If you missed out on a trip this summer, your wallet might thank you. Fall is famously a more affordable time to travel, and this off-season means plenty of deals. To get inspired for cheap autumn breaks in September, October, and November, here are eight affordable destinations for everything from seasonal weekend getaways to cheap fall family vacations.
Editor’s Note: Airfare and nightly rate estimates are accurate as of time of publication. Some of the links featured in this story are affiliate links, and SmarterTravel may collect a commission (at no cost to you) if you shop through them.
Visiting Chicago in the fall will have you seeing the Windy City in a whole new light. Admire the famous Cloud Gate amid the gorgeous foliage in Millennium Park or take an architecture cruise to see famous buildings surrounded with autumn colors.
Getting There: According to Kayak, the cheapest month to fly to Chicago is October. Google Flights shows roundtrip airfare in the $100 to $200 range from several major airports, with many offering fares cheaper than $100.
Where to Stay: Opened in September of 2021, The Selina Chicago is new on the scene. However, the building itself had a nearly 200 year history as the Tremont Hotel before The Selina opened its doors, lending the property a distinctive historic charm. Rooms are available from $132/night.
Things to Do: Plan your trip for the last weekend in September to attend Chicago’s Oktoberfest and get a little taste of adventuring abroad in your domestic travels. Closer to Halloween, check out Arts in the Dark, an evening of visual and performing arts in Washington Park with a spooky seasonal twist.
New England is famous for its spectacular autumnal foliage, so make Boston with its leafy city parks your home base for a fall getaway. Make time for a day trip to Salem or take leaf-peeping road trips up the coast of New England.
Getting There: Find roundtrip airfare from major hubs to Boston in the $100-$300 range, with many flights coming in under $250.
Where to Stay: Located in Brighton, Hotel Boston is for travelers who want quick access to the city via the Green Line but a quiet retreat when the day is done. Opt for a suite and save money on meals by using the in-room kitchenette. Rooms start at $175/night in September.
Things to Do: Iconic activities in Boston include lots of walking— meandering along the Freedom Trail Foundation’s 2.5-mile trail past 16 historical sites or a stroll along the 40-plus-mile Harborwalk. Reward yourself for those calories burned with a free tour at the Sam Adams Brewery and Tap Room or a trip to one of the North End’s many Italian restaurants.
New Orleans, Louisiana
New Orleans is bustling with activity this upcoming fall season, from the Burlesque Festival to the citywide NOLAxNOLA concert series. Explore the city at the tail end of its off season with nice (less humid) fall weather, including temperate days and cooler evenings.
Getting There: You can find roundtrip airfare to New Orleans from several major hubs for under $200 this coming fall, with Google Flights showing options under $100 in September and October.
Where to Stay: The Aloft New Orleans Downtown places you in the heart of the city, within walking distance of iconic areas like the French Quarter and Bourbon Street. It’s pet-friendly, features an on-site convenience store for all the toiletries you forgot to pack, and Marriott Bonvoy members can use their points for further discounts on their stay.
Things to Do: Listening to jazz and live music is a must while in the Big Easy, as is feasting at Cajun and Creole restaurants like Commander’s Palace. To experience a bit of nature beyond New Orleans’ beautiful architecture, tour a bayou via boat and try to spot gators.
San José, Costa Rica
The rainy season in Costa Rica lasts from May to December with peak months in September and October. Traveling during this time can be a gamble, but the rewards are worth the risk. The extra precipitation allows for lush jungle scenery you’ll miss in the dry season, and these months are a prime time to see wildlife.
Getting There: Most fares for the season are in the low to mid-$300 range, but if you book strategically you can find fares as low as $250.
Where to Stay: Put a pop of color in your vacation at Hotel Fleur De Lys, a colorful and warmly welcoming hotel in the cultural district of San José. The property brings the natural beauty of Costa Rica into its design, with each room named after a local flower and several atriums for guests to explore. Standard rooms and Junior Suites are available for less than $90/night.
Things to Do: There are plenty of activities in Costa Rica that are actually improved by the rainy season. Book a white water rafting tour or explore local waterfalls while the water is flowing. If you’re an animal lover, plan your trip further west of San José to visit the Ostional National Wildlife Refuge and see the arribadas, or large-scale arrivals, of nesting sea turtles in September and October.
