Is there going to be a problem packing a suitcase inside a suitcase to my destination - I'm buying a lot of stuff at my destination and want to avoid the 2nd bag fee until the return?

I've done this many times when flying. Put small samsonite into the big one...and even put small trolleys into it. It's not going to be a problem. Last time went to IAD on UA and went into the US with 1 bag..... return to LHR with 3 bags

No. I do it regularly.

I do it as well. It's never been an issue.

Thanks I am cleaning up on Carhartt work wear at Sierra Trading Post in Reno- going yhz-rno then sfo-yhz return - so will pass through customs !

The suitcase will be considered a personal item, just like anything else you have in tow at customs. As pointed in previous answers, not an unusual behavior.

I was in their outlet in Cheyenne and kind of surprised at the small selection. You might try ordering off their website and using their free ship to store option. Also, don't order anything until you've signed up for their DealFlyer emails. The have sales all the time 30 to 45 percent off.

excellent idea and has been done lots of times and perfectly legit

has anyone done a suitcase within a suitcase within a suitcase? I could see easily fitting a 80 Lt duffel in there.

I did order only and shipped to store to make sure what I wanted was there thanks for the tip !

I always wondered if they would give me a hard time if I used an extra large leather tote bag and put my purse inside that. I like to bring a book, a movie and other things My purse is only medium in size and I bring my readers as well as my sunglasses in it. By the time I do that I don't have any room for hardly anything else. I usually take my makeup and Lysol wipes out of my freedom baggie once I get through so called security and put them in my purse along with other women things. It's a battle trying to get all this in.

My luck, the TSA would tell me it is against policy to put a purse in a tote and a battle would ensue, so I never tried it. Now I know it's "legal" and will start doing this. Logic tells me I can put anything that isn't against the law in my carry on, including a spare purse, but as we all know there is no logic when going through THE LINE.

Not weird at all. We have a couple large but collapsible duffels that sometimes get stuffed into other bags if we know we're bringing back more than we departed with. Usually our clothes go into the duffels and whatever we're bringing back goes into the more durable luggage.

I've also checked empty wine cases on trips where we know we'll be bringing back wine. Now that airlines charge most passengers for checked bags, the airline-approved shipping cases have gotten a lot harder to find, even in places like Napa where they used to be available at any liquor store, vineyard, or package supply store. So we keep reusing ones we already have.

I took two extra duffels in a suitcase when I went to Thailand. All 3 came back full

That reminds me of the old Marx Bros. movie, "Coconuts." Groucho is manager of a hotel and Chico is checking in with suitcases:
:
Groucho: "Hey, these bags are empty."
Chico: "That's ok, we' fill 'em up before we leave."

I do it every time I fly. It's safer to have my purse zipped inside my tote than
hanging off my shoulder.