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I tried several times with DS before it actually worked. I would say, once you make up your mind to end the swaddle, commit entirely and give it at least one full week. I kept giving in with DS and going back to swaddling, and I think that prolonged the whole process. Here's the methods we tried, and how well they worked for us:

1. Cold turkey; just completely stopped swaddling. This didn't not work at all, and DS had a major meltdown.

2. Swaddling one arm in and leving one arm out. Same result as #1 for us.

3. Replacing swaddling with a small lovey so they have something to do with their hands. This worked for DD, but not for DS.

4. Swaddling looser each day until the swaddle is no longer needed. This did not work for DS because he liked to be wrapped up very tightly.

5. Replacing swaddling with tucking into bed. This is the only thing that worked for DS. I put him into bed, and then tuck a crocethed blanket very tightly around him. At the beginning, I'd wrap the blanket around the mattress and tuck it underneath so it was very tight; now, I just tuck it loosely into the sides of his crib. It also keeps him from scooting all over his crib and getting caught/stuck in the crib slats.

ETA: Once we committed all the way, he was actually sleeping better unswaddled than he had been swaddled within 3 days. The first night he woke up like 5 times; the second night it was 3 times; the third night it was 1-2 times.

We waited until she seemed ready, and at just after 5 months I went cold turkey and started putting her to sleep on her belly. She did fine.

We did it cold turkey with sleep training and have never looked back ever since.

We transitioned with the Magic Sleepsuit (because I was so scared of how badly he would sleep unswaddled) at 4 months and then into jammies at 5 months. Both transitions were seamless and his sleep didn't change although I thought my LO was nowhere close to rolling as he would just lay on his back for floor time. Once we transitioned to pajamas he started rolling and sleeping on his side.