For groups of 8 or more needing a Sprinter van or multiple vehicles, we’d recommend booking 1-2 weeks ahead, since larger luxury vehicles are simply in shorter supply than sedans, both in our fleet and across Chicago generally.

During busier stretches — big conventions, holiday weeks, or wedding season weekends — 3-4 weeks out is a safer bet, since Sprinters and minibuses tend to be the first vehicles to book up.

Group reservations also take a bit more setup on our end than a single ride: confirming headcount, luggage, whether everyone’s on the same flight, and assigning one chauffeur to track it all through our chauffeur service. That coordination is part of why earlier booking matters more for groups than it does for an individual trip.

If your travel dates fall during a known busy period in Chicago, it’s worth reaching out before locking in other event details like a venue or hotel block, so transportation isn’t the piece that ends up scrambled last. For groups planning a longer day together rather than a single pickup, our hourly limo service is often the better option. You can reach out directly through our Chicago limo service, or for weddings specifically, our wedding limo page walks through typical planning timelines in more detail.