Weekend getaway: Labor Day destinations to round out your summer travels

Both summer holiday weekends so far — Memorial Day and Fourth of July — brought with them some of the biggest crowds that airports have seen in years. That trend will likely continue as the unofficial end of summer draws near. Meanwhile, travelers can only hope that the operational challenges seen during those holiday weekends will not be repeated on Labor Day weekend, which is now less than two months away.

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Here at TPG, we dreamed up some ideas for how you might spend your final summer weekend. And for those concerned about long lines and lost bags at airports, one of our options is to take the train. Remember, prices are likely to go up the closer we get to the holiday, so now is a good time to book if you want to get away Labor Day weekend, which runs from Friday, Sept. 2 through Monday, Sept. 5.

New York travelers: Berkshires weekend trip

This is a getaway we noted when Amtrak announced it was launching a direct summer weekend train service to the region and could be something to consider for a nice getaway from the city.

You can catch the Berkshire Flyer out of Manhattan on Friday afternoon, with service to Pittsfield, Mass. You’ll probably need to rent a car in order to explore the region, but the train is certainly a cost-effective option for making your way to the rolling hills of western New England at just $45 each way.

You’ll be in the Berkshires in time for a late dinner on Friday and can catch the train back to New York late Sunday afternoon.

If you've got a haul of points you're ready to use and are looking for a wellness-oriented weekend, check out Hyatt’s Miraval Berkshires.

With nightly rates often over $1,000 (and priced at $1,149 per night for Labor Day weekend), it’s not cheap, though a lot of what you’ll need for the weekend is included in the rate. You can stay at the property on Labor Day weekend for 50,000 World of Hyatt points per night, which are worth about $850, according to TPG’s points and miles valuations.

For more affordable options, Marriott and Hilton each operate properties nearby, though not their top-level brands — think Courtyard, Fairfield, and Hampton Inn. Prices at those hotels generally fell in the $300 to $400 per night range for the holiday weekend. You might also see what home-rental sites like Airbnb have for a stay in a more remote location in the region.

Related: 7 must-visit mountain towns in Massachusetts

Chicago travelers: New Orleans

Check the prices to New Orleans Louis Armstrong International Airport (MSY) from where you live whether that's Chicago or another city. We’ve seen some excellent fares to the Big Easy lately. Your biggest hurdle for this trip might be the heat and humidity — I found the humidity rather stifling when I visited the city on New Year's Day, for that matter. But unlike my visit during the holidays or one you might make during, say, Mardi Gras, you should have a lot less difficulty finding a seat at a prominent French Quarter bar to listen to jazz or getting a restaurant reservation.

The airfare I found for the holiday weekend isn't comparable to the sub-$150, round-trip prices we've seen recently for non-holiday weekends. However, you can get a round trip from Chicago's O’Hare International Airport (ORD) to New Orleans for $248 on United nonstop in each direction, a price far below average summer domestic round trip fares which regularly soar over $300.

One of the tips we talked about when it comes to both holiday weekend getaways and those trips centered around a major event like the Final Four in New Orleans earlier this year is that you can really save when you shift your trip days just a little bit. That goes for both cash and miles fares.

Check out how many United MileagePlus miles you’ll save if you return from your trip on Wednesday.

For the Saturday departure and Wednesday return, your total comes to 21,900 miles – not an incredible redemption, but pretty comparable to the cash fare.

If you’re looking to book a weekend stay using points, try the Le Meridien New Orleans. It has a rooftop pool with poolside cabanas and is within walking distance of the French Quarter, the World War II Museum, the Mississippi riverfront and area casinos.

While you’ll pay $368 per night for the four-night stay, consider booking using points. The award stay comes to an average 34,750 points per night, which is worth about $278 according to TPG’s valuations. That's a nice improvement over the cash fare.

Related: 10 TPG-approved hotels in New Orleans

Miami travelers: Puerto Rico

Here’s an option for South Florida travelers who might want to book flights with cash.

You can get a round trip to San Juan, Puerto Rico, aboard low-cost carrier Spirit Airlines for a $185 base fare. You’ll have to watch out for those added fees, but if you can go without seat selection for the relatively short flight, your biggest fee would be baggage.

On this itinerary, it looks like it’s cheaper to actually check a bag for $77 round trip instead of bringing a full-sized carry-on, making your round trip total $262.

Once in Puerto Rico, one lodging option for enjoying its beaches is the Hyatt Regency Grand Reserve. This sprawling property boasts beautiful pools and easy ocean access.

TPG reviewed the resort in 2021 and found it's an ideal property for a weekend stay. You can get a room for $280 per night or if you’ve got World of Hyatt member with points accrued (or transferrable points) you can book for 15,000 points per night.

It’s worth noting, that the 15,000 points per night rate is only 3,000 points above the off-peak rate (a points difference worth about $51 per TPG’s valuations) so you’re really not shelling out too many additional points for the benefit of booking on a U.S. holiday weekend.

Related: A beginner’s guide to visiting Puerto Rico

Los Angeles travelers: Seattle

Temperatures in Southern California won't cool off too much by winter, and they sure won't be cooler by Labor Day weekend. That could make it a great time to visit the Pacific Northwest. In Seattle, the average September high temperatures hover around 70 degrees.

I wasn't a fan of either coffee or seafood when I last visited Seattle as a teenager, but that's changed — which is why the Pike Place Market and coffee scene are just two of the reasons Seattle is on my short list of U.S. cities I hope to soon visit if a great redemption opportunity comes on my radar.

For Labor Day weekend, you could get a round-trip flight from Los Angeles International Airport (LAX) to Seattle/Tacoma International Airport (SEA) for $230 aboard Seattle's hometown carrier, Alaska Airlines. Again, that's a price well below the average summer domestic fare.

Related: A Hyatt hop through Seattle

Try staying at the Kimpton Hotel Monaco in downtown Seattle. You can get the stay for 58,000 IHG One Rewards points per night, worth about $290 according to TPG’s valuations — in contrast to the $340 nightly cash rate.

The hotel is within walking distance of the Public Market and original Starbucks location. If you get tired and want to eat on-site one night, you could enjoy locally-sourced cocktails and what I'd describe as elevated bar food at the Outlier Restaurant. There's also plenty of outdoor seating to enjoy the (hopefully mild and clear) Pacific Northwest weather.

Bottom line

While it remains to be seen if airlines will make it through Labor Day weekend without major hitches, there’s excitement in having more flexibility to plan travel in 2022 after a couple of years when it was more risky and unpredictable. While some of the inconveniences and uncertainties surrounding this year's summer travel months aren't likely to disappear completely on the season's final holiday weekend, they will hopefully get better as the airlines and airports address operational issues and ramp up staffing.

If you're apprehensive about traveling on the last big weekend of summer though, we still have some good news. Prices usually go down around Labor Day and stay lower through the autumn months. And crowds will be thinner as children head back to school. So if you don't book a getaway in early September, watch for an opportunity later that month or in October and November before the Thanksgiving holiday season is here.