Some friends recently said I reminded them of Emily in Paris. At the time, I hadn’t watched the show, so I laughed and replied, “More like Drea in Chicago.” Fast forward to me binge-watching all four seasons - and honestly, they weren’t wrong. Like Emily, I’ve got a love for storytelling, a flair for style, and a knack for finding the best spots in every corner of the city. But here’s the twist: while Emily is navigating a new world abroad, I am the local. I know the backstreets, the best bites, and the magic behind the scenes of Chicago.
Welcome to Drea in Chicago: The #SummertimeChi Edition- your personal guide to exploring the city like a local.
As a proud Chicagoan and Business Development Manager at CSI DMC, summer in this city isn’t just a season, it’s a whole different vibe: a time to merge culture, creativity, and community into awesome experiences. Whether you're planning an event, scouting a venue, or looking for inspiration, these are my favorite ways to tap into the warmth of summertime Chicago and introduce guests to a city that knows how to show off.
Rise Pilates Club: Morning Movement, Beachside Backdrop
There’s no better way to rise, literally and figuratively, than with Rise Pilates Club’s summer beach series. Fridays at 6AM on Oak Street Beach (May 30–August 8), you’ll find me flowing to the rhythm of waves and sunrises. It’s the kind of energy that sets the tone for the whole day. And let’s be real, if I’m up and moving before coffee, it better be worth it. Spoiler alert: it is.
Lakefront Trail: Where Movement Meets Memory
Chicago’s 18.5-mile lakefront trail is more than a scenic path; it’s a high-energy corridor perfect for movement-based breakout sessions or team-building strolls. Rollerblading along the lakefront trail seemed like a great idea to me … until it got very real, very fast. One minute I’m vibing, the next I’m airborne and sand bound. But hey, it’s #SummertimeChi. You roll with it.
Offshore Rooftop: Sky-High Strategy
Some come for the views - I am the some! As the world’s largest rooftop bar (feel free to fact-check me here), Offshore Rooftop offers jaw-dropping city views and lakefront scenery. If you’re going to meet in Chicago this summer, you’ll want to do it where the city meets the lake. If your event needs elevation this flexible space to sip and connect, is it.
🍸 Ideal for cocktail receptions, client mixers, or a dinner gala with a view.
Navy Pier Fireworks: The Ultimate Spark
We all know Navy Pier is one of Chicago’s top spots for private events - with lake views, flexible venues, and that unbeatable skyline backdrop. But when I’m off the clock? You’ll find me posted up for the public show. Every Wednesday at 9PM and Saturday at 10PM (May 24–August 30), Navy Pier lights up the lakefront with a free fireworks display that brings all the summer energy. It’s the kind of feel-good moment that reminds you why #SummertimeChi hits different.
✨ Want fireworks at your next private event? Let’s talk - I know just how to bring the spark.
Millennium Park Music & Film Series: Culture Meets Community
If it’s not obvious by now—Chicago knows how to do summer. And free live music and movies under the skyline at Jay Pritzker Pavilion? That’s just showing off. Every Monday and Thursday (June 26–August 7), you’ll catch jazz, soul, global beats, indie vibes, and more - all for the low price of absolutely FREE. Then on Tuesdays (July 1–August 26), the giant screen comes alive with films that pair perfectly with skyline views and popcorn under the stars.
🎶 Great for: team picnics, client outings, or inspiration for immersive cultural programming.
Chicago’s Street Fests: Hyperlocal, Highly Fun
From Do Division to Logan Square Arts Fest and Taste of Randolph, Chicago’s Street Festivals have range. Each fest represents the vibe of the city’s neighborhoods - filled with local makers, live music, and spontaneous dance breaks. It’s where you catch culture in its rawest, realest form. Let me know if you want to go to one together - I always know where the best vendors are!
🎡 Think: scouting local vendors, or guest itinerary add-ons.
Soho House Rooftop: Exclusive, Elevated
#SummertimeChi doesn’t get chicer than Soho House & Co. With skyline views and cocktail clinks, it’s where events get done in style. It’s members-only - but lucky for you, CSI DMCs got the key. Let’s connect and catch a vibe.
🥂 Private receptions or high-touch experiences feel right at home here.
Paradise Park: Pizza, Flamingos, and Full Vibes
I mean, it’s in the name… PARADISE! Located in Wicker Park, this spot delivers on fun. From rooftop pizza to flamingo-filled patios, Paradise Park blends playfulness with personality.
Full disclosure: I might be biased because I live walking distance from the Wicker Park location. But even if I didn’t, this place would still be top tier.
🍕 Team happy hour? Informal welcome night? Yes, and yes.
The 606: Urban Exploration with Edge
The Bloomingdale Trail at The 606, winds through Chicago’s coolest neighborhoods - offering an active, creative tour for teams. You’ll find locals, skyline views, street art, and maybe even a few future business ideas along the way.
🚴 Use it to explore the city, reenergize, or rediscover your next big idea.
Royal Palms Shuffleboard: Game On
Retro vibes, frozen cocktails, and fierce competition - The Royal Palms Shuffleboard Club is the team outing venue you didn’t know you needed. From the flamingo wallpaper to the frozen cocktails served with little umbrellas, Royal Palms is not your grandma’s shuffleboard. This is where retro fun meets real competition -and yes, I’m keeping score (although I'm terrible).
🏓 Perfect for client fun nights, team building, or quirky off-sites.
Starved Rock: Nature’s Reset Button
Just 90 minutes outside the city, Starved Rock offers an escape to nature. We’re talking canyons, waterfalls, and views that’ll have you questioning why you ever paid for a nature sound app. It’s the kind of place where your phone goes to “No Service,” but your soul says, “Thank you.” Starved Rock is #SummertimeChi’s wild side, and sometimes, nature is the best meeting room.
🌲 Because sometimes, the best team outing includes moss and a waterfall.
Let’s Connect in #SummertimeChi
Chicago doesn’t just do summer - it owns it. Whether you're designing a program, curating experiences, or just looking for your next great meeting moment, let’s create something amazing. You bring the vision. I’ll bring the vibes (and maybe a mimosa).
Andrea Taylor, CITP, Business Development Manager, andrea.taylor@csi-dmc.com