Half-off Samsonite Weekenders, One of Our Favorite Totes, and More Prime Day Travel Deals
October Prime Day is here, and we’re updating this story hourly. To find the best deals in every category, follow all of our October Prime Day coverage.
I probably don’t need to tell you that flights are more expensive than ever, as are suitcases and other travel accessories. In fact, going on vacation has never felt like more of a luxury, but today and tomorrow’s Prime Big Deal Days (otherwise known as October Prime Day) are here to help. Over the past few hours I’ve spotted some unusually good deals (frankly far better than last year’s ones) on suitcases (including options from Away and Samsonite), flight-ready totes (that are big enough to fly personal-item-only with), backpacks, and in-flight accessories (like AirTags, sleep masks, and airplane pillows). Many of our Best in Class top travel picks are on sale, including our best overall carry-on suitcase, sleep mask, and travel pillow.
I’ve listed the best luggage and travel gear on sale for Prime Day below, and will continue to update this guide as items go in and out of stock. Indeed, the whole Strategist team is online all day today and tomorrow to highlight new Prime Day deals as they come up. Head to the main Prime Day hub and check them out, and don’t forget to sign up for the Strategist Deal Freaks Daily newsletter to receive each day’s best deals in your inbox, including some that we save just for newsletter subscribers.
Deals I personally think are the best
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Amazon's sub-$50 suitcase is surprisingly indestructible.
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Although Away's version comes with a lifetime guarantee.
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Why pay more for a weekend bag?
Totes, duffels, and backpacks
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According to our contributor Katie Stone, this is the “tote bag to end all tote bags.” It holds everything you need it to, slips over the handle of a suitcase, and is smart-looking enough to bring to work as well as the airport.
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Away the Everywhere Bag
If you’ve been looking for a companion for your Away suitcase, the DTC travel brand’s personal-item bag is the perfect size and 30 percent off.
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Samsonite’s weekender bag is nearly 50 percent off and just as capacious as the pricier picks above.
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Got a few fall weddings coming up? Halfday’s clever suit-and-gown-preserving garment duffel is under $100 right now.
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Lots of bags from Bellroy (a brand often recommended to me by business travelers) are 20 percent off, including these two personal-item-size options.
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And the tech-protecting (it’s got room for a 17-inch laptop and is highly water-resistant) backpack that made our Menswear Hall of Fame is also 20 percent off.
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The iconic Kanken makes for a surprisingly good personal item, as its rectangular shape slots nicely under plane seats.
Suitcases and luggage sets
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Believe it or not, this sub-$50 Amazon Basics carry-on is life coach Jay Shetty’s favorite suitcase. He’s not alone; many well-traveled people have recommended it to us over the years.
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The second-generation version (the third only just launched and sadly isn’t on sale yet) of our best overall suitcase is 30 percent off. A great deal, especially considering the lifetime guarantee that comes with it.
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This slightly smaller size is a better choice if you’re flying a lot of short-haul European routes; airlines over there offer less generous carry-on allowances.
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For longer trips or just more outfits (I’d never judge you) on your short ones, Away’s checked luggage is also 30 percent off.
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We love Away’s suitcases, but Samsonite’s are nothing to sniff at — and they’re much more affordably priced, especially on Prime Day.
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Suitcases from Travelpro, the utilitarian travel brand that’s popular among pilots and flight attendants (as well as Strategist staffers and readers), are also on sale. This sturdy two-wheeler is currently just $106 and comes with a lifetime warranty.
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Or here’s one with four spinner wheels, if you prefer to glide through security.
Travel accessories
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Drowsy Silk Sleep Eye Mask
Our best overall sleep mask’s fan base includes actress and comedian Kate Berlant, who once told us, “I worry that my dependence on this thing will alter the course of my life,” as well as Natasha Rothwell, who owns no fewer than ten.
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Trtl Travel Pillow
Our best overall travel pillow rarely dips below $50, so now’s your chance to finally fall asleep in economy class.
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Never pay for those tinny airline earbuds ever again — the AirFly connects to your Bluetooth headphones, allowing you to watch Nolan epics on the small screens they weren’t intended for.
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$24 is a smaller price to pay than usual for the peace of mind that Bluetooth luggage tracking provides.
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Bellroy Hanging Toiletry Kit 3L, Travel Toiletry Bag - SeaKelp
This nylon Dopp kit looks sharp but is less precious than a leather one.
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“I don’t know what I’d do without these under-eye patches to help hide the fact I woke up at 3 a.m.,” says Food Network star Maneet Chauhan, whose filming schedule has her flying between New York, Texas, California, and Tennessee.
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Merrell Women’s Nessa Moc
These aren’t strictly travel shoes, but Merrell’s slip-on Mocs are just perfect for airports. They’re a vacation staple for many Strategist staffers, as well as the likes of fashion designer Sandy Liang.
More Prime Day Deals
- A Buy-It-for-Life Vacuum Is On Sale for October Prime Day
- Levi’s, Tevas, and More: The Best Prime Day Deals Under $50
- Hydro Flasks, Headphones, LEGOs, and More: Prime Day Deals That Make Great Gifts
- Prime Day Is Back, and I Found All the Best Deals
The Strategist is designed to surface useful, expert recommendations for things to buy across the vast e-commerce landscape. Every product is independently selected by our team of editors, whom you can read about here. We update links when possible, but note that deals can expire and all prices are subject to change.