To 1 stop or drive and non stop, that is the question

Thoughts about the following are really appreciated. I’m having a hard time with these decisions.

We haven’t flown since 2016. We can’t do carryon only for a number of reasons. The airlines we are willing to use do not have direct flights from Milwaukee to Orlando but do have them from Chicago. Right now which of the two situations would you recommend assuming the overall cost of travel will end up being the same? Though refundable vs not may be an issue.

A) Fly with the 1 stop to Orlando with switching planes but not airlines
Pro: easiest from home
Con: potential for missed luggage right now in particular

B) travel to Chicago take nonstop from Chicago to Orlando
Pro: much less likely to have luggage lost though probability is not zero
Con: need to get to Chicago plan for that via rideshare or shuttle

I won’t drive our car because I don’t want it sitting at the airport. It’s safest in our garage. Plus I’d like to avoid being the one driving in Chicago because Chicago.


How long would the layover be in Chicago? Also, how far from Chicago is Milwaukee driving? Not sure you’d be able to find a ride share willing to do that, but you might be able to find a town car service


Isn’t there a train from Milwaukee?


at 1:15 est. drive time from Milwaukee to O’hare I’d go with the drive+direct flight.

Heck, drive time from JFK airport to New Jersey could easily be more than that, and I’ve done it occasionally if the flights are better.

Edit: airtags in your checked baggage are a cheap form of insurance against the airline having no clue where your bag is.

Edit2: on reflection, it’s not close. I’d rather do a nonstop flight from JFK than a 1-stop from EWR, which sounds similar to your situation. Ie nonstop from ORD vs 1-stop from Milwaukee.


I wouldn’t trust getting to Chicago without driving myself and giving myself a lot of time to do so. Is there something about airport parking lots that would prevent you from parking there?

If driving yourself is out of the question I would do the connecting and pack half of your stuff in each others bags in case one gets lost. I’d also bring a carryon each with essentials for a couple days in case of the worst case scenario.


Yes, but it doesn’t stop at Ohare. We would need to get transportation from Union Station in Chicago, and means dealing with our own baggage etc.

It varies but at least an hour. We have a company go rite way that has vans that would be doable price wise. According to the person I talked to today. They used to do shared shuttles but stop because Covid. ETA: Maybe a bit $$$. Sigh.

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I don’t want to pay for parking and I don’t want my car broken into. I don’t do it in Milwaukee so I’m definitely not doing it in Chicago.

I know about cross packing and will be doing that anyway because I’m paranoid lol. Ok just anxious. Maybe.


Definitely am thinking of the AirTags anyway. Though we may need to upgrade our phones. :woman_facepalming:

Also, not all the 1 stops go through Chicago, but that’s the only other airport that is feasible to do a nonstop from.

I have too many options. Sigh.

Edited: The airlines have made it have too many options. I hate what air travel has become with the nickel and diming and not including things that used to be included. :face_with_symbols_over_mouth: Double sigh.

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I used to only fly SWA out of MKE until rates skyrocketed, so we too found better options out of ORD (assuming you’re going there and not MDW). But for me, it’s not much more time getting there vs over to Mitchell.

I totally get not wanting to drive to and park in Chicago. Gotta be careful there. I will say we have been happy with parking at Loews in Rosemont about 5 miles from O’Hare and using their free shuttle that runs every 15 min. It’s self park, covered, cameras (I think), on a high level, and need reservation to get through gate into ramp, so pretty secure.

But if definitely not up for driving/parking, I’d probably look into something like the Coach USA bus that runs several routes daily between Waukesha, Brookfield, MKE, Racine, and O’Hare. And there’s Amtrak, but that might have to deal with a Union Station transfer. There could be a good option I’m not aware of. Hope it all works out. I would lean toward getting to Chicago to have a nonstop flight though.


Thanks so much for this information!! I will definitely look into your suggestions.

It used to be so easy to do all this, but things have changed so much, even pre-Covid, since the last time we flew.

Another question. Is getting a refundable ticket redundant if getting trip insurance? Thoughts?

Refundable tickets are essentially cancel-for-any reason with minimal hassle. There will be some redundancy with travel insurance.

My approach is generally to make as much of the trip refundable as possible, or at least cancellable and rebookable, and dispense with the travel insurance, because of the hoops you have to jump through to file a claim.

Many credit cards will include some travel insurance for free for travel charged to the card.


Where would you switching planes?

Have you considered doing an overnight layover? That way your luggage only needs to arrive, not be transferred which is where most of the problems seem to be these days.

Probably only required on the way to Orlando. So it would add a day to your plans.


Where I live I can get a direct flight into Sanford via Allegiant. However, their flight schedule is confining, so I have never done it.
I fly Southwest on a direct flight out of Indianapolis. Same situation as you → I have to get to Indianapolis somehow. It’s a two hour drive. I have driven it and just stayed overnight at a hotel where I leave my car and take their shuttle to the airport. Ideally, I prefer my husband to drive, but with solo trips I don’t like to put him out like that. This past February I used a shuttle service. It was convenient, but nerve wracking because the driver’s driving skills were suspect.

My favorite scenario is when my husband goes on the trip, he drives us to Indy and we leave our vehicle at the hotel. My second favorite is shuttle - if I can trust the shuttle driver. :face_with_raised_eyebrow:
Least favorite option is me as the driver, so I understand your dilemma.
I also understand the dilemma with leaving your vehicle at the airport. In 2018 we took a trip to Vegas and left my husband’s pickup at the hotel for the week. It was stolen!!! And we had to rent a car to make the two hour drive home.

Sounds like your best option is to take the connecting flight and cross your fingers your bags make it safely. The saving grace about lost bags is the options you have with being able to go off property to buy clothes/essentials. When I first started going to WDW in the 90’s leaving something at home (sunglasses - been there, done that) or a lost bag meant you were screwed unless you had a car. Uber/Lyft have changed the game tremendously.


Rumblestrip Randy lives rent free in my head always.


If you watch the news, it sounds like no one’s luggage makes it but I think there are plenty more times that it does. I asked my TA about it and she said she has not had any clients have their luggage lost this year.

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I know of two people whose bags were lost on a direct flight to Orlando. One had theirs turned up a day or so later, the other one never turned up. Both domestic flights too.

And @melcort10 ’s stroller had an interesting “vacation” that lasted longer than her own vacation. But that did involve Heathrow, so won’t affect @mathhound .


Thank you everyone for offering suggestions, opinions and questions!! You all helped me navigate my situation and feelings about air travel right now.

I did relook at the 2 trips I had already booked flights for and tried out various scenarios. They are both on Delta with fully refundable tickets and comfort plus (DH needs the leg room).

The DL trip in October is from Milwaukee and currently has a 2 hr layover in Minneapolis. The times are decent and I think we will be upgrading our phones so AirTags will be used. I decided to keep this because the seats on any direct flight from Chicago were iffy on the extra leg room now.

Our January WDW trip is similar with a similar 2 hr layover (so far) in Minneapolis. Again, switching to Chicago wasn’t great once I factored in the seating situation again. Also, Jan/Feb travel in the Midwest is a crap shoot and driving to Chicago could be as problematic as flying so, keeping those plans.

Where things changed was for our GSC trip in March. I will be using Coach USA as recommended by @Tall_Paul1 to get us to and from Chicago. From there we will be nonstop to Orlando on United. Which compared to a 1 stop Delta trip at the same time, I think saves us a little bit of money.

That ends our travels for quite some time and I am happy about that. I do truly hate what air travel has become (starting pre-Covid). Thanks for all your help!