O'Hare to Midway mid afternoon on a Thursday?

knick1959

Level 2 Member
#1
I need to get my wife and myself from ORD to CLE. I am expecting that a decent flight option for us might be out of Midway. This on a Thursday (and never mind that it's in January!)

Screwed up the times on my original post. Our international flight doesn't land until 2:25pm. How much time would I need to get to Midway, please, if I can find a viable flight?

I see some shuttles run between, and I can always take a cab. Or rent a short-term car? Does anyone do this on a regular basis?? TIA
 
Last edited:

italdesign

Level 2 Member
#2
I did ORD-MDW I-D once but it was with an overnight. I took the subway and it probably took 1.5 hours. Imagine traffic wouldn't be too bad around 3pm on a weekday.

I would book multiple Southwest awards if possible. They refund points even if you miss the flight (at least was the case last year). So book for multiple times, factoring in possible delay, and refund the ones you didn't take after the fact.
 

knick1959

Level 2 Member
#3
I did ORD-MDW I-D once but it was with an overnight. I took the subway and it probably took 1.5 hours. Imagine traffic wouldn't be too bad around 3pm on a weekday.

I would book multiple Southwest awards if possible. They refund points even if you miss the flight (at least was the case last year). So book for multiple times, factoring in possible delay, and refund the ones you didn't take after the fact.
Thanks for the reply. Turns out I was right with the original post; flight landing time was correct - it's 12:25. The third time I had listed in my spreadsheet was 14:25 which I took at quick glance as the real landing time. After some sleep and checking the email receipt - it lands at 12:25pm and the flight time is 14:25 (or 14:35 ... not much difference).

So. I have SW non-stop options at 4:55pm and 7:50pm. I had figured roughly an hour to get off the plane, collect bags and make it through customs/immigration. Just a guess but in the US and with GE I don't recall taking more time than this. There is a shuttle between airports that claims usually 60 minutes. That puts us there at 2:30 or even 3 which is plenty of time to catch the 4:55pm. HOWEVER, I think your suggestion is even better. I don't have the miles so will have to transfer UR. But now that we're SW experts (14 months so far with the CP) I know we can make use of a small RR pool left over from canceling one of those flights. They are pretty cheap to boot ($ or miles) ... or will be as I'm looking at flights a month before, the schedule doesn't extend that far out until end of this month.

Thanks again.
 

projectx

Level 2 Member
#4
I did ORD-MDW I-D once but it was with an overnight. I took the subway and it probably took 1.5 hours. Imagine traffic wouldn't be too bad around 3pm on a weekday.

I would book multiple Southwest awards if possible. They refund points even if you miss the flight (at least was the case last year).
They still do. This technique saved our Caribbean cruise in March when a snowstorm cancelled our initial flight.

Edit: Do not book for the same day. Southwest will cancel one of the flights.
 
Last edited:

knick1959

Level 2 Member
#5
I did things a little differently given time to think.

First, after doing the math, I opted to PAY for an AA direct flight from ORD to CLE that leaves at 3:05pm. I would have preferred using points but any option there was unrealistic (too points-pricey, no saver level awards).

However, I am still a little nervous with the time. While the time between flights seems convenient (land from HKG now at 12:20, leave at 3:05pm), if anything unusual happens we could be in trouble. Am I wrong in this thinking? This should be enough time to clear customs getting bags and to recheck, yes?

Well, just in case I did book that SW flight at 4:55 on miles. If it looks like we won't make the 3:05 for any reason at all, we'll bee-line to MID and shoot for that one. If things go smoothly, I'll cancel that SW flight and reclaim the few miles I had to invest (13.5k for 2).

Thinking a little further, as a backup perhaps I should change this to the somewhat later flight. I mean, if we're screwed with option #1, we should have room to maneuver for the backup plan. I'll recheck the flights and see how much later the next option leaves.

Thanks for all of the feedback.

[Update] Checking, the next nonstop option leaves at 9:25, 4.5 hours even later. I'm going to hold and take my chances with the 2 flights as booked.
 
Top