Rebooking a Hotel Reservation to Save Money

Please note this site has financial relationships with American Express and this post may contain affiliate links. Read my Advertiser Disclosure policy here to learn more about my partners.

I have a work trip to Chicago coming up soon and so I needed to book a hotel room for the night.  I have loved all of my stays at the Park Hyatt Chicago, but I can’t justify the points or cost for that hotel on this short trip.  So, I turned my search to other Hyatts in the area since I want to use my Diamond perks, and need to earn another stay credit toward re-qualifying for elite status.  I found some fair rates at the The Hyatt Chicago Magnificent Mile and decided to go with that property due to cost, location, and the fact that they recently underwent a pretty massive $25 million dollar renovation.

Hyatt Mag Mile Mommy Points

Room at the Hyatt Mag Mile in Chicago

The rate for the night when I first booked was $159.20 + taxes and fees.  That seemed fair for a night in downtown Chicago, but of course I always want to do better and keep more money (or points) in my pocket.  As the trip got closer I would go back to periodically and check the rates again.  Earlier this week I saw the property available for the same night I needed for $139.30.  I quickly checked the cancellation rules on my reservation and confirmed I could still cancel without a penalty.  I made a new reservation at the lower rate and cancelled the old one.  I was pretty excited about saving $20 for just a few minutes of research.  Fast forward a couple of more days and the same room at the same hotel was now available for $104.30, so I repeated the same process and have now saved $55 from the original booking.

I will keep checking, but would be shocked if the room price dropped below $100 per night.  If I didn’t want to do the work monitoring the rate myself, I could book with and they will automatically check and refund the difference to your credit card if they see the price for your room has dropped.  I don’t personally use tingo mainly because I want to ensure that I get hotel points and status credit for my stays and that can’t be guaranteed via most third parties.  They also don’t offer discounts like AAA, AARP, etc, so you may be able to get a better price elsewhere. However. I do like the auto-rebooking component that tingo offers as some people don’t have the time or patience to keep rechecking rates.

I’m good with the old-fashioned way of regularly checking the rates myself, so as a trip approaches I make sure to spend a little time checking to see if the price has dropped.  In this case it had, and my 5 minutes I probably devoted to these checks in total resulted in $55 saved.

This is by no means a new or “secret” type of trick, but it is one that is tried and true and deserves a reminder every now and again.  Re-checking the price can also help on stays that were originally so expensive the best option was to use points, but the price may have dropped to a level where using cash and earning points is the better approach.  In fact, I have an upcoming stay at the soon-to-open Andaz Maui at Wailea where the price has been dropping to the point where it is now a toss-up whether to use points or cash since the return I am getting per point is now a bit below below 2 cents per point (my threshold for Hyatt points).

Do you re-check your reservations as the date appears?  If so, I’d love to hear any tips you have learned along the way!

The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. Yep, I do it all the time. I’ll even switch hotels if I see rates dropping elsewhere. I was in France for the past 12 days, and I must have cancelled and rebooked three or four times at least. It makes sense, and as you say, takes only a few minutes. It is also the reason I never book a hotel room that I can not cancel. At worst, the AAA rate can always be cancelled, which gives me flexibility.

  2. Constantly! And for car rentals as well. In fact, I am picking up a car today that I cancelled and rebooked for $80 less for the week.

  3. I always recheck! For car rentals too!

    We are going to Orlando for a weekend in October. I had a room booked at a Marriott for $99. I just happened to check on it earlier this week and they were having a 48 hour sale and offering rooms for $69! I rebooked and saved myself $90 for the 3 night stay! What luck that I happened to check on it that day!

  4. I’m actually staying at a Hilton now that I did just that. The price dropped $15 a night last week so I called Hilton and they rebooked at new rate.

    I also have some reservations in Europe later this year on points and points dropped 10000 points one night for each room so I cancelled and rebooked at lower rate.

  5. In many locations hotel rates are their lowest 3 to 10 days before date of arrival.

    I rarely book a hotel more than one week in advance, but if I think rates may go higher I book a hotel earlier with a no cancellation penalty rate and then check periodically and usually find a lower rate at that hotel or some other hotel nearby.

