Disclaimer: Don't be that person who is obnoxious and demands an upgrade. You are not entitled to an upgrade — they're usually given based upon availability.
We've been traveling a lot the past month and tested a few methods to see how to get free hotel upgrades. Here are our learnings about what you can do to increase the chance of getting an upgrade, depending on availability. These tips do not guarantee an upgrade.
1. Have status at the hotel group
If you have status with the hotel group you're staying at, your chances of getting a free upgrade increases. Traditionally, people earn status from hotel stays. In order to earn Gold status at the Ritz-Carlton, you'll need 50 nights or 5 meetings. That's a lot of nights!
To get around this, certain credit cards like the Ritz-Carlton, Amex SPG, and the Amex Platinum card will give you certain status levels for free.
2. Don't be a jerk
There are a ton of people who approach the front desk staff acting like they're entitled to an upgrade. Being nice increases your chances of getting an upgrade.
Follow the Golden Rule: treat people how you would want to be treated.
3. Have a reason for the upgrade
This one is a bit grey area, but if you have a special occasion to celebrate like an anniversary or honeymoon, it may increase your chances of getting a free upgrade, depending on availability. We don't personally do this, but we have heard success stories from friends.
4. Check-in late
It's counter-intuitive, but for all of our stays where we received a free upgrade, we checked-in on a weekday and relatively late (after 8 pm).
The Ritz-Carlton, Laguna Nigel: Checked-in at 10pm, we were offered 3 different complimentary upgrade options.
The Ritz-Carlton, Los Angeles: Checked-in at 6pm, got a free upgrade to a corner room junior suite.
Hilton Double Tree, NYC: Checked-in at 7pm, booked through Hotels.com because there was a good deal, but we were denied a free upgrade because it wasn't booked directly through Hilton. We showed Gold status through the Hilton app on our phone and we were still denied an upgrade.
They assigned us a room on a lower floor, and when we requested a room on a higher floor, the staff granted us a free upgrade to the Hhonors floor.
5. Book directly with the hotel when possible
Some hotel groups won't honor status if you book a reservation through a third-party website. Whenever possible, book the reservation directly with the hotel and be sure to enter your status.