To review discussion from 2016-2019 click HERE.

Overview
Many Chase cards, including Sapphire Preferred and Reserve and MileagePlus Explorer, come with three different kinds of travel protection:

Trip Delay: This reimburses you for incidental expenses if your travel is delayed, for example by weather, mechanical, or missed connection. It only covers new expenses such as hotel, local transit, taxis, meals, toiletries, clothes, etc. that are caused by the delay. It does not (usually) cover the cost of onward travel or any pre-paid expenses. Max: $500

Trip Cancellation: This reimburses you for travel expenses (tickets, hotels) you have to cancel because of covered reason (illness, etc.). It only covers pre-paid expenses, not new expenses. If you re-use your old tickets, it covers the change fee (but not fare difference). Max: $10,000 for CSR/CSP, $1,500 for MPE

Trip Interruption: This is similar to Trip Cancellation, but reimburses you for travel expenses (tickets, hotels) you have to cancel because you cut your trip short for a covered reason (illness, etc.). It mostly covers pre-paid expenses, not new expenses. Exceptions: If you re-use your old tickets, it covers the change fee (but not fare difference); it covers charges to return rental cars early to a different location; and covers up to $250 to get to/from the airport or medical facility. Max: $10,000 for CSR/CSP, $1,500 for MPE

No coverage on the Chase cards will pay for new expensive tickets home.

How to file a claim:
- go to http://eclaimsline.com/ , or
- call 1-888-675-1461

Guide to Benefits:
Read it! CSR - CSP

Trip Delay FAQ and experiences

This reimburses you for incidental expenses if your travel is delayed, for example by weather, mechanical, or missed connection. It only covers new expenses such as hotel, local transit, taxis, meals, toiletries, clothes, etc. that are caused by the delay. It does not (usually) cover the cost of onward travel or any pre-paid expenses. Max: $500

How long does the delay have to be? 6 hours for CSR, 12 hours for CSP and MPE, check your guide to benefits for other cards. Also kicks in if the delay is "overnight".
Are delays because of weather and mechanical problems covered? Yes.
Who is covered? Only you, your spouse, your dependent children under 22. For large meals (multiple main courses), people have been asked what portion of the meal was consumed by covered travelers.
Does it cover Authorized Users? Apparently yes, as long as their name is "embossed on the card", as well as their spouse and dependent children.
I bought reward tickets but paid taxes/fees with my card, am I covered? Yes.
I bought reward tickets with Chase UR points, am I covered? Yes.
Do I have to buy the flight that is delayed with the Chase card? Yes.
Do I have to use my Chase card to purchase hotel/meals/etc. I am hoping to have covered? No, you can use any card, or cash. Just keep your receipts.
Does the travel have to be round trip? Yes, but your ticket does not have to be. You must depart from your place of residence and return to your place of residence within 1 year. The round-trip travel can involve different tickets on different carriers, open jaws, etc.
Does it cover alcohol? Recent reports indicate yes; some older reports of alcohol being denied.
Does it cover tips? Recent reports indicate yes, up to 20%; some older reports of tips being denied.
My airline is offering a voucher for a hotel, but I skipped the voucher line and booked my own hotel. Am I covered? Reports point to yes, as long as you did not actually take the airline up on their offer.
Rather than staying in a hotel, I'd rather rent a car / buy a walk-up fare on another airline. Will this be covered? Mixed reports. In general this coverage is meant for expenses incurred during a delay, not onward travel.
How do I show the reason for the delay? The coverage requires a statement from the carrier indicating the cause of the delay. If your document doesn't state the cause of the delay, it probably will not work. One possibility is to get a military excuse while at the airport; another is to screenshot the carrier's website or app if it shows the cause. You can also write after the fact to get a delay letter: United: [email protected] , Delta , American. Make sure to request that the delay letter state the cause of the delay. For other carriers contact their main customer service.
Am I covered if my flight is cancelled and I am rebooked on a later flight? Yes
Am I covered if my flight is slightly delayed and I miss my connection, causing a longer delay? Yes
Am I covered at my home airport? Maybe. This report of someone being covered after appeal for hotel in Newark when EWR flight was delayed, lives in NJ but not Newark. Guide says "You are not covered for any Covered Hazard delay that was made public or known to you prior to the departure for the Covered Trip [a period of round-trip travel (meaning departing from and eventually returning to your primary residence) that doesn’t exceed three hundred and sixty- five (365) days away from your residence to a destination other than your city of residence.]".
I was delayed on my outbound and claimed $500. Now am I delayed on my inbound. Am I covered? One report on this thread of two reimbursements for two different delay incidents on a single ticket. Chase says "per trip" on the phone, but Guide says "per ticket". So a round-trip ticket may not cover two delays, but two one-ways could. Need more data on this.

