Have you ever walked into a hotel room and felt that sinking feeling? You know the one—when you open the door to find just a basic room with a view of the parking lot, while you imagine other guests are living it up in suites with stunning views and extra perks. The truth is, there’s a hotel secret that can change everything, and it’s ridiculously simple: just ask for an upgrade. It sounds too easy, but this one straightforward approach has transformed my travel experiences, and it can change yours too.
Why most people never get upgrades
Most travelers don’t realize that hotels often have unsold premium rooms sitting empty every night. Hotels hate vacant rooms because they represent lost revenue that can never be recovered. Once a night passes with an empty suite, that potential income is gone forever. This creates a perfect opportunity for savvy travelers. Hotel managers would rather put you in a better room for free than let it sit empty, especially if you’re likely to spend money on other hotel services or become a loyal customer.
Yet most people never think to ask for an upgrade, assuming it’s only for the wealthy or those with elite status. They don’t understand that front desk staff often have surprising freedom to upgrade guests on the spot. According to hotel industry professionals, about 78% of hotel guests never ask for anything beyond what they initially booked, leaving free perks and upgrades unclaimed. By not asking, you’re potentially missing out on hundreds of dollars in free value that could make your stay more comfortable and memorable.
The exact words to say at check-in
When you arrive at the check-in desk, timing and approach matter more than you might think. Wait until there isn’t a line of people behind you, make eye contact, and smile genuinely. Then, try this simple phrase: “I was wondering if you happen to have any complimentary upgrades available today?” That’s it. No demands, no entitled attitude. This polite, direct question works because it’s respectful of the staff member’s authority while clearly stating what you’re hoping for. If they respond positively, thank them warmly. If not, accept the answer graciously—remember, you’ve lost nothing by asking.
Hotel employees consistently report that how you ask matters more than what you ask for. Being friendly, making conversation, and treating staff with respect can dramatically increase your chances. One front desk agent told me, “If you’re nice to me, I’m much more likely to be nice to you. I remember the guests who treat me like a person.” This approach has gotten me everything from corner rooms with better views to multi-room suites with private terraces—all without paying a penny more than the standard room rate I originally booked.
The best time to check in for maximum success
The timing of your hotel arrival can significantly impact your chances of scoring that coveted upgrade. Late afternoon to early evening (between 4:30 and 6:00 PM) is often the sweet spot. By this time, most of the day’s check-ins have been processed, giving the front desk a clear picture of which rooms will remain vacant. They’re also more likely to know which guests with reservations won’t be showing up. This knowledge gives them more flexibility to offer upgrades without risking overbooking premium rooms.
Weekdays typically offer better upgrade opportunities than weekends, especially at business-focused hotels where premium rooms may sit empty. Similarly, shoulder seasons—the periods just before or after peak travel times—present excellent opportunities as hotels have more inventory available. I once checked into a downtown Chicago hotel on a Tuesday in April around 5:30 PM, and what started as a standard king room booking turned into a corner suite with floor-to-ceiling windows and a separate living area, simply because I asked at the right time.
The special occasion strategy that works every time
Hotels love to help guests celebrate special occasions, and mentioning one can significantly increase your chances of an upgrade. You don’t need to make something up—there’s almost always something worth celebrating in life. Maybe it’s a birthday within a few weeks, an anniversary, a promotion, a reunion with friends, or even the start of a much-needed vacation after a stressful period. Sharing these details creates an emotional connection and gives the staff a reason to make your stay special.
When mentioning your special occasion, be specific but brief: “We’re celebrating our fifth anniversary this month,” or “This is our first vacation since having our baby.” According to hotel managers, staff members genuinely enjoy enhancing special occasions when they can. A hotel general manager in Puerto Rico notes that if a suitable room is available for guests celebrating an anniversary, staff will “go above and beyond to make your stay special” with upgrades and other amenities. This approach has worked consistently for me, resulting in not just room upgrades but also complimentary champagne, late checkout, and other thoughtful touches.
Book directly with the hotel
Where and how you book your room significantly impacts your upgrade chances. Hotels pay substantial commissions to third-party booking sites—often 15-30% of the room rate. When you book directly through the hotel’s website or by phone, they save this commission, making them more inclined to reward you with upgrades or additional perks. Direct bookers are also viewed as more valuable potential repeat customers who might become loyal to the brand rather than the booking platform.
