Chicago Outdoor Advertising
We work with companies like…
Prices
Billboard advertising in Chicago starts as low as $1,000 per month for posters in residential areas, with billboards along the I-90/94 through downtown running up to $14,000. Digital billboards in the Loop and River North typically fall between $3,500 and $8,000, and wallscapes start at $15,000 and up. Chicago is a competitive major market — strong reach across a highly diverse, transit-heavy metro. Prices reflect four-week campaigns (excluding wallscapes, which have extended durations) and are based on recent market averages.
The City
Chicago is the third-largest city in the United States and one of the most important billboard markets in the country. Known for its iconic architecture, diverse neighborhoods, and a population that spans every demographic, Chicago offers advertisers access to a broad, engaged audience across a dense urban core and sprawling suburbs. From the Loop to Lincoln Park, Wicker Park, and the South Side, Chicago’s neighborhoods each draw a distinct and passionate local audience.
The I-90/94, I-290, I-55, and Lake Shore Drive carry millions of commuters daily between the city and its suburbs, creating consistent, high-frequency exposure for billboard campaigns across the entire region. If you’re considering billboard advertising in Chicago, Evanston, Oak Park, or anywhere across the greater Chicagoland metro, we know this market. Let us help you find the right locations and lock in competitive pricing for digital, mobile, and traditional outdoor advertising.
the Landscape
Chicago is home to a population of 2.7 million in the city proper and over 9.5 million across the greater metro — the third-largest DMA in the United States. The market is highly diverse, with a strong mix of Black, Hispanic, White, and Asian residents spanning a wide range of income levels and industries. Major employers including Boeing, United Airlines, and Hyatt have headquarters in the city, creating a large professional audience alongside Chicago’s famously loyal neighborhood communities.
The Chicago market features billboards concentrated along I-90/94, I-290, I-55, and Lake Shore Drive, with a strong digital presence in the Loop, River North, and Wicker Park. For brands looking to reach a diverse, urban, and highly engaged Midwest audience, outdoor advertising in Chicago delivers strong results at competitive prices.
Chicago Billboards
DASH TWO
Dimensions:
Billboards measure 48 feet wide x 14 feet tall.
Dimensions
The majority of posters measure 22 feet wide x 10 feet tall.
Dimensions
Digital bulletins measure 48 feet wide x 14 feet tall, other sizes of digital inventory are also available.
Chicago, IL
Population: 2.7 Million
500+
Billboards
places to advertise
Traffic jams can have people sitting for minutes or even hours throughout the city. Based on our experience, here are some of the best locations for Chicago billboards:
Sunset Blvd Afterpay Mural
The Loop
The Loop is Chicago’s central business district and the heart of the city’s commercial activity. With millions of commuters, tourists, and residents passing through daily via the CTA El, bus routes, and pedestrian corridors, billboard placements here deliver unmatched visibility. Top advertising categories include financial services, entertainment, retail, and hospitality.
I-90/94 (Dan Ryan / Kennedy Expressway)
The I-90/94 is Chicago’s busiest expressway, running through the heart of the city and connecting the North and South Sides. With hundreds of thousands of vehicles daily, billboards along this corridor deliver massive reach and frequency. Top advertising categories include consumer products, automotive, healthcare, and major brand campaigns. See how billboard advertising performs on high-speed corridors like the Dan Ryan.
Glow Recipe
River North
River North is one of Chicago’s most upscale and high-traffic neighborhoods, home to galleries, restaurants, nightclubs, and luxury residential buildings. Billboard placements here reach an affluent, trend-conscious audience. Top advertising categories include luxury goods, dining, nightlife, real estate, and lifestyle brands. Explore digital billboard options in River North.
I-290 (Eisenhower Expressway)
The I-290 connects downtown Chicago to the western suburbs, carrying heavy commuter traffic daily between Oak Park, Cicero, and the Loop. Billboards along this corridor deliver strong reach into both the city and suburban markets. Top advertising categories include retail, home services, healthcare, and local businesses. Contact us to check current availability on I-290.
