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Aspen ⛷️ in $200s-$220s RT

By late July, the summer feels a little endless. But pretty soon, the mountains of Colorado will be covered in perfect powder...

...and it couldn't be easier to reach! A single non-stop flight followed by an airport shuttle to your resort, and you're ready to hit the slopes (or go straight to the après).

Aspen sure doesn't skimp on the ski resorts, with options ranging from sleek stays with seasonal cocktails to historic spots with major star-appeal. Snag December dates and the town itself will be just as alluring, with holiday lights glowing off the snow.

Winter sports not your thing? We've got late summer and fall dates too — ideal for hiking and mountain biking through some of the most scenic mountains in the country, no snowpants required. 

And lastly, a little bonus for LA: We spotted tickets to Vail for the same price, but they're with United so they don't include a carry-on. We prefer this Aspen route, but if you REALLY want to see Vail instead, that's a pretty decent deal too :-)

Taking off ✈️

Tip Published: Jul 31, 2025

To:

  • Aspen (ASE)
From:

  • Chicago (ORD) - $229
  • Los Angeles (LAX) - $209 (inc. NYE, Xmas)
Flight Details

Travel Dates

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Airline

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Standard Fare

$400 (non-stop)

Bags & Fees

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Flight Notes

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How to Book

    This is a Premium deal for Jack's Flight Club members only. For step by step instructions on how to book it you'll need to login or upgrade to Premium membership.

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