Fly Southwest: MDW to Missoula, Montana

Hey there, fellow globe-trotter! If you've got your sights set on an adventure from the Windy City of Chicago to the untamed beauty of Missoula - and you're considering hitting the skies with Southwest Airlines - I reckon you'll find this read right up your alley. Let's delve into the nitty-gritty from the comfort of our seats, shall we?

Sit tight as we start from square one - flights. Now, who doesn't enjoy the comfort and convenience of direct flights? Embarking on a journey can be taxing in itself, without the additional worry of juggling connecting flights. Sadly, Southwest does not offer direct flights from Chicago to Missoula at present, although I've no doubt we'd all love a non-stop escape from the bustling city to the tranquillity of Montana. But hey, everyone loves a good layover, right? Take it as an opportunity to stretch your legs, grab a bite, and maybe even explore a bit if time permits.

Your airfare is the next pressing issue on the agenda. Isn't it just a game of timing? The best time to book is without a doubt the million-dollar question here. If you're looking to get the most bang for your buck (aren't we all?), you might want to consider keeping an eye out for any potential flight deals or last-minute flights - just remember, patience and persistence are key!

Moving onto the fun stuff - in-flight services! Southwest endeavors to keep it casual and friendly—just your typical Midwestern vibes in the air. An array of snacks to pick from, non-alcoholic beverages on the house, and there's WiFi onboard for a nominal fee, in case you can't bear to be disconnected, even at 35,000 feet.

As seasoned travelers, we're only too familiar with the infamous check-in line dance. With Southwest's two free checked bags policy, part of their baggage allowance, you can save those extra bucks and maybe splurge on something more gratifying, like a post-flight dinner at Missoula's finest. If you are someone who travels a lot, Southwest's frequent flyer program, Rapid Rewards, is worth considering. It provides perks like faster boarding, more baggage allowance, and priority security lanes - the whole nine yards.

Now to touch on the not-so-glitzy bits. Flight cancellations can be a real drag. Luckily, Southwest's flight cancellation policy is quite flexible, offering passengers the option to use the funds from a canceled flight for future travel, provided it's within a year from the original flight date. It's a handy silver lining if things go sideways.

I am aware that there's a lot of info packed in here. But remember, this isn't just about planning a trip; it's about embracing the journey, thriving amidst the unexpected, and making stories out of experiences. So here's to your upcoming adventure from Chicago to Missoula - may your flights be safe, your airfare budget-friendly, and your journey nothing short of phenomenal.