5 of Our Favorite Summer Destinations on Southwest

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Lyn writes about how to fly free on Southwest on her GotoTravelGal.com blog, and has written a free ebook that walks you step-by-step through how to earn the coveted Southwest Companion Pass.  If you can earn it, the Southwest Companion Pass lets 1 person fly nearly free with you for up to 2 years! 

Lyn:  Our kids are out of school, and we’ve started our summer travels!  Yea!  How about you?  If you’re still looking for a last-minute getaway this summer, I’ve rounded up my family’s all-time favorite destinations that are reachable via Southwest for your consideration.

5 Fabulous Summer Destinations on Southwest

1.   San Diego

One of my family’s favorite places on earth is San Diego.  You simply can’t beat the 70-degree temperatures nearly every day, plentiful beaches, and so many outdoor and family-friendly activities.  La Jolla is 1 of our favorite spots in the city where you can walk right up to sea lions, hike down into a sea cave, and kayak in the ocean.  Pacific Beach is an affordable family-friendly spot for some beach time, or book a stay on Coronado Island for the ultimate beach vacation.

5 Of Our Favorite Summer Destinations On Southwest
San Diego Is 1 of Our Favorite Cities to Visit!

Of course, San Diego has an awesome zoo, SeaWorld, LEGOLAND California, gorgeous Balboa Park, and the hip and happening Gaslamp Quarter downtown.  Oh, and don’t miss a great Italian meal in the city’s Little Italy!

Here’s my list of 29 Suntastic Things to Do in San Diego.

2.   Rocky Mountains (Denver)

Because my family owns a condo in the Beaver Creek area of Colorado (just west of Vail), we have visited the Rocky Mountains many times.  Our favorite time to fly to the Rockies (via Denver on Southwest) is during the summer months, as we love to hike, fish, bike, and just breathe in the mountain air.

5 Of Our Favorite Summer Destinations On Southwest
Hiking in the Rocky Mountains Near Vail, Colorado, on a Gorgeous Summer Day

The mountains bring me great peace and I could spend days camped by a rushing mountain creek and wandering through the aspens, pine trees, and gorgeous scenery at every turn.  Top spots on my list for Colorado include Colorado Springs, Telluride, Aspen, Vail, Crested Butte (check out this amazing Crested Butte to Aspen day hike!), Ouray, and, of course, Beaver Creek.

3.   New York City

What can I say, a part of my heart belongs in New York City.  I’ve been visiting this metropolis since I was a dancer in high school.  I fell in love the minute I took a dance class overlooking Broadway at the Broadway Dance Center and saw my first Broadway show!

5 Of Our Favorite Summer Destinations On Southwest
I Love Using Miles & Points to Take My Family on Trips All Across the US!

We return here year after year, only to discover new parts of the city to love (and some NOT to love).  We recently visited on our way to Rome and stayed in the Meatpacking District, closer to downtown, at the Gansevoort Meatpacking Hotel.

It was fabulous and in a super convenient location.  We hopped on the High Line (which is 1 of my favorite activities in the city), wandered into the Village, and explored Soho and Chelsea, and managed to see Aziz Ansari at the Comedy Cellar.  He just “showed up” to try some new material!  Did I mention I love New York City? 😉

4.   San Francisco

While San Francisco can be a bit on the cooler side in May and June, it makes for great weather for wandering this hilly city.  My husband and I visited in May 2017 and loved it.

5 Of Our Favorite Summer Destinations On Southwest
My Husband and I Enjoyed a Wonderful Weekend Getaway to San Francisco – Just the 2 of Us!

I’d recommend climbing to the top of Coit Tower for fab views of the city, hopping on a Big Bus Tour to catch all the city’s top sites (getting off to explore and hopping back on when you’re ready), taking a dinner cruise of San Francisco Bay, and of course, riding a cable car.  Though you’ll have better luck catching it downtown than uptown.

Southwest flies into 3 airports in the San Francisco area, including Oakland, San Jose, and San Francisco.  Be sure to compare fares to see which has the cheapest flights from your destination.

5.   Chicago

We live in Indianapolis, so Chicago has long been a frequent haunt for my family.  In fact, we got engaged there a million years ago along the Chicago River!

5 Of Our Favorite Summer Destinations On Southwest
Exploring Chicago

One of my favorite activities in Chicago is a river cruise.  But you can hop on a water taxi for many of the same views at a much lower cost.

Kids will love the Shedd Aquarium, Adler Planetarium, and the Field Museum (lots of dinosaur bones!).  The Bean in Millennium Park is a must-do, and if you have time, get tickets to a Chicago Cubs game.  Seeing a game at Wrigley Field is a once-in-a-lifetime experience.

There are lots of great places to stay in the city, but my favorites include ACME Hotel Company and Kimpton Hotel Monaco (they have awesome window seats overlooking the Chicago River!).

Lastly…DEEP DISH PIZZA!!!  Try Lou Malnati’s or Gino’s East.  And check out Harry Caray’s Italian Steakhouse for another great place to eat.

Bottom Line

There’s no shortage of fantastic destinations to see this summer when you’re flying Southwest.  Choose from a big city getaway to New York City, San Francisco, or Chicago, get some peace and quiet in the Rocky Mountains, or enjoy some sunshine and the beach in San Diego.

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Million Mile Secrets is a contributor to Million Mile Secrets, he covers topics on points and miles, credit cards, airlines, hotels, and general travel.

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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