Let’s be honest business trips don’t have to be all boardrooms and boxed lunches. If you’re already flying out for work, why not stretch the trip just a bit and sneak in a little fun?
Welcome to the world of bleisure travel, where savvy professionals blend work and leisure to get the job done and make some unforgettable memories while they're at it. Whether you're jetting off to pitch a client or attending a big industry event, here's how to turn your next business trip into something that feeds both your career and your soul.
Don’t Just Travel—Strategize
Before you book that flight, ask yourself: “Can I extend this trip by a day or two?” If the answer is yes, you’ve just unlocked time for sightseeing, dining out, or simply decompressing. Coordinate meetings early in the week or late in the day to leave space for leisure time.
Quick tip: Many companies are fine with you tacking on personal days as long as you’re covering your own costs. Just double-check your company’s travel policy.
Pick the Right Home Base
Skip the airport hotels. You’re not just sleeping—you’re living a little! Book accommodations in a lively neighborhood close to both your meetings and the action. You’ll save time and get a better feel for the city.
Look for hotels with business-friendly features (hello, high-speed Wi-Fi) and easy access to local hotspots, whether that's trendy restaurants, historic districts, or a rooftop bar with a view.
Pack Like a Pro (Not a Tourist)
You don’t need two separate wardrobes. Bring versatile outfits that work double duty—think a blazer that looks sharp in the boardroom and pairs well with jeans for a night out. Don’t forget comfy shoes and a power bank. Trust us, your phone battery will thank you.
Schedule Downtime Like It’s a Meeting
If you don’t block time off your calendar, it won’t happen. Set a hard stop for your workday and actually plan your downtime. Whether it's catching a show, checking out a museum, or just wandering through a new neighborhood make room for moments that aren’t on the agenda.
Treat Yourself to Hassle-Free Transportation
Want to instantly level up your bleisure trip? Skip the rental counter chaos and book a chauffeured ride. It’s one less thing to worry about—and one more way to stay cool, collected, and on time.
Make It About More Than Work
Your hotel isn’t the only place to recharge. Try the local cuisine, join a walking tour, or strike up a conversation with someone outside your industry. You never know where those connections—or experiences—might take you.
Bleisure travel isn’t about slacking, it’s about creating balance. You show up for your job and show up for yourself.
You’ve worked hard to get where you are. Why not enjoy the journey too? Bleisure travel is your chance to turn routine business trips into opportunities for discovery, rest, and a little joy along the way.
Bonus Tip: Ride in Style with Chicago Original Limousine
Make your trip as effortless as it is exciting. Whether you’re heading to a meeting or taking a detour to a local landmark, let Chicago Original Limousine handle the ride. It’s reliable, professional, and just luxurious enough to make your trip feel like a treat.

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