Signing-up for credit cards through partner links earns us a commission. Here’s our full Advertising Policy.
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.
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!
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!
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.
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.
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.
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.
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!
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.
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.
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.
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.