How to hike from Aspen to Crested Butte for (nearly) free

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Have you checked out our Guide to Hiking from Aspen to Crested Butte?  Maybe you’ve thought that this would be an awesome adventure, but you worry about the cost of a trip like this? Even if you don’t live in Colorado, it’s still possible (and even quite easy) to conquer this classic hike without breaking the bank by using the strategies described here and by opening just a single credit card! Keep reading to find out more.

Part 1 – Flights
If you are lucky enough to live in Colorado you can skip this section, pick an open weekend, hop in your car, and be in Aspen in a matter of hours. However, for those coming from other areas of the U.S. it isn’t nearly as easy to get to the trailhead. The trip typically involves flying into Denver, renting a car, and driving the 4ish hours to Aspen. This can be costly and requires a lot of your valuable time just to get to the start of the hike. However, if you open just one credit card, the Chase Sapphire Preferred, you’ll be able to fly directly into Aspen and still have miles left over to help cover your lodging in Aspen or Crested Butte and even rent a car.

Your first step is to open the Chase Sapphire Preferred, which currently offers 50,000 bonus miles after spending $4,000 within the first 3 months of opening the card. Chase miles are incredibly valuable because, not only can you book travel directly through Chase’s website, but you can also transfer your points to their many travel partners, like United Airlines. This gives you lots of options to save big on your trip. After you open the card, simply put all of your normal spending on it to meet the $4,000 spending requirement within the first 3 months. At this point you’ll have at least 54,000 Chase miles in your account (the 50,000 miles bonus plus the 4,000 points you’ll get for your normal spending). Now it’s time to book your flight.

When booking United Airlines flights within the mainland U.S., you’ll want to look at the United Award Chart to know how many miles you’ll need to redeem. You can find the United Award Chart here.  The chart is organized  with your departure region on the y-axis and your destination region on the x-axis. Simply locate where you are leaving from (in our case the mainland U.S.) and follow that row until you find the mainland U.S. column. That box will tell you how many miles you’ll need for a one-way award ticket.

Locate your departure and arrival region to determine how many miles you’ll need for a free flight.

As you can see, you’ll need 12,500 United miles each way for flights within the U.S. at the Saver level. We only book award flights at the Saver level since the cost for other awards is simply not a good deal. Given this info, we now know that you’ll need 25,000 United miles to book our round-trip flights.

Now, let’s say that you’re coming from Chicago. You’ll head over to, enter Chicago as your departure city and Aspen as your arrival city, being sure to check the “Search for award travel” check box.

Enter your flight info and be sure you’ve checked “Search for award travel”

Looking at specific dates,  I was able to find a round-trip flight from Chicago to Aspen for 25,000 miles plus $11.20 in taxes and fees (this is what I mean by nearly free). Fights into Aspen’s tiny airport can often run in excess of $500, so to get this flight for only $11 is an incredible value!

Lots of great flights from Chicago to Aspen for only 12,500 United miles
Plenty of options for your return flight from Aspen to Chicago

At this point you might be wondering how all those Chase miles you’ve accumulated are going to help you book a flight that requires United miles. Lucky for you, the Chase miles you’ve received from opening the Chase Sapphire Preferred are transferable to your United account. All you have to do is login to your Chase account, select the  number of miles you want to transfer (in our case, 25,000), enter your United account info and voila! you’ve now got 25,000 United miles to book your flight.

Part 2 – Hotels and Rental Car

After transferring your Chase miles to United to book your flight you should still have 29,000 Chase miles remaining from your Chase Sapphire Preferred sign-up bonus. One of the great features of this card is the ability to book travel through Chase’s website and get 1.25 cents per point for any travel that is bookable through the Chase portal. I’ve found that Chase’s portal has a good selection of hotels that are all competitively priced. So, if you want to save on your hotels for Aspen and Crested Butte all you’ll need to do is log in to your Chase account and find a hotel that will meet your needs. Given that you will get 1.25 cents per mile, you’ll have roughly $362 to book your hotels. This deal gets even better if you have a travel partner who does the same because you’ll double the number of Chase miles that you have remaining, giving you over $700 between you to book your hotels. With over $700 left to spend, you should easily be able to book your hotels and will  likely  be able to also rent a car through Chase’s portal. The result? A nearly free trip!

So there you have it. The information above walks you through  how we used the incredible world of collecting miles and points through credit card bonuses to hike from Aspen to Crested Butte, including a direct flight into Aspen, for nearly free.

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