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Alaska Airlines from Midway International Airport to Monterey

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It's time to start exploring the world without emptying your wallet with Alaska Airlines!

Discover our wide selection of affordable Alaska Airlines tickets that provide both quality and comfort.

Anna B.

Allegiant Airline Flights from Chicago to Monterey

OMG! Booking online was a breeze. Super informative and very user-friendly site. Nice going, unnamed booking co!

Barry L.

Allegiant Airline Flights from Chicago to Monterey

Excellent service over the phone! Unnamed booking co never disappoints. Smooth booking process, kudos guys!​

Top tips for flying out of Midway International Airport (MDW) on Alaska Airlines to Monterey (MRY)

 Popular things to do in Monterey, California

EXPLORE THE MONTEREY BAY AQUARIUM

EXPLORE THE MONTEREY BAY AQUARIUM

Indulge in the unrivaled beauty of marine life at Monterey Bay Aquarium. With over 200 exhibits, this underwater wonder showcases a world teeming with diverse species.

REVEL IN THE CANNERY ROW

REVEL IN THE CANNERY ROW

Step into the legendary Cannery Row, the historic heart of Monterey. It offers an eclectic mix of world-class dining, unique shops, and scenic ocean-side beauty.

EXPERIENCE THE 17-MILE DRIVE

EXPERIENCE THE 17-MILE DRIVE

Discover the spellbinding scenery on a 17-Mile Drive. This dramatic coastal route boasts of stunning beaches, awe-inspiring cliffs, and iconic landmarks such as the Lone Cypress.

VISIT THE PEBBLE BEACH GOLF LINKS

VISIT THE PEBBLE BEACH GOLF LINKS

For golf enthusiasts, a visit to the world-renowned Pebble Beach Golf Links is a must. The prestigious seaside link is recognized as one of the most beautiful golf courses worldwide.

ENJOY WHALE WATCHING

ENJOY WHALE WATCHING

Monterey Bay is a prime spot for whale watching. Experience the thrill of marine giants at play between April and December, the peak migration periods.

HIKE AT POINT LOBOS STATE RESERVE

HIKE AT POINT LOBOS STATE RESERVE

The Point Lobos State Reserve offers incredible hiking experiences. With its rugged coastline and rich wildlife, it's a gem for nature lovers seeking an adventurous escapade.

FAQs for booking flights from Chicago (MDW) to Monterey (MRY) on Alaska Airlines

Is there a time machine involved in booking flights with AirBookr, or just good old-fashioned mouse clicks?

While the AirBookr team is composed of wizards and witches, time travel remains beyond our reproach. For now, vacationers will have to settle for our highly optimized online platform and dedicated phone service to book their flights from Midway to Monterey on the beloved Alaska airlines.

Will using AirBookr to book my flight make me so popular that I'll need to hire security?

Well, regrettably we can't guarantee instant fame, but what we can guarantee is a hassle-free and delightful booking experience. So while you may not need to hire a security detail, you will definitely be the talk of the town when everyone hears how smoothly your flight booking went!

Does booking my flight with AirBookr come with a pre-flight skydiving crash course?

Haha, cheeky! While we at AirBookr are adventurous at heart, we prioritize safety over excitement. So, no skydiving sessions - just a smooth, seasoned booking process that feels closer to lounging on the beach than jumping out of a plane. And hey, that's the kind of thrill we can get behind.

What if I've accidentally booked a ticket to the moon on AirBookr instead of Monterey?

Unless Richard Branson has recently come on board, then we're safe! You'll have options to perfectly tailor and confirm your trip details before the final booking. Moreover, with our 24/7 customer service, if something does go wrong (like accidentally ticking off moon as your destination), we're here to swoop in and rectify it!

Does AirBookr provide disco balls and dance grooves for post-flight celebrations?

While we're all for the party spirit, technically we aren't equipped to hype up your post-flight celebrations with disco balls and groovy music. However, in terms of punctuality, cost-effectiveness, and A-class service, we promise to keep your spirits high during your flight booking process.