When booking directly, take advantage of the “special requests” or “comments” section to mention any preferences or celebrations. You can write something like, “Looking forward to our stay! We’re celebrating our anniversary and would appreciate any available upgrades if possible.” This plants the seed before you even arrive. Then follow up with a friendly email to the hotel a few days before check-in, reiterating your excitement about your stay. This two-step approach has dramatically increased my success rate with upgrades at both boutique hotels and major chains.
Join the hotel’s loyalty program
Even if you’ve never stayed at a particular hotel chain before, signing up for their loyalty program before your stay can instantly increase your upgrade chances. Most loyalty programs are completely free to join and immediately provide benefits. Front desk staff can see your member status in their system, and they’re typically instructed to prioritize members—even new ones—for available upgrades. This simple step takes just minutes but signals to the hotel that you’re interested in building a relationship with their brand.
The benefits extend beyond just room upgrades. Many hotel loyalty programs offer immediate perks like free WiFi, late checkout, or welcome amenities even to entry-level members. As you build status, these benefits improve dramatically. During a recent stay at a major chain hotel, I signed up for their loyalty program the day before checking in. At the front desk, the agent specifically mentioned seeing my new member status and offered me a room on a higher floor with a better view. This small change made a noticeable difference in my stay without costing anything extra.
Ask about hidden amenities
Beyond room upgrades, hotels often have an array of free amenities that they don’t advertise prominently. These can range from practical items like phone chargers, yoga mats, and humidifiers to more unexpected offerings like musical instruments, gaming consoles, or specialty pillows. At higher-end properties, you might be surprised to find they offer complimentary pressing services, shoe shines, or even local transportation. The key is knowing that these perks exist and simply asking for them.
The front desk or concierge should be your first stop for these requests, but house cleaning and room service can also help with certain items. Some hotels have created dedicated travel essentials programs where they stock hundreds of items guests might have forgotten. I’ve borrowed everything from a high-quality hair straightener to a humidifier during my stays. One hotel even lent me a Nintendo Switch when I mentioned my kids were bored on a rainy day—a perk I would never have known about if I hadn’t asked what family amenities they offered.
The $20 trick that can transform your stay
While asking politely works well, some travelers swear by the “$20 trick” (also called the “sandwich trick”) to increase their upgrade odds. This approach involves discretely sandwiching a $20 bill between your ID and credit card when handing them to the check-in agent, while simultaneously asking if any complimentary upgrades are available. The key is to be subtle and not make the staff member uncomfortable. If they can’t provide an upgrade, they’ll typically return the cash, so there’s minimal risk involved.
This method is particularly common in Las Vegas but works in many tourist destinations. The amount should vary based on the hotel category—$20 might be appropriate for a mid-range hotel, while $50-100 might be more suitable for luxury properties where potential upgrades are more valuable. While some consider this approach controversial, many hotel employees view it as a standard practice and appreciation for their service. I’ve used this approach selectively at resort properties with great success, often receiving upgrades worth hundreds of dollars more than my small tip.
The email template that gets results
For travelers who prefer planning ahead rather than asking at check-in, sending a pre-arrival email can be highly effective. The best time to send this email is 2-3 days before your stay—close enough that the hotel has a good idea of their availability, but not so last-minute that they’ve already assigned rooms. Address it to the general manager or front office manager when possible, as they have the most authority to approve upgrades. Keep your message friendly, brief, and specific about the occasion and what you’re hoping for.
A simple template might read: “Hello, I’m looking forward to staying with you this weekend to celebrate my partner’s birthday. We’ve heard wonderful things about your property and are excited to experience it. If possible, we’d love to be considered for any complimentary room upgrades that might be available during our stay. Thank you for considering our request, and we look forward to meeting your team soon.” This approach works because it’s polite, mentions a special occasion, and makes a clear but humble request. I’ve received everything from room upgrades to welcome amenities and personalized notes using this method.
The next time you check into a hotel, remember that the difference between an ordinary stay and an exceptional one might be as simple as asking the right question. You have nothing to lose by politely requesting an upgrade or special amenities, yet you could gain tremendous value that enhances your entire travel experience. Whether you’re traveling for a special occasion or just need a comfortable place to rest, these strategies can help you access the hidden perks that hotels offer but rarely advertise. So go ahead—ask for that upgrade and see how it transforms your next stay.
