Have you looked into car service or Uber? If you're talking about 2 tickets at 100 per then I would think for not much more than $200 you could get a 1-way service to Milwaukee.

For example I just plugged in the route on Uber Estimator and $200 is a good budget.

 

I'm surprised that they even fly ORD-MKE. It's only 67 miles between the two airports.

 

If uberESPANOL guarantees a Spanish-speaking driver, what kind of service is uberBLACK? (and yes, I know that uberBLACK is their luxury version, but the chosen service names look a bit weird when mentioned in the same conversation.)
They really should be more careful with their choice of service names...

 

I can personally verify transportprof's statement. I lived in Wisconsin for several years and regularly flew MKE-ORD-XXX and reverse, and your parents will be far more comfortable on the bus (or car service). The CR2s are horribly cramped aircraft, while the bus is actually quite nice.

Definitely do NOT take the CTA to downtown and then Amtrak up -- it's a pain in the butt, time-consuming, and not a comfortable ride.

Further complicating the situation is that when an itinerary involves two different tickets (even on the same carrier), you are asking for trouble. Baggage "inter"lining, IrrOps, lots of little things that can go wrong and you're not protected since the tickets are entirely independent as far as the CoC is concerned.

It may be too late at this point since you already bought the ORD-MKE tickets, but in the future I would recommend any of several other options.

 

And there's probably very few (if any) O & D pax. This is almost all to service connections from destinations. It's probably faster to take the train, and definitely to drive if just doing Chicago-Milwakee.

Besides, we'd lose those all the great threads on people doing HCT and how to get their bags short-checked just to ORD, etc.

OT a bit, but on short flights, we used to fly YYZ-FLL, with a stop in MIA (same plane) on Eastern, and then DL took it over (IIRC). I don't know if the carriers actually sold the MIA-FLL segment and vv on its own, but believe at the time the open skies agreement didn't allow a non-stop to FLL from Canada.

 

It's been years since I flew ORD-MKE, and I remember they are all tiny planes, but I have taken the bus recently over the last Christmas holiday. The bus is very tight on the knees, and I can't remember ever having such little room on a plane. I have to sit sideways on the bus. So if they are both cramped, the advantage would be a 20 minute flight vs an 1.5 hr bus ride.

The last time I took the bus to Ohare from Milwaukee, the bus actually broke down for over an hour, just a mile or two from the airport. There were several people on the bus that missed their flights.

 

Booking elderly parents on 2 separate tickets though a congested, delay-prone airport with 1 hour between the tickets sounds like a total disaster in the making.

What kind of contingency plans do you have for IRROPS?

 

I think there are many connecting flights at O'hare that are 1 hour apart. Worst case would have been they missed their flight and either got on the next one a few hours later or have taken the bus.

I understood the risks when I booked the tickets, but it still sucks when it doesn't go as planned. Thanks for taking the time to read.

"irrop = irregular operations." You'all and your acronyms! Its almost as bad as the military.

 

Your initial post {doesn't} seem to align with this new admission.

 

And you understand that taking the next flight would be an extremely expensive proposition? On separate tickets, UA is not obligated to rebook your parents if they misconnect.

 

I think flat tire rule would probably work for them. They just have to show up at the counter late and not mention they're on a connecting flight.

 

Back in the day MKE/xxx routing with a connection at ORD could be much less expensive than ORD/xxx.

I'd often book MKE/xxx, shlep up to MKE and then just skip the final ORD/MKE leg. One time in a weather situation I was able to get them to just dump the initial MKE/ORD leg and keep the rest of the itin intact.

On at least one occasion it was cheaper to fly a RT ORD/MKE on one ticket followed by a MKE/ORD/xxx/ORD/MKE itin (skipping the last leg of both tickets.)

 

If UA blows a connection on a single PNR, then they're on the hook to rebook you on as easy alternative as possible. With two PNRs, there is no obligation at all. You're just late for your flight and you can rebook or hang out for standby.

With same day changes, on their departure day, you might be able to change the final leg to a later flight. Personally, I would just get a rental car at ORD and be done with it. They would probably be in Milwaukee long before they would get another flight from ORD.

 

OP, Try this.

Put a towel in your mouth (to avoiding breaking your teeth due to the pain) and call UA back.

Do not discuss the other flight, do not even mention it. Simply say they have moved the flight to MLK an hour and this does not work for you. Ask for another flight or a refund.

No guarantees, but if UA wants to imitate DL it could work.

EDIT: Have no clue who flies this leg, but if they changed operating carrier they must refund you.

 

Except OP notes a change to the BTV-ORD flight, not the MKE one.

So, problems here:

- As KF booked the first segment, they are the ones who must make changes. Not sure who's COC they use to determine what hey are required to do. But UA has set 90 minutes as the SOP change threshold, IIRC, or if MCT is broken. OP being on two tickets mean MCT is irrelevant. Not sure what KF uses as a change threshold.
- KF has to make the change, as it's their ticket. UA (well, UAX) only operates the flight.
- KF may not have a stipulation where a change in operating carrier allows for a full refund.
- finally, none of this solves the end problem of OP getting on the flight they want if there's no (award) space on it. So even if SQ were to agree to a change, OP won't get on the flight they want unless SQ can convince UA to open space on it. Not impossible, but very unlikely. Or if they are willing to purchase it, which we don't know.