Letting go of plans—and walking and running everywhere—allowed me to experience a new city in a more meaningful and spontaneous way than I ever thought possible.

By Cassie Shortsleeve
Updated: September 01, 2017
Photo: Cassie Shortsleeve

I like to think I've done a fair amount of traveling. I've visited most of our country's biggest cities: I've lived in New York, flown to Los Angeles for business, crossed the Golden Gate, spent time shuttling between restaurants exploring Denver's food scene, and even hiked a crater outside of Honolulu during a flight delay.

Often, my travels are for work. Jam-packed with dinners, tours, and events, trips are planned out to a tee ahead of time. They fly by. I'm moving from the minute my plane touches down till the time I'm off again. I've spent a lot of hours in cars on highways in traffic in new cities.

While amazing in their own ways, sometimes upon returning, the trips can seem a bit of a blur. (We've all had those days when you look back and wonder where exactly the day went.)

So this summer, when cheap flights between Boston and Chicago (one of the major U.S. cities I had yet to make it to!) popped up, my sister and I decided to book on a whim. My goal: a quieter vacation.

All we really knew was where we were going to stay and eat: at the Ritz-Carlton, Chicago, which BTW, has a killer gym with floor-to-ceiling windows overlooking Navy Pier. (The hotel's restaurant, Torali Italian-Steak, is full of organic and locally-sourced options, to boot.) The property is also primely positioned on the Magnificent Mile, easy access to many of Chicago's hot spots.

Given that my sister and I are both runners, we also knew we wanted to log some miles. Often, when I'm on-the-go, this isn't always an option. A packed itinerary can mean only an hour of free time for a long beach run or a jog through a city. But with no schedule to stick to, we decided to spend Saturday simply exploring the city by foot, seeing where we wound up.

After a good night's rest, we started the day. First up was Wrigley Field. As a Red Sox fan, I'd always wanted to see it. We hit the Lakefront Path (and saw Lake Michigan for the first time!) and began the 4.5-mile trek. When we arrived at Wrigley after some unplanned pit stops-small stores selling Cubs apparel, a health grocery store for a smoothie-we found a pre-game calmness. Because we were up and out so early, we also arrived before the restaurants even opened. The streets were quiet.

By the time we looped around the park and sat down for breakfast, we had just about six miles under our belts.

In Boston, where I live, this easily would have been a distance that I'd have chosen to drive. At home, I have a car and an active Uber account. Plus, it's all too easy to hop in a car and zone out on Instagram until you arrive. But being on our feet, we took in the scenery, noticing as the baseball crowd (and the noise) slowly started to grow.

When we slipped out, en route to Lincoln Park Zoo-another two miles or so away-we didn't look at a map or sign up for an activity. We simply walked (for free!) through exhibits of flamingos, crossed small bridges, and trekked along scenic pathways. We talked through my upcoming wedding, my sister's return to college, and everything in between.

We also stumbled upon an indoor/outdoor Lou Malnati's (a famous pizza parlor for Chicago deep dish) and made a last-minute decision to swim in the lake at Oak Street Beach, which happened to be on our way home.

When it was time to shower and change for dinner, we'd logged about 10 miles. And dinner, which we knew we wanted to eat on the waterfront, was another mile or so trek away. When we arrived in the area, standing on the DuSable Bridge (after a few pit stops for shopping), we'd practically completed a half-marathon worth of steps. (Looking for an even more active getaway? Learn how to plan an epic adventure vacation from one thrill-seeker who knows all about it.)

But I knew exactly where we took each one of those steps. And while I was a far way from being able to give directions to a passerby, I knew right where we were after only being in the city 24 hours or so. I knew the name of the street we had to look for when arriving at Wrigley, I knew the turns off and onto the Magnificent Mile, I had started to grasp the different neighborhoods.

It was then that it hit me. How often do we go through the day following Google Maps, set schedules, and tight itineraries, never looking up to see where we are? How often do we visit cities without seeing them? Of course, maps and plans certainly have their place in travel (I am the biggest planner of them all). But looking up (and slowing down) for just one day showed me just how much I had been rushing-be it in cars between activities or through fast showers to make it to dinner reservations.

It's a habit that keeps us from discovering some of the little things-the morning sun reflecting off of people's swim caps in the lake, the way one of the country's most famous ballparks feels when it's empty, the conversations you have when surrounded only by nature. These are the things that make a trip. (Related: These Incredible Pools Will Make You Want to Swim Some Laps.)

Of course, seeing a city by foot to take in these things is nothing new. The popularity of companies such as Marathon Tours & Travel, which curates active trips for traveling runners; City Running Tours, a group that takes people on "sightrunning" trips; and top-notch travel companies such as Context Travel that offers walking tours, are proof of that.

But our no-plan plan worked for us. It allowed us to make mistakes, too. I think we clocked an extra two miles just trying to find one particular riverfront restaurant that we had eyed from the Chicago Architecture Foundation's River Cruise the day before. We went up and down staircases countless times, wound up in a mini marina at one point, asked for directions (and then asked for them again), and eventually gave up, settling on an entirely new place to eat.

It was 9 p.m. by the time we finally sat down. But because we'd missed the dinner crowd, the waitress took us right to a table perfectly-positioned next to the railing separating the restaurant from the river. In front of us, a family left the eatery by way of their boat. We sat there for hours eating a much-deserved dinner, drinking wine, and watching the boats cruise by and the lights across the river.

Leaving, we (finally) hopped in an Uber. We looked out the windows, reliving our journey, the whole ride back.



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