Halloween Week Travel Deals from Play, Southwest, Expedia, Marriott, and More

It’s Halloween week, and while we’re still a month or so out from the palooza that is Black Friday and Cyber Monday, the cold-weather travel deals are starting to flow in.

Noteworthy Halloween sales to snag this week include cheap flights from Icelandic airline Play and a flash sale from Southwest. It’s a good time to book hotel stays, too: Expedia’s regular rotation of deals are rich with great properties this week; Aqua-Aston’s Oahu, Maui, Kauai, Big Island, and Orlando properties come with one night free; Marriott’s five-night-stay deal is reaching its October 31 deadline; and weekend getaways booked through apartment platform Sentral are deeply discounted.

Outside of the deals world, money savvy travelers may also be interested to learn how to retroactively redeem Amtrak points—truly, this is one of our most game-changing pieces of intel in recent weeks. If you’re interested in that, you’ll also likely be curious why Wednesday is the best day of the week to fly. Finally, we have your back with holiday shopping, and compiled this list of the 41 best travel gifts that money can buy for under $25.

Below, our list of the most valuable travel deals to book while you can. 

All listings featured in this story are independently selected by our editors. However, when you book something through our retail links, we may earn an affiliate commission. This article has been updated with new information since its original publish date.

Deals from Icelandic airline Play will make you want to book a last-minute trip to Europe.

Günter Wicker

Flight deals 

Icelandic airline Play offers scary-low airfare for Halloween

There’s something extra spooky about the grey, cold-weather climes of northern Europe in the fall and winter, and from October 26-31, as part of a booked roundtrip itinerary, flights to Iceland start at $99 and flights to London, Dublin, Copenhagen, Paris, Berlin, and Liverpool start at $129. Athens is the newest destination that Play is servicing, and when booking roundtrip flights, tickets are as low as $199.

A Southwest monster fare sale with $49 one-ways

Now through Friday, October 28 at 11:59 p.m., for nonstop flights taking place between November 29 and March 8, Southwest is celebrating Halloween with big discounts. One-way flights are as low as $49. (Of note, blackout days range from December 16, 2022, to January 9, 2023.)

From Westchester County Airport, one-way flights for as little as $29

New Yorkers, take notice! If you have any west coast travel in the books, consider jumping on these $99 flights to Los Angeles. You can save on all kinds of domestic destinations with this deal, including $29 flights to Nashville, Tennessee, Charleston, South Carolina, and Savannah, Georgia. The promotion from newly created domestic airline Breeze is valid for flights purchased before October 31, 2022, on travel taking place from November 1 through February 14, 2023.

23-year-olds are now eligible for United’s young adult discount

23-year-olds, everyone thinks you’re still babies! And the downside is that you often have to pay under-25 fees for car and vacation rentals (if the company or host will take you at all)—but there’s good news too: You can now fly for cheaper with United. The airline’s young adult deal has existed since 2019, but previously only included 18-22-year-olds. The five percent-off discount, which applies for certain flights, can be booked through the United app.

Rocky Mountaineer

Courtesy Rocky Mountaineer 

Train deals

Couples get $400 off Rocky Mountaineer’s train and plane trips to Las Vegas 

To book an epic American Southwest journey (whether it’s with your bestie or your boo) at a steep discount, visit Rocky Mountaineer’s site before 2022 ends and purchase one of their Rockies to the Red Rocks Las Vegas with Flightseeing packages. These trips are transportation experiences you’ll get nowhere else in the world—you’ll see the Southwest from the earth and from the sky. The two-day package begins with a journey aboard the Rocky Mountaineer from Denver, Colorado to Moab, Utah, and then a flightseeing transfer to Las Vegas, floating 2,000 feet above Capitol Reef National Park, Zion National Park, and Valley of Fire State Park. 

