How to effectively ask for compensation when your trip falls short of expectations

Imagine you’re ready to board your flight with your carry-on, but the gate agent announces the overhead bins are full and asks you to gate-check your bag. You reluctantly hand it over, only to arrive at your destination and discover your bag never made it to Paris with you. 

You spend over $200 on emergency toiletries, a change of clothes, and a warm jacket (that was packed in your suitcase) until your bag finally arrives three days later. When you ask the airline for reimbursement, they offer you a $50 voucher and tell you that’s “standard policy.”

You’re not alone, and you shouldn’t accept that offer. Whether it’s a gate-checked bag that goes missing, a hotel room with broken air conditioning, or a cruise excursion that never happened, travelers are often owed compensation—but many don’t know how to ask for it, or worse, don’t ask at all. With travel disruptions on the rise (thanks in part to the current government shutdown affecting TSA and air traffic control), knowing how to politely but firmly request what you’re owed has never been more critical. 

This guide will walk you through when you’re entitled to compensation, how to request it effectively, and what to do if the company says no.

Know When You’re Honestly Entitled to Compensation (and When You’re Not)

Not every travel hiccup warrants compensation—but many do, and knowing the difference can save you hundreds (or even thousands) of dollars.

Airlines

If your flight is significantly delayed, canceled, or you’re bumped from an overbooked flight, you may be entitled to compensation. 

In the US, airlines must compensate passengers for involuntary bumping (up to $1,550 depending on delay length). If you’re flying to, from, or within the EU, EU261 rules can entitle you to up to €600 for delays over three hours or cancellations. 

Lost or delayed baggage also qualifies. Airlines are liable for up to $3,800 for domestic flights, but there are many catches.

Reality check on baggage claims:Delayed baggage (the most common and easiest to claim):

• Airlines reimburse “reasonable expenses” for toiletries, clothing, and essentials while you wait
• Most airlines informally cap this at $50/day, though legally you’re entitled to more
• You must keep all receipts and file them within specific timeframes (often within 21 days)
• The success rate is relatively high if you follow procedures and have documentation

Lost baggage (21+ days missing):

• Airlines compensate based on depreciated value, not replacement cost
• You need receipts to prove the value of the contents – yes, even for your lost clothing
• The $4,700 is a maximum; most claims settle for far less
• The process can take up to 3 months

Damaged baggage:

• Must be reported within 6-24 hours (varies by airline and ticket issue date)
• Often disputed, especially if damage could be from overpacking (although having a picture of your bag before the trip can help with this)

How often can travelers actually claim?

According to the Bureau of Transportation Statistics, airlines mishandled about 0.75% of bags as of 2023.

• Delayed bags are by far the most common (and most successfully claimed)
• Lost bags (21+ days) are rare but do happen

Most travelers who follow proper procedures and keep receipts do get reimbursed for delayed bag expenses

Bottom line: The delayed baggage compensation is legitimate and worth pursuing—especially for immediate expenses (toiletries, clothing). The lost baggage maximum is real, but rarely paid in full.

Hotels

If your room isn’t as advertised (broken AC, construction noise, unsanitary conditions), you have grounds to request a refund or room change. The same applies if the hotel fails to honor your confirmed reservation. Document everything with photos and timestamps.

Tour Operators & Cruises

If excursions are canceled, itineraries are drastically changed without notice, or promised amenities aren’t delivered, you’re entitled to a partial refund or credit. Read your contract carefully—many operators include force majeure clauses, but those don’t cover poor service or misrepresentation.

When airlines, hotels, or tour operators invoke force majeure, they’re essentially saying: “We can’t fulfill our contract due to circumstances beyond our control, so we’re not liable for compensation.”

Key Distinction: There’s a difference between “inconvenience” and “breach of contract.” A crying baby on your flight? Inconvenience. An airline canceling your flight and offering no rebooking options? Breach of contract. Compensation is owed when a company fails to deliver what you paid for.

Pro tip: Always read the fine print in tour operator and cruise contracts. Many include broad force majeure clauses that can limit your recourse if trips are canceled. Travel insurance with “cancel for any reason” coverage can help protect against these situations.

Note: The US government shutdown affects travel services, so some compensation claims may take longer to process. Document everything, keep all receipts, and consider travel insurance that covers trip interruptions and delays for added peace of mind.

How to Properly Request Compensation

When your trip goes wrong, how you ask for compensation matters just as much as what you ask for. A polite, well-documented request usually gets results, while an angry rant usually doesn’t. Because why should that behavior be rewarded?

Document Everything Immediately

The moment you notice a problem, start creating a paper trail. Take photos with timestamps: the broken AC unit, the construction outside your hotel window, the unsanitary bathroom, and your delayed baggage claim ticket. Screenshot confirmation emails, booking details, and any communication with the company. Save every receipt for expenses you incur because of the issue. This documentation is your leverage.

Report the Problem Right Away—In Writing

Always report issues while you’re still traveling, not after you get home. 

• For airlines, file the paperwork at the airport before you leave. 
• For hotels, speak with the front desk manager and ask them to note the complaint in your reservation. 
• For tour operators, notify your guide or tour manager immediately. 

Follow up every verbal complaint with an email or written note—this creates a record that you reported the problem in real time.

