Alaska backpacking: Chilkoot Pass vs Denali National Park?

I've hiked both of those areas, backpacked some in and Around Denali and done a LOT of hiking around the Kenai Peninsula.

For the "oh-wow" factor, Denali wins. Nowhere else in North America can you see a 20,320 foot mountain. Nowhere else in the world can you see a mountain rise 18,000 feet from it's base. Nor can consistently see so many large critters anywhere else without being in a zoo (or maybe the semi-tame stuff in Yellowstone). You're sure to see Dall sheep, Caribou and Grizzlies. Possibly also moose, wolf, fox, and golden eagles. Denali also wins for connections. Fly in Anchorage and drive 250 miles. Or hitch. Or take the train. Or fly into Fairbanks and drive 150 miles.

Skagway is harder to get to. You can drive there off the Alaskan highway but that 1500 miles or so from Seattle. Of Fly to Juneau or Gustavus and take the Alaska State Ferry. Or fly Whitehorse (Yukon Territory) and rent a car.

An advantage (or disadvantage) to the Chilkoot is that it is a TRAIL. In Denali, you pull a permit for an AREA and then crash through the willow bushes and over the braided streams however you decide. So if you want to meet other people and don't want to deal with routefinding - the Chilkoot. If you want to leave it all behind and feel like you're in the middle of nowhere all by yourself - Denali

I agree with the other poster that the Resurrection Trail is much easier (physically, logistically). About a 90-mile drive from Anchorage, the northern portion is 40 miles long (Hope to Cooper Landing). Crossing the Sterling Highway in Cooper Landing lets you take it another 35 miles south to Exit Glacier out of Seward. (But the last 15 miles hasn't been maintained and has at least one tough river crossing). I do each of those as a day hike, but I lean heavily towards high-mileage outings. They are each more reasonable 3-5 day trips. You'll see other people but not a lot (until you get a few miles from Cooper Landing. I've hiked 25 miles on it before seeing another person. There are forest service cabins that you can reserve (6 months in advance and the trick is to be on-line THAT night, 6 months in advance. A 12' x 15' cabin with cut wood, wood stove and bunks is a lot nice place to wait out some rain than a backpacking tent. Some are on lakes and one or two of them are equipped with boats.

Food, lodging, attractions:

Denali: It's a National Park! For good reason. Lodge, visitor's center, interpretive programs, etc. Outside the park you can also river raft, buy souveniors, or stay in upper-end hotels.

Chilkoot: Skagway is a cute town to look around in for a day. Whitehorse is more interesting to me. If I were going to/through Skagway, I'd book passage on the State Ferry and sightsee in various SE AK towns on the way there or back.

Resurrection Trail: You can raft the Kenai out of Cooper Landing or find a room to rent. In Seward, there is a great aquarium and day cruise of Kenai Fjords National Park. Continuing on to Kenai would let you try for salmon. Going to Homer would give you great views, art galleries, halibut charters, and sea kayaking options. Several good resturants too.

It's not in a city. It's in a national preserve that is somewhere between Anchorage and Fairbanks. It's quite remote.

Resurection Pass is also nice and easier to get to than either of the other two.