YTO-ORD, thoughts?
 

Hey all,

I'm trying to decide on a flight between Toronto and O'Hare, and I was wondering what you all thought of my situation. (I'm posting this here because much of my decision depends on the feasibility of ground transportation in Toronto).

General constraints:

-I have a 10% possibility of needing to be at UofT Downtown at 1:00pm for around 5 minutes.
-I'll be flying out on Thursday
-I'd like to make 4:30 bus from O'Hare to Rockford (although there is a 5:30 and a 6:30 bus in case I miss it).
-I don't mind running, and missing a flight isn't the worst thing in the world to me (but I'd really rather not).
-I have Nexus

Possible flights:

YYZ-ORD on AC 14:30-15:14 $206

Pros:
Cheapest option
I easily make the bus (maybe even make the 3:30 bus if I run)

Cons:
Super tight connection if I have to be at UofT at 1
I don't collect miles on *A (at least not yet)

YYZ-ORD on AA 15:16-16:07 $287

Pros:
I have status/collect miles on AA
I don't have to worry about making it from UofT

Cons:
Super tight connection in ORD
Most expensive

YKF-ORD on AA 15:20-15:58 $230 *I do have a car*

Pros:
I have status/collect miles on AA
Never been to YKF before

Cons:
Super tight connection in ORD (especially considering the lack of Pre-Clearance in YKF)
I'd rather not pay for parking in YKF if I can help it (If I don't have to be at UofT at 1, I'll take Via to Kitchner).

If anyone has any insight I haven't thought about, or if you could say which you'd prefer to do, that'd be really appreciated.

More facts:
How are you planning to go UofT to YYZ
What part of UofT will you be at? big difference at Spadina/College vs St George Station.

1305h from UofT to YYZ for a 1430h departure sounds not doable considering check in, CBP and CATSA.

Spadina/College, and TTC (or Uber if I have to). I've been lucky--CATSA/Immigration usually takes me 10 mins tops with Nexus, but I understand it can take longer.

YKF has no pre-clearance FYI, so you land in ORD Int'l terminal (T5?), at least you should get in quickly via Global Entry
but YKF is super small, very easy/quick between check-in/security/boarding

Also, you can redeem 4500 Avios one-way on AA (American Eagle) instead of cash fares
YKF/YYZ-ORD 4500 Avios + $60

Take the cheapest flight and use a cab to Rockford if you miss the bus.

Don't forget if OP is still considering a cash fare, it may very well be cheaper to buy YTO-CHI-XXX instead of only YTOCHI.

what about Midway?
 

Have you considered YTZ-MDV? $174.30 CAD, tons of availability in April:
https://www.flyporter.com

The OP's bus connection is from ORD and the cab fare to ORD would be a lot. Transit would require a change of els in the Loop and about 90 minutes.

How much is Via to Kitchener compared to parking there?