The 6 Best Shoulder Season Trips to Book With Cash, Points and Miles
Summer Fridays may be ending soon, and the kids heading back to school can certainly put a damper on family travel — but fall is actually the best time of year to take advantage of off-season savings. Places traditionally thought of as summer or winter destinations are often just as good (or better!) in autumn, when the weather cools off and less demand drives down airfare and hotel rates. Of course, there are some places where your dollars (and points) go even farther in the shoulder season.
To help you find the best fall getaway, we examined flight data from Skyscanner; reviewed Booking.com's extensive hotel rate data; rounded-up destinations with ample points properties; and studied airline award charts. The results of our almost scientific study? The six best places to plan a vacation — and to score a solid deal — this autumn.
Chicago
If you're traveling with cash
If you’ve been contemplating a trip to the Windy City, fall is the time to go. In an analysis of average monthly prices from 2017, the hotel booking site Booking.com found that the most inexpensive month to visit Chicago is November, with an average savings of 30% if you go in either October or November. Likewise, Skyscanner found that from Sept. 22 to December 21, flights to Chicago are on average $20.95 less expensive than other periods. Fall is also the perfect time to visit Chicago’s cultural attractions, such as the Art Institute of Chicago and the new Chicago Architecture Center, which is moving from its long-time home across from Millennium Park to a new Mies van der Rohe building overlooking the river on Aug. 31.
The Chicago Athletic Association Hotel is celebrating its 125th anniversary with $125 in gift cards to all seven food and beverage outlets — and a tote full of CAA swag — when you stay through Oct. 31. Just use the code 125WAYSTOPLAY when you book.
If you're traveling on points and miles
United saver award space is available from New York City-area airports or LAX to ORD for 25,000 miles (plus $5.60) round-trip — as is American Airlines' economy MileSAAver award space. Delta flights from Newark Liberty International Airport (EWR) are available for only 12,000 miles (plus $11.20) round-trip to Chicago Midway International (MDW) right now, or from LAX to either ORD or MDW for 19,000 miles (plus $11.20). Both Delta options have stops.
To sweeten the shoulder season deal, the Category 5 JW Marriott Chicago (35,000 points per night)is also offering a daily food and beverage credit of up to $250 when you book a suite through Dec. 31.
San José del Cabo
If you're traveling with cash
Looking at the period between Sept. 22 and Dec. 21, flight booking site Skyscanner found that flights to San José del Cabo are, on average, nearly $20 cheaper than at other times of the year.
Once you get there, soak up the stunning scenery, savor the margaritas and chill out at the area’s plush resorts. In addition to tried-and-true favorites like the One&Only Palmilla, there’s the sleek new Viceroy Los Cabos (formerly known as Mar Adentro).
If you're traveling on points and miles
We found great deals from New York City and Los Angeles to Los Cabos International Airport (SJD). Delta has flights from New York City's John F. Kennedy International Airport (JFK) to SJD for 30,000 miles (plus $103.68) and from Los Angeles International Airport (LAX) to SJD for 12,000 miles (plus $98.08). A cool 35,000 miles (plus $33.51) will get you from multiple New York City-area airports, LAX or Chicago's O'Hare International Airport (ORD) to SJD with United saver awards. But the best deal comes from American Airlines, which has economy MileSAAver award space from both LAX as well as New York City's LaGuardia Airport (LGA) to SJD for just 25,000 miles (plus $5.06 in fees).
In September, Marriott is debuting Solaz, the first Luxury Collection Resort in Baja California Sur. The Category 7 property is available from 60,000 Marriott points per night.
Copenhagen
If you're traveling with cash
Why not visit the Danish capital as it transitions from all-out summer fun to winter-time hygge? Skyscanner found an average savings of $189.78 — hardly pocket change — on flights to Copenhagen between Sept. 22 and Dec. 21, while Booking.com reported an average of 30% savings on hotels during the months of October and November.
Even with Noma sold out for the season, there are plenty of other incredible places to eat. Check out Amass, where Noma alum Matt Orlando serves a tasting menu of inventive dishes made with vegetables and herbs from the on-site garden in a dining room covered in street art murals. Or sample elevated takes on traditional Danish smørrebrød at Selma.
Get inexpensive cash flights on WOW Air from the West Coast when the prices plummet from more than $500 to less than $180 one-way in September and October (think: SFO and LAX).
If you're traveling on points and miles
Availability is limited, but you can also use point and miles to enjoy an inexpensive trip to Copenhagen this fall. Delta has scattered availability from EWR to Copenhagen Airport (CPH) for 38,000 miles (plus $80.91); from LAX to CPH for 30,000 miles (plus $75.31) round-trip; and MDW or ORD from 28,000 miles (plus $80.91).
Barcelona
If you're traveling with cash
Barcelona gets downright steamy in the summer, so fall is a great time to take advantage of cooler temps and thinner crowds. Skyscanner found an average savings of $144.06 if you travel in the fall, and Booking.com calculated a 43% savings when traveling to Barcelona in October and November, with November offering the best deals overall. Foodies and night owls will be in heaven in this buzzing Spanish city known for its fantastic restaurants and nightlife. Do as the locals do and start the evening with an aperitif of vermouth and olives at the low-key Antic Teatre, a cultural center and bar with courtyard seating. For an amazing meal, book a table at Disfrutar, a Michelin-starred restaurant by three El Bulli alums with a laid-back vibe and next-level tasting menus. It recently jumped to No. 18 on San Pellegrino’s World’s 50 Best Restaurants list.
