VIP Ground · @Frank Miulli
A Vail ski trip is better with your ski crew, whether that’s a Chicago ski club, a group of college friends, or group of famlies. It’s also harder to pull off. More people means more flights to line up, more bags and ski gear, and more ways for one late arrival to throw off the whole first day.
VIP Ground began in Chicago and now runs group transfers across the Vail Valley every winter. Here’s how Chicago groups can get to and from the mountain.
Booking Flights for a Group from Chicago
The goal is simple: get everyone landing close together, ideally at the same airport. Your two realistic choices are a seasonal nonstop from O’Hare into Eagle County (EGE), about 35 miles from Vail, or a flight from O’Hare or Midway into Denver (DEN), about 120 miles away.
- Eagle County works best for smaller groups that can all fit on the same one or two nonstop flights. You’ll be on the slopes the same afternoon.
- Denver works best for larger groups or anyone with tight budgets. There are far more flights from both Chicago airports, so it’s easier to find seats for 10 or 15 people.
- Ask about group fares. Most airlines offer group bookings for 10 or more travelers on one itinerary, which can lock in seats before holiday fares climb.
- If arrivals are spread out, cluster them. Pick two or three arrival windows instead of letting everyone book separately. It keeps ground transportation simple and affordable.
Why Rental Cars Don’t Work for Ski Groups
A group of 12 usually means three or four rental SUVs, these SUV’s would not be equipped with 3 peak mountain rated tires. Then three or four drivers navigating I-70 in winter, and a lot of skis that won’t fit inside. Add Colorado’s Traction Law, which applies on I-70 September through May, and the plan gets complicated fast.
A private group transfer solves all of it:
- One vehicle, one crew. VIP Ground’s Sprinter vans seat up to 14 passengers, so most groups travel together in a single van. For larger groups, we run multiple vans on the same schedule.
- Room for gear. Skis, boards, boot bags and luggage ride with you, not on a roof rack.
- Nobody draws the short straw. No designated driver after a long travel day. Everyone relaxes from the airport curb.
- Mountain-experienced drivers. We drive I-70 and Vail Pass all winter and plan around weather and closures.
- Flight tracking. If part of your group is delayed out of O’Hare, we adjust pickups instead of leaving anyone stranded.
- Simple cost splitting. One booking, split among the group, often compares well with multiple rentals plus gas and resort parking.
Chicago-to-Vail Group Trip Checklist
- Pick one trip organizer to handle flights, lodging and transportation
- Lock in dates early, especially for Christmas, MLK weekend or Presidents’ Day
- Choose one arrival airport for the whole group (Eagle County or Denver)
- Book flights in two or three arrival windows, not a dozen separate times
- Collect everyone’s flight numbers in one shared list
- Reserve group ground transportation as soon as flights are booked
- Count skis, boards and bags so the right vehicle shows up
- Book lift tickets and rentals in advance for group pricing
- Schedule the return transfer with extra time for mountain weather
Book Your Group’s Chicago-to-Vail Transfer
From ski clubs to multi-family holidays, VIP Ground gets your whole crew from the airport to the mountain together. Send us your group size, arrival airport and flight times, and we’ll put together a plan.
Request a group quote at vipgroundtransportation.com.
