I'm fairly new at this frequent flyer stuff, so hear me out please.
My family and I (three people) are going to Chicago for me to take a test at DePaul University. We already have our hotel booked, and it is right on the Magnificent Mile. We are now figuring out how to get there.
We will be flying out of CLE after work on Friday, December 2, and returning late evening Sunday, December 4 (the test is over at 5PM). If at all possible, we would like to avoid flying one of the cramped little regional jets, which seem to be by far the most common.
Up until now, we have only flown CO, and neither of the two flights that I am looking at is with them. Of the following two flights, which would you suggest? One is WN, and one is UA - the WN flight is $300 less.
Southwest Airlines Flight #2632?Depart CLE 12/2/2005 5:35 PM, Arrive MDW 12/2/2005 5:55 PM?Boeing 737-300
Southwest Airlines Flight #892?Depart MDW 12/4/2005 8:15 PM, Arrive CLE 12/4/2005 10:20 PM?Boeing 737-700
or
United Airlines Flight #79?Depart CLE 12/2/2005 4:46 PM, 12/2/2005 Arrive ORD 5:25 PM?Boeing 737-300
United Airlines Flight #1202?Depart ORD 12/4/2005 9:20 PM, Arrive CLE 12/4/2005 11:33 PM?Boeing 737-500
The UA flights would be $700.20 for the three of us, which seems a little steep for a 300 mile trip. The WN flights would be $410.70.
Also, we are not currently members of any of the *A programs. If we were to do the United flights, which member airline's program would you recommend? We will hopefully be redeeming the miles on ANA, not UA, but it would be nice to have the perks for both if we ever made Elite.
Finally, we've never been to Chicago before. Shuttle service for us would end up being about $120 each way, by my calculations, wheras taking the train would be $1.50 per person each way, which is a HUGE savings. Would it be easy/safe enough to take the train with one suitcase and one backpack?
Thanks in advance for the help!