If you're traveling on points and miles
We found that 60,000 miles (plus $5.60) will get you from ORD, EWR, LGA, JFK and LAX to Barcelona-El Prat Airport (BCN) on either United or American Airlines. But if you don't mind a stop (or two) Delta fliers can travel from LAX to BCN for 40,000 miles (plus $57.31) and from either EWR or LGA to BCN for 39,000 miles (plus $52.81) — though you'll have to fly in the wrong direction, to Atlanta (ATL), first.
Book a room at the brand new Barcelona EDITION for 60,000 Marriott Rewards points per night.
San Diego
If you're traveling with cash
Let’s face it — San Diego is great year-round, but the upside of visiting in the fall is that you won’t have to contend with high prices and oversized crowds. Of course, you can still enjoy outdoor activities like surfing, snorkeling, kayaking, hiking, hang gliding and exploring Balboa Park. The city also has a great craft beer scene. Booking.com reported an average of 32% savings in October and November, with November being the cheapest month for hotels. Skyscanner found an average savings of $15.58 on flights from Sept. 22 to Dec. 21.
If you're traveling on points and miles
New Yorkers can fly to San Diego International Airport (SAN) this fall on either United or American starting at 25,000 miles (plus $5.60). Delta loyalists can get deals from EWR for 22,000 miles (plus $11.20) and from MDW for 20,000 miles. Spend the night at the Hotel del Coronado, a Curio Collection property where the Hilton Honors points per night needed for a room drops from approximately 95,000 to approximately 70,000 in late October and early November. If you'd rather cash in World of Hyatt points, the Park Hyatt Aviara Resort, Golf Club & Spa and the Andaz San Diego both start at 20,000 points per night.
Boston
If you're traveling with cash
A trip to Beantown offers plenty of autumnal fun, whether you stay in town or use it as a jumping off point to explore Salem or Cape Cod and the islands. Skyscanner.com calculated an average savings of $34.62 on flights to Boston from September 22 – December 21 and Booking.com found an average of 31% savings on hotel rooms in November.
With fall comes the Boston Symphony Orchestra’s return from its summer home in Tanglewood, and baseball season will be going strong through the end of September (go Sox!). If you decide to combine the city and the islands, the Nantucket Island Resorts are offering savings of up to 20% on Sunday, Monday and Tuesday nights before shutting down at the end of October. You can celebrate the Cranberry Festival on Nantucket on Oct. 6, run the Nantucket Half Marathon on Oct. 7 and even go lobstering aboard the Wauwinet Lady.
If you're traveling on points and miles
Check out two recently refreshed properties — The Ritz-Carlton Boston and the Kimpton Nine Zero — if you want to make use of points during your Boston getaway. Stays at the Kimpton Nine Zero are available from 60,000 IHG points per night this fall, while rooms at the Ritz start at 60,000 Marriott Rewards points.
TPG featured card
Rewards
| 4X | Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 4X | Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 3X | Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com. |
| 2X | Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com. |
| 1X | Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases. |
Intro offer
Annual Fee
Recommended Credit
Why We Chose It
There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits. (Partner offer)Pros
- 4 points per dollar spent on dining at restaurants worldwide and U.S. supermarkets (on the first $50,000 in purchases per calendar year; then 1 point per dollar spent thereafter and $25,000 in purchases per calendar year; then 1 point per dollar spent thereafter, respectively)
- 3 points per dollar spent on flights booked directly with the airline or with amextravel.com
- Packed with credits foodies will enjoy
- Solid welcome bonus
Cons
- Not as useful for those living outside the U.S.
- Some may have trouble using Uber and other dining credits
- You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
- Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
- Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
- Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
- $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
- $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
- $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
- $120 Dining Credit: Satisfy your cravings, sweet or savory, with the $120 Dining Credit. Earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. Enrollment required.
- Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
- No Foreign Transaction Fees.
- Annual Fee is $325.
- Terms Apply.
Rewards Rate
| 4X | Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 4X | Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 3X | Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com. |
| 2X | Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com. |
| 1X | Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases. |
Intro Offer
You may be eligible for as high as 100,000 Membership Rewards® Points after spending $6,000 in eligible purchases on your new Card in your first 6 months of Membership. Welcome offers vary and you may not be eligible for an offer.As High As 100,000 points. Find Out Your Offer.Annual Fee
$325Recommended Credit
Credit ranges are a variation of FICO® Score 8, one of many types of credit scores lenders may use when considering your credit card application.Excellent to Good
Why We Chose It
There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits. (Partner offer)Pros
- 4 points per dollar spent on dining at restaurants worldwide and U.S. supermarkets (on the first $50,000 in purchases per calendar year; then 1 point per dollar spent thereafter and $25,000 in purchases per calendar year; then 1 point per dollar spent thereafter, respectively)
- 3 points per dollar spent on flights booked directly with the airline or with amextravel.com
- Packed with credits foodies will enjoy
- Solid welcome bonus
Cons
- Not as useful for those living outside the U.S.
- Some may have trouble using Uber and other dining credits
- You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
- Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
- Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
- Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
- $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
- $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
- $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
- $120 Dining Credit: Satisfy your cravings, sweet or savory, with the $120 Dining Credit. Earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. Enrollment required.
- Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
- No Foreign Transaction Fees.
- Annual Fee is $325.
- Terms Apply.