20 MONTEREY COUNTY WEEKLY JUNE 4-10, 2026 www.montereycountynow.com For now, direct flights between ORD and MRY are on Saturdays only. That gives you a week. As a former Monterey County resident transplanted to Chicago, here’s my recommended itinerary: SATURDAY EVENING: Fly into O’Hare around 8:40pm. Hungry from the flight? Look no further than Tortas Frontera (Terminals 1, 3 and 5; United Airlines flies into Terminals 1 and 2), which made the New York Times’ latest “25Best Restaurants in Chicago Right Now” list. Hail a ride. Check in and settle into lodging. SUNDAY DAY: Take an architecture boat tour; if you have time, do one that takes you out onto Lake Michigan. This is something locals like to do on occasion. SUNDAY EVENING: Take the Blue Line to Logan Square to have dinner at Reno Chicago or Lula Café, and afterward get a nightcap at the craft cocktail bar Billy Sunday. MONDAY DAY: Go to the Art Institute of Chicago, regularly voted one of the best art museums in the world. MONDAY EVENING: Check out Zanies (Old Town) or the Lincoln Lodge (Bucktown) to see live, local stand-up comedy; if you go to Zanies, stop for dinner at Twin Anchors for the ribs. TUESDAY DAY: Visit the (free) Lincoln Park Zoo, but first stop at nearby Beacon Donuts, which is hidden in the alley and slings the best— and all-vegan—donuts in the city. TUESDAY EVENING: Get tickets to the Chicago Crime Tour, a bus tour that begins and ends on the Magnificent Mile (Streeterville) and stops at historic crime spots (the evening tour also includes a slice of traditional Chicago-style deep-dish pizza). WEDNESDAY DAY: Walk around “The Loop” to find public art by Picasso, Chagall and Miro, and get coffee at Happy Monday, which is also in the Loop. WEDNESDAY EVENING: Go to The Green Mill jazz bar (cash only) in Uptown to see Alphonso Ponticelli & Swing Gitan play gypsy swing jazz from 8pm-midnight. The Green Mill is also a solid option on Fridays for happy hour with Chris Foreman, the blind singer who plays the organ behind the bar and on Saturdays at 3pm for the standing-room-only Paper Machete variety show featuring local musicians, comedians and actors alternating their acts between the main stage and the stage behind the bar. THURSDAY DAY: Visit the Field Museum (Museum Campus) to see 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. A Week Away A suggested itinerary for a trip from Monterey to Chicago, from a former local. Story and photos by Gabriel Skvor dioramas and an extensive collection of dinosaur skeletons and fossils including Sue, the most complete Tyrannosaurus Rex specimen in the world. THURSDAY EVENING: Go to The Wiener Circle for a traditional Chicago-style hot dog (beware when ordering the $20 chocolate shake…if you know, you know) and then head to iO Theatre for an improv show. FRIDAY DAY: Spend a day at Montrose Beach on Lake Michigan (one of Chicago’s legal surf spots). FRIDAY EVENING: If you can get a reservation, go to Kumiko for either the tasting menu or for the basement whiskey bar, regularly voted one of the best bars and bar programs in the world. SATURDAY MORNING: Cry tears of joy because you just fell in love with Chicago and your flight leaves at 8:40am. You should be back in Monterey by lunch time. SUMMER FUN The city skyline as seen from Promontory Point on Chicago’s South side. Tiffany Dome at the Chicago Cultural Center. Cloud Gate, aka “the bean,” reflects the scene in Millennium Park. A lovely day on the Chicago River as seen from the Michigan Avenue bridge. The writer takes a selfie next to one of the lions flanking an entrance to the Art Institute of Chicago. Public art adorns a highrise off Michigan Avenue in downtown Chicago. Flying continued from pg. 19
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