Experiences:

• 01/2014 - Delayed in MSP overnight due to mechanical issues. ~$300 for Hotel Ivy downtown, meals, and ground transportation covered with no issues. Benefits applied to AMEX FHR. Claim processed within 1 week. [Full Report]
• 02/2014 - Flight was cancelled due to weather; booked Amtrak with points, which was then delayed because of downed electrical wires; rented a car and drove home. Used print out from flightaware.com to show flight was cancelled, claimed non-points dollar amount for Amtrak ticket, got Chase (not insurance) to request receipts from vendors that weren't saved by OP. All was covered. Full report
• 04/2014 - Delayed in DTW overnight due to crew member time-out. ~$400 for DTW Westin and meals covered with no issues. Claim processed within 1 week. Full Report
• 07/2014- Delayed in MSP overnight due to weather at destination. Booked Marriott Mall of America for $120, and meals for 3 and a shirt were all covered. Recommend keeping new and old boarding passes.
• 12/2014 - Trip delay in WAS (flight was delayed because of MX causing misconnect and overnight. Reward flight with taxes+fees on Chase card. OP + wife were covered $632 for a for a room, dinner, and taxi roundtrip from the airport. Gratuity was not reimbursed and could not convince them to after a phone call. Hotel Was $380 after tax and this was not a problem.
• 07/2016 - Delayed in YYC overnight due to mechanical problems. Claim paid out ~$300. Full report.
• 7/2017 - Delayed in EWR due to thunderstorms. ~$390 for hotel, uber, meals. Claim processed within a week, no issues. Full report.
• 9/2017 - Delayed in EWR due to Harvey. ~$499 for hotel, ubereats. Claim processed in 7 business days
• 1/2017 - $625 covered on two tickets on JetBlue award flight with taxes+fees on Chase in FLL. Missed connection due to Mx. Incl. $65 at Walgreens, r/t uber to hotel, uber home, $265 hotel, $180 meal. Tax, tip, and alcohol covered.
• 06/2017 - $258 covered for overnight delay hotel/dinner. Did not cover $50 to pick a seat on next day's flight. Full report
• 08/2017 - covered during ATC equipment failure leading to cancelled flight
• 08/2017 - covered with flightaware showing delay, no direct statement from carrier. Booked dummy return flight on Southwest to 'comply' with r/t requirement.
• 12/2017 - covered for forced overnight due to ATL "Power Outage". Entire ticket, including taxes, was paid for using Ultimate Reward points through my Reserve account. There was no credit card charge showing on my account.
• 1/2018 - covered for $500 including hotel tips, a drink, and minibar snacks w/ no receipt (but showed credit card statement with purchases listed)
• 1/2018 - covered rental + gas to drive to int'l gateway when feeder flight was cancelled.
• 3/2018 - covered int'l phone calls, roaming cell phone data (submitted phone bill), storage locker, and hotel.
• 4/2018 - covered hotel, meals/snacks, cold medicine, Uber ground transport for overnight due to weather. Award ticket with taxes/fees on CSR.
• 5/2018 - covered $250 in hotel, uber, two meals after missing a connection in a "painless but slightly drawn out" process. Had to request a different delay letter because first one didn't state cause of delay. Total turn-around time 40 days including re-requesting delay letter.
• 11/2018 - covered $300+ in hotel, 2 Ubers, 3 meals; did not cover seat charge or Uber home; originally booked with UR points (no CC charge)
• 7/2019 - covered $400+ in hotel, rental car, 3 meals, clothing/toiletries for me, wife and son for 24 hour delay; award tickets with taxes/fees in CSR.
• 01/2021 - covered $225 in meals, hotel, Uber for myself for overnight due to weather; used voucher and paid small amount on the Sapphire Preferred.
• 01/2021 - covered ~$100 for meals and toiletries purchased during a 7+ hour daytime delay.

(A previous thread that dealt with travel delay compensation has been closed and all future issues with travel delays & cancellations will be handled here. The last 4 posts from that thread have been merged into this one. The closed thread can be found here.)

For one overview of when you're covered and how to file a claim, read this blog post. The Milewriter @ Saverocity compiled a lot of information from this thread, and thanks all the contributors.

