even in a crowded corridor, the right brand can cut through.

Or look at Giordano’s, whose bold roadside billboard grabbed attention with crave-worthy visuals and a simple message. Placed along a major traffic corridor, it reminded drivers that Chicago-style pizza doesn’t need explanation - just timing and reach.

This is where OOH thrives. When the right food hits the right street at the right time.

OOH That Speaks the Language of Chicago

In Chicago, credibility matters. Brands that don’t sound like outsiders get noticed.

The AT&T billboard that read “It’s a 312 Thing” didn’t need anything more. Locals knew exactly what it meant. The simplicity was the strategy, and the area code nod gave the campaign cultural weight without a single extra word.

Then there’s McDonald’s “Roll with the arches” board: designed like public art but unmistakably brand-driven. It blended fast food, fan loyalty, and a distinctly Chicago sense of humor all into one larger-than-life canvas.

These are more than executions. They’re reminders that when creative speaks in a voice the city recognizes, it doesn’t feel like advertising. It feels like a statement.

Messaging That Moves With the City

OOH works best when it moves with the audience. Few cities move like Chicago.

But that doesn’t just mean roads. The Chicago Symphony Orchestra ad at O’Hare Airport wasn’t loud or flashy. It was refined, elegant, and perfectly tuned to travelers’ headspace between flights. A cultural institution speaking to a global audience in a high-dwell, high-impact space.

Back in the heart of the West Loop, United Airlines took over 500 W. Madison. The creative didn’t just show up, it wrapped around commuters' daily experience. From the escalators to the entrances and concourses, United delivered an immersive message that moved with its audience, adapting to their pace and energy. It was a smart use of placement, repetition, and tone; an OOH moment built for a crowd on the go.

On the west side of the city, Miller Coors claimed a massive wallscape near the Salt Shed, a popular music venue and mixed-use space. The board is impossible to miss, and is seen by drivers on the Kennedy Expressway and pedestrians headed into shows or nearby restaurants. It’s a textbook example of how brands can use scale and setting to command attention from multiple types of commuters at once.

When brands understand how and where their audience moves, OOH becomes part of their routine.

Timeless Takeovers

Some billboard campaigns are so well-placed and so well-timed they become part of the city’s memory.

These campaigns weren’t just visible. They were impossible to ignore. They showed that when a billboard is done right, it doesn’t just deliver a message. It leaves a mark.

Built for Chicago, Backed by Experts Who Know It

OOH works in Chicago because it meets the city where it lives—in movement, in culture, and in tone. Whether it's a roadside billboard catching Cubs fans on the way to Wrigley, or a perfectly timed placement in a commuter hub like 500 W. Madison, location and context make the difference. That’s why Clear Channel Outdoor offers more than media space. Our award-winning creative team helps brands translate bold ideas into memorable, locally relevant campaigns. And our Chicago-based team lives the market every day. We know what works here because we’ve helped brands across industries find the message, the moment and the audience that moves the needle.

If you're looking to make a lasting impression in this city, we’re ready to help you show up in the way Chicago expects: clever, confident, and right on time.