5 Great Deals on Southwest This Summer

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Lyn writes about Southwest on her GotoTravelGal.com blog and has written a free guide on how to quickly and easily earn the Southwest Companion Pass.  I’ve asked her to share some of the best deals on Southwest flights to help you get Big Travel with Small Money this summer.

Lyn:   I love Southwest for many reasons, including the fantastic low prices they regularly offer to many of my favorite destinations like Denver, Florida, California, and New York City.

Southwest Airlines Summer Sale 2017

Southwest Has Great Deals – Both in Dollars and Points – to Terrific Destinations Throughout the US

I’ve compiled some of the best Southwest deals to help you stretch your points (and cash) in your summer travels.

Southwest Summer Sale 2017

Link:   Southwest Fare Sale Page

The summer months are typically NOT the best time of year for low airfares, but there are still cheap fares on Southwest to lots of fun destinations.  And even a few new ones for the airline.

Southwest is a good choice for peak summer travel, because as long as there’s a seat for sale, you can book it with points.  And everyone gets 2 free checked bags!

Southwest Airlines Summer Sale 2017

Whether You’re Looking for a Tropical Escape or a Vacation Closer to Home, Southwest Has Good Deals on Summer Travel

You can book these deals using Southwest points or by transferring Chase Ultimate Rewards points from the Chase Sapphire Reserve, Chase Sapphire Preferred, Chase Ink Business Preferred, Chase Ink Plus (no longer available), or Chase Ink Bold (no longer available) to your Southwest account.

If you have the Chase Sapphire Reserve, you might get a better deal redeeming Chase Ultimate Rewards points for Southwest flights through the Chase Ultimate Rewards Travel Portal.  That’s because you’ll get 1.5 cents per point when you book your flight through the portal.

But you can’t book online.  To book Southwest flights through the Chase Ultimate Rewards Travel Portal, call 866-951-6592.

1.   Grand Cayman Island

Beginning June 4, 2017, Southwest will fly to Grand Cayman Island from Fort Lauderdale, and you can get there for cheap!

Flights from Fort Lauderdale to Grand Cayman cost ~5,000 Southwest points, or ~$100, each way through most of the summer.  The price drops even lower after mid-August to ~2,100 Southwest points, or ~$60, per direction!  What a steal!

Southwest Airlines Summer Sale 2017

Play With Stingrays on Grand Cayman Island With One-Way Flights From Just ~$60 on Southwest!

There’s plenty to keep you busy in the Cayman Islands.  Grand Cayman, where Southwest flies, is the largest of the 3 Cayman Islands and offers many fun activities.

Swim with sting rays at Sting Ray City, wander through George Town and marvel at the Caribbean architecture, and, of course, sip a rum cocktail on the beach beside crystal blue waters.

2.   Washington, DC

Get an education in our government with a trip to our nation’s capital, Washington, DC, on the cheap.  Southwest flies to both Dulles and Ronald Reagan airports with prices ranging between 2,000 and 6,000 Southwest points each way from cities like Providence, Atlanta, and St. Louis, making it an outstanding destination to really stretch your points.

Southwest Airlines Summer Sale 2017

Visit the National Museum of African American History and Culture in Washington, DC, This Summer

The Smithsonian’s new National Museum of African American History and Culture Museum is worth a visit!   It houses nearly 37,000 artifacts, like an airplane flown by the Tuskegee Airmen, Nat Turner’s Bible, and shards of stained glass from a bombed church in Birmingham.  

Don’t miss the Sweet Home Cafe, where you can sample cuisine from 4 geographic areas, including the Creole Coast and Agricultural South.  Admission is free, but the museum requires timed passes for entry, which are available on site the day of your visit.

3.   Denver

If you prefer mountains, consider a trip to Denver!   Southwest has many daily flights which regularly cost ~6,000 to ~10,000 Southwest points, or ~$100 and ~$160, each way.  There are even cheaper flights originating in Tulsa, Oklahoma City, and Phoenix.

In Denver, check out The Crawford, a modern hotel inside the city’s beautiful Union Station, with massive floor-to-ceiling windows looking out onto downtown.  Grab a burger and shake at nearby Hopdoddy Burger Bar.

Southwest Airlines Summer Sale 2017

Hike the Breathtaking Maroon Bells in Aspen, the Most Photographed Place in Colorado, After Flying Into Denver

We love to head into the Rocky Mountains each summer for hiking and outdoor adventures in mountain towns like Beaver Creek, Aspen, Telluride (one of my favorite places on the planet), and Ouray, (pronounced “you-ray” like “hooray”) which is known as the Switzerland of America.

Colorado Springs is also a fantastic option, just a little more than an hour south of Denver with tons of activities.  Take the highest Cog Railway in the world up to Pikes Peak, wander through the red stone monoliths at Garden of the Gods, and meander through the 500-million-year-old Cave of the Winds at 6,000 feet elevation.  Check out the full report of our 2-week trip to Colorado last summer.

