Oh…HARE – Tips (And Tales Of) Escaping Chicago’s Infamous Airport

Filed Under: Advice, Travel

Anyone who flies regularly knows that delays and cancelations happen, and there’s often very little that we can do about it in advance – other than plot our flights very, very carefully. As a general rule, I try to avoid Chicago’s O’Hare like the plague – I’ve even gone so far as to use it as a criteria for my airline loyalty. But when I have work in Chicago, this is hard to achieve. And unfortunately, on a recent business trip to the windy city, my low expectations were…met.

Now, I realize that a delay at O’Hare is about as news-worthy as the sun rising in the east or Delta devaluing their award redemptions (love you, Delta!) but this trip had a few extra…complications that made it interesting.

So I figured I would regale you with tales from O’Hare, as well as some of my favorite tips for avoiding (or at least surviving) these routine – and routinely frustrating – delays and cancelations.

And if you’re not up for Storytime with Steph and are just here for the tips, that’s cool, too – feel free to scroll right down to the “What to do if you’re delayed” section. Otherwise, let’s raise our seatbacks, stow our tray tables away, and buckle up for this turbulent ride.

Weather, Delays, & Cancellations (Oh My!)

Right from the start, the trip was fraught with disaster, beginning with a three-hour delay out of New York’s La Guardia (LGA). We managed to arrive around 2 AM (thankfully, I had a later start the next morning and some very understanding colleagues).

The return trip was no better. I had been watching my weather app religiously, knowing that the slightest rain can often mean Armageddon at ORD, so when I went to check into my return flight, I was pleasantly surprised to see that United had proactively offered me the option to switch to an earlier flight at no cost. I jumped on the opportunity to take the earlier, 7 PM flight out.

But sure enough, the email notification for my canceled flight came right around 3 PM. I immediately checked to see what was available, but it was already slim pickings. The best I could come up with for same-day departure was a 9:30 PM flight to Denver, followed by a redeye back to LGA.

In a middle seat.

This sounded about as appealing as a root canal, but options the following day were limited to 8 PM flights or later, and I wanted to jump on the sure thing while it was there.

I also wanted to keep the costs down rather than staying another night – normally, I have some flexibility to expense these fiascos, but I knew that this client was already on a tight budget and I didn’t want to push my luck.

So I grabbed a seat on the Denver flight, told myself that it was a mileage run (whatever it takes!), and figured I would reevaluate my other options once I was done with our program.

Trip Delay Insurance to the rescue

I tend to look for any opportunity that I can to use some of my credit cards’ less-talked-about perks, and it dawned on me that my United MileagePlus Explorer card offers trip delay coverage. More specifically, the card offers up to $500 of trip delay insurance, provided that you paid for part of the trip with the card in question (check) the delay requires an overnight stay (check) or the delay is 12 hours or more (this ended up being a check, barely).

I did a quick Google search to make sure this was accurate, and changed to the best late-morning flight on the following day that I could find. I figured $500 would buy me enough for a night in Chicago, a meal or two, and some fodder for at least one or two blog posts.

In hindsight, I should have been spending that time searching for lodging.

Where have all the hotels gone?

While I was busy researching trip insurance policies cleaning up from our event, apparently the entire city of Chicago sold out of hotels for that night. To make matters worse, every hotel booking app that I’ve ever used started showing phantom availability, akin to what we sometime see on award bookings.

I probably clicked through 30 or 40 hotel listings that looked available but showed as “sold out” – and the few available motels near O’Hare were retailing for over $800 per night. I was ready to spend – but not quite that much.

I checked to see if I could get back on that original flight to Denver, but by then, it was long-gone. I was seriously contemplating taking a flight to SFO and then a redeye back to Newark, but decided to take one last look at hotels.

And then I found the answer to my prayers: The Bridgeview Inn.

Sure, it was 25 miles south of O’Hare, and yes, it had a 4.5 out of 10 on Kayak, but they had a room available, they accepted my credit card, and they retailed for the low low price of $67.19 per night.


In hindsight, I might have been better off taking that SFO flight.

