18 MONTEREY COUNTY WEEKLY JUNE 4-10, 2026 www.montereycountynow.com Left: United Airlines flight 485 coming in for landing at Monterey Regional Airport on Saturday, May 23. Right: Officials from various local agencies gathered to celebrate the arrival of the first direct flight to MRY from Chicago O’Hare. Unlike other United flights locally that contract with SkyWest, this is a mainline route, meaning flights are staffed by United employees, rather than third-party contractors. SUMMER FUN A dispatch from the skies on the inaugural direct flight between Chicago and Monterey. By Gabriel Skvor Photos by Nik Blaskovich Flying High 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 Michelinstarred and James Beard Awardwinning 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-plusyear-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
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