Skip to content

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

July 16, 2022
10 min read
southwest plane in air clouds
This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. Terms apply to the offers listed on this page. For an explanation of our Advertising Policy, visit this page.

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.

For more TPG news delivered each morning to your inbox, sign up for our daily newsletter.

Summer travelers wait in line at a TSA checkpoint at Tampa International Airport (TPA). (Photo by Sean Cudahy/The Points Guy)

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.

Sign up for our daily newsletter
The Berkshires. (Photo by DenisTangneyJr/Getty Images)

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.

(Screenshot from amtrak.com)

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.

(Photo by Chris Dong/The Points Guy)

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 French Quarter in New Orleans. (Photo by Sean Cudahy/The Points Guy)

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.

(Screenshot from united.com)

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.

(Screenshot from united.com)

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.

(Screenshot from united.com)

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.

(Screenshot from marriott.com)

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.

(Screenshot from marriott.com)

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.

(Screenshot from spirit.com)

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.

(Photo by Chris Dong/The Points Guy)

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.

(Screenshot from hyatt.com)

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.

(Screenshot from hyatt.com)

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.

Pikes Place Market, Seattle. (Photo by Lonnie Kishiyama/Getty Images)

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.

(Screenshot from google.com/travel/flights)

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.

(Screenshot from ihg.com)

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.

(Photo by Diana Robinson Photography/Getty Images)

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.

Featured image by (Photo by Sean Cudahy/The Points Guy)
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

TPG featured card

Best starter travel card
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards

1 - 3X points
3XEarn 3 Points per $1 spent at Restaurants and Supermarkets
3XEarn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
1XEarn 1 Point per $1 spent on all other purchases

Intro offer

Earn 80,000 ThankYou® points60,000 points
For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening

Annual Fee

$95

Recommended Credit

670-850
Excellent, Good
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.

Why We Chose It

The Citi Premier’s 3 points per dollar spent across a wide range of popular categories is one of the more lucrative offerings in the world of points and miles. The Citi Premier comes with a $95 annual fee and is currently offering a solid sign up bonus of 80,000 points after you spend $4,000 on purchases within the first three months. It also has some valuable transfer partners to make the most of your rewards. Add in access to Citi Entertainment plus a $100 hotel credit for any single-stay hotel booking that exceeds $500 or more, excluding taxes and fees, booked through the Citi travel website, there are few reasons why the Citi Premier should not be in every traveler’s wallet.

Pros

  • Earns 3x points on restaurants, supermarkets, gas stations, air travel and hotels.
  • $100 annual hotel savings benefit (on single hotel stay bookings of $500 or more, excluding taxes and fees, booked through thankyou.com)
  • Points transfer to 16 airline programs, from JetBlue to Virgin Atlantic.
  • World Elite Mastercard benefits, extended warranty, damage and theft protection.

Cons

  • $95 annual fee
  • Lacks travel protections that other travel rewards cards come with
  • For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening
  • Earn 3 Points per $1 spent at Restaurants and Supermarkets
  • Earn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
  • Earn 1 Point per $1 spent on all other purchases
  • Annual Hotel Savings Benefit
  • 80,000 Points are redeemable for $800 in gift cards when redeemed at thankyou.com
  • No expiration and no limit to the amount of points you can earn with this card
  • No Foreign Transaction Fees on purchases
Best starter travel card
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards Rate

3XEarn 3 Points per $1 spent at Restaurants and Supermarkets
3XEarn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
1XEarn 1 Point per $1 spent on all other purchases
  • Intro Offer
    For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening

    Earn 80,000 ThankYou® points
    60,000 points
  • Annual Fee

    $95
  • Recommended 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.

    670-850
    Excellent, Good

Why We Chose It

The Citi Premier’s 3 points per dollar spent across a wide range of popular categories is one of the more lucrative offerings in the world of points and miles. The Citi Premier comes with a $95 annual fee and is currently offering a solid sign up bonus of 80,000 points after you spend $4,000 on purchases within the first three months. It also has some valuable transfer partners to make the most of your rewards. Add in access to Citi Entertainment plus a $100 hotel credit for any single-stay hotel booking that exceeds $500 or more, excluding taxes and fees, booked through the Citi travel website, there are few reasons why the Citi Premier should not be in every traveler’s wallet.

Pros

  • Earns 3x points on restaurants, supermarkets, gas stations, air travel and hotels.
  • $100 annual hotel savings benefit (on single hotel stay bookings of $500 or more, excluding taxes and fees, booked through thankyou.com)
  • Points transfer to 16 airline programs, from JetBlue to Virgin Atlantic.
  • World Elite Mastercard benefits, extended warranty, damage and theft protection.

Cons

  • $95 annual fee
  • Lacks travel protections that other travel rewards cards come with
  • For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening
  • Earn 3 Points per $1 spent at Restaurants and Supermarkets
  • Earn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
  • Earn 1 Point per $1 spent on all other purchases
  • Annual Hotel Savings Benefit
  • 80,000 Points are redeemable for $800 in gift cards when redeemed at thankyou.com
  • No expiration and no limit to the amount of points you can earn with this card
  • No Foreign Transaction Fees on purchases