Getting Uber-lost

Don’t worry – we’ll get to the Bridgeview Inn experience in a minute. But first, I had to get there. I was pleased to see that there was an Uber less than two minutes from my restaurant, and while the driver’s rating was a little lower than I’m used to, he was a pleasant conversationalist and got me on my way pretty efficiently.

We got south of the city and that’s when things started to get weird – I noticed my time starting to increase. My route was starting to deviate off of the highway – I initially refrained from saying anything, because I thought maybe the driver knew something that I didn’t.

Until he pulled up in front of a group of (pretty unsavory-looking) residences and asked me “Is this good?”

According to the app, we were still 11 minutes away from the hotel.

At that point, I was more interested in getting to the hotel in one piece than I was in the inner workings of Uber, so I offered to navigate him via Google Maps. He said something about the app timing out, and then followed my turn-by-turn directions the rest of the way to the hotel.

I found out later that a colleague of mine had had a similar experience with Uber earlier that day, so in the end, I really don’t fault the driver – although I do wish he had asked before driving up to some random houses.

But who said travel was easy?

Welcome to the Hotel California

If anyone out there still thinks that business travel is glamorous, or that contributors to this blog get any kind of preferential treatment, then hi, nice to meet you, and I’m here to put those myths to bed once and for all.

In a sense, I can’t fault the Bridgeview Inn too much – you certainly get what you pay for, and the guy who checked me in was really nice – like, surprisingly so.

But the positives end there.

Bridgeview Inn check-in

Upon check-in, I was given a room key, as well as the remote control to the TV in my room, with the warning that I would need to turn the tv on manually.

Bridgeview Inn room

I told myself that the stains on the floor were marker…

Bridgeview Inn room

And took a moment to admire the local “art:”

Bridgeview Inn room

The whole thing felt a bit like an episode of Breaking Bad, Chicago-style.

Honestly, I was happy for a place to sleep for the night, but the biggest issue can’t be depicted in photos. During my approximately four minutes total outside of the room, I had two separate people ask me for a cigarette, so it should come as no surprise that everything in the room (including me, by the end) reeked of ashtray.

I would have loved a long, thorough shower in the morning, but sadly, shampoo wasn’t included with the price of my stay.

Bridgeview Inn amenities

But when your hotel only costs $2 more than your Uber to the airport, I suppose all of this is to be expected.

A safe return home

Fortunately, some further finagling with the United app got me onto an earlier flight, and I made it to O’Hare with no drama in the morning (save for some Chicago traffic – yikes!) I did end up in the middle seat in the second-to-last row of the plane, but honestly, at that point I would’ve ridden in the cargo hold for that two-hour flight.

Given that my hair still reeked of smoke, maybe my neighbors would have liked that, too.

What to do if you’re delayed

First off, for those of you who skipped ahead to this section, welcome back!

At this point, you’re probably wondering what you can do when you know you’re just not taking off that night. Some things, like weather (and lost Ubers, and bad hotel room graffiti), simply fall out of our control. But with the right strategy, technology, and credit cards, there are certainly plenty of things that we can do when we get that notification.

Get in front of the issue

It’s not uncommon for airlines to proactively offer to waive change fees when weather or other issues strike en masse. What they don’t tell you is that you may be eligible for a free flight change, even if they technically haven’t offered it yet

I’ve done this with Delta many times, but I’ve had Gold or higher status with them for years, so that isn’t necessarily an accurate metric. But over the past month, both United and American have allowed me to change a flight, free of charge, before any waivers were issued.

Last month, American Airlines let me negotiate a change to an earlier flight at the check-in counter, because there might be weather in the future.

And just this week, United allowed me to change my flight on the app before the waiver went out.

And I currently don’t have status with either airline. 

Now, I should probably note that both of those aforementioned flights were eventually canceled, but it sure is nice to know that the option is there, even for non-elite fliers.

When in doubt, if you think your original flight might be delayed or canceled, don’t be afraid to ask to move.

Leverage your apps

I don’t fly United that often and I’m not about to break up with Delta, but I’ll give due credit here – their interface for rescheduling on the app was awesome. I changed my flight a grand total of five times throughout the evening, and each change took two minutes, tops.

