7 Last-Minute Labor Day Weekend Getaway Ideas

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The unofficial end of summer is near.  Where did the time go?!  Hopefully, you’ve been able to enjoy quality time off and a vacation or two!  We’ve shared some recent trip reviews from the Million Mile Secrets team, including Meghan’s weekend at the Loews Regency San Francisco.

If you’re searching for last-minute “tripspiration” this Labor Day Weekend, we put together a list of fun cities and destinations that includes something for every type of traveler!

You Can Check Out a Major League Baseball Game While Traveling This Labor Day Weekend!

Before planning your last-minute getaway, be sure to check out these guides for tips to save money on travel:

Here are 7 last-minute Labor Day Weekend trip ideas to consider!

1.   Enjoy Amazing Food and Weather in Chicago

Summertime is without a doubt my favorite time to visit Chicago.  You can soak in the sun while cruising the Chicago River on a boat tour or even by kayak.  There are also awesome lakefront beaches, which I always find to be so neat given the city skyline is right behind you.

Chicago also has endless dining options for the foodies out there.  Alinea, which has been ranked World’s Best Restaurant, is supposed to offer a dining experience like none other.  Team member Joseph has this restaurant high on his dining bucket list.  He’ll be sure to share a review if he goes!

If you’re a brunch person and don’t mind splurging on a meal, check out Sunday Brunch at The Peninsula.  It’s buffet style and includes sushi and seafood stations.

If You Enjoy Fancy Meals, Be Sure to Enjoy Sunday Brunch at The Peninsula! It’s Pricey at $75 per Person, but It’s an All You Can Eat Buffet and Includes Sushi and Seafood Stations.

While in Chicago, don’t miss other sightseeing attractions like the Skydeck, located on the 103rd floor at Willis Tower.  Keep in mind, you can save on the price of admission and get the same great skyline views by visiting The Signature Lounge instead.  It’s located on the 96th floor of the John Hancock Building and the cocktails are delicious!

2.   A Scenic Weekend in Monterey

Earlier this year, my wife and I took a trip to Big Sur, Carmel-by-the-Sea, Monterey, and Pebble Beach.  The scenery at each stop was breathtaking!  If you’ve watched the HBO series Big Little Lies, you may have already been thinking about a trip to this region of Northern California, which is the setting for the show.  It’s an excellent destination whether you’re a solo travel, couple, or family!

The Views Near Monterey and Big Sur Were Absolutely Breathtaking!

If you’re flying to California, you can drive to the Monterey region in less than 2 hours from the airports in San Francisco or San Jose.

And you won’t have any trouble filling a weekend itinerary exploring the area.  You can hike in Big Sur, go on wine tastings in Monterey, or play a round of golf at Pebble Beach.  Be sure to pencil in time to catch a Pacific Coast sunset!

3.   Visit a National Park

After recently reading about Lee Abbamonte visiting ALL 60 US National Parks, I’m definitely inspired to start spending some more time outdoors.

The National Park Service website makes it easy to plan a trip and check the conditions at each park.  For example, due to the devastating California wildfires, many parts of Yosemite are currently closed.

Plan a Road Trip to a National Park This Labor Day Weekend to Enjoy Amazing Scenery

Be sure to check out Million Mile Secrets team member Meghan’s review from her 2,500+ mile road trip through YosemiteDeath Valley, Red Rock Canyon, Zion, and Bryce Canyon.

4.   Travel to the Caribbean

Folks living in many East Coast cities are just a short flight away from many fantastic Caribbean islands.  I have friends in New York City who recently booked last-minute trips to the Atlantis in the Bahamas.  You might also considers Turks & Caicos, Grand Cayman, or Jamaica!

Celebrate the Unofficial End of Summer by Sipping Cocktails Surrounded by Beautiful Turquoise Waters!

If you collect flexible credit card rewards like Chase Ultimate Rewards points, check out our post with how to book travel through the Chase portal.  Airlines usually blackout award flights during peak travel dates, like Labor Day Weekend.  But with Chase points, you can book airfare, hotels, and rental cars without having to worry about blackout dates!

5.   Experience Southern Charm in Charleston

Charleston is near the top of my travel bucket list.  Unfortunately, it’s not the easiest place to get to from the West Coast so I won’t be able to make it there this Labor Day.  But I’ve never heard a bad review from anyone who has traveled to this historic city.  You can enjoy live theater, walking tours, historic mansions, museums, top-rated restaurants, and great shopping.

Million Mile Secrets reader Melanie told us she used hotel points to stay free in Charleston and enjoyed “3 glorious nights in a city with hospitality, great views, and terrific food!”

Spend Your Labor Day Weekend in Historic Charleston, South Carolina!

Don’t forget about a trip to Swig & Swine, the best BBQ in South Carolina according to team member Joseph’s recent rankings!

6.   Journey to Our Nation’s Capital

Washington, DC, is much more than just dysfunctional politicians.  If you’re a baseball fan, you can watch the Washington Nationals take on the Milwaukee Brewers at Nationals Park on Sunday, September 2.

Or you can consider other family-friendly activities, like a Washington Monuments river cruise.  Or ride on the Capital Wheel to take in incredible views of the city.  There’s also the National Symphony Orchestra’s Labor Day Concert, which is a free event.

There are plenty of museums and fantastic restaurants to enjoy throughout the city as well.  I’m usually not a fan of hop-on hop-off bus tours, but I think Washington, DC, is a good city to consider booking this type of tour because there are so many sights to see.

Washington, DC Offers Plenty to Do Beyond Museums and Government Buildings! There Are Lots of Wonderful Restaurants, Nightlife, and Outdoor Activities!

7.   Enjoy the Pacific Northwest in Portland or Seattle

Since moving to the West Coast, I’ve really enjoyed the opportunity to explore Portland and Seattle, which are less than 2 hours flying time from Los Angeles.  If you’re also on the West Coast, you can consider a trip to these fun Pacific Northwest cities this Labor Day.

If you like wine, especially Pinot Noir, a visit to Willamette Valley in Portland is a must.  My wife and I booked an amazing wine tour through A Great Oregon Wine Tour and it was such a fun experience!  And there are plenty of fantastic day trips you can take from the city, including a trip to the Oregon Coast or Mt. Hood.

Enjoy Wine Tours and Tastings in the Willamette Valley Wine Region Just Outside of Portland!

And if you’re in Seattle, there are tons of fun (and free) spots to enjoy the Emerald city.  You can check out Pike Place Market, Pioneer Square, and all of the wonderful parks.  A trip to the Space Needle is also a tourist favorite, although the lines can be excessive.  I waited for ~2 hours and didn’t think it was worth it.

Kerry Park Offers an Incredible Setting to Watch the Sunset Over the Seattle Skyline!  On a Clear Night, You Can See Beautiful Mount Rainier in the Background!

We’d LOVE to hear about your Labor Day Weekend travel plans in the comments below!

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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