Departures from Midway

September 26, 2017 1:15 PM

I am going to be flying in/out of Midway in a few days. I've flown out of O'Hare several times, never Midway, though. The company I'm doing business with has changed my itinerary, such that my last meeting with them is 3:30-4pm and my flight departs at 5pm. Convince me that this is not a terrible idea.

The last meeting of the day is with the director of the division, and the coordinator (who emailed me the updated itinerary just now) said, "I will let him know to keep that last meeting short." Per Google Maps, the place in question is about half an hour from Midway assuming no traffic, but I'm guessing there will be some degree of rush hour traffic leaving the city at that hour. This is the last flight back to my home city that day (there was a 7:20pm, but it is sold out). I must be back for work the next day, no exceptions. I find airports and flying pretty stressful on a good day, and this seems like folly, honestly. I am seriously regretting taking the company up on their offer to book my flights. On the plus side, I will not be checking a bag.

Chicagoans, how bad is security at MDW? Is there any way I will actually be able to make this flight? Any suggested wording for gently pushing back to their coordinator without actually saying, "This is not going to be possible?"

posted by basalganglia to Travel & Transportation around Chicago, IL (25 answers total)

Terrible idea. Security lines can be so long they extend out into the airport's parking garage.
posted by agregoli at 1:16 PM on September 26, 2017 [14 favorites]

You can't even physically get to your gate from the office in that hour window and have any realistic chance of getting on the plane. Even assuming you left on the dot of 4:30, got a ride with no traffic, were already checked in and only had carry on luggage, you'd be hard pushed to even walk through the terminal to get to your gate before they closed the door for departure.
posted by Brockles at 1:19 PM on September 26, 2017 [10 favorites]

This is a deeply terrible idea.
posted by ArbitraryAndCapricious at 1:21 PM on September 26, 2017 [4 favorites]

Response by poster: OK, that's what I thought. Suggestions for wording? I have a draft email "Thanks, but [company] is 30-45 minutes from Midway Airport, and I assume longer with rush hour; I'm having trouble understanding how I can get from [company] to the airport and through security before the boarding doors close at 4:45. I don't mean to be difficult, but I do want to make the flight!"
posted by basalganglia at 1:26 PM on September 26, 2017 [1 favorite]

Google Maps will give you an estimate of how long it takes to get somewhere with typical traffic at some particular time. For example, a trip from Shedd Aquarium to Midway on that Wednesday at 4 p.m. is estimated to take between 30 min and 1 h. This means it is likely that you will arrive at the airport after your flight is left, not even counting the time waiting in line for security, the security checkpoint, sprinting to your gate, and the fact that airlines can and will give away your seat if you aren't there at some preset time before departure.

In no universe is this a good idea.
posted by grouse at 1:29 PM on September 26, 2017

I'd note the time that you need to leave to be comfortable getting to your flight.

"I'd like to be accommodating, but the proposed scheduling just won't work for me. I will need to leave by 2pm. Thanks!"
posted by CoffeeHikeNapWine at 1:31 PM on September 26, 2017 [6 favorites]

I'm also team Bad Idea, but Midway security is always a total breeze in my (white) experience. And I travel with a pet and opt out of the pornoscanner. The only time it's ever taken longer than about 10 minutes is when I was a stupid idiot and wore giant baggy overalls covered in metal findings that kept setting off the metal detector and made me nearly Ungropable™.

The choke points at Midway are check-in and sloppy personal TSA prepping.
posted by phunniemee at 1:51 PM on September 26, 2017

(OP mentioned that the last MDW flight to her home city is 7:20pm, and it's sold out.)

Would the client be willing to buy you a one-way ticket out of O'Hare after 8:00pm (if that itinerary is possible)?
posted by JoeZydeco at 1:51 PM on September 26, 2017

Just adding to the chorus: I fly out of Midway a lot, have pre-check, and usually cut things pretty close, and I would never ever ever show up later than 4:15 for a 5 p.m. flight. Never.
posted by goodbyewaffles at 1:52 PM on September 26, 2017 [1 favorite]

"I appreciate your willingness to keep the meeting short, but even leaving at the time the meeting is scheduled to begin will not enable me to make my flight. As I'm sure you know, just traveling to Midway that time of day will take xx minutes. Unless I can get a later flight at O'Hare, I will need to be able to leave by xx. Thank you for your consideration."

(I am not super clear on who schedules your flight - your home office or the people you're meeting with.)
posted by FencingGal at 2:04 PM on September 26, 2017 [2 favorites]

I'm assuming you are representing a company, and meeting with another in Chicago? This is a business priority question between the client company's coordinator and your own manager. If it's important business, then your manager needs to be cool with you taking the first available flight the following day. If getting back in time trumps the meeting, then you decline the meeting.
posted by mikeh at 2:06 PM on September 26, 2017 [6 favorites]

For the email draft:
It appears that the 7:20 flight out of Midway is sold out. I would be more than happy to fly out of O'hare on $AIRLINE any time after 6:30* pm. Alternatively we could rearrange the itinerary such that I depart [company] no later than 3:15 and take the 5pm flight from Midway.