Most importantly, I didn’t have to spend a single minute dialing an 800 number.

I haven’t tried to change a flight on the latest version of the American app, mainly because I usually have to flat-out rebook on another airline, but historically, their app hasn’t been all that easy to use, even for simple things like changing seats. Unfortunately (or maybe fortunately), I don’t have enough experience changing flights with the non-legacy carriers, but I’m sure there is plenty of experience out there 🙂

I would say that by comparison, the Fly Delta app is almost as good for changing flights – but United’s one-click multi-city search interface gives it the slight edge.

Speaking of airport choices…

Check out all of your airport options

Weather delays are usually pretty widespread, but sometimes, there are other factors at play. For example, La Guardia (sort of) has a midnight curfew, whereas Newark does not. I ultimately wound up on a flight back to LGA, but the Newark alternative did open up some other possibilities.

I could have also flown to my home airport (Hartford’s BDL) and rented a car back to La Guardia (where my car was parked) if I had wanted to. That prospect sounded about as appealing as a redeye in a middle seat, but if I was in dire straits, that could have been another way to get creative and get home.

Don’t forget about trip delay reimbursement

I’m probably in the small minority who intentionally carries airline co-branded credit cards, which are mainly there to ease the pain when I don’t have status. But in this case, my United MileagePlus Explorer Card and the accompanying trip delay reimbursement may have saved the day.

I’m looking forward to reporting on the outcome of my claim once it gets resolved, and I plan do a deeper dive into the overall concept and the corresponding cards in an upcoming post, similar to my rental car insurance series.

But in the meantime, it’s important to remember that some of our favorite cards also offer a whole slew of benefits that we hope to never have to use.

Prioritize hotel reservations

If there’s one area here where I seriously misfired, it was with my hotel reservations. For all the overnight delays that I’ve encountered, even in places like Philly, Atlanta, and D.C., I’ve never been in a position where the entire city was sold out.

The biggest surprise to me was the sheer amount of phantom availability that displayed on some of my favorite booking sites, including Kayak, Priceline, Hotels.com, TripAdvisor, HotelsTonight, and both the Hyatt and Hilton websites.

The jury’s still out as to whether my final hotel outcome was lucky, or at my own peril, but I was kicking myself all night for not jumping on something sooner.

Moral of the story? Just because something looks available doesn’t necessarily mean that they actually have rooms.

And to that end…

Don’t give up

Sia’s “The Greatest” was my theme song for the evening as I constantly refreshed my flight search – and it eventually paid off. While hotels are unlikely to open up availability once they’ve sold out, airline seats often change faster than the price of bitcoin.

Case in point – when I started my search, the earliest flight available on the following day was a flight that got in at 10. I eventually found myself on an 11 AM flight with a two-hour layover in Cleveland, and by the end of the evening I was on an 8 AM flight scheduled to arrive at 11:07.

We even got in a few minutes early.

I think the big takeaway here is that once your flight has been flagged as eligible for rebooking, you pretty much have carte blanche to change it as many times as your heart desires – which means that other people are likely doing the same. So if things start to look bleak, just keep hitting refresh – and you may be handsomely rewarded.

Final thoughts

At the end of the day, I love a good story at the expense of almost any personal comfort, so it’s all good on my end. And as much as I take issue with some of United’s other service flaws, their app – and their timeliness in reporting the cancelations that day – really impressed me.

That said, hopefully it’s not a feature that I have to use again anytime soon.

Were any of you stuck in Chicago with me this week? What are your go-to moves when you know that a flight will be delayed or canceled? Sound off below! 

  1. No joke I know exactly where the Bridgeview Inn is. Right next to JB Hunt trucking company and Walmart a block away. Unfortunately im from Bridgeview you should have tried for the Super 8.

  2. Which moron decided to put a large hub in a place where related delays are unavoidable.

    Weather related delays should not be exempt from compensation.

  3. Bridgeview Inn, the type of place where B grade porno’s are shot. Still, $60 per night ain’t bad.

  4. The last time I flew out of ORD my flight was canceled as well. Thankfully I had close friends in Chicago and spent the night with them.

