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When I booked my October honeymoon in Madagascar roughly six months in advance, I knew my journey to the East African island would involve an 11-hour layover at Chicago’s O’Hare International Airport (ORD). As a Hyatt loyalist who holds the World of Hyatt Credit Card, I booked a night in a Hyatt hotel near the airport with points. Then I sat back to get excited about my trip, knowing the planning was done.

Imagine my surprise when, the morning we were supposed to leave for our trip of a lifetime, I got an automated email asking me to check in online — at the Hyatt Place Chicago/Midway Airport, a 45-minute drive from ORD. How could I have made such an obvious mistake? And could I rebook us at the right hotel without forfeiting my points?

What happened?

To cut myself some slack, the booking process for our flights had been rather challenging. After booking our flights to Madagascar on points, we’d had a lot of trouble finding flights home due to a quirk in Ethiopian Airlines’ partner award flight policy. It had taken several days of online searching to get our returning flights squared away — and in that time, I had forgotten the details of our outbound flight. I knew we flew through Chicago, but I forgot which airport.

This is one of the few downsides of playing the points and miles game. When you use points and miles to book free travel, things can get a little more complicated, making it easier to overlook small mistakes like this.

Thankfully, my flight left late in the afternoon, giving me plenty of time to address the issue.

Hyatt’s cancellation policy

I immediately logged into my account to look at my reservation. I had redeemed 8,000 World of Hyatt points for a “standard” night at the Category 2 Hyatt Place Chicago/Midway Airport. There was an almost identical property near ORD: the Hyatt Place Chicago/O’Hare Airport. This hotel is also Category 2, but apparently it classified my date as “peak,” so it cost a slightly higher 9,500 points for one night.

I had no problem paying a few more points to get a hotel where we could easily crash after our flight landed around 11 p.m. However, according to the hotel’s cancellation policy, if I canceled within 24 hours of 11:59 p.m. local time, I would be charged one night’s fee. Oh, well — I figured I’d rather pay 8,000 points for my mistake than the $264 I would have paid with cash.

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But when I called a World of Hyatt representative, I learned the cancellation policy is a little different from what I expected. Apparently, when you cancel a points booking after the deadline, your points will be refunded — and your card on file will be charged the current room rate for one night’s stay. Yikes.

Help from Hyatt

But just in case there was a way to avoid paying this cancellation fee, I tried explaining the situation to the representative. I didn’t want to cancel my booking, exactly; I wanted to transfer it to a property closer to the right airport.

The representative started by checking with the second hotel to confirm they had availability. Then she called the first hotel to explain that I was rebooking at another Hyatt, and they agreed to waive the cancellation fee. They canceled my original reservation, and the 8,000 points immediately appeared back in my account. Thanks, Hyatt!

I didn’t have enough points in my World of Hyatt account for the representative to book the new 9,500-point hotel (I had spent them all on my upcoming European Christmas trip), but I told her I could transfer them from my Chase Ultimate Rewards account. Thankfully, because of Chase’s (typically) superfast transfers, the extra points I needed were in my World of Hyatt account a few minutes later, and I was able to book a night at the Hyatt Place Chicago/O’Hare Airport. The cash rate was $295 before taxes and fees, giving me an excellent value of 3.1 cents per point (compared to TPG’s December 2024 valuation of 1.7 cents for Hyatt points).

The entire process took less than an hour, and I had the rest of the morning to pack and prepare for my Madagascar trip before we headed to the airport. Overall, I’m glad Hyatt sent me the check-in email and I realized my mistake early. If I hadn’t noticed it until we arrived at the airport at 11 p.m., it could have been much harder — and more stressful — to fix.

What if I hadn’t been able to get my points back, or the Hyatt I wanted had been fully booked?

My husband and I wouldn’t have had to start our honeymoon by spending the night in ORD, Tom Hanks-style. There are plenty of hotels nearby. I could have transferred Chase points to Marriott Bonvoy to book an award night at the Marriott Chicago O’Hare, for example, or paid cash at the Hilton Chicago O’Hare Airport. Worst case, if there had been absolutely no rooms open around ORD, I could have simply paid for a 45-minute Uber ride to and from my original Midway hotel.

But thanks to Hyatt’s customer service and a few extra Chase points, I was able to make our night in Chicago as streamlined as possible without spending a dime.

Bottom line

Lesson learned: Don’t assume that a city has only one airport or only one international airport. Don’t book the first hotel with “airport” in the name, like I did. And when you finish booking a trip, double-check all your reservations to make sure the dates and locations line up.

Also, if this happens to you, don’t simply rebook online and pay the cancellation fee. It’s worth trying the phone helpline first — they may be more generous than you expect.

Lastly, it’s always a good idea to have some extra transferable points saved up for situations like this. And we recommend setting up any hotel and airline accounts you may use in the future and linking them to your transferable points account now, as this will speed up the process if you end up needing to transfer your points last minute.

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