4.   New York City

As much as I love the isolation and peace of the mountains, the city also calls me and the Big Apple is one of my favorites.  Southwest flies to LaGuardia and Newark airports and offers excellent deals all year long.

We took our kids to New York City last year for the first time and used our AMEX Starwood card to book 4 second row tickets to see “School of Rock” on Broadway for the price of one!

Southwest Airlines Summer Sale 2017

Use Your AMEX Starwood Card to Book Tickets to a Broadway Show Like the Family-Friendly “School of Rock”

Stay within walking distance to Times Square, but out of the center of the craziness, at EVEN Hotels Times Square South (one of my all-time favorite hotels).  It’s an IHG hotel close to Madison Square Garden, and entirely wellness-themed, down to the in-room workout center and stand-up desk.

We also enjoyed the classy and comfy Hotel Elysee boutique hotel, part of the Library Hotel Collection, in the Midtown North area, not far from Central Park.

Southwest Airlines Summer Sale 2017

Work Out in Your Hotel Room at the EVEN Hotel Times Square South

If you can only do ONE thing in New York City, I recommend walking the High Line in Chelsea, which is completely FREE.  This former railway line-turned-elevated-park starts just below EVEN Hotel Times Square, and offers fantastic architecture, people watching, and views of the Empire State Building.   Stop in the Chelsea Market for local eateries and boutique shopping.

5.   Fort Myers

Fort Myers is one of our favorite destinations in the US when we are ready to get warm after a Midwestern winter!  The airport is small and easy to get around, and serves as the gateway to gorgeous Florida destinations like Naples, Marco Island, and even the Florida Keys.

Southwest regularly has deals to Fort Myers from cities like Indianapolis, Baltimore / Washington, Chicago, Pittsburgh, and Columbus, Ohio.  Prices range from ~$100 to ~$130, or ~6,000 to ~7,500 Southwest points, per way.

Southwest Airlines Summer Sale 2017

Enjoy Ocean Views and Jet-Skiing Through the Ten Thousand Islands at the JW Marriott Marco Island With Marriott Points

You can book the JW Marriott Marco Island, ~30 minutes south of the airport, with Marriott points.  Jet-ski right from the beach through the Ten Thousand Islands National Wildlife Refuge to see plentiful dolphins, birds, mangroves, and even manatees up close.

Bottom Line

Southwest has plenty of awesome deals to destinations around the US and the Caribbean this summer.

Be sure to book your flights during Southwest summer sales to save the most money and points, and have fun lounging at the beach, hiking in the mountains, wandering through museums, and exploring the busy city!

Note:   Some accommodations and activities were provided to us at no cost in exchange for a fair and honest review.

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565 responses to “5 Great Deals on Southwest This Summer

  1. Going home to see my boyfriends grandma “Meemaw”

  2. Maria Boswell

    Visiting our son in Los Angeles!!! Thank you so much for the heads up to get the Companion Pass by using my Marriott Reward Points!!! What a great deal 🙂

  3. I use the points to meet family in places like Las Vegas during peak season.

  4. I love using Southwest for their new International destinations.

  5. Southwest Airlines is actually our favorite airline when it comes to domestic travel. We always find they have the best deals. Also, the website as well as the phone app are so easy to navigate. In addition, I’m in the process of earning my Southwest companion pass. I’m halfway there. Woohoo . I’m planning to use my Southwest points to travel to New York and Florida this year. For my spouse and I, our favorite tropical spot is Hawaii. So hopefully Southwest would fly to Hawaii soon.

  6. I use Southwest points to go to Ft. Myers FL and hit up the beach in Naples.

  7. Michael Burke

    I love using Southwest for their new International destinations like Cancun and Cabo.

  8. I really like the fact that Southwest lets you sit where you want with no assigned seats.

  9. Benjamin LeRoy

    Quick weekend trips to Chicago!

  10. For going places in the US: Michigan, Houston, and NY, Orlando in 2018 with 2 companion passes for our family of 5.

  11. My favorite use of southwest points is to take my companion to a vacation of her choice.

  12. Getting kids back and forth to college. Our only college requirement has been that they are on a Southwest route. Just celebrated a graduation in Spokane, Thanks Southwest for letting us use points to get everyone there.

  13. Brian Wimberly

    I love to use Southwest points when I go on camping trips. That way I can get 2 free checked bags when I really need two big checked bags full of camping gear!

  14. Travel to Costa Rica

  15. My favorite way to use points are on flights that are super cheap…higher redemption value!

  16. I love using Southwest points for connecting in the continental U.S. when i fly from Hawaii.

  17. I love flying Southwest direct to Cabo or Cancun for a beach vacation!

  18. FLY TO LA

  19. Shonuffharlem

    Vegas so I have flexibility if I want to stay later

  20. Short business hops are so easy using SW points!

  21. Visiting my son in Fla.

  22. I want to take my husband to Cabo for a fishing vacation after fire season with Southwest points!

  23. I like to fly Southwest to BWI to visit family

  24. Our family uses Southwest points to stay connected. Will folks spread out over the US, Southwest is our ticket to giving those hugs in person!