  5. Ha, I think I like “Storytime with Steph.”

    I wonder, though, at what point would you have just given up and slept in the airport?

  6. Ahhhh Chicago. One of my first “solo” experiences with weather disruptions was there, way back in the mid-90s during my college days.

    My dad had to be in Chicago around Christmas time for work, so for whatever reason it was decided that we’d do our family Xmas celebration in Chicago that year. My parents flew in from India and I flew up from Atlanta after my college finals.

    I had decided to make a day trip from Chicago to Madison to visit a friend there on 23rd December, so I made my way back to O’Hare that morning for a 730am flight on United (operated by an Air Wisconsin BAe146). We departed for Madison on time but due to heavy snowfall, the airport closed while we were en route and after an hour of circling we diverted to Milwaukee around 945-10am. United organised buses for us and we got to Madison around 1230pm.

    Of course, due to the weather my flight back to Chicago scheduled for around 5pm had also been cancelled and there were no flights leaving Madison at all that day. Renting a car and driving back to Chicago in the snow was not practical for a 19 year old either. So we decided to head to my friend’s house past Wisconsin Dells and see what the next morning brought.

    Early morning, phone calls to all the airline’s 800-numbers (this was before the era of airline apps, or indeed smartphones or internet booking) brought news that Madison airport was still closed but it looked like American was still flying from LaCrosse. So we drove out to LSE airport after breakfast. Unfortunately, by the time we got there it turned out that O’Hare was closed and the American Eagle Saab 340 had not yet departed. I spotted a Northwest flight to MSP leaving around lunchtime and successfully begged the counter staff to accept my UA paper ticket to get me out to MSP on that flight, and then standby on a later flight to Chicago if the airport opened later.

    I made it onto the DC9-10 and into MSP, but Chicago was still closed. Spent most of the afternoon at MSP airport (I remember spending around $20 on the NBA Jam arcade game on the old “Blue” concourse) until I finally made it as a standby onto an A320 to Chicago around 6pm. Finally got back to our hotel downtown after 9pm but just in time for Christmas.

    So yeah, that taught me a lesson about Chicago weather disruptions that I still haven’t forgotten 20+ years later!!!

  7. This is almost identical to what happened to me in the first week of June at ORD. flight delayed in toORD from YYC so missed connection to Madison. HSBC Premier Mastercard World Elite Insurance wouldn’t cover the cost of hotel or rerouting. Went to Hertz as PC, and they said as it was a walk-in booking no loyalty benefits and charged $256 for less than 12 hour rental to drop of in Madison.
    ! A real shocker!

  8. You are a experienced traveler, a female traveling alone and you did this? Very naive. @snic is right you should have slept in the airport, which would have been safe. If you know anything about Chicago or any large metropolitan US city like that you should know that 25 miles outside the city can be good, bad or very dangerous. Not something which you should gamble on. I am glad you lived another day to write. You are very – very lucky.

  9. LGA to ORD….ouch

    I’ll go out of my way to avoid both, but for me, LGA has been so much worse than any other airport

  10. These are the situations in which I enlist help. I have had good success with Amex Platinum services being able to take good care of me. For situations like this with hotels, it’s great to have an experienced travel agent on call 24/7 with access to the GDS.

  11. Flew into ORD on Thursday when they had more rain issues. Was good to be 1K in that case as I was able to get booked onto and earlier (delayed) flight with 1 seat left even though that flight was showing full and wasn’t an option in the app for rebooking.

  12. Another bad airport for weather is SFO – always a crap shoot.

    I once had a trip from Milan to San Diego that took three days. Five hour delay at MXP for an ATC blackout over London. Arrived at Newark just in time to miss the last flight to San Diego. All hotels were sold out. Found a place (just like Steph’s) an hour outside of Newark. Returned to the airport at 5 am for my flight to Houston which was cancelled due to weather at Newark. Waited ten hours for another flight. Arrived Houston in time for a hurricane warning and cancelled flights. Fortunately, found a Hyatt close by. The following day I got out at noon to San Diego. This was my last flight with United; I realize that most of this wasn’t their fault but the rebooking was a never-ending nightmare. All this happened in the normally weather safe month of September.