The Chatwal in New York City

Courtesy Dream Hotel Group

Hotel deals

Save 20 percent on winter getaways through the apartment-stay platform Sentral

Sentral, a new platform that offers design-forward furnished apartment accommodations for flexible lengths of time—short-term stays, long-term stays, and anything in between—has a Halloween deal worth scooping up. The 20 percent-off discount is valid to book through October 31. November and December Denver stays start at $141 per night; December Chicago stays start at $119 per night; December Austin stays start at $102 per night; and December Nashville stays start at $120 per night.

Scan Expedia for fast-moving hotel deals up to 50 percent off

Expedia always offers a running list of last-minute deals on its site—but be prepared to act fast, since they move quickly and only apply to travel within the next two weeks. Right now, top discounted properties include the Chatwal in New York, Zoetry Agua Punta Cana (50 percent-off stays), Pendry Chicago, The Palazzo at The Venetian Resort in Las Vegas, and dozens of others. You’ll find even more last-minute deals with hotel stays up to 50 percent off in New York City, Aruba, San Francisco, and more of our favorite places, towns, and cities. 

View from Aston Kaanapali

Courtesy Aqua-Aston

Add on a free night at Aqua-Aston’s Hawaii hotels and condos

Aqua-Aston Hospitality is offering one night free for stays at its Hawaii and Orlando properties booked before November 7, and taking place through December 20, 2022. Included hotels and condominiums are located on Oahu, Maui, Kauai, the Big Island, and in Orlando. Use code FALLNIGHTS to save. Note that minimum-night stays vary for each property and are listed on Aqua-Aston’s website below.

Save on stays of five or more nights at Marriott Hotels 

There’s nothing quite like savoring a long vacation. Select Marriott hotels are offering big savings when you stay a minimum of five nights at hotels, or seven nights at resorts, and book by October 31, 2022. This deal is valid on hotel stays now through November 6, 2022. Use code LTS to save.

Watch Hill Inn

Stay at top-notch Rhode Island hotels for less 

It’s the perfect time of year to visit coastal New England. The ocean breezes are brisk, the leaves are red and gold, and the crowds are few. The Watch Hill Inn in Rhode Island is offering a third night free, valid through October. The all-suite-style rooms have full kitchens, living rooms with fireplaces, and outdoor terraces, making them ideal for a family weekend trip. Another Rhode Island hotel, the Weekapaug Inn, is offering a $100 resort credit per day now through November. These stays, respectively, are three- and four-time Readers’ Choice Awards Winners.

Banyan Tree Mayakoba

Banyan Tree Mayakoba

World of Hyatt members can earn double points on select stays 

Good news for World of Hyatt members—with the Bonus Journeys offer, travelers can earn double points on stays of two or more nights at participating Hyatt hotels around the world. Register by November 15, and stay at participating Hyatt hotels any time until December 20, 2022. 

Atlas Ocean Voyages

Courtesy Atlas Ocean Voyages

Cruise deals

Your guest sails free to Antarctica on Atlas Ocean Voyages

Dreaming of a 2023 voyage to Antarctica? Now might be a good time to book, considering that for trips booked with Atlas Ocean Voyages before December 31—for expeditions taking place in November 2022 through March 2023—two guests sail for the price of one. Atlas Ocean Voyages’ small, sleek, yacht-style cruises hit far-out, wintry destinations that include the Antarctic Circle and Peninsula, the Falkland Islands, South Georgia and the South Sandwich Islands, and the South Shetland Islands, where visitors will find penguins, albatross, black sands, calderas, and hot springs. 

Save up to 50 percent off your child’s voyage with Hurtigruten 

Hurtigruten is offering a major deal for families: Travelers can save up to 50 percent off of a child’s voyage on their next family cruise with this Young Explorers deal. Take advantage of the deal on select expedition cruises and Classic Coastal Norway departures. The highest discount applies when the child occupies a cabin with at least two adults. (When the cabin has just one adult, the savings go down to 20 percent off.) This makes cruising with family members of all generations even better—and easier on your wallet.

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