  25. My favorite way to use Southwest points is for a weekend getaway.

  26. Visiting my dad in Albuquerque. Non stop (sometimes) from Portland

  27. I love Southwest points to visit each of our 5 children, and 10 grandchildren, who are scattered around the U.S. We also have the companion pass which makes flying twice as good!

  28. Use SW points to go to Cancun. Thanks

  29. Visiting my family!

  30. I love using Southwest points for cheap flights, where they often have the best value!

  31. I love using Southwest points for cheap flights, where they often have the best value!

  32. Fly to Aruba

  33. A favorite use is a short trip to see a Boston sports teams on the road. Just did Red Sox in Milwaukee and will do the Patriots in New Orleans. Go Southwest!

  34. I LOVE Southwest Air ever since I received my Companion pass last year. What a great deal! Thanks Million Mile Secrets for your tips on how to earn that pass. I recently used my SW points to book at trip from Oregon to Hartford, CT at the last minute to see my mom who is in hospice. It was a great way to fly since if I had to pay out of pocket it would have cost me a pretty penny since I was planning the trip at the last minute. Thanks SW AIR!

  35. I luv to use my southwest points to go to Arizona in the middle of winter.

  36. Las Vegas

  37. I prefer SWA for short domestic flights from my home airport.

  38. Southwest looks more interesting all the time.
    The Grand Cayman is my pick !

  39. I would love to take my family to Cayman! I love that we can fly Southwest during peak times.

  40. My 3 sisters and I live in opposite corners of the US. Lucky for us, Southwest reaches each destination and allows me to spend quality time with them for an affordable price. Now that I have a 4-year old, affordability on such a family-friendly airline is mission critical! Thanks to your blog, we are also now working on securing the Companion Pass to make quality family time even more frequent. 🙂

  41. I use the points to visit my daughter in San Francisco once or twice a year. (I live near Chicago.)

  42. Going to disney or universal!

  43. My favorite use of Southwest points is booking Midway (Chicago) to McCarran (Vegas). Nice schedules offered almost every hour, easy to get to your destination after landing, Southwest employees are THE BEST, and well …. the weather is always better then ours:)

  44. Favorite place to visit is Las Vegas

  45. Florida, to the beach!

  46. I like to use my Southwest miles to fly to Orlando to go to Disney World or to visit family in California and yes I do have a companion pass for my wife.

  47. I love to use Southwest to fly to Panama City, FL to see my daughter!

  48. Flying anywhere with a beautiful beach!!

  49. Seeing my daughter in Los Angeles CA and getting her to Florida for the Christmas Holidays! SW is our first choice for travel!

  50. I love southwest and my companion pass – means my husband and I can take double the trips to see our daughter in NYC

  51. My favorite use of Southwest points is taking advantage of the Companion Pass so my girlfriend and I can attend as many friend’s weddings as possible.

  52. Southwest is by far my favorite airline. First of all, the no change fee is huge, in case your travel plans change AND they say it best in their recent marketing campaign, they’re not trying to come up with new fees. I always fly Southwest if I can!

  53. the last 3 summers, ive taken my faamily to akron twicw and indianapolis once, all FREE on southwest!!

  54. Love traveling this great country, driving trips up the coast, mountains. Trying to figure out what to do this summer. Love to travel!

  55. Flo-ri-da!

  56. I loved my first trip to Georgia to see my military son. Flying in and out of Jacksonville was easy….easy and now saving up again for a trip once their baby arrives.

  57. Can’t wait for Southwest to fly to Hawaii from California!

  58. Love to fly to NYC to celebrate my daughter’s sweet 16 birthday!

  59. Surprising my wife for her milestone bday with a trip to Vegas! We have not had a trip alone together since starting our family!

  60. My favorite use of points is to visit my sister in Austin, Texas who is a teacher and can’t take too much time off. I enjoy spending time with her while also flying Southwest to go visit her!

  61. Going to visit the parents! Best use of points, especially with the no fee refunds.

  62. I Live in Hawaii – so ideally I would be able to use SWAL points soon to Fly to Los Angeles.
    I AM SO WAITING FOR THE ANNOUNCMENT that Soutwest will be coming to Hawaii?
    Or I’d fly from LA to Vegas and then on to my ol’ stomping grounds in Dallas & Austin Texas.
    I remember living in Houston, Texas waaaaaaay back when Southwest flights were only Dallas, Houston, and San Antonio. I Love Southwest and wish they’d hurry up and get to Hawaii.

  63. sandra peterson

    Getting away to my vacation home in PHX! We have companion pass 4 years running now, so hubby and I can go for a quick weekend without spending a fortune in airfare from MDW.

  64. We LOVE to go to NYC using our SW Companion Pass, to see our daughter and her family, including our rowdy 5 yr. old twin grandsons!