Review: Southwest Airlines 737-800 & 737-700 (Economy); Maui to Atlanta (via Oakland)

Southwest Airlines / Hawaiian Airlines


Introduction: Dream Trip for My Wife (and daughter) To Hawaii

Review: Delta Airlines 767-400 (Business); Detroit to Honolulu 
Review: Delta Sky Club Lounge (Detroit)
• Review: Hyatt Centric Waikiki Beach (Honolulu)
• Review: Southwest Airlines 737-800 Inter-Island (Economy); Honolulu to Maui
• Review: Fairmont Kea Lani (Maui)
• Review: Southwest Airlines (Economy); Maui to Atlanta (via Oakland)

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After spending a few enjoyable days in Maui is was time to return home. We would be traveling from Maui to Atlanta (via Oakland).

Maui – Oakland – Atlanta

Again, this flight review will be slightly different than other flight reviews as I assume most people have experienced a Southwest Airlines economy flight.

This review will have qualities of a normal trip report but I want to focus more on the “experience” than the flight details.


Unfortunately, Southwest does not have favorable connection times to Atlanta, so we would have to spend the night in Oakland.

Southwest flies to several west-coast locations from Maui (OGG) including:

  • Honolulu
  • Kailua–Kona
  • Oakland
  • Sacramento (begins March 7, 2020)
  • San Diego (begins April 14, 2020)
  • San Jose (CA)

Although, we could’ve redeemed points to fly business class on our return home. We (or at least I) chose the opposite route – an economy flight with an overnight stay in Oakland and I wanted to take a non-stop flight to Oakland, another non-stop flight to Atlanta.

Ultimately, I wanted to compare if it was better to book a 10 hour, non-stop business class flight with an infant or better to fly 4 hours to Oakland, adjust to the time difference with an overnight stay, and then continue the next morning.


I redeemed points for the entire return flight. I redeemed 14,035 Southwest points for the flight from Maui (OGG) – Oakland (OAK)

Maui – Oakland

And I redeemed 9,772 points from Oakland (OAK) to Atlanta (ATL).

Oakland – Atlanta

Southwest is unique in the fact that the number of points required for a redemption are tied to the price of the ticket. It’s impossible to extract extreme value out of the points because it depends on the price the ticket.

However, I have the Southwest Companion Pass so, my wife (aka – my companion), my infant daughter and I would all flying for 23,807 Southwest points total.

Southwest Airlines Economy Class 737-800 Review

Southwest Airlines Flight 588
Maui (OGG) to Oakland (OAK)

Scheduled Departure: 4:50PM
Scheduled Arrival: 12:50AM (+1)
Duration: 5hours
Aircraft: Boeing 737-800
Seat: No assigned seats on Southwest. Just pick one! (Economy Class)


Southwest Airlines Flight 178
Oakland (OAK) to Atlanta (ATL)

Scheduled Departure: 11:35AM
Scheduled Arrival: 7:10PM
Duration: 4hours 35min
Aircraft: Boeing 737-700
Seat: No assigned seats on Southwest. Just pick one! (Economy Class)

We arrived at the car rental facility at 2PM. The process was simple and we were able to return our cars within minutes.

Maui Car Rental Center

There is a small electric train that connects the rental car facility to the main terminal. When we arrived at the main terminal, the Southwest Airlines check-in counters were located to our right.

Southwest Check-in (OGG)

Similar to our check-in experience for our flight from Honolulu to Maui, we were welcomed at the counter by a cordial representative. Check-in was easy and within minutes we were given our tickets and directed to our flight out of Gate 9.

Again, the staff were extremely helpful, directed us to the security lines, and we breezed though security in a matter of minutes. Interestingly, the airport was rather empty.

Maui (OGG) Concourse

Southwest has really made an impact on air traffic from the Hawaiian airports and appeared to have advertisements on every wall.

Maui (OGG) Concourse


Flying Southwest from Hawaii is just like flying Southwest anywhere else: either you like it (or at least tolerate) open boarding and all-economy class or you don’t. Southwest already flies some transcontinental routes, and if you’ve ever flown between the coasts, the flight time from Hawaii to the mainland isn’t substantially different.

