It is now possible to spend Saturday morning surfing at Carmel, Asilomar or Lovers Point, dry off and drive to Monterey Regional Airport, hop on the new nonstop flight to Chicago and wake up to surf Lake Michigan the next morning.
The nonstop flight between Chicago’s O’Hare International Airport and Monterey Regional Airport is exciting for more reasons beyond the novelty of surfing onshore, wind-driven freshwater waves on Lake Michigan. One of California’s most vibrant coastal towns is now connected to one of the world’s great cities. Chicago is a “Goldilocks” metropolis: not densely packed and vertical like New York City and not sprawling and congested like Los Angeles. Chicago boasts Michelin-starred and James Beard Award-winning restaurants, efficient public transportation, world-class comedy, music and theater, and the familiar expanse of a seemingly endless body of water bordering a skyline that gave birth to the modern skyscraper.
Spend time in Chicago’s many neighborhoods outside of downtown and “The Loop,” and there’s a comforting small-town feel from family-owned shops and eateries among the 100-plus-year-old brick, graystone and brownstone buildings, where walkability and bikeability are key features built into urban design.
May 23 marked the takeoff of this direct route, currently offered only on Saturdays and on a seasonal basis. (Although that season has already been extended – originally set to end Aug. 15, United Airlines will keep it going through Sept. 19.)
To write this story, I had a seat on both first flights.
My morning started in Chicago’s Andersonville neighborhood. I plopped my weary bones into a Lyft at 6am to be on the inbound flight to Monterey, departing O’Hare at 8:40am. Having previously lived in Monterey County for nine years and now in Chicago for 12 years, this was more than a freelance travel assignment for me; it’s a personal link connecting two wildly different and stunningly beautiful, lively places.
My Lyft dropped me off at 6:30am and I was through airport security by 6:40am. I had now two hours to kill before my flight due to zero traffic and my irrational fear of being late and missing a flight. Saturday mornings at O’Hare – aka “the busiest airport in the world,” according to Chicago Mayor Brandon Johnson’s periodic message on the airport’s PA system – are eerily sleepy and smooth.
At our gate, a Portland, Oregon resident named Isaac was taking photos and had a GoPro mounted to his backpack – he was also documenting this flight. He told me he was an aviation enthusiast who flew to Chicago simply to collect the experience of being on this inaugural flight; he also grew up in Monterey. As we exchanged pleasantries, he asked, “I wonder how many of these people know this is the inaugural flight?” I didn’t have an answer, but no one else waiting for our flight looked as excited.
WITH ALL OF MY EXTRA TIME, I made sure to visit the gate attendant and ask for any available upgrades.
No first-class seats remained, but the kind United Airlines employee gave me an entire row in Economy-Plus – with extra legroom – at no extra charge. Advice: jump on these flights before they’re popular to take advantage of the extra space. My flight appeared to be about 60-percent full; I wasn’t the only one with my own row.
Now in “couch class,” I could choose to sit at the window, in the middle seat or on the aisle, and switch seats with reckless abandon, playing a human shell-game of sorts for the flight attendants who would not be able to guess where I’d end up when it was time to put our tray tables and seat-backs into their upright and locked positions.
Everything was going smoothly until we learned we were delayed for 10 minutes, then 30 minutes – not due to weather, not due to mechanical issues, but because the software on the plane hadn’t yet been updated to include Monterey as a destination.
Then we took off and cruised for four hours. As we were descending, with 10 minutes to go before landing, the captain came over the PA to thank everyone for being on this “inauguration” flight from Chicago to Monterey. For a split second, my mind jumped forward to Jan. 20, 2029 and greener (hopefully) political pastures on our national stage.
And yes, there are direct flights between ORD and Washington, D.C.
WHILE THERE WAS NO FANFARE LEAVING CHICAGO FOR THIS FLIGHT – or when I returned to O’Hare later that evening – passengers exiting onto the tarmac in Monterey walked through a colorful arch welcoming us with people cheering, press photographers snapping photos and a KSBW reporter grabbing Isaac from Portland for an interview; he made it onto their broadcast later that evening.
All passengers were gifted United Airlines-branded golf Ts and a branded tote bag commemorating the flight filled with gifts like a large stuffed sea otter toy from the Monterey Bay Aquarium, a “Monterey” baseball cap, a water bottle and a few brochures and stickers; truth be told, I took two gift-filled totes because I couldn’t come home with just one otter to a household with two children under age 6.
Passengers on our flight were invited to the airport’s observation deck where dignitaries like Monterey Mayor Tyller Williamson and U.S. Rep. Jimmy Panetta, D-Carmel Valley, made remarks. Attendees were invited to sample a buffet filled with iconic Chicago food items like Italian beef sandwiches, deep dish and tavern-style pizzas, Chicago-style hot dogs – with no ketchup – and Garrett’s popcorn.
Isaac from Portland may have received the celebrity treatment on the local television news, I got mine on the other side of security as friend, travel guide writer and former Weekly staff writer Stuart Thornton was waiting to snap a few photos of me for posterity.
After a few minutes at the busy event on the observation deck, we opted for bay-view dining and local flavor a few steps away at Woody’s Restaurant and Bar with the time I had left.
With less than an hour before my departure, I ordered the sand dabs and calamari combo – with Chicago’s comforting fare having followed me two time zones to the observation deck, going with an only-in-Monterey lunch seemed prudent. On this auspicious day of firsts, this first for me was the most delightful. I had always heard about how great Woody’s was, but now I could confirm that, along with the view of the runway and the bay (plus seeing old friends), that the sand dabs are worth the trip. ✈