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For a family of four flying round trip from Chicago, Aeroplan's published chart starts at 80,000 points in economy on United (10,000 per person each way for 501–1,500 miles), plus taxes and a partner booking fee. A five-night Hilton stay booked with points could cost around 200,000 points with an elite fifth night free (hypothetical). Park tickets, food and transport are cash. Expect roughly 280,000 points plus a few hundred dollars for flights and hotel, then the park budget on top.
What we'd do first: pick your dates around school holidays, search flights for all four travelers on those dates, and only then price the hotel.
The flights: what Aeroplan publishes
Aeroplan prices flights within North America by distance flown. For 501 to 1,500 miles, which covers Chicago–Orlando nonstop (about 1,000 miles), flights on Air Canada and "Select Partners", which include United, start at 10,000 points one way in economy, with a published median of 15,000 (Aeroplan Flight Reward Chart, PDF, checked 13 Nov 2026, 21:47 Lima). "Starting at" amounts "are not guaranteed".
For four people round trip that's 80,000 points at the starting price, or 120,000 at the median. Aeroplan's policy adds a CAD39 partner booking fee per ticket when a flight is operated by an airline other than Air Canada and its regional brands, so United flights carry it (Aeroplan Flight Reward Policy, checked 22:27 Lima). The TSA security fee is \$5.60 per one-way trip, capped at \$11.20 per round trip (TSA: Security Fees, checked 21:45 Lima).
An alternative for Southwest flyers. If someone in your family has, or is close to, a Southwest Companion Pass, a companion flies for taxes and fees on the same flights. Our guide to the Companion Pass under the 2027 rules explains the thresholds.
The hotel: what Hilton publishes
Orlando has many Hilton hotels, and Hilton's rules help families. Its help center says standard award nights cost "as few as 5,000 Points per night and no more than 95,000 Points per night", with select properties up to 120,000 (Hilton Help Center: Fifth Night Free, checked 13 Nov 2026, 22:01 Lima). Its terms say members on reward stays "booked using all Points… will not pay resort fees", that elite members (Silver and up) get the "5th Night Free on Standard Room Reward Stays", and that award rooms are priced at the "double occupancy room rate", with extra occupants possibly charged (Hilton Honors Terms & Conditions, effective July 15, 2026, checked 22:01 Lima).
That last point matters for four people: ask the hotel about extra-person charges before booking, and confirm the room has two beds.
The plan: five nights for four (hypothetical hotel and cash)
| Part | Points | Cash (hypothetical except where noted) |
|---|---|---|
| Flights, Chicago–Orlando, 4 round trips | 80,000 (published starting price) | ~\$90 taxes incl. TSA \$11.20 per person (published); 4 × CAD39 partner fee |
| Hotel, 5 nights at 50,000/night, fifth free | 200,000 (hypothetical rate) | Resort fees waived on all-points stays (published); extra-person charge if any |
| Park tickets, 4 people | – | Cash, set by the parks |
| Food, transport | – | Cash |
The full cost
At an assumed 1¢ per point yardstick (our assumption, not a market value), flights and hotel come to 280,000 points (\$2,800) plus about \$200 cash for the flights (about \$90 in taxes and about \$110 for the four CAD39 partner fees at a hypothetical exchange rate), with no resort fee on an all-points Hilton stay: about \$3,000. If flights price at the median, add 40,000 points. If the hotel prices higher or you don't have Hilton elite status, the hotel could cost 250,000 points or more for five nights. Park tickets are extra, often a large part of an Orlando budget. All hotel and cash figures are hypothetical.
A first step
- Fix your dates. School holidays are busiest; search a few date options.
- Search flights for four. Look on Aeroplan for United flights and note seats for all four on both directions.
- Transfer only when seats show. Amex, Chase, Capital One and Bilt transfer to Aeroplan; transfers are final. See our guide to transferable points.
- Book the hotel. Check the points price, the fifth-night benefit if you have status, and extra-person charges.
- Buy park tickets separately. Points programs don't cover them in this plan.
A worked example: the booking sequence (hypothetical)
Suppose you hold 300,000 Chase points and plan a week in late January, outside the busiest school holidays. You search Aeroplan for Chicago–Orlando on United and find economy at 10,000 points each way for four on a Saturday out and the following Thursday back. With seats confirmed for all four, you transfer 80,000 points to Aeroplan and book, paying taxes and four partner booking fees. Next you search Hilton for five nights; a hotel with two queen beds prices at 50,000 points a night. Chase points don't transfer to Hilton, so in this example a family member with Hilton points and Silver status books it, with the fifth night free: 200,000 Hilton points. You'd still have 220,000 Chase points for another trip. Every hotel figure here is hypothetical, and we don't claim seats or rooms exist on any date.
When to pay cash instead
- Cheap fares. If round-trip fares from your airport are low, points may be worth more on a longer trip.
- Low hotel rates. Off-season cash rates near the parks can be modest; compare with the points price at your yardstick.
- Theme-park hotel perks. If early park entry or transport matters to your family, a cash booking on-site may be worth more than a free points hotel off-site.
Mistakes to avoid
- Booking two seats and hoping for two more. Search for all four before transferring.
- Forgetting extra-person charges. Hilton's award rate is for double occupancy.
- Paying for a resort fee you don't owe. Hilton's terms say all-points stays don't pay it; check your folio.
- Leaving tickets until last. Park tickets and reservations can sell out on busy dates.
Trade-offs
- Points for flights vs hotel. Short domestic flights can be cheap in cash; check whether points give good value using our cents-per-point guide.
- On-site vs off-site hotels. Theme-park hotels can offer early entry or transport, which a points hotel may not. Weigh the perks against the points saving.
- One room or two. Four people in one room may need two beds and could trigger extra-person charges; two rooms double the points.
Fallback
If award seats for four aren't available, split the family across two flights only if you're comfortable with that, book two travelers on points and two in cash, or try another nearby airport. If Hilton prices are high, compare with the Hyatt award chart or use a free night certificate for one of the nights.
Orlando on points: FAQs
Can I use points for theme-park tickets?
Not in this plan. Some card travel portals sell tickets; check the price against buying direct.
Do kids pay the same points for flights?
On Aeroplan, children with their own seat need their own Flight Reward; infants on a lap under 2 travel on a separate ticket with any applicable fees, per Aeroplan's policy.
Will Hilton charge a resort fee?
Hilton's terms say not on stays booked using all points.
Is the fifth night free for everyone?
Hilton lists it for Silver, Gold, Diamond and Diamond Reserve members on all-points standard room stays.
Which card points reach Hilton?
In our research, Amex and Bilt transfer to Hilton; Chase doesn't. Check your issuer's partner list before planning.
Which airport should I fly into?
Orlando International is the main one; check the distance band and prices for nearby airports too.