Planning a Spring Trip? Best Places to Visit from Chicago with a Rental Van

Christmas and New Year Road Trips from Chicago for Big Families

  • Rental Vehicles
published on 13 November 2026 | updated on 13 November 2026
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Flights for six, eight or twelve people at Christmas add up fast, and the airport is the most stressful place to be with a big family in December. A passenger van turns the trip into part of the holiday: the kids watch a movie, the grandparents get a comfortable seat, and the presents ride along in the back. This guide pulls together our holiday road trip ideas from Chicago and the practical side of renting a van for them.

Pick the right van for your family

  • Up to 7 people: the 7-passenger minivan, starting at $50 a day, with about 2 ft of luggage space behind the third row.
  • 8 to 12 people with suitcases: a 12-passenger van keeps luggage space behind the last row. Ford Transit starts at $120 a day; Mercedes-Benz Sprinter at $180 a day.
  • 13 to 15 people: a 15-passenger van. The 15-passenger Sprinter keeps about 4 ft of luggage space; the 15-passenger Ford Transit has none, so it suits groups traveling light.
  • Long drives in comfort: the Grand Recliner and Golden Chariot Sprinters have reclining seats, and every Mercedes-Benz Sprinter has a smart TV and an Xbox.

Every van we rent, up to 15 seats, drives on a regular driver's license, and you plus two additional drivers are included at no charge - so the long stretches can be shared.

Holiday road trip ideas from Chicago

We have written a full guide for each of these winter favorites, with stops, places to visit and what to pack:

Distances are approximate one-way road miles from Chicago. Split the longest drives over two days and plan a hotel stop with parking for a tall van.

Do the mileage math before you book

Every rental day includes 250 free miles, and extra miles are $0.35 each. A round trip to Orlando is roughly 2,300 miles; on a 10-day rental you have 2,500 free miles, so the drive is covered. A shorter trip with lots of driving - say Miami and back in seven days, about 2,760 miles against 1,750 free miles - would add about 1,010 extra miles, or around $350. Adding a day or two to the rental often costs about the same and makes the trip less rushed.

Pick-up, return and the holiday calendar

  • Office days: our Melrose Park and Berwyn offices are open 7 days a week, 8 AM to 5 PM, except Thanksgiving and Christmas Day. New Year's Day we are open.
  • Coming home late: return the van at any hour with the 24/7 key drop box at our offices.
  • Family flying in for the holidays? We deliver the van to the O'Hare or Midway terminal 24/7, 365 days a year. On weekends, national holidays and outside 8 AM to 5 PM a special after-hours fee applies; picking up at our offices avoids it.
  • Rental tax: renting from our suburban offices costs less in tax than renting inside the City of Chicago - 12% in Melrose Park and 11% in Berwyn, versus 26% plus $0.50 per rental in the city.

Winter packing list for the van

  • An ice scraper and snow brush, warm blankets and water for each passenger.
  • Phone chargers - the Sprinters and the minivan have Apple CarPlay and Android Auto.
  • Snacks in a bag up front, so nobody has to dig through the luggage.
  • Presents packed low and toward the front of the cargo space, with the heaviest bags on the bottom.
  • A printed copy of your route and hotel booking, in case cell service drops in the mountains.

Driving through snow on the way? Read our winter checklist for driving a 15-passenger van in snow before you go.

Holiday van rental: quick questions

How far ahead should we book a van for Christmas?

As early as you can. Christmas and New Year's are among the busiest weeks of the year for 12 and 15-passenger vans, and the van you want may be gone close to the date. You can reserve online at any hour.

Are your offices open on Christmas and New Year's Day?

Our offices are closed on Christmas Day (and Thanksgiving) and open on New Year's Day, 8 AM to 5 PM. Plan your pick-up for a day the office is open; you can return at any hour with the 24/7 key drop box.

How many free miles do we get on a long holiday trip?

250 free miles for every rental day. A 10-day rental includes 2,500 free miles - enough for most round trips to Florida. Extra miles are $0.35 each.

Can we drop the van off in Florida?

One-way rentals are possible anywhere in the USA for a one-way fee, which covers bringing the van back to Chicago. Email info@chicagovanrentals.com for a quote.

Ready to plan? Choose your van and your dates on our booking page to see the exact price, or call (773) 800-9898, 7 days a week, 8 AM to 5 PM.

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