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✈️ Avoid Southwest Baggage Fees with AI: Smart Travel Hacks You Haven’t Tried

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✈️ Avoid Southwest Baggage Fees with AI: Smart Travel Hacks You Haven’t Tried

Spoiler: Southwest is one of the rare airlines that actually gives you two free checked bags — but if you’re flying internationally, with a codeshare, or lugging oddly shaped gear, those fees can still sneak in. Here’s how to dodge them — AI style.

🤖 1. Use AI to Auto-Find “Free Baggage” Fare Classes

Airfare search tools like Google Flights or Kayak often hide the fine print on baggage fees. Use a free AI assistant (like ChatGPT or even a custom GPT you create) to analyze fare rules in plain English.

Prompt idea:
“Compare these three fare classes on Southwest and tell me which one includes free baggage or avoids overweight fees.”

🧳 2. Create a Packing Assistant Bot

Overweight bags = $100 fee. Avoid that by using AI tools like ChatGPT + Google Sheets to build a personal packing assistant:

  • Input your trip length, weather, and activities.
  • Let AI suggest what to pack — and how to split items between bags.
  • Optimize weight distribution to avoid any overage charges.

Bonus: Use a free app like PackPoint or build your own packing prompt in Notion with AI plugins.

🧠 3. AI Image Recognition for Size Compliance

Southwest carry-on rules are generous — but go over 24x16x10 inches, and you might be forced to gate check. Take a photo of your bag next to a ruler or tiled floor and use AI tools like Google Lens to estimate dimensions before you leave home.

📦 4. Compress with AI Repacking Tips

Use YouTube and ChatGPT to find smart folding hacks based on your luggage type:

Try prompts like:
"What’s the best way to fit 10 days of clothing in a 40L duffel for a Southwest flight?"

Then follow AI-generated packing tutorials or get dynamic packing diagrams.

🪄 5. Automate “Early Bird Check-In” with an AI Reminder Bot (Step-by-Step)

Southwest doesn’t assign seats — instead, it uses a boarding position system based on when you check in. The earlier you check in (starting exactly 24 hours before your flight), the better your boarding group — and that means more overhead space, so you're not forced to gate-check your bag.

Here’s how to automate your check-in reminder using Google Calendar and Zapier:

  1. Create a Google Calendar Reminder
    - Open Google Calendar
    - Create a new event titled “Check in for Southwest Flight”
    - Set the date/time to 24 hours before your flight departure
    - Add a notification alert for 5 minutes before the event
  2. Set Up a Zapier Automation (Optional but powerful)
    - Go to Zapier.com and sign in
    - Create a new Zap: “When Google Calendar event starts → Send text/email”
    - Add filters: only trigger if the event title includes “Southwest”
    - Choose an action like sending yourself an SMS or email with a check-in link
    - You can also include the Southwest check-in URL for quick access
  3. Bonus: Use Notion AI or ChatGPT
    - Ask ChatGPT to build a packing and check-in tracker for your trip
    - You can embed the reminder links and details into Notion for central trip planning
    - Use prompts like: “Create a Southwest trip checklist with check-in reminders, packing list, and carry-on rules.”

💡 Deeper Dive: Using Point.me to Avoid Fees with Miles + AI

Point.me is an AI-powered award search engine that finds flights across multiple airline loyalty programs, helping you:

  • Find free flights (including on Southwest via partner programs)
  • Avoid checked bag fees by booking through airlines with better baggage policies
  • Spot “sweet spots” — like using British Airways Avios on American, or Turkish Miles on United

AI Tip: Use ChatGPT to analyze search results. Paste the results into ChatGPT and ask:
"Which of these redemptions gives me the lowest baggage fees and best check-in experience?"

Try this with a combination of AwardHacker + Point.me to compare options even faster.

🤖 Travel GPTs: The Future of Baggage-Free Flying

Did you know there are custom GPTs built for travelers?

Search GPTs or assistants that specialize in:

  • Fare Class Analysis: Tells you what’s included in “Wanna Get Away” vs “Anytime” fares
  • Reward Route Planning: Finds the cheapest award route with the least baggage restrictions
  • Trip Optimizers: Balance check-in windows, weather, carry-on size, and loyalty perks

You can build your own GPT like:
"A travel assistant that checks fare classes, alerts for check-in, and reminds me to pack."

Start with ChatGPT Custom GPTs or tools like Roam Around.

Prompt idea:
"Help me avoid baggage fees on Southwest flying from LAX to JFK on July 5th using my Chase Sapphire points."

Want a downloadable checklist or AI-packing template?
Let me know by commenting on this Youtube video on my channel — I’ll make it for you! ✨

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