Be Specific About What You Want

Don’t just complain—state clearly what resolution you’re seeking. “I’d like a refund for the two nights affected by construction noise” is far more effective than “This hotel was terrible.” Be reasonable in your request. If one meal was cold, don’t demand a full refund for a week-long cruise. Match your request to the severity of the problem.

Use the Right Tone: Firm but Polite

You’re more likely to get results if you’re respectful. Start with phrases like “I’m writing to request compensation for…” rather than “I demand…” Explain the impact the problem had on your trip without being dramatic.

“The broken air conditioning made it difficult to sleep, which affected our ability to enjoy the activities we’d planned,” is more persuasive than “This ruined our entire vacation!”

Know the Deadlines

Every company has different timeframes for filing complaints. 

• Airlines typically require baggage damage claims within 6-24 hours and delayed baggage claims within 21 days.
• Hotels may have 30-day windows. 
• Tour operators vary widely. 

Check the company’s policy and submit your claim well before the deadline. Late claims are almost always denied.

Follow the Chain of Command

Start with customer service, but if you’re not getting anywhere, escalate. Ask to speak with a supervisor or manager. 

• For airlines, you can contact the Department of Transportation’s Aviation Consumer Protection Division. 
• For hotels booked through third parties, contact the hotel and the booking platform.
• For cruises, escalate to the corporate office if the onboard staff can’t resolve the issue.

Consider Your Payment Method

If you paid with a credit card, you have additional protection. Many credit cards offer trip delay coverage, baggage delay reimbursement, and purchase protection. If the company refuses to compensate you fairly, you can dispute the charge with your credit card company, though this should be a last resort after you’ve exhausted other options.

Be Persistent but Patient

Companies often take weeks to process claims. If you haven’t heard back within the specified timeframe, send a polite follow-up email. Keep records of all your communications. Persistence pays off—many travelers give up too soon and leave money on the table.

Finally, Say Thank You 

When you receive a fair resolution, send a quick thank-you email mentioning the specific individuals who helped you. Customer service representatives rarely get recognition for doing their jobs well, and your note might help them professionally. Plus, you’ll have established a positive relationship if you travel with that company again and encounter issues.

When Your Request Is Denied, Don’t Give Up

Sometimes, despite your best efforts, the company says no. Don’t give up—you have options.

Ask Why and Get It in Writing

If your claim is denied, request a written explanation. Companies are often vague in their initial rejections. A specific reason gives you something to address. If they claim you missed a deadline, check your records—they might be wrong. If they cite a policy exclusion, read the fine print yourself to verify.

Escalate Within the Company

A frontline customer service agent doesn’t have the final say. Ask to escalate your case to a supervisor, manager, or corporate customer relations team. Be polite but persistent: “I understand your position, but I’d like this reviewed by someone with more authority to resolve the matter.” Higher-level staff often have more flexibility to approve compensation.

File a Formal Complaint with Regulatory Agencies

For airlines, file a complaint with the Department of Transportation’s Aviation Consumer Protection Division. While they can’t force the airline to pay you, airlines hate having complaints on their record and often settle to make them go away.

Check if hotels or tour operators are members of industry organizations like the American Hotel & Lodging Association or the United States Tour Operators Association. These groups sometimes have dispute resolution processes.

Dispute the Charge with Your Credit Card

If you paid by credit card and the company refuses to refund you for services not rendered, you can file a chargeback dispute. This works best when you have clear documentation that the company breached the contract—like an uninhabitable hotel room or a tour that was canceled without a refund.

Be aware: chargebacks should be a last resort. Use them only when you’ve genuinely been wronged and the company won’t make it right. Frivolous chargebacks can damage your relationship with the merchant and your credit card company.

Leverage Social Media (Carefully)

A polite, factual post on the company’s social media pages can sometimes get results when other methods fail. Companies monitor their public image closely. 

Keep it brief, professional, and stick to facts: “I’ve been trying to resolve a baggage claim with [Airline] for 45 days with no response. Case #12345. Can someone help?”

Avoid ranting, exaggerating, or making threats. You want to look like a reasonable customer seeking a resolution, not someone looking for attention.

Consider Small Claims Court

Small claims court might be worth it for larger amounts (typically over $500). You don’t need a lawyer, filing fees are low (usually under $100), and the process is designed for regular people. Airlines, hotels, and tour operators often settle rather than send a representative to court.

Check your state’s small claims limit—it ranges from $2,500 to $25,000 depending on where you live. You’ll need solid documentation, so this is where all those photos, receipts, and emails pay off.

Know When to Walk Away

Sometimes, the fight isn’t worth it. It might be time to move on if you’ve exhausted reasonable options and the amount in question is small. Leave an honest review to warn other travelers, make a note never to use that company again, and chalk it up to experience.

Learn from the Experience

Whatever the outcome, use this as a learning opportunity. 

• Did you skip travel insurance when you should have bought it? 
• Did you book through a third party that made resolving issues harder? 
• Did you fail to document the problem in real time? 

Apply those lessons to your next trip.

The Bottom Line

Requesting compensation isn’t about being difficult—it’s about holding companies accountable when they fail to deliver what you paid for. Most of the time, a polite, well-documented request gets results. When it doesn’t, you have tools to push back. The key is knowing your rights, following the proper procedures, and being persistent without being unreasonable.

Safe travels, and may your bags always arrive on time.