Ten Reasons Chicago Reigns as Best Big City

Author

Sydney Stiegel

Senior Marketing Coordinator

When Condé Nast Traveler named Chicago the Best Big City in the World for the ninth year in a row, we weren't surprised—but we were proud. From Travelzoo to Frommer's to WalletHub, the accolades keep rolling in. But what makes Chicago truly exceptional isn't just the awards. It's what our PRA Chicago team experiences and shares with clients working and living in sweet home Chicago.

We asked Heather Brown, April Pranske, and Alli Rush from our Chicago team: “Why is Chicago the best? What is it about this city—our corporate headquarters’ home—that keeps winning over travelers, planners, and locals alike?"

It's not just one thing. It's ten things. (Actually, eleven. We couldn't help ourselves.)

By the Numbers

• Airport: O'Hare is officially the busiest airport in the country by number of flights
• Architecture: Home to the tallest building in the world designed by a woman (Jeanne Gang's St. Regis Chicago)
• Green Buildings: 400+ LEED-certified buildings—among the highest in the U.S.
• Sports: Six major league sports teams; Host of the 2026 WNBA All-Star Game and 2027 MLB All-Star Game

Top Ten: Why Chicago Is the Best Big City

1. The Biggest Small Town

"I moved here from a small town of 3,500," Heather says. "Twenty-seven years later, what keeps me here is that Chicago is the biggest small town I've ever lived in. I run into people I know everywhere I go. I feel safe. It has everything I loved about my small town, but with all the opportunities and excitement of a major city."

That juxtaposition—intimate yet expansive—is rare. Chicago offers the approachability of a tight-knit community with the scale and sophistication of a world-class city. For events, this means attendees feel welcome and comfortable while still accessing top-tier venues, restaurants, and experiences.

2. You Never Repeat the Same Day

"All these years later and I still find myself looking up as I'm walking through this city," Heather explains. "There's always something new to experience. That's what makes it feel exciting and fresh every day."

Alli agrees: "Every single person who visits or lives here can have a totally unique experience. There are 1,000 different concerts, art exhibits, tours. You can wander around and get lost in a new neighborhood and try new food. Not many cities have that level of accessibility to different cultures, cuisines, and experiences."

For planners, this diversity is gold. Whether you're designing an incentive trip, a corporate retreat, or a multi-day convention, Chicago gives you endless options to keep programming fresh and attendees engaged.

3. The Food Scene

You can't talk about Chicago without talking about the food. World renowned deep-dish pizza. A Chicago-style hot dog at a baseball game—no ketchup. Italian beef sandwiches dripping with au jus. The culinary scene here is iconic.

"The accessibility to so many different cultures and cuisines is incredible," Alli says. "You can find authentic food from every corner of the world. From Michelin-starred restaurants to neighborhood spots, the quality is consistently high."

This means your food & beverage options are practically limitless for events. Want a progressive dining experience through different neighborhoods? A pizza-making competition? A rooftop reception with skyline views and craft cocktails? Chicago's culinary depth makes it easy to create memorable food-forward programming that attendees will talk about long after they leave.

4. Built-In Identity

"We have such a built-in identity," April says. "The architecture, the river, the lake, the iconic venues—it creates this ecosystem of really strong suppliers. When people come to Chicago, they already have a mental image. Our job is to exceed it."

Chicago's skyline, Navy Pier, Millennium Park, the Riverwalk—these aren't just attractions. They're instantly recognizable symbols that give your event instant credibility and excitement. Attendees arrive with high expectations, and Chicago consistently delivers.

5. Turnkey Spaces and Suppliers

"It's a dream doing what we do here," Heather notes. "We have lists of amazing suppliers to choose from—transportation partners, AV partners, décor partners. Chicago has some of the best veteran industry suppliers in the country. That sets us apart."

April adds: "Our suppliers are always reinventing themselves to make sure they're at the top of their game. We've got tried-and-true museums and venues, but we've always got something new and fresh to keep it exciting."

Translation for planners: you get reliability and innovation in one package. Whether you need a historic ballroom or a cutting-edge experiential venue, Chicago delivers with professionalism and creativity.

6. Central Location

Chicago's location in the center of the country makes it accessible from both coasts. And with O'Hare now officially the busiest airport in the U.S. by number of flights, attendees have more direct flight options than ever before.

Plus, Chicago's robust public transportation system—the 'L,' buses, bike shares—makes it easy and affordable to navigate the city. Many neighborhoods are pedestrian-friendly, so attendees can explore on foot.

7. Four Seasons That Don't Stop the City

"People talk about Chicago winters," Heather laughs. "But Chicago in winter is beautiful. We just had a huge event a few weeks ago, and our city didn't shut down when so many other cities did. We're built for snow and cold. We know how to handle it."

But it's the seasonal variety that really shines. "Chicago in the summer, spring, and fall? Magical," Alli says. "Four different, really unique experiences."

As an event planner, it means you can design seasonally themed programming—rooftop summer parties, fall foliage tours, winter holiday markets, spring blossoms at the parks—and know the city infrastructure will support you year-round.

8. Inclusive and Accessible

Chicago is highly rated for inclusivity and accessibility for visitors with disabilities and members of minority groups. Choose Chicago's new Department of Inclusive Tourism and Community Engagement ensures that inclusion is at the center of marketing, partnerships, and building a visitor economy that benefits every community.

For corporate groups focused on DEI initiatives, Chicago walks the walk. From accessible venues to inclusive programming options, the city makes it easy to create events that genuinely welcome everyone.

9. Sustainability and Green Building

Chicago is a leader in sustainability and green building practices. With over 400 LEED-certified buildings—one of the highest counts in the country—the city makes it easy for planners to align events with corporate sustainability goals.

The city also has an impressive number of protected parks and green spaces, especially downtown. From Millennium Park to the Lakefront Trail to the 606, Chicago balances urban development with environmental stewardship.

10. Major League Sports

The Chicago Sports Commission is driving economic impact and global visibility by securing high-profile national and international sporting events. Chicago is hosting the 2026 WNBA All-Star Game and the 2027 MLB All-Star Game, bringing thousands of visitors and major media attention to the city.

Events can access world-class sports venues with and the energy that comes with being in a major sports city. Whether it's a private suite at Wrigley Field or a corporate outing to a Bulls game, Chicago delivers.

Bonus #11: “Never Done, Never Outdone”

“Choose Chicago has a slogan: Never Done, Never Outdone," Heather says, and I think it really sums us up. We're always striving to be better, but we are never outdone. We feel like we're the best, but we're always pushing to be even better."

Through the "Never Done, Never Outdone" campaign, Choose Chicago is sharing the city's authentic story and elevating voices, culture, and creativity across every neighborhood. It's a mindset that permeates the entire events industry here—constant innovation, relentless excellence, and a refusal to rest on past success.

The Second City is Number One

Nine years running as Condé Nast Traveler's Best Big City isn't a fluke. It's the result of a city that continuously reinvents itself while staying true to itself.

As the home to our corporate headquarters, we're biased—but we're also right.

Chicago gives you everything you need: world-class venues, veteran suppliers, iconic architecture, diverse neighborhoods, inclusive values, and a team of professionals who genuinely love what they do.

Come see why Chicago keeps winning.