  6. Check all the time and have saved a nice chunk of money doing so. The only drawback is that if I rebook a reservation using one of my wife’s accounts, she get upset when I cause her to receive four different e-mails from the same hotel for the same room.

  7. I just stayed at this hotel. It was great, newly renovated and just became a Hyatt. Only one block from Michigan Avenue shopping!

  8. I do it all the time too – for hotels and cars. I always get a reservation for both as soon as I get my plane tickets, just in case there turns out to be something in the city like a big convention that would later fill all the rooms or drive rates up. But that first reservation is almost never what I end up using!

  9. @ric does this 3-10 days rule of thumb work with destinations like Disneyland? I re-check sometimes, but only seem to find prices going up. If it goes down at all, it is only due to a deal through a third party booking portal.

  10. Just a quick note; there has been a lot of criminal activity on Chicago’s Magnificent Mile lately. Seems like I read about Facebook gangs purse snatching and crowds of young kids running wild in that area and tearing up a McDonalds. I could be wrong but I think it would be worth checking out b4 going.
    Might explain why the rates are so low also.

  11. I always set up hotel and car rental reservations once I have a trip planned and have my flights booked. I am often particular about where I want to stay, and I feel that I MUST have reservations “I can live with” even if the rates are higher than I’d like. I would always rather have a reservation made & take advantage of price drops than wait and find the prices are even higher as it gets closer to the trip. I NEVER book nonrefundable rates and I ALWAYS check multiple times as my trip approaches for lower rates. You must be careful, however, when doing lots of rebooking that you keep careful track of all of your reservations and cancellations. It is easy to lose track of things. I print out a paper copy of each reservation & mark it on a calendar near my computer right when I make it. If I cancel a reservation, I put a big X through it on the calendar & staple the copy of the cancellation to the original reservation. If I modify a reservation, I staple the newest version on top of the original!

  12. I’m not sure about Hyatt, but with Club Carlson you can go in and change room type (even after no cancel date). After confirming go back and switch back and confirm. You will have the same room with the new rate without cancelling (or if you couldn’t still cancel).

    Of course if you have sufficient status you’re getting a room upgrade anyway, so you could possibly skip the changing back of the room type.

  13. I just booked via phone with Starwood, for the 7&8th of August, for the Westin Dawn Beach in St. Maarten. The website prepaid rate was $169, on the phone I was offered $129 for a breakfast package. So checking rather last minute by phone, can also yield significant savings at times.

  14. I saved 10,000 Starpoints but doing this, although it was AwardWallet that tipped me off. I’m not sure how it was triggered, but they pulled that the week we were staying had downgraded from a high points booking to a low points booking. The next week it was back up to the high rate. My guess it is it was either a technical glitch or some magic rubric on the back end that said the hotel was going to be at low capacity and they were trying to fill it with points stays.

  15. So true about doing this with Southwest, rental cars, and more. The diligent worm keeps the cash…or points.
    Ric, I believe that to be true, but with a family I would never not make a back-up reservation somewhere that would work. Of course make it a refundable reservation in most cases, but then keep looking as 3-10 days does seem to be a sweet spot in some situations.

  16. Yea you!! Yes, I check an re-check. Significant savings at Hyatt Orange County a couple years ago over Thanksgiving. Rates kept going down, so I’d cancel and re-book. I’m going to follow SgFm’s advice from now on and call last minute to see if I can secure a more favorable rate. Great job, everyone!

  17. that’s an awesome rate! We live in the suburbs of Chicago, and often go in to the city for a weekend or a night. I’m looking at that exact hotel in a few weeks and the lowest I’ve seen so far is $190. I haven’t booked it, because it’s supposed to be a night out with friend, but it’s not going to happen unless we get a good deal. Which $190 unfortunately doesn’t qualify as, though it is a very reasonable rate. So, crossing my fingers that the rate goes down in the next week or so.

  18. I was able to save $200 on a hotel reservation in New York using the hotel deal monitor. It found a better price for the same room. All I had to do is rebook and that’s it! Saving $200 with a few clicks…

Leave a Reply

Your email address will not be published. Required fields are marked *