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.
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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!

Unless you plan on significant flying in the future (at minimum, elite stauts with one carrier) and are not planning on making CO that carrier, save the money and fly WN.

I'm not sure where you checked on fares but using Orbitz.com for the dates and times showed UA/AA/CO all with fares of $137 or lower.

Regarding transportation the blue line train is safe and simple to use...as long as your luggage isn't too heavy.

Enjoy your time in Chicago!

がんばってください

I am also from Cle and will be taking the jlpt except mine at Columbia. I am trying for level 3 ..we shall see if I can pass it .. The best of luck to you

The "el" trains from both ORD and MDW are safe, inexpensive, and convenient. I wouldn't consider anything else.

I was looking at flying a 737, not an RJ, so that is where the prices came from.

At this point, I think I'll probably be going with WN.

今年私は４級をします。来年３級をすると思います。
I picked Chicago only because I was originally planning on driving, but certain circumstances have made that impractical.

あなたも頑張ってください！