A fall trip to Ontario could be a great and affordable combination of city (Toronto) and country (hiking and biking in Ontario’s forests). Autumn colors are at a peak in the region in September and October, painting a beautiful backdrop for your seasonal adventures.
Getting There: Roundtrip flights to Ontario for the fall season sit mostly in the $200 to mid-$300 range.
Where to Stay: The all-suite Azure Hotel & Suites Trademark Collection by Wyndham offers rooms from just $98 in September. Amenities include early and mobile check-in, free breakfast, and a luggage hold for guests who want to explore the area before check-in without the burden of bags.
Things to Do: For fall leaf peeping, stay in Toronto and take a ferry to Toronto Island Park or go for a road trip to parks like Algonquin Park (or splurge on a train tour of Agawa Canyon). Quirkier fall activities in Ontario include cranberry harvest festivities at Muskoka Lakes Winery.
San Juan, Puerto Rico
Fall is considered the low or shoulder season in sunny Puerto Rico, which averages 80-degrees days all year round. But be prepared that the good deals also coincide with the possibilities of hurricanes.
Getting There: Roundtrip airfare to San Juan from major airports can be found between $100 and $200, with nonstop service on Spirit from Miami (MIA) dipping as low as $110.
Where to Stay: New hotel Palacio Provincial brings modern decor to a beautifully restored building, with airy rooms starting at $135 a night in September. For a family-friendly San Juan lodging option, the Verdanza Hotel in Isla Verde starts at $161 for the same time period, and includes a water spray park for kids in the pool area.
Things to Do: Taking photos in scenic Old San Juan and near El Morro fortress is a must, as is visiting Puerto Rico’s beautiful beaches including Playa Condado or Isla Verde. It’s also worth making a trip to explore the lush El Yunque National Forest, the only rainforest in the U.S. National Forest System.
If you’re a risk-taker (that is, you don’t mind the possibility of rain or even hurricanes), Cancún in the rainy season of August to October could lead to some good deals on this classic, white sand Mexican beach destination on the Yucatán Peninsula.
Getting There: You can find roundtrip service to Cancún for under $300 in September and October, with prices edging toward the mid-$300 range in November, according to Google Flights.
Where to Stay: Where you stay in Cancún depends on how you want to spend your days, from all-inclusive resorts to simple haciendas. For families, kids might love the newly-revealed Nickelodeon Hotels & Resorts Riviera Maya with a themed water park. For more of a spring break vibe and a bit of a splurge, check out Krystal Cancun, with October rates starting at $217.
Things to Do: Swimming, sunbathing, snorkeling, and scuba diving all top the list of activities in Cancún. Beyond the sea, book a package to visit historic sites like the Chichén Itzá Ruins or take a street food tour to try tacos and mezcal.
After the crush of tourists in Greece in the summer, September through October are known as some of the best times to find a deal while exploring the delicious Mediterranean meals and impressive ruins in Athens. Plus, the weather is just as delightful, with temperatures in the seventies.
Getting There: Fall is the best time to visit Athens, with particularly favorable ticket prices in October. Crossing the Atlantic makes this trip a bit pricier than other options on this list, but you can still find fares to Athens from major US airports in the mid-$500 range.
Where to Stay: Stay near the Acropolis and other sightseeing destinations at the small boutique destination Sweet Home Hotel, a bright pink hotel where rooms start at $129 for October. For more modern decor, there’s Coco-Mat Hotel Athens with rooms in the $150 range or for a bit more of a splurge, the centrally-located Royal Olympic Hotel.
Things to Do: Known as the birthplace of democracy, there’s more history in Athens to explore than anyone could fit into one visit—from the Parthenon to Hadrian’s Arch. Don’t skip more recent Greek culture either, as seen in the recently renovated National Museum of Contemporary Art Athens.
Carol McPherson contributed to this story.
You Might Also Like:• The 8 Best Ticket Websites for Booking Day Tours and Travel Activities
• The Ultimate Camping Packing List: 29 Essentials
• 10 Underseat Carry-On Bags You Can Take on Any Flight
• The 9 Best Sites to Book a Cruise
• Flash Sale Alert! Save up to $100 on Summer Flights to Europe & Other Hot Destinations
We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.