*6:30 or whatever time = transit time from[company], preferably on blue line + 1hr after 4pm.
posted by Cold Lurkey at 2:07 PM on September 26, 2017 [1 favorite]

*8:00. Make 'em buy you dinner at Tortas Frontera before the flight home. =)
posted by JoeZydeco at 2:12 PM on September 26, 2017 [6 favorites]

"If it's important business, then your manager needs to be cool with you taking the first available flight the following day. If getting back in time trumps the meeting, then you decline the meeting."

mike is correct. travel is a part of your work time. simply by being at the airport in the morning, you are at work. If that's not acceptable to your employers, your day availability in Chicago ends by 2pm, not a minute later.
posted by mwhybark at 2:16 PM on September 26, 2017 [2 favorites]

Just to add one more factor on why you'd never make a 5pm flight after a 3:30-4pm meeting: I have never yet seen a meeting that ends promptly on time. So no, you wouldn't even have a full hour to call a cab/dash to the airport/race through TSA/run for your plane.
posted by easily confused at 2:24 PM on September 26, 2017

Response by poster: Few clarifications:

Flights were booked by the company I'm going to be meeting with. They originally suggested flying out after 7pm (which is how I searched for and found the now-sold-out 7:20) but then they booked the 5pm. The original meeting schedule they sent me ended at 2:30pm, which would be fine, but this afternoon they sent me an "update" which ends at 4. (Same general schedule, just with random interspersed breaks, I assume because of availability of the people on the other end.) The last meeting of the day in both itineraries is with the biggest decision-maker, so I really don't want to "cut it short," as their coordinator suggested. But if this is an indication of how they do business, maybe my/our decision is already made.....

I've already alerted my own manager to let her know that depending on what happens I might have to "work from home" on the day after this trip; this means canceling other meetings or setting them up via Skype, so there is a domino effect on other people I'd like to avoid if possible. O'Hare is a good suggestion; they have a couple flights that leave closer to 10pm -- this would get me home well after 2 AM, which is not ideal for me but I've emailed their coordinator and left her a follow-up voicemail.

Ugh, fingers crossed. I will bow out now and try de-stressing exercises. Thanks all.
posted by basalganglia at 2:30 PM on September 26, 2017 [2 favorites]

My pulse skyrocketed just reading your question.

I'd have serious second thoughts about these people, whatever your involvement with them is. That's horribly inconsiderate to you and everyone you work and/or live with; their plan is, objectively, to abandon you to a travel epic.
posted by Dashy at 2:57 PM on September 26, 2017 [4 favorites]

A side suggestion: Don't ever put a line in an email like you proposed that says "I don't mean to be difficult". You're NOT being difficult. You're being reasonable. They're being difficult. Why would you suggest to them otherwise? Be matter of fact about pushing back and don't apologize. It makes you sound tentative and unsure of your position. You're in the right here. Be the hammer, not the nail.
posted by Kangaroo at 3:40 PM on September 26, 2017 [16 favorites]

I bet that the meeting reschedule has been based on the old info of the 7:20 flight. When you word it, make sure you say "my flight at 5" to avoid confusion.

Are they able to drive you to the airport and meet whilst there?
posted by freethefeet at 3:55 PM on September 26, 2017 [2 favorites]

Yeah I would be a little less accommodating in my email. Your suggestion:

"Thanks, but [company] is 30-45 minutes from Midway Airport, and I assume longer with rush hour; I'm having trouble understanding how I can get from [company] to the airport and through security before the boarding doors close at 4:45. I don't mean to be difficult, but I do want to make the flight!"

My suggestion

"Thanks, but boarding doors close at 4:45 for my 5 pm flight at an airport that is at least 45 minutes away and is known for long security lines. I can't make this work. I can either fly out of O'Hare later and I'll take a few hours comp time the next morning (since I'll get home at 2 am), or we can shift the meetings again?"

They may not know just how inconvenient this is. Alternatively, they may not care which is a different set of problems.
posted by jessamyn at 4:28 PM on September 26, 2017 [1 favorite]

Just tell them that the meeting needs to be moved to no later than 1:30pm (I'm assuming it could go as long as an hour.) I wouldn't even get into asking them to book a later flight if you need to be at work the following day. They'll have you home in the middle of the night.
posted by fingersandtoes at 4:37 PM on September 26, 2017 [1 favorite]

The only way this could possibly work is if your meeting is being held at the airport, after security. Even if you got a police escort through traffic and there wasn't a single person in line at TSA, you still wouldn't make a 5pm flight leaving at 4:30. Heck, a TSA employee probably couldn't leave work that late and still board on time.
posted by kevinbelt at 5:38 PM on September 26, 2017 [1 favorite]

Speaking as someone who arranges travel for others as my job, nobody on the planet with any familiarity with any airport at all would expect this to work out. You don't need to stress about wording. Just tell them the timing involved here and let them figure out how to fix it.
posted by something something at 5:55 PM on September 26, 2017 [1 favorite]

With the admission that I don't fully know your dynamics with the Chicago company ...

Don't apologize. Don't be overly deferential. Just be pleasant and professional.

"Thank you for my updated itinerary. Unfortunately, the new schedule does not leave me enough time to make my flight out of Midway. To make my flight, I'd need to leave by 3pm [or whenever]. I'm happy to either move our schedule up, or leave on a later flight out of O'Hare [assuming you are willing to do that]. Please let me know which one you'd prefer."
posted by Betelgeuse at 7:08 PM on September 26, 2017 [3 favorites]

Wondering how this worked out.

You shouldn't be chewing your limbs off about it. Clearly they screwed up in booking your flight, and you need to be out of there at 2:30 or 3:00 as originally planned.
posted by intermod at 1:41 PM on September 27, 2017