Sunset Blvd
Digital Billboard
Wicker Park / Bucktown
Wicker Park and Bucktown are two of Chicago’s most culturally vibrant neighborhoods, attracting a young, creative, and brand-conscious audience. Street-level posters and wallscapes perform particularly well here. Top advertising categories include fashion, food and beverage, music, entertainment, and lifestyle brands. Learn more about wallscape advertising in Chicago’s trendiest neighborhoods.
Client Testimonials
“
We needed digital ad services, expertise in programmatic advertising, and help with traditional media buying. DASH TWO really came through for us in all areas.
Brian Shafton
RBC Records
“
DASH TWO’s marketing services are great to work with! They are prompt, professional, and simply put — they get it. Our results have been fantastic!
Renee Frank
Marketing, Frank Productions Inc.
“
DASH TWO is an excellent boutique media buying shop. If you need programmatic advertising and digital ad services, I highly recommend them.
Josh D’Amore
300 Entertainment
Ready to get started?
Thinking About Billboard Advertising in Chicago?
Contact us to learn more about billboards in Chicago. Whether you’re targeting the Loop, the expressways, or local neighborhoods, we can help you build a high-impact outdoor campaign that fits your budget and goals.
Why DASH TWO
Chicago is a market that rewards relationships. The city’s competitive billboard inventory, high demand along the lakefront and expressway corridors, and neighborhood-by-neighborhood audience shifts mean that buying outdoor media here requires more than just a rate card. Knowing which operators control the best locations, what fair market pricing looks like on the Dan Ryan versus a surface street in Wicker Park, and how to structure a campaign around Chicago’s commuter patterns — that’s where experience makes the difference.
DASH TWO has spent 15+ years building relationships with the major outdoor operators in the Chicago market, including Clear Channel, Lamar, and Outfront. We know what’s available before it hits the open market, and we have the leverage to negotiate competitive rates on your behalf — whether you’re booking a freeway bulletin on I-90/94 or a wallscape in River North. We don’t just book boards — we monitor campaign performance in real time and make adjustments to ensure your spend is working as hard as possible from day one.
Whether you’re a Chicago-based business looking to reach locals or a national brand activating in the Midwest, DASH TWO gives you a single point of contact for everything from strategy and buying to creative and reporting. We treat every budget — startup or Fortune 500 — like it’s our own.
Rates vary by format and location.
A minimum spend of $5,000 applies, which can be spread across multiple displays and time periods.
Chicago has five main formats: billboards, posters, digital billboards, mobile billboards, and wallscapes. Each serves a different audience and campaign goal — from high-speed expressway placements to street-level urban posters.
Chicago’s audience is one of the most diverse in the country — 33% White, 29% Hispanic, 29% Black, and 7% Asian. The metro spans a wide range of income levels, industries, and neighborhoods, giving advertisers access to virtually every consumer demographic in a single market.
No — your advertising partner handles all permits, zoning compliance, and installation logistics through the City of Chicago Department of Planning and Development. You don’t need to navigate any of that on your own.
Static (vinyl) billboards display a single printed ad 24/7 for the duration of your campaign. Digital/LED billboards rotate your ad among several advertisers and allow for quick creative updates without print production costs. Digital boards are ideal for:
Most billboard campaigns run on four-week cycles, though digital boards can be booked for shorter windows. Wallscapes typically require longer commitments.
Coverage spans Chicago plus:
Key corridors include:
Yes — creative and design services are available, including free graphic design for qualifying campaigns. Billboard ads should be simple, bold, and readable at highway speeds. Contact us to learn more about design services.
Billboards work across a wide range of industries, including:
Chicago residents spend significant time commuting, making outdoor advertising a cost-effective way to build reach and brand recall.
Digital and Outdoor Advertising Agency. Expertise in the science of digital and the art of the outdoor.
214 S. Locust St. #200
Inglewood, CA 90301
Copyright 2026 © DASH TWO, INC. All rights reserved.