There’s an unmistakable rhythm to Chicago—whether it’s the energy at McCormick Place, the steady flow of Michigan Avenue, or the excitement before a concert at the United Center. Managing a group in the middle of all this shouldn’t feel like work. That’s why, for Group Transportation Chicago is capable of taking the stress off your shoulders. With more than 45 years of experience, Pontarelli keeps groups together, comfortable, and right on time. From corporate teams to wedding guests and friends in town for a celebration, we make sure every ride feels effortless—whether it’s a quick airport pickup or a full evening of city stops.
When people need to move together, details matter—but your focus shouldn’t be on timetables or parking spots. Our Chicago Group Transportation service frees you from those worries. Imagine a team dinner in River North or a group arriving at Navy Pier for an evening event: everyone steps out at once, refreshed and ready, without the hassle of multiple cars or rideshares.
Behind the scenes, our team keeps everything synced so your group stays focused on the occasion—not the commute. We stay one step ahead—adjusting routes if traffic changes, keeping everyone informed, and making sure nothing feels rushed. The result? Peace of mind, less waiting around, and more time to enjoy the reason you came together.
No two groups move through Chicago the same way. One day it’s executives flying in for back-to-back meetings, the next it’s a team heading to a company dinner. Sometimes it’s VIP travelers stepping off a private jet. With Pontarelli, no one is left waiting or scrambling. Your group arrives together, at ease, and ready for what comes next.
Here are just a few group transportation services Chicago clients rely on us:
That’s why our transportation services bend around your plans—not the other way around.
The right vehicle does more than get you from place to place—it shapes the experience of your day. That’s why our fleet is built around comfort, flexibility, and Chicago’s unique demands. Every ride is clean, quiet, and built for comfort—because group travel should never feel crowded or chaotic.
Guests enjoy the calm, spacious feel of our Lincoln Aviator and Lincoln Navigator SUVs for smaller groups or VIP clients. For mid-sized groups, our Executive Vans make boarding and drop-offs quick and easy, especially for multi-stop routes. Larger gatherings call for our Luxury Mini Bus or Motor Coach, with roomy seating that lets conversation and connection continue on the road.
Every vehicle is paired with a professional chauffeur—trained, background-checked, and experienced in Chicago’s streets. They bring discretion when it’s needed and attentiveness when it matters most.
Visit our fleet page for more information and details on additional vehicles.
Since 1977, Pontarelli Companies has helped thousands of groups move confidently across Chicago—whether for business, celebration, or once-in-a-lifetime events. As a certified WBENC Women’s Business Enterprise, we take pride in pairing professionalism with personal care. Clean vehicles, timely service, and a highly trained team are the foundations of what we do.
Our clients say it best. One review recently shared: “We used Pontarelli for 2 trips for an executive team in Chicago. They were timely, professional & friendly from the first interaction. Very easy to book, good rates & great fleet.” You’ll find many similar endorsements across our Google reviews, each reflecting the same commitment to service you can expect.
If you’re planning group transportation Chicago is the ideal destination. So, let us help make it simple. Call us at 312-361-4111, email info@pontarellischicago.com, or send us a quick reservation request. With Pontarelli, your next group trip will run smoothly from the very first pickup.
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