Trip Cancellation / Trip Interruption

This reimburses you for travel expenses (tickets, hotels) you have to cancel or interrupt because of covered reason (illness, etc.). It only covers pre-paid expenses, not new expenses. Max: $10,000 for CSR/CSP, $1,500 for MPE

Trip Interruption only covers a few new expenses: If you re-use your old tickets, it covers the change fee (but not fare difference); it covers charges to return rental cars early to a different location; and covers up to $250 to get to/from the airport or medical facility and from the airport to your home.

What are covered reasons? Illness or injury or death (with documentation) of you or family, severe weather, change in military orders, terrorism, jury duty or subpoena, uninhabitable dwelling, quarantine, or if your travel supplier goes bankrupt. Pre-existing medical conditions are not covered.
Who is covered? CSP/CSR: Extended family: You, your Spouse or Domestic Partner and their children, including adopted children or step-children; legal guardians or wards; siblings or siblings-in-law; parents or parents-in-law; grandparents or grandchildren; aunts or uncles; nieces or nephews. MPE: You, spouse/domestic partner, dependent children.
Does it cover Authorized Users? Apparently yes, as long as their name is "embossed on the card", as well as their extended family / immediate family depending on the card.
I bought reward tickets but paid taxes/fees with my card, am I covered? Yes.
I bought reward tickets with Chase UR points, am I covered? Yes.
Do I have to buy the travel arrangements with my card to be covered? Apparently now this is "yes", you have to pay for "some portion" of each travel arrangement (hotel, flight, etc.) for that arrangement to be covered.
What kinds of pre-paid travel arrangements are covered? "airline tickets, train tickets, bus tickets, prepaid tours, hotels, and rental cars."
What kinds of pre-paid travel arrangements are not covered? "Event Tickets or prepaid fees to theme parks, museums, golf courses, or other points of interest"
I got ill during a trip and had to buy really expensive tickets to fly home. Will I get reimbursed? No. If you can't use your original tickets, this will reimburse you for those -- but new tickets are on you. If you change your original tickets, this will cover the change fee only. It does not pay for fare difference or new tickets. It will pay up to $250 to get you to/from the airport or train station, medical facility, and to your residence after you land at your home airport.
I got ill and need to cancel my trip / return early. What documentation do I need? Generally a letter from a physician or other medical person. There is a special claim form for the doctor to fill out but a sufficiently detailed letter from the doctor can work too.
Does the travel have to be round trip? Yes, but your ticket does not have to be. You must depart from your place of residence and return to your place of residence within 60 days. The round-trip travel can involve different tickets on different carriers, open jaws, etc.
My flight was cancelled. Am I covered? Probably not. Only if it was cancelled due to weather or transit strikes, and only if you didn't get reimbursed by the carrier. However, see Trip Delay above.
I cancelled my trip and the airline has given me one year to use my tickets, but I can't use them. How do I get reimbursed? Several reports indicate that you must wait for the unused tickets to expire, then file another claim. You can get the change fee covered right away. Other reports say if you demonstrate you won't use the tickets, they'll cover full amount right now. YMMV.
Am I covered if I'm taking a road trip, with no flights or common carrier? Yes. However the online claim form requires flight info; just fill it out with dummy flights and explain your other documents that there was no common carrier.
I am pregnant and no longer want to travel. Am I covered? Maybe. Generally, unexpected complications with non-IVF pre-26th week single pregnancies are covered. Non-IVF multiple pregnancies (twins, triplets) are not covered unless you get pregnant after purchasing your tickets. IVF pregnancies are not covered. The guide says you are not covered for "Travel arrangements that are scheduled to take place after the twenty-sixth (26th) week of pregnancy; or when any multiple pregnancy, with or without complications, occurs prior to the initial deposit date or booking date of the Trip; or any pregnancy associated with an assisted reproductive program, such as in vitro fertilization"
There is civil unrest at my destination, am I covered? Maybe. Generally you are covered if there is a Terrorist Incident or State Dept travel warning during your trip (Trip Interruption) or in the 30 days leading up to your trip (for Trip Cancellation) for within 25 miles of any place along your trip itinerary or your home, as long as the incident or warning didn't happen before you booked your tickets. Not covered is "War, undeclared war, civil war, insurrection, rebellion, revolution, warlike acts by a military force or personnel". Also not covered is "Trips booked to any area known to be associated with Terrorist Activity" (meaning multiple Terrorist Incidents or travel warnings in 12 months) and "disinclination to travel due to civil unrest [or] an epidemic or pandemic".

Experiences: