Longhaul trip on AC; need positioning help from ORD to YYZ
 

I am trying to book ORD-YYZ-BOM but its priced better without married segment i.e. ORD-YYZ/ YYZ-BOM as different journeys. Since both would be separate tix, would it minimize risk in case of a misconnect f both flights were operated by same carrier?
I am traveling in winter and bit concerned about weather woes. UA and AC are both *A but not sure if having separate tix will make it an issue.
My other option could be to take a cheaper flight the night before on miles and stay by the airport.... not sure if that equates to much $ savings though.

Any suggestions?

Not to be a stickler for nomenclature, but you are not connecting as you are on separate tickets. You have two fully-independent flights. You don't say how much time you plan to leave between these flights, but if you do not present yourself in time for check-in/boarding of the AC flight, that entire ticket will auto-cancel and AC will not be under any obligation to accommodate you. You must also consider whether you have checked luggage, in which case you'll need to collect this and pass through security again, as you cannot assume that UA will check through to the AC final destination on separate tickets. To make a long story short, you should certainly plan to arrive the night before. This gives you some better options in case weather or cancellations make your life difficult. Whether this extra time, cost, and hassle is something you are prepared to accept is something only you can decide.

You are right. This is not a connection nor I intended to present that way. Also, I was going to keep a gap of 4-6hrs at YYZ but if there is a misconnect from bad weather, few hours can go by pretty fast. From your answer it seems, conventional wisdom prevails. I'll plan to arrive the day before atleast.

And stay downtown. There area around the airport is a dump with nothing to do.

There are many airport hotels near YYZ with post-tax prices typically around 100 USD. I would do that if on separate tickets. You can then get in the mood for BOM early with some decent Indian food around Missisauga.

edit: I see now the YYZ-BOM flight is timed for 9pm. I might feel comfortable taking an early morning ORD-YYZ in that case. Or if going the night before, indeed it would be better to stay downtown. For the above I was thinking arrive in the evening and depart in the morning.

That's where I was coming from as well but neither ORD or YYZ are known for favorable weather conditions. And if on separate tickets, I don't want a "misconnect" (for lack of better term).
Last I remember, the only good way to get from YYZ to downtown was a ($20?) shuttle. Still the same case?

There's a Light Rail Transit service called the Union Pearson Express.

https://www.upexpress.com/

best way to get downtown by far. I think it’s about $12 each way (can’t remember...I just tap my Presto card and it takes off whatever it’s supposed to) and gets you downtown in less then 1/2 hour. Toronto traffic is also horrible, and you never know when it’s going to be bad, which can be any time of day.

as for the ticket, have you tried searching multi-city ORD-YYZ and YYZ - BOM instead of. ORD - BOM. It can change the pricing (sometimes for the better, sometimes...not), but if it’s pretty close to the same, would also keep you on one ticket. Just an idea.

I have done BOS-YYZ-BOM before and I would say a 6 hr connection is good enough. Try and keep both separate tickets on the same ticket stock if you can, that can help during irops. Also, I have been able to get an end-on-end before with BOS-YYZ in Y then YYZ-FRA-BLR in C. Have you tried if you can get it on 1 ticket?

Thanks for the tip.

That's what i am working on here as well.

That's a good point. Should I book YYZ-BOM and then maybe call AC to add ORD-YYZ leg? I am not sure if ORD-YYZ/ YYZ-BOM can be booked together without married segment pricing.

At this point, positioning flight cost is quite similar between AC, UA, AA. So it's totally worth trying.

Try it with Matrix. Or post date/flight details and someone can check. It used to be always possible with YYZ, but they added some end-on-end restrictions more recently.

I would try to stay within *A. AA operates out of T3, while AC and UA from T1. The transfer from transborder to international within T1 is a lot of easier than inter-terminal transfer from T3 to T1, especially if there are delays and/or you are running low on transfer time. Good luck.

The biggest problem with OTA and online engines is mixed cabin pricing. I am trying to make YYZ-BOM as PEY and ORD-YYZ as Y. Except for kayak (which doesn't give best results either), other OTA or search engines don't even give mixed cabin options. Second best results came from Google flights, which only puts it as 2 tickets.

AC ticket is PEY refundable. Maybe I can try booking it online and see if AC agent can help?

Matrix should have no problem with those constraints. There are a lot of end-on-end restrictions which is probably the issue.

I think this might be it... got from EF. How do I make sure I am looking at correct fare basis (just going my closest $ here)