    Having spent many nights in airports, I’d take a seedy motel given the choice.

  13. cracking up at the note taped to the wall the Bridgview inn photo

    “DO NOT RENT” list

    Will it soon include a blogger who posted photos that put the hotel’s cleaning and carpet/furniture replacement cycles in an unfavorable light?

  14. There are ways to travel through Chicago and minimize your chances of being delayed. Chicago and O’Hare was my home airport until I just recently moved to Houston. Obviously weather delays you can’t do much to avoid. If you want to get through O’Hare with the least chance of being delayed leave early in the morning.

    You also talked about flying into a different airport to get home, but did you look at flying out of Midway instead of O’Hare.

  15. Fly to MKE. Amtrak has a stop that serves the airport. Unfortunately with most of what was Midwest Airlines/Republic/Frontier long gone avoiding a connection at ORD is more difficult.

  16. Steph what a nightmare! I fly out of ORD internationally once a month and have had a heck of a time with logistics (I live in Milwaukee and have opted never to get a connecting flight ever from MKE to ORD for all of the delays – I was averaging a 50% cancellation rate on my return connection to MKE). Some options for stay in hotels for future reference is to look at the Western Suburbs (Schaumburg, Woodfield, Oak Brook, Vernon Hills, or even Rosemont to the East) which although a fair distance away from the airport you can get a Go Airport Express shuttle or Uber to. You can also check flights at Milwaukee (MKE) airport which is accessible by Coach USA bus which leaves hourly from ORD to MKE. I recall an issue awhile back where the computer systems went down and all flights out of ORD were suspended. People managed to rebook out of MKE. While ORD is convenient to Chicago MKE is such an easy airport to get in and out of and has direct flights to LGA. It is about 1:15 to ORD direct by car or you can also grab the Amtrak train at the airport to get you downtown Chicago Union Station. Still thinking of how scary it must have been to be in the hotel you stayed at. Glad you made it home!

  17. Experienced traveler. Really? Starting with booking LGA-ORD as if they are the only transportation choices in cities of 13 million and 7 million, and then seeming blown away when things don’t go well? “Experienced travelers “ have known about both LaGuardia and O’Hare for decades, and work around them unless travel conditions like weather, holidays, time of day for travel, etc seem to not be complicating factors. Yes, weather. You can usually get a decent idea of potential weather problems as far as two weeks ahead of time; if you’re booking your travel 3 months in advance, then you get what you get at LGA or ORD, when flights on that same day in the same weather will have a lower chance of on-time success than at EWR or MDW. If you want to hedge the bet, Newark and White Plains and Midway and Milwaukee look pretty good right from the start of trip planning. Then randomly riding out to Bridgeview with no idea about it other than there’s a $60 hotel room available? ($60 rate being another small clue missed when decent basic hotel rooms in NYC and CHI are typically 2-3X that rate.) It’s all very cute and knock yourself out if you’re gonna travel without a common sense plan, but don’t represent yourself and your story as “advice from an experienced traveler” to whoever might be (god forbid) a less-experienced traveler, with the amount of bonehead moves made on this misadventure.

  18. If you are Marriott Plat. aren’t they supposed to get you a room if they are out?

    Travelled all my life for business, and yes before uber and gps. I have stayed many time in those “holes”. Often wondered if my car would be on blocks. Slept in my clothes because you know those top comforter did not get changed, much less the sheets.

    And the family at home thinks Dad is on vacation.

  19. I have travelled to and from ORD probably a hundred times but will soon be making my first connection there. Tortas Frontera during a flight delay will puts ORD on top of the other options.

    And I think the United app is fantastic.

  20. Thanks all for the suggestions re: alternate airports and otherwise. I normally do what I can to avoid both LGA and ORD at all costs, but with a last-minute client schedule change, tight budgets and razor-thin timelines, most of my other go-to options were off the table this time around.

    And for those of you concerned with safety – first off, thank you (really) for your concern. I did spend some time waffling between sleeping in a fleabag motel or on an airport cot with my laptop bag by my side in a public place, and ultimately the privacy won by a (small) margin. Had I felt truly unsafe, I would have had no problem telling the Uber to turn right back around (and probably would have done so if my hotel had been at the original drop-off location that he attempted). In the end, while I was skeeved out and unamused, I never felt that my safety was threatened.

