Connecting at EWR from Terminal C (UA domestic) to B (International departure SQ)

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For 3. the easiest is taking the monorail between terminals. From terminal C - B it is 2-3 minutes and this train runs every 5 minutes i think. here is the link to the airtrain map

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Is 2hr 30mins enough for transfer?

I don't think so. This feels very risky, especially given the consequences of missing an ultra long haul flight.

I believe I can ask to "join" the ticket for a baggage check-thru at UA check in counter?

I'm not sure if that's possible. Life would be a lot easier if this can be "joined" into a single ticket but this may trigger a change fee and re-pricing at the new ticket price.

Does the air-side shuttle bus from Terminal C to B run in the morning?

Per current information from various websites the answer is "no". I found the bus availability to be dicey and website info not always be up to date.

Unless you can turn this into a single ticket (where the airline takes responsibility for a missed connection), I would not do this. It's quite likely that you have to collect your bags in Terminal C, take the train to terminal B, check the bags at the SQ check in counter and re-clear security. SQ check in closes one hour before departure.

My last few flights into EWR domestically where considerably delayed. It's hard to predict but this feels too risky to me. Consider flying in the night before and grabbing an airport hotel.

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