1) Those are the official dates. The Transit Card Vending machines will stop selling new cards on May 1 and stop recharging old cards on June 1. At this time there is no reason to believe that they will not stick to those dates.

We went through this once last fall, but the system was such a disaster that they extended the deadline. However, as the deadline to purchase Transit Cards approached, they did let the machines fall into a state of disrepair and they let them run out of Transit Cards. They are being less cavalier about the transition this time, so we will see how they do.

2) I haven't been to Midway recently, so I hope someone else will answer. At O'Hare they have two Transit Card machines left and at least one of them is out of order each time I pass through lately.

Just to clarify, the Ventra Card machines are up and running right now. The reason I told you to get a Transit Card was so you could pay $2.25 rather than $3.00. The Ventra machines accept cash and US credit cards. The Transit Card machines accept only cash. NO change is given by either machine.

3) Visitors like the day passes because of the convenience of not having to figure out how much they need to spend in advance and because they don't have to take a college course in how to pay your fare which the other alternatives require. Unfortunately, they usually end up overpaying since the other options would be cheaper.

I assume you are saying that the total would be $25 for all three of you combined, not $25 per person? When figuring the total, remember that when you pay via Transit Card or Ventra Card, the train fare is $2.25, but the bus fare is only $2. And also for an additional 25 cents you get to ride two more buses or trains within a 2-hour period from when you boarded the first bus or train. So you can take a round trip ride on the bus for just $2.25 if you board the return bus within 2 hours of when you boarded the original bus. Does this information change your calculations?

In your original post, you said your riding was going to be over a two-day period. A one-day pass is good for 24 hours from when you first use it.
So if you first use it at 4:00 pm on Tuesday, you have until 4:00 pm Wednesday to finish using it. Will you be able to get all your riding finished in this 24 hour period?

Let me suggest an alternative: Buy a Ventra Card. A single Ventra Card can be shared by up to 7 people. The advantage of this is that for the same price (or less) you won't have a 24 hour deadline and you can use the card again if you visit Chicago within the next 5 years. (There is a $5 monthly inactivity fee after 18 months of non-use. But the fee does not reduce the balance below zero.) This video illustrates how to buy a Ventra Card at the Midway Station. There are two ways to proceed with this:

a) Buy a Ventra Card for $25 plus the $5 card fee. This is the same cost as three one-day passes.

b) Buy a Ventra Card for $20 plus the $5 card fee. When you get to your hotel, register your Ventra Card and $5 will be credited to your Ventra Card account which you can use immediately. This video shows how to register your card over the internet. You can also register by phone by calling 1-877-NOW-VENT.

To share a Ventra Card at a train station, each passenger taps the card on the reader before passing through. To share on a bus, first tell the bus driver that the three of you want to share a single Ventra Card. The bus driver will push a button on his console and then you tap three times.

I'm afraid I can't make the decision for you. These are the facts. You need to decide whether a one-day pass works for you and if you want to pay extra for simplicity and whether you want a Ventra Card to take home with you and use again the next time you visit Chicago.

4) Transit Card Machines do not dispense day passes. If you want a 1-day pass, you'll need to get it at the Ventra Card machine. This video shows how to buy a 1-day pass (it's called a 1-day "ticket") at the Ventra machine. You may pay by cash or US credit card.

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This video has some shots showing the interior of the train cars and people with luggage. Unfortunately, it mixes scenes of O'Hare and Midway service without making it clear which is which. But the train cars are the same.

Basically, each car of the train has a cabin for the operator. The cabin is at the front of the lead car, the back of the second car, the front of the third car, the back of the fourth car, etc. Immediately in back the cabin is a space with no seat that is for wheelchairs. You will hardly ever see anyone in a wheelchair on the train. This is the space that bicyclists use to take their bikes on the train and it's also a great space for bulky luggage. If you can't get to that space, each door has sideways-facing seats on both sides of it. These are great for traveling with luggage because you have extra room without getting into the aisle. But be sure you stick close to your luggage!

You won't have a problem boarding at Midway since it is the end of the line.
You might have a problem on the Red Line. Do your best to squeeze in someplace. The train should empty out at Jackson where you can run and grab a good seat and then the train will start refilling again at Jackson and north of there.