    And obviously I’m trying Tortas Frontera next time I’m in ORD (and my husband concurs that it’s awesome.)

  21. I realize your post was probably written with the best of intentions, but instead of containing constructive advice (book early departures when possible, reject itineraries with short connections, or such), it just leaves the reader with a throwing out the baby with the bath water-type of “don’t fly via ORD”.

    I have flown transcontinental itineraries regularly now for eight years, and often choose ORD as the transfer point. Never had any major issue there, except one time when all flights were late – but then it just ended up that my connecting flight was proportionately late, so no missed connection then either. ORD is an advantage actually, because there is such a redundancy of flights in case you do miss a connection. And five runways, soon to be six, have improved reliability – and the ability to recover from irregular operations quicker – substantially.

    Looks like you had dark cloud chasing you that day, and I’m sorry about that. But don’t place ORD as the primary culprit in that chain of events.

  22. Was in a 7 hour delay on Wed with AA ORD to DFW. 5 hrs due to weather and 2 more for a mechanical delay(with a equipment change). Was expecting AA to pull the plug any minute but we left after midnight and arrived close to 3am at DFW. Was surprised to get an email from AA the next day with 6000 miles.

  23. ^Agree with Marco, I’m from the Chicago suburbs and honestly have never had a major issue of all my times. Yes, there will be times when weather is bad either in the winter or summer, but that can happen anywhere in the Midwest. I would disagree with the “any little bit of rain causes delays at O’Hare” even if it’s an exaggeration, it would only be for major thunderstorms with large amounts of lightning in the area…it’s not like the airport is super paranoid and shuts down during the lightest bit of rain.
    Also there are unquestionably plenty of better hotels in the suburbs west and southwest of O’Hare that I doubt would have been sold out even if there had been a large weather delay (i.e. Naperville, Schamburg, Lombard, Aurora, etc.), so I really believe your misfortune of staying in a ghetto motel was largely due to your lack of knowledge of the Chicago geography.
    This post would have made more sense if you focused on things like the lack of amenities, how far you have to walk from one terminal to another, how horrible Terminal 5 (International) is. O’Hare is definitely not a “nice” airport but I don’t think it deserves the title of this report based on a one-off experience you had…now if this happened MULTIPLE times you’ve gone through O’Hare, please write away on how horrible it is.

  24. This happened in May 2018. Reading in your column about Turkish Air. I had booked two business class seats to Odessa Ukraine with a stopover for a week in Istanbul. We live in Alaska. We booked a flight from Anchorage to O’hare on Alaska Air and planned to then fly Turkish Air to Istanbul. Our flight from Anchorage to Seattle was uneventful. The flight from Seattle to Chicago ran into weather. Chicago was closed for incoming and we were diverted to Milwaukee. While we were on the ground I used my cell phone to call American Express Travel Service to change our flight to the next day. Good to have 24 hour coverage by a tour company. They called Turkish air before our flight left Chicago. The travel agent called me back and said regardless of weather my change fees for my wife and I would be $1,000. Not pleased but charged it to my Amer Exp (AX) card. Got into Chicago later that evening , the Turkish flight was long gone and all the hotels in all my apps and phone calls were sold out. We walked to the Hilton in the O’Hare airport. Gave him my most sorrowful blue eyes look, gold status and my platinum AX card. They found a room. The next day I was unable to print out our Turkish Airline tickets. Called my AX travel agent. They called Turkish Air. They stated since they we had missed our flight they had cancelled the rest of our round trip ticket. However they would be pleased to restore it for $5000 dollars. No pleas made a difference or alternative options. I expected to be taken at “the grand bazar” but not before I had left O’Hare. We cancelled our trip, got the $1000 original change fee back and contacted the tour guides and hotel. Most were understanding when we told them our Turkish Air experienc. Our AE Travel agent is working to get our original $6,000 tickets refunded. FYI, AK Air changed our return back to Alaska at no charge (We are MVP gold) . The O’Hare Hilton is a 5 star hotel. For us it was worth the money after a long long frustrating flight

