Chicago to Vail Transportation

Few transportation companies can say they know both Lake Shore Drive and I-70 like the back of their hand. VIP Ground can. VIP Ground Transportation started in Chicago, where we spent years driving executives, families, and private aviation clients across Chicagoland. When we moved our home base to the Vail Valley, we kept our Chicago operation running. Today we’re the bridge between two places our clients love: the city where they live and work, and the mountains where they ski, celebrate, and recharge.

That means one company handles your whole trip. We pick you up at your home or office in Chicago and get you to O’Hare, Midway, or your private terminal on time. When you land in Colorado, our Vail Valley team is waiting to take you straight to the slopes. You get one point of contact, one reservation, and the same level of care on both ends.

Chicago families have been heading to Vail and Beaver Creek for generations. We built our service around making that trip easier: fewer handoffs, no rental car lines, and no wondering whether your driver will actually show up.

Suv & Sprinter picking up passengers at Vail Rental.

The arrival experience

How It Works: Chicago Door to Vail Door

  1. Book once. Tell us your travel dates, flights, group size, and gear. We set up both legs of your trip, Chicago and Colorado, in a single reservation.
  2. Chicago pickup. Your chauffeur arrives at your home, office, or hotel anywhere in Chicagoland, loads your luggage and ski bags, and drives you to O’Hare, Midway, or your private jet terminal.
  3. We track your flight. Our Colorado team monitors your flight in real time, whether commercial or private. Early, late, or diverted, we adjust.
  4. Colorado arrival. Your Vail Valley chauffeur meets you at Eagle County Regional Airport (EGE), the Vail Valley Jet Center, or Denver International Airport (DEN) and handles your bags.
  5. Straight to your door. We drive you directly to Vail Village, Lionshead, Beaver Creek, Bachelor Gulch, Arrowhead, Cordillera, Edwards, or your private residence.
  6. The trip home. When it’s time to go home, we reverse the whole process, from your mountain door back to your Chicago door.
  7.  Skip the rental car counter, the parking fees, and the white-knuckle drive over Vail Pass. With VIP Ground, your trip is handled from the moment you leave your Chicago home until you walk into your lodge in Vail or Beaver Creek, and all the way back again.

WE ARE HERE TO SERVE YOU

FAQs

We guarantee an
unparalleled experience

Yes. That's exactly what this service is built for. We operate in Chicago and the Vail Valley year round so one reservation covers your pickup at home and your arrival in the mountains.
Eagle County (EGE) is much closer to Vail, about 35 to 45 minutes. Denver (DEN) usually has more flight options, but the drive takes about 2 to 2.5 hours in good conditions, 4 to 5 hours on a peak holiday weekend with snow. We serve both, and we're happy to help you weigh them.
Yes. We work with private aviation clients at Chicago-area FBOs and at the Vail Valley Jet Center at EGE along with Denver FBOs ( JSX, Net Jets, Flex Jet etc.)
We track every flight and adjust your pickup to match. You won't be left at the curb.

Yes. We provide local in town transportation around Vail, Beaver Creek, and the rest of the valley.

For holiday and spring break weeks, book as early as possible, ideally when you book your flights. For other dates, a few weeks' notice is usually enough, but contact us anytime.
Winter weather is part of mountain travel, and we plan for it. We monitor road conditions and closures, adjust timing as needed, keep you updated, and do our best to detour around any closures. If your plans have to change, we'll work with you on a new pickup.

Peak holiday dates may have different terms, and we'll spell them out when you book.

Yes, We believe tips should be earned. Our flat-rate pricing is competitive with local providers, the only addition is a 5% admin fee, with no layered pricing or surprise charges. Gratuity is entirely up to you, and if you’re happy with your driver, a tip is always appreciated.