
Historic Route 66 Ski Vacations
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Top Ski vacation packages in Historic Route 66

The Royal Sonesta Chicago River North
Reviewed on Aug 22, 2025



Trump International Hotel & Tower Chicago
Reviewed on Aug 19, 2025

5* Ski vacations in Historic Route 66

Trump International Hotel & Tower Chicago
Reviewed on Aug 19, 2025


The Langham, Chicago
Reviewed on Aug 12, 2025
3 Night Ski vacations in Historic Route 66

Hotel Riu Plaza Chicago
Reviewed on Aug 21, 2025

Trump International Hotel & Tower Chicago
Reviewed on Aug 19, 2025

The Inn at Vanessie
Reviewed on Aug 22, 2025
4 Night Ski vacations in Historic Route 66


The Inn at Vanessie
Reviewed on Aug 22, 2025

The Hacienda & Spa at Hotel Santa Fe
Reviewed on Aug 18, 2025
Planning your Historic Route 66 ski vacation
What are some things I should consider when booking a Historic Route 66 ski trip package?
Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in.
How can I find cheap Historic Route 66 ski packages?
Fly down the slopes during low or shoulder season, either side of , for a ski package to please your purse. Right now, ski trips start at just $431. Prices and availability are subject to change. Additional terms may apply.
Can I book a beginner ski package in Historic Route 66?
Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Historic Route 66. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow.
How much does a ski trip to Historic Route 66 cost?
Sensational ski trips to Historic Route 66 start from $431. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply.
When’s the best time of year to plan a ski trip to Historic Route 66?
The best time to hit the slopes in Historic Route 66 depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days.
Can I book Historic Route 66 ski packages with airfare?
Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly.
Can I book a Historic Route 66 ski trip with free cancellation and/or flexible dates?
Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options.
Why should I book a ski package in Historic Route 66 with Expedia?
Simple search and fantastic filters make it easy to find, build, and book your dream Historic Route 66 ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.