Where to use your points and miles this fall

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Fall is one of my favorite times to travel, and it can also be a smart time to use your points and miles. In some destinations, summer crowds have faded and temperatures are finally comfortable. In others, fall is the sweet spot for warm weather before peak-season prices kick in.

Whether you're craving a European getaway, a beach escape, or a city break, these fall hotspots are worth considering for your next rewards redemption.

Keep in mind these are just examples. Availability can change overnight, and the exact award prices for flights can vary widely depending on your home airport. Searching Google Flights with the Points Path browser extension can help you surface the best award deals, and don’t forget about positioning flights if you find a great deal from an airport other than your home hub.

If you're dreaming of a beach getaway, Punta Cana is a great option, particularly in November. Temperatures remain warm, and hotel prices tend to be lower than during the winter high season. The trade-off is that September and October land in the peak of Atlantic hurricane season, so storms and rain can also be more common.

For sample travel dates in November, I found award flights on Delta for just over 30,000 miles round-trip from Chicago.

On the hotel side, Hyatt has several options, including the all-inclusive, adults-only Bahia Principe Escape Aquamarine, bookable for 15,000 points per night. Remember that you can transfer Amex points to Delta and Chase points to Hyatt — though the Chase-to-Hyatt ratio drops from 1:1 to 4:3 on October 1st, 2026 for Sapphire Preferred and Ink Business Preferred cardholders who applied before June 15th, 2026. Anyone who applied on or after that date is already transferring at 4:3, and Sapphire Reserve cardholders keep 1:1.

Award flight: Chicago O'Hare (ORD) to Punta Cana (PUJ) round-trip November 13th to 19th with Delta SkyMiles (31,300 miles plus $149.27 per person)

Award hotel: Bahia Principe Escape Aquamarine with World of Hyatt on November 13th to 19th (15,000 points per night with double occupancy)

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Athens is an awesome fall destination; you can explore Greece without dealing with the summer heat and crowds. September can still be quite warm, while October brings more comfortable temperatures and fewer visitors.

At the time of writing, American Airlines was offering award flights between Boston (BOS) and Athens (ATH) from 60,000 miles round-trip for travel dates in early October. Note that this itinerary includes one stop — annoying, but it could be worth it for the mileage savings. My search also flagged that the class of service may not be available on every segment, so confirm before you transfer any points.

AAdvantage miles are harder to stockpile than most, because Citi is the only issuer that transfers into the program: 1:1 from annual-fee cards like the Citi Strata Premier and Citi Strata Elite, and 1:0.7 from Citi’s no-annual-fee cards.

I also found award availability at the Adia Aluma Athens, Curio Collection by Hilton, for 65,000 points per night in early October. You can transfer points into the Hilton program from Amex Membership Rewards at 1:2 — meaning that 65,000-point night runs you 32,500 Membership Rewards points — or from Bilt Rewards at 1:1. You may also already have a stash of Hilton points from a card like the Hilton Aspire.

Award flight: Boston (BOS) to Athens (ATH) round-trip October 6th to 13th with American AAdvantage (60,000 miles plus $158.23 per person)

Award hotel: Adia Aluma Athens, Curio Collection by Hilton with Hilton Honors on October 6th to 13th (65,000 points per night)

Fall gives you plenty of ways to experience Italy, whether you're interested in Rome's historic sights, the famous art of Florence, or Tuscany's food and wine. September and October can still be busy, but the season brings cooler temperatures than the peak of summer, plus harvest and wine events. Push into November, and the crowds thin out further.

It’s worth comparing cash prices with award rates for travel to Italy, since demand and hotel prices can vary significantly by city and date.

I found a round-trip between New York and Rome for 37,500 miles on Flying Blue. For those same dates, the Comfort Hotel Bolivar was available for 20,000 points per night. It’s a Choice Privileges property, and you can transfer Capital One Miles or Amex points, among other options.

Award flight: New York (JFK) to Rome (FCO) round-trip November 3rd to 10th with Air France/KLM Flying Blue (37,500 miles plus $391.93 per person)

Award hotel: Comfort Hotel Bolivar with Choice Privileges on November 3rd to 10th (20,000 points per night with double occupancy)

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Remember that fall in the U.S. means spring in Buenos Aires. September through November brings warmer temperatures, blooming trees, and a lively atmosphere as the city emerges from winter. Spring is also a good time to explore Buenos Aires on foot, whether you're visiting parks, neighborhoods, or outdoor cafes.

I found an American Airlines AAdvantage award flight for 56,000 miles round-trip (departing from New York), though the outbound routes through Miami and runs close to 25 hours with a long layover; the return is a nonstop redeye.

As for hotels, the high-end Palacio Duhau - Park Hyatt Buenos Aires is available for 30,000 points per night.

Award flight: New York (JFK) to Buenos Aires (EZE) round-trip November 11th to 18th with American AAdvantage (56,000 miles plus $106.83 per person)

Award hotel: Palacio Duhau - Park Hyatt Buenos Aires with World of Hyatt on November 11th to 18th (30,000 points per night)

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