I'm a tad bit nervous. Could AirBookr kindly sort me a therapy dog to accompany me on my flight with Alaska?

While we at AirBookr are dog lovers to the fullest, sadly our virtual platform isn't equipped with fluffy companions. Yet, in terms of support, we ensure a smooth and stress-free booking experience – we'll be by your side (virtually speaking) from Midway to Monterey!

Will AirBookr turn my flight into an episode of 'Who Wants to be a Millionaire'?

Although a million-dollar prize sounds pretty enticing, we specialize in thrilling plane tickets, not thrilling game shows. We assure you that our fares are competitive and budget-friendly, that it'll feel like you have saved a million dollars!

Flying on Alaska Airlines from Midway International Airport to Monterey

Calling all wanderlusters, vagabonds, itinerants, and habitual vacation indulgers! Behold the gloriousness that is soaring through the sky on a magic metal bird from Midway International to the illustrious Monterey via Alaska itself. Now, before you smother your cough with your hand, yes, you did read it right! You're not hallucinating because of those last minute 'medicinal' mojitos at Midway's Miracle bar. Allow this humble scribe to enlighten you to the delightful eccentricities of embarking upon this route.

First, it's imperative to discuss the lesser known, and mostly overlooked marvel: layovers. Some might sneer at these intervals, brand them as the plague of a journey. "Direct flights are the way to go!" they cry. Well, let me tell you, my friends, Alaska Airlines partakes in the unsung brilliance of the layover. The sparkly souvenir shops, the overpriced hors-d'oeuvres, the chance encounters with exciting strangers, all of which are part and parcel of layovers and connecting flights – an adventure within an adventure.

Not to mention the sheer thrill of Alaska Airlines' first-class luxuries. Imagine a leather throne, surrounded by room enough to practice your Tai Chi without elbowing your neighbor in the nose. Now add refreshments that include everything but the mythical ambrosia of the gods (because that would just be silly). Isn't it worth chucking your budget out of the window at 35,000 feet?

I’ll let you in on a little secret to ensure your wallet doesn’t levitate out of the window. There ARE such things as flight deals. More elusive than a Yeti sighting, these delightful things pop up more frequently than Halley's comet if you proclaim your loyalty to the airlines. Yes, my globetrotting associates, the frequent flyer mileage program is your golden ticket, magically reducing your airfare from 'gastronomically horrifying' to 'mildly alarming'.

Moving on, let's turn the spotlight on the flight duration. These flights are no ordinary ordeals of getting strapped in economy class with your knees hugging your chest. No sir! These are leisurely aerial jaunts, long enough for in-flight services to woo you with irresistible edible witchcraft and charm you with dazzling duty-free goodies. An opportunity to forget about the world beneath you, and succumb to the magic of soaring above the clouds!

And how, you may ask, are these flights scheduled? My dear sojourning compatriots, Alaska Airlines masterfully conducts its flight schedule with the elegance of a seasoned orchestra conductor (if conductors wielded airplanes instead of batons). Always perfectly timed, in sync with the rhythms of the universe, and perhaps a little mercy towards those of us who sprint for the last-minute flights!

Now, let's pause for a moment of appreciation for our intrepid carrier, Alaska. An airline named after a state with a land area of 663,268 square miles, larger than the combined area of the smallest 22 U.S. states, it sure knows a thing or two about traversing vast expanses. I mean, doesn't the mere thought of flying with an airline that represents such an impressive bit of trivia give you a little thrill?

So, let me reiterate, folks! If you're bound from Midway to Monterey, may I heartily recommend the zany, not at all straight (flight)-lined pathway via Alaska Airlines? Embrace the layovers, the delectable in-flight services, and the charm of first-class. It's a one-way ticket to a flying experience so saturated with joy and delight that even the staunchest round-trip advocates won't want to return. Happy soaring!

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