I say give Cyndaquil a try if you are torn between him and Chikorita. I picked Chikorita on my last playthrough of Soul Silver because I think this line is the most pleasing to the eye to have as a pokemon following you in the overworld. It is cute, but it also takes the most work to raise. Chikorita has a type disadvantage in the first gyms against the flying and bug pokemon of Falkner and Bugsy. The matchups just get harder and harder as the story progresses, since you have ice, steel, dragon and ghost gyms coming up, and Team Rocket's poison pokemon. Even just walking through the world can use up a lot of potions and healing from the early route flying pokemon, the zubats in caves, crossing the waters and encountering poison moves from countless tentacool to finding your way through the ice path. You'll have to have other strong pokemon on hand to support your Meganium and cover her weaknesses since she doesn't have many coverage moves. Chikorita is definitely for the brave.
If you just really love Chikorita for its design and personality, and don't mind doing some grinding then you should go for it. But if you want to keep it a more casual playthrough then Cyndaquil is the fastest and has the most attacking power and doesn't have any gyms that its typing is weak against. It also learns a very strong move in Eruption and can also always land against the evasion tactics of Clair's Kingdra with swift. I say get Cyndaquil or Totadile to play it safe, and if you want to test run a pure grass pokemon in Johto then add a Bellossom on your team, its also very cute. If you like it then maybe use Chikorita next time.