  25. I have a separate itinerary for SAT-ORD then ORD-MUC. I originally planned on being in Chicago for 2 days leading up to my flight to Munich but last minute changes actually have me in San Antonio so I had to purchase a one way UA ticket to ORD. I am very stressed about the idea of making my Munich flight on Lufthansa as the connection is 2 hrs 30 minutes. I know I can through check my bags since it’s an all Star Alliance itinerary but getting to Chicago is a whole different matter. This is a 70k mile business class ticket on Lufthansa and it would be a shot to the stomach if couldn’t get to ORD. I am actively searching for award space with SAT-MUC so I can rebook and just take the losses on my one way flight. Well worth the peace of mind but as of now there is nothing for the date I’m looking for. Great article

  26. Hello,

    June 18 HKG-JFK-YYZ.

    Took me 15 hours HKG-JFK on CX
    Took me 30 hours JFK-YYZ on AA

    18th June JFK to YYZ cancelled last minute on AA

    I was rerouted to ORD and connect to YYZ.

    On the flight to ORD we were diverted to STL as ORD closed weather.

    Reached ORD and YYZ connection long gone.

    AA rebooked me 8.3am flight next morning ORD-JFK. When I enquiried about bags said check with bags enquiry desk.

    I asked for bags, said too late to pull bags now. They will be checked forward.

    I get hotel room $500 downtown only. Around 1am on my way (20 mins later) I get email to say my 8.30am ORD to YYZ is cancelled and airline has rebooked me via New York to YYZ via LGA.

    Also airline email confirmation full of mistakes. Places me with 10 minute layover and marks aircraft type as “A380” clearly airline has lost control of its booking system.

    At this stage I feel like a first class passenger “on the titanic”

    I give up. I buy new ticket 8am on AC ORD to YYZ for US$1200 one way. Cost nearly as much as my HKG to JFK R/T ticket in premium economy.

    I get 3 hours sleep after my long trip front Hong Kong in my $500 a night room and head back to airport.

    6am I am at AA baggage desk to get my bags. I am promised my bags will come out “within 2 hours”

    I change my AC flight to 10am and wait.

    My bags NEVER come.

    I switch my AC flight to 6pm.

    Every hour I check with the baggage enquiry desk and spend the entire day sitting in front of them. They all say it’s coming, it’s coming, it’s coming. It never ever came. I am then told my bags already have made it to YYZ.

    Finally I left and flew to YYZ. Upon arrival I check and my bags are not in YYZ.

    I file missing bags enquiry and it’s 5 days already and still no bags. I’ve come on an international business trip with no clothes and no samples. I lost my entire week by the time my office scrambled and couriered my replacements.

    Unfortunately, my story is worse than even OMAATS story. I probably fly 200k miles a year and have been doing so for 18 years. This is my worst experience I can recall.

    Luckily I have travel insurance.

  27. What a coincidence, I happened to fly into ORD for the first time in my life this week. Our flight got diverted to IND due to thunderstorms in the Chicago area and the plane needed fuel. Missed the last flight of the day to NYC.
    Had to spend the (short) night at the Hyatt Regency ORD.

    Will try to avoid ORD next time

  28. EWR as a hub for UA or JFK as a quasi-hub for DL (and less so every month for AA) are far, far worse connecting points than ORD. As noted the add’l runway a few years ago led to a good on-time arrival gain, and to this day I think it’s ~10 points higher than any NYC airport.

  29. Maybe I’ve just been lucky, but I’ve never had major issues flying through ORD. If anything, I like connecting there because I have somewhere around 425 alternatives from O’Hare or Midway to get back to Dallas if something goes wrong.

    As far as things to do proactively, I always keep a close eye on the weather about a week out. If it looks like there might be problems on the return, I’ll find a hotel near the airport with a 6 pm same-day cancellation policy and book a room a few days before. Never had to actually use it but at least I know I’ll have a place to sleep and have a meal.

  30. I rarely have difficulties flying through O’Hare. Also, there are thousands of hotels within 30 min from the airport – don’t really see a concern.

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