Sometimes spur‑of‑the‑moment travel delivers the best surprises. A few years ago, on a random Wednesday, my partner asked if I wanted to go to Chicago for the weekend. Sure. Why not? Three days in the Second City turned into a fast-paced, invigorating escape — architecture tours, deep-dish pizza, art museums, comedy clubs and all the things you simply can’t do in little old Deerfield or Greenfield. It felt good to be in a real city again.
It’s only a two-and-a-half‑hour flight west from Boston, and before long we were stepping off the plane at O’Hare and onto the CTA Blue Line. So many U.S. cities — except the ones in New England — have figured out how to make airport access easy. Chicago’s Blue Line whisks you straight downtown for five bucks, 17 stops from the middle of the city right to the airport monorail. Try that in Boston. Our hotel, the Cambria, sat right in the theater district with a comfortable lobby and decent-sized rooms. A perfect home base.
First order of business: deep-dish pizza. Lou Malnati’s Pizzeria, with its subterranean dining room and perpetual crowds, delivered exactly what we hoped for. We grabbed two bar seats, and soon those thick disks of pie landed in front of us. All the toppings were buried inside the sauce, and these pizzas and the crusts were thin and buttery, different and tasty.
Walking around downtown afterward, we were struck by how carefully tended the flower beds were — hydrangeas, hostas and bright plantings lining the streets, all well-watered and thriving. The lack of litter and graffiti made the city feel welcoming. Locals kept telling us the architecture boat tour was a must, and they were all right. Four different companies run the same route, all packed, but the perspective from the Chicago River is unmatched. You learn the stories behind the skyline, spot the city’s iconic flag with its four stars and two bars, and come away with a deeper sense of what makes Chicago tick. At $50, it’s worth every penny.
Saturday morning brought a different kind of treat: Japanese soufflé pancakes at Hanabusa. The line outside was long, but the payoff was huge — towering, jiggly pancakes made from whipped egg whites, topped with custard or sugar torched to a crackly finish. When you slice into one of these pillows, it’s like you’re taking a bite of air; it is so good and worth the wait. And they give you no more than about 15 minutes to finish and leave. People are waiting.
Families filled the streets, kids splashing in fountains at Millennium Park, college-age travelers roaming with iced coffees and weekend energy. Chicago, it turns out, is topping the charts this summer as the number one American city for meetings and events from April through June, and you could feel that buzz everywhere.
We made our way to the Art Institute of Chicago, where a standout exhibit featured Georgia O’Keeffe’s paintings of New York City. The museum’s collection is vast — room after room of impressionist masterpieces — and then the Thorn Miniature Rooms, a gallery of 68 meticulously crafted interiors built at one‑twelfth scale. These tiny rooms, made from the same materials as full-sized spaces, even include original works of art. They’re like portals into another era, and absolutely worth seeking out.
After checking off two of Chicago’s biggest attractions — the boat tour and the Art Institute — we went hunting for another classic: the Chicago beef sandwich. Mr. Beef on Orleans, made famous by “The Bear,” is a cramped, no-nonsense joint plastered with dusty celebrity photos. None of the photos were more recent than 2000, but the wall made its point. This was one of the most non-BS joints. You can imagine. Cash only, no substitutions, no bathrooms, no trays, no questions. Those slowed down the line, all laid out in a tongue-in-cheek sign. You get it. It’s all part of the charm. The roasted, thin-sliced beef with peppers is savory, messy and unforgettable. One bite and you understand why this place has a cult following.
Chicago is a great walking city, and throughout the Loop, downtown and Old Town, we felt safe and energized. The only quibble: Chicago’s downtown is increasingly overwhelmed by obnoxious three‑wheel motorcycle caravans that roar through the streets with blaring music and modified exhausts, a noisy weekend ritual the city has tried — and failed — to rein in.
For Saturday night, we hopped a bus to Old Town, where the skyscrapers give way to low-rise buildings, clubs, bars, and restaurants. We found the Old Jerusalem Cafe, an inexpensive spot serving Middle Eastern dishes at outdoor tables. A few blocks away sat Zanies, where the 11:15 p.m. stand-up show was already filling up. We squeezed into our seats and enjoyed six comedians — only a couple duds in the mix, which is a pretty good batting average for late-night comedy.
By Sunday, we felt like we’d packed a week’s worth of experiences into a long weekend without breaking the bank. Chicago delivered exactly what we needed: a jolt of city life, great food, memorable art, and the thrill of discovering new corners of a place that’s constantly reinventing itself. City breaks are one of the best ways to inject excitement into your summer, and Chicago proved to be the perfect choice.
Max Hartshorne is the retired editor of GoNOMAD.com Travel in South Deerfield. Follow his posts on his Substack at substack.com/@maxdeerfield.
