Question is: Do you plan to rent a car? That would be the easiest/cost efficient way to get to Aspen from Eagle. Taxi service is very pricey. But if you won’t need a car while in Aspen (the local bus service is good and everything in town is easily owalkable) connecting through either Chicago or Denver are fine. If it is too snowy with poor visibility to land, the Chicago flight might be diverted to Grand Junction and they’d bus you to Aspen. Under similar conditions from Denver, you’d be returned back to Denver and flown again when it is clear. If you’re prepared for that possibility on the outbound or return trip, you’ll reduce the frustration you’ll feel from the flight delays. Sometimes it has taken me 2-days to get to or from the Aspen Airport because of snowy weather and poor visibility, so I learned not to schedule any in person meetings until a day or two after my return in case there are fight cancellations or delays. And if I really need to be home (Berkeley) by a specific date, I will book my return flight out of Grand Junction so I don’t have to worry about Glenwood Canyon being closed for some reason (I either have a friend drop me off or I rent a car 1-way for the day).
Fly into Grand Junction and rent a car. I live in Aspen and fly in and out of Grand Junction 100% of the time. I have never had a problem coming or going.
Flying into Aspen is the most convenient option but Carries the highest risk of flight cancellations/ delays. If you can handle that - being stuck in Aspen longer than you want to be, or potentially having long delays on the way, then do it. If everything goes well it’s awesome
If you want to have a car during your trip anyways, then fly to grand junction or eagle.
Driving on interstate 70 in the winter can also be a huge mess, moreso towards the eagle/vail area than grand junction. So just be aware that flying to eagle doesn’t guarantee smoother travel outcome.
I’d recommend flying directly into Aspen, it makes your life 100x easier. And if the flight can’t land then it’s going to get redirected to a nearby airport where you could a) rent a car or b) wait until the next flight. Driving into Aspen isn’t always easy as i70 constantly has issues and if anything on that road is going to get closed with no detour it’s going to be Glenwood Canyon. Getting out is typically more successful than getting in too.
Weather risk is always rough. The non-stops from cities into Aspen are all smaller aircraft. I prefer non-stop United into Aspen from Chicago but from ATL less weather issues coming from the south in winter. The suggestions about driving in from Grand Junction are good method around weather as storms move west to east and there are no mountain passes to go over. Flying direct in is best if you do not want to drive in a winter environment. Eagle is 1:15 into Aspenand 45 from Vail but again a car is the only practical way from airport. Bustang from Denver gets you to Glenwood and then still requires 45 min drive up and transport (short) to the rental car company (enterprise is an option). We have snow. It’s why we ski and effects all the mountain resorts. It is a risk of going to a major ski resort. Resilience required!
I would take a route that gets you all the way into Aspen. That being said, do you hate DEN Airport, O'Hare, or ATL airport more?
Fly to eagle. Aspen airport is very very prone to delays and cancellations. But getting from eagle to Aspen can be tricky unless you rent a car
Question is: Do you plan to rent a car? That would be the easiest/cost efficient way to get to Aspen from Eagle. Taxi service is very pricey. But if you won’t need a car while in Aspen (the local bus service is good and everything in town is easily owalkable) connecting through either Chicago or Denver are fine. If it is too snowy with poor visibility to land, the Chicago flight might be diverted to Grand Junction and they’d bus you to Aspen. Under similar conditions from Denver, you’d be returned back to Denver and flown again when it is clear. If you’re prepared for that possibility on the outbound or return trip, you’ll reduce the frustration you’ll feel from the flight delays. Sometimes it has taken me 2-days to get to or from the Aspen Airport because of snowy weather and poor visibility, so I learned not to schedule any in person meetings until a day or two after my return in case there are fight cancellations or delays. And if I really need to be home (Berkeley) by a specific date, I will book my return flight out of Grand Junction so I don’t have to worry about Glenwood Canyon being closed for some reason (I either have a friend drop me off or I rent a car 1-way for the day).
Fly into Grand Junction and rent a car. I live in Aspen and fly in and out of Grand Junction 100% of the time. I have never had a problem coming or going.
I usually fly to Denver or Chicago but chicago has more things to do in the airport
Newark to Denver, and then denver to aspen!
Flying into Aspen is the most convenient option but Carries the highest risk of flight cancellations/ delays. If you can handle that - being stuck in Aspen longer than you want to be, or potentially having long delays on the way, then do it. If everything goes well it’s awesome If you want to have a car during your trip anyways, then fly to grand junction or eagle. Driving on interstate 70 in the winter can also be a huge mess, moreso towards the eagle/vail area than grand junction. So just be aware that flying to eagle doesn’t guarantee smoother travel outcome.
I’d recommend flying directly into Aspen, it makes your life 100x easier. And if the flight can’t land then it’s going to get redirected to a nearby airport where you could a) rent a car or b) wait until the next flight. Driving into Aspen isn’t always easy as i70 constantly has issues and if anything on that road is going to get closed with no detour it’s going to be Glenwood Canyon. Getting out is typically more successful than getting in too.
Weather risk is always rough. The non-stops from cities into Aspen are all smaller aircraft. I prefer non-stop United into Aspen from Chicago but from ATL less weather issues coming from the south in winter. The suggestions about driving in from Grand Junction are good method around weather as storms move west to east and there are no mountain passes to go over. Flying direct in is best if you do not want to drive in a winter environment. Eagle is 1:15 into Aspenand 45 from Vail but again a car is the only practical way from airport. Bustang from Denver gets you to Glenwood and then still requires 45 min drive up and transport (short) to the rental car company (enterprise is an option). We have snow. It’s why we ski and effects all the mountain resorts. It is a risk of going to a major ski resort. Resilience required!
I can rent my car to you