One of my favorite things about traveling is that I almost never have to try to get my steps in. Put me in a walkable city, and before I know it, I’ve logged 15,000 steps without ever feeling like I exercised. Chicago is definitely one of those cities.
I was there for a convention, but every chance I got, I headed outside to explore. Beautiful architecture, parks, Lake Michigan, amazing food, and some of the best public transportation I’ve used made this one of the easiest—and most fun—cities I’ve ever visited without renting a car.
✈️ Getting There
I flew from San Diego into Midway Airport and, after boarding, strapped on my Firefly Recovery devices. This was my first test to see how they’d handle a full travel day. Between flying, dragging luggage, conference sessions, and thousands of steps, I expected to be sore. Surprisingly… I wasn’t.
https://youtube.com/shorts/VrexGEjtshc?is=vlPn3dGFyXcT80wr
I’m still testing Firefly, but it’s definitely earning a spot in my travel bag.
🚆 Skip the Rental Car
One of my favorite discoveries? Chicago’s “L” train. After landing at Midway, I simply followed the signs to the Orange Line, and for just a few dollars, I was downtown and within walking distance of the Hilton Chicago.
https://youtube.com/shorts/T7vlu5iOJ74?is=JG1uXZuhwGsIq5PC
Easy. Affordable. Air-conditioned. Done. If you’re comfortable using public transportation, I’d skip the rental car altogether.
🏨 Hilton Chicago
The Hilton Chicago was the perfect home base. My room overlooked Lake Michigan, had plenty of room to spread out after conference days, and—something I’ve never seen before—two bathrooms!
https://youtube.com/shorts/A4zC73V1oew?is=2ghASsX6HA81nEh4
As many of you know, I like to keep moving while I travel, and the Hilton made that easy. The fitness center has everything you need: cardio equipment, strength machines, free weights, and even an indoor jogging track.
https://youtube.com/shorts/n7dtHR8tPBE?is=Sqb3ZYYWMZ6B45_z
Then there’s the pool… Three lap lanes, two wonderfully warm whirlpools, and massage jets that felt amazing after spending all day on my feet.
https://youtube.com/shorts/zcmDG5eSvu0?is=EnjCgk-bb9x1XQIu
👟 The Best Way to See Chicago
Here’s my biggest piece of advice. Walk. Seriously. One afternoon I wandered from the hotel through Grant Park and along Lake Michigan, stopping whenever something caught my eye. Gardens. Fountains. Public art. Beautiful skyline views. Every few blocks there was another photo waiting to happen. Before I knew it, I’d sailed past 10,000 steps.
https://youtube.com/shorts/9Hn-fvTZYKo?is=ailg5RVI8kovd8s-
That’s one of the reasons I love travel so much. Sometimes the best workout isn’t in a gym—it’s simply exploring a beautiful city.
🍽️ Tapas with Friends
One evening, several of us shared dinner at Café Ba-Ba-Reeba, and it ended up being one of my favorite meals of the trip. Instead of ordering individual entrées, we shared tapas.
Warm goat cheese with tomato sauce and crusty bread, Stuffed mushrooms, Seafood paella, And my favorite—a beautifully cooked steak that arrives hanging from a metal rack before being carved at the table.
Everything was delicious, but what made the evening memorable wasn’t just the food. It was the laughter around the table. Those are the meals you remember.
⚾ A Chicago Ballgame
No visit to Chicago feels complete without catching a baseball game, so one evening a group of us hopped on the “L” and headed to Rate Field to watch the White Sox. One more reason I loved Chicago? The train dropped us off just a block and a half from the stadium. No fighting traffic. No paying for parking. Just a short walk to the ballpark.
https://youtube.com/shorts/AGm6JOJy4c4?is=Ul7MUOvp_2y2HToZ
I’ll admit it—I wasn’t there because I’m the world’s biggest baseball fan. I was there for the experience. There’s just something special about sitting in a ballpark on a warm summer evening, cheering with thousands of fans, and soaking in the energy of the city.
And of course… the food.
I fully leaned into the ballpark experience and tried a little bit of everything: a bratwurst, a churro, and a classic Chicago-style hot dog—which is a must if you’re visiting the city. A true Chicago dog comes on a poppy seed bun with mustard, chopped onions, bright green relish, tomato slices, a pickle spear, sport peppers, and a dash of celery salt. One important rule… absolutely no ketchup!
One of my favorite parts of travel is saying yes to experiences I might not normally do at home. Sometimes it’s a museum. Sometimes it’s live theater. And sometimes it’s spending a summer evening at a baseball game. Whether you’re a baseball fan or not, I’d recommend catching a game if you’re visiting during the season. It’s a fun—and very Chicago—way to spend an evening.
🎭 The Highlight of Chicago
If you’ve followed WanderLyn for any length of time, you probably already know what’s coming… Go see Drunk Shakespeare.
https://youtube.com/shorts/MOISB28QP3U?is=PS4dPCRIfbh0LcLk
A few colleagues and I caught the city bus over one evening, and it was hands-down the funniest show I’ve seen in years. The actors are incredibly talented, the audience becomes part of the performance, and somehow Shakespeare and complete chaos work perfectly together.
We laughed until our cheeks hurt. I think we all need more nights like that. Life gives us enough responsibilities. Make time for fun.
🚉 Heading Home
Getting back to Midway Airport was just as easy…well…almost.
https://youtube.com/shorts/Z7vczYjBjQU?is=8jIALeQdd6I0kmh0
I confidently boarded my train and then realized I was heading in the wrong direction. Totally my fault. More than one train serves that station, so make sure you’re paying attention before you hop on.
Luckily, I had plenty of time. I simply got off, caught the correct Orange Line train, and continued to the airport. Even with my little travel blunder, I’d take the “L” again in a heartbeat.
✨ Final Thoughts from WanderLyn
Chicago, you were such a joy.
From long walks along Lake Michigan to wandering through the city streets, hopping on the “L,” sharing incredible meals, and laughing until my cheeks hurt at Drunk Shakespeare, this trip was everything I love about travel.
I found myself logging 15,000 steps a day without even thinking about it. No treadmill. No plan. Just curiosity, movement, and a beautiful city inviting me to explore. That’s the magic.
So lace up those comfortable shoes, trust your sense of adventure, and step outside. The best experiences are often just around the next corner.
Until next time…
Eat well. Move well. Wander well.
Lyn @ WanderLynTravel
Follow along on social media @WanderLynTravel
No comments:
Post a Comment