After arriving at our gate, we waited about 60 minutes before boarding was called. The photo below was taken a few minutes before boarding. You can see that the plane was not full by any means.

Gate Area
Southwest Airlines / Hawaiian Airlines

As with any Southwest flight, you are assigned a boarding group (A, B, or C) and position (1-60+) upon check in. Your unique group and position combination (for example: A35) will be displayed on your boarding pass and represents a reserved spot in the boarding group at the gate.

We were assigned B6 and B7 despite checking in at the check-in counter and not on the app. Southwest Airlines has “family boarding” after A’s are done boarding (but before B’s are called to board). We boarded with the families so we were able to board the plane a few spots earlier than expected.

While I was attempting to board the plane with my bag, my daughters bag, and the car seat, the flight attendant at the door of the plane asked to assist me. She grabbed the car seat and followed us to Row 23 A, B, &C.

I inquired the load factor and she responded “Feel free to spread out. All of our flights have been busting at the seams, however, school has just started so we’re not as busy as we usually are.”

After strapping my daughter into her car seat, the pilot welcomed us on our “fight back to reality” and encouraged us to sit back and enjoy our 4 hour and 25 minute journey to Oakland.

Ready For Takeoff

Given the flight was not completely full, the boarding process was fast and efficient. And within minutes, we were being pushed back and in the air as the sun set over Hawaii.

Southwest Pushback

These days, economy class passengers don’t get many frills on the major US carriers. Southwest doesn’t get major frills either — though on the plus side, I do find their crews to be a bit friendlier than other US carriers (on average).

In fact, during the announcements, it was notable when a flight attendant said, “We’re here for your safety and service”. I could be wrong but I don’t believe I’ve ever heard that last part — and service — on any airline in quite a while. It was a nice touch.


Now, here’s the good part. Southwest offers better snacks on these routes than they do on their normal flights.

For example, their “snack pack” includes: wheat thins, white cheddar spreadable cheese, fruit snacks, pretzels, and tic-tacs and with many families aboard this plane, I saw snack packs being handed out frequently.


Admittedly, it’s not Singapore Airlines’ lobster thermidor and Krug, but you probably you didn’t have those expectations when you booked Southwest.

Southwest Snacks

And yes, I agree….

Southwest Napkins


We arrived at 12:30AM (PST), exhausted from our long day and long flight.

Southwest Oakland Airport (OAK)

We stayed at a local hotel and returned to the airport the next morning for our flight.

Southwest Oakland Airport Check-In
Southwest Airlines
Southwest Airlines

To be honest, I would like to say that I remember the staff being nice but I was so tired that I don’t remember much about our flight to Atlanta.



I did not take a screen shot of the actual price of our flight from Maui to Oakland nor Oakland to Atlanta. However, it’s worth noting that I have at least 100,000 Southwest miles from the Southwest Companion Pass, so redeeming ~25,000 in order for my whole family to travel from Hawaii to Atlanta represents great value to me.


So let’s address the obvious question…was it better to take the 10 hour direct flight in business class or readjust with the time difference and have a connection on the west coast?

Although, I love Southwest Airlines, hands down…10 hour direct!!

While we’re addressing concerns, it’s also worth noting that on the 737-700 (my flight from OAK-ATL), the only changing table is located in the bathroom at the front of cabin.

In my experience, families tend to move to the rear of the plane so that is completely inconvenient. It’s time to refurbish the bathrooms SWA!

Again, while some will invariably look at flying Southwest with dread, it’s worth a reminder that even if you’re slightly uncomfortable, the juice is likely worth the squeeze.

Those who don’t mind flying Southwest domestically will be pleased that the experience flying from Hawaii isn’t much different.

For those who haven’t flown Southwest lately, I’d say this: having flown Alaska, American, Delta, and United in economy class over the past month, I don’t find flying Southwest to be substantially different (apart from the boarding process) in any negative way.

In fact, two free bags with Southwest, whether inter-island or on the mainland, sweetens the pot for me personally.

And for those who would never set foot on a Southwest plane, take comfort in competition.

Have you ever flown Southwest? What was your experience?

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