There are two ways to visit a city. You can check into a hotel, follow the guidebook, and move from one famous attraction to the next, or you can pretend you actually live there. In Chicago, my wife Stephanie and I chose the latter this time.
We flew in from Toronto with Porter Airlines, riding the kind of first-timer excitement that would make any local roll their eyes. We wanted baseball, deep-dish pizza, jaw-dropping architecture, and the best views the city had to offer.
We booked our stay through HomeExchange.com, the home-swapping platform that has saved us thousands of dollars over the years. This time, it landed us in a luxury condo in the South Loop, and it came with something no hotel concierge could offer, our host’s actual neighbours.
Before we’d even unpacked, one of them was walking us through a mental map of the neighbourhood, the absolute best restaurants, which grocery store to use, which subway entrance to take if we wanted to skip the crowd, and the neighbourhoods we should avoid. It was like a secret key to the city and removed much of the rigmarole of local travel.
On the Waterfront in Chicago
Our first real introduction to Chicago came from the river. We boarded the Architecture Center’s river cruise aboard Chicago’s First Lady, and spent ninety minutes gliding past a skyline that seemed determined to outdo itself at every bend.
This tour came highly recommended from a number of sources and it was easy to see why. Our guide talked us through a century of styles and the rivalries and ambitions behind them. Glass towers reflected older stone facades, bridges lifted and dropped above us, and each turn in the river handed us another version of the skyline. For first-time visitors, it did something a guidebook can’t, it showed us how the city actually fits together.
Afterwards, on a tip from our host’s guidebook that they left available in the condo, we headed to Lou Malnati’s in the Wrigley Building. Stephanie and I have done a lot of traveling over the years, but believe it or not we had never tried deep dish pizza.
A thick, buttery crust holding up layers of cheese, toppings, and sauce was brought to our table. We ordered one veggie and one pepperoni, and even though these were supposed to be “personal” pizzas, we were completely unable to finish everything, it was fantastic.
It’s important to note that Chicago has an incredibly unique and diverse food scene. Some of the more notable eateries include Al’s #1 Italian Beef, Mario’s Italian Ice, Molly’s Cupcakes, Lao Sze Chuan and Evie.
Go Cubs Go!
No first trip to Chicago felt complete without a visit to the iconic Wrigley Field for a Cubs Game. We took the Red Line north from our apartment, by now a route we could navigate without checking our phones, and surfaced in Wrigleyville, where the whole neighbourhood was exploding with people and vendors of all kinds.
Opened in 1914, Wrigley Field is the second-oldest park in Major League Baseball, and you feel it the second you walk in with the ivy-covered walls, the hand-operated scoreboard, and the rooftop seats peering in from across the street. The Cubs lost to the Cardinals in a huge blowout of 17 – 1 that afternoon, but we ate authentic Chicago hot dogs in the sunshine so the activity was a big win for us.
The next day we skipped lunch knowing full-well that our upcoming visit to the Museum of Ice Cream on Michigan Avenue was on our list.
The museum is as subtle as its name suggests, with brightly coloured rooms, unlimited (and very decadent) ice cream, a sprinkle pool, and yes a complete history of the iconic dessert. It’s unapologetically silly, which was a welcome change.
Then, with a belly full of ice cream, we thought it would be a great idea to visit Flyover Chicago at Navy Pier. Flyover is an immersive ride that uses a massive spherical screen, moving seats, and gusts of simulated wind to send you soaring above the city. Within minutes we were sweeping over skyscrapers and racing the Chicago River from an angle that would otherwise require a helicopter. It was truly incredible and a must see for thrill seekers.
We chased one more angle at 360 Chicago, on the 94th floor of the tower once known as the John Hancock Center. More than a thousand feet up, the observation deck opens onto the Magnificent Mile and Lake Michigan stretching to the horizon. Some of the braver visitors tried TILT, a glass platform that slowly leans out over the edge of the building. As for Stephanie and I, we were satisfied with the views and enjoying a drink from CloudBar, which is their signature cocktail lounge area.
Pinball Wizard
The final day of our adventure was a personal favourite, as I am a huge pinball enthusiast. Most people don’t realise that Chicago is the pinball capital of the world, as it has been the manufacturing and engineering hub of the game for decades.
We left our condo early that morning and took two subways and an Uber to Elk Grove Village, where we were fortunate enough to get a private tour from Zachary Sharpe, the Senior Director of Marketing for Stern Pinball. Stern is the largest and most dominant pinball manufacturer in the world, having created iconic games for decades including Star Wars, Godzilla, Transformers, Pokemon, and a laundry list of others.
Walking the aisles on the manufacturing floor of their enormous facility, we got to see pinball machines being made by hand, with all the artistic and engineering elements on brilliant display. Afterward, we were able to play many games in their extensive arcade that sits right in the middle of the lobby.
The pinball extravaganza did not end there, because that evening we headed over to The Flip, which is Chicago’s playable pinball museum. When we arrived we found a dedicated team of individuals who love all things pinball, curating, fixing and caring for some of the rarest, most incredible pinball games in existence. If you love the game, or even if you just enjoy it, this museum is a must-see.
Two other honourable mentions in the must-see department are the iconic Cloud Gate (bean) sculpture that is synonymous with Chicago’s identity, and the very awesome Adler planetarium. Both are worth the effort.
The Quiet Parts of Chicago
By the time we packed up, we’d seen Chicago from the river, from 94 floors up, and from the middle of a simulated flight above it. We’d eaten deep dish, watched the Cubs, and learned more about pinball manufacturing than we ever expected to.
But some of my favourite moments were the ones in between with no attraction attached. Figuring out which subway car to stand near for the fastest exit, running into the same cashier twice at the grocery store, and sitting on the condo’s balcony at the end of a long day, tired in the specific way you only get from a city that rewards walking. Staying through HomeExchange didn’t just save us money, it gave us a version of Chicago that started at street level, with actual neighbours pointing us toward the places they loved.
Getting back to our home city was effortless, as Porter flew out of Chicago Midway into Billy Bishop Toronto City Airport, which meant skipping the usual chaos at Pearson International. The free snacks and drinks on-board, as well as the amazing staff, also made both flights pretty sweet. Porter has a number of weekly flights to the windy city, so check them all out and find the one that fits the best.
Chicago surprised us with its enormous buildings and neighbourhood bars, century-old ballparks, unique museums, famous food, and a pinball factory. For a few days, thanks to a condo in the South Loop and a few good tips from the neighbours, it actually felt like we lived there.