How a Business Trip to Chicago Became the Trip I Looked Forward to All Year
When I first started traveling to Chicago on business trips, I was thrilled. Finally, a chance to spend time in and explore one of America’s great cities! This was definitely one of the upsides to traveling for work. The sad reality? I flew to O’Hare, stayed in Rosemont (the village directly adjacent to the airport), and took meetings in only nearby villages. Every night, I ate at the same restaurants, all of which were conveniently located along my meeting route. After 4 or 5 trips, I realized I’d never even seen the Chicago skyline up close, much less visited Millennium Park, the Riverwalk, or one of Chicago’s many famous urban neighborhoods. Could I even really claim that I’d been to Chicago?
The view I’d somehow never seen. The Chicago skyline from Lincoln Park.
Photo: SeanPavonePhoto / Adobe Stock
The Questions I Ask Before Booking Anything
Back then, my priorities were time efficiency and convenience. In, out, no time wasted. But after too many trips where I rushed from a flight straight into a meeting (often changing in the taxi on the way), arriving home more tired than when I’d left, and never really learning anything about the place I was going, I started to ask myself if I had it backwards.
What if these work trips were an opportunity to be time efficient, just in a different way? What if I could show up rested instead of rushed, and arrive home caught up instead of doing double the workload? What if I could plan for my rare weekend off to happen while I was away and take in some sights instead of passing out on my sofa, too tired to even enjoy being home?
This is how I first learned that there’s a difference between what a traveler wants and what they actually need. Nowadays, among the first questions I ask, before dates and budgets and locations, is: “What’s most important in your life right now? Is something missing? If this trip could do anything for you, what would that be?”
The Business Part: Rosemont, Done Right
The practical logistics for my Chicago business trips were relatively easy. The InterContinental on River Road (which has since been taken over and re-branded as Loews) was walking distance to my main work event, had a restaurant with your choice of a made-to-order breakfast or a decent buffet, and was close to several very good restaurants. Rooms came with a desk which made work easy, had very comfortable mattresses & pillows, and were usually quiet at night since the hotel catered to business travelers. It didn’t hurt that it allowed me to bank points with one of my preferred hotel brands but, to be honest, that was the least important factor for me. Comfort and convenience won out, especially when my work trips needed to move from draining to rejuvenating.
Meals to Remember
The food in Chicago is famously hearty, comforting, and generously portioned. Finding great food wasn’t difficult, even if my main qualifiers at the time were ‘walking distance’ and ‘edible’. From an on-site steakhouse that first introduced me to a Delmonico steak drizzled in aged balsamic and staff that remember my name and favorite menu items (thank you Capital Grille), to what is still my favorite Mexican restaurant in America (and I’ve lived in Arizona AND California), Rosemont crushed it in the food category. I have many fond memories of post-show meals with my suppliers and the conversations that connected us beyond the business we did together.
The Year I Extended My Business Trip
After a handful of perfectly acceptable and efficient work trips to O’hare (I had to stop saying Chicago—it felt like a lie), I decided it was time to do something that felt like a real splurge: extend my trip. I kept it simple that first time: I showed up a day before my meetings and stayed a day later. My priority was to find some time to rest so that I went home feeling better than when I’d left. It felt like a selfish decision, and I almost talked myself out of it several times, but I eventually pulled the trigger and made the booking. Thinking back on it, I’m pretty sure the one person who needed convincing was myself.
The Follow-Up Morning (Why the Extra Days Are Part of the Work)
What made the decision easier was that these trips involved hours of post-meeting follow-ups, paperwork, and emails which could be done from anywhere. Why not do them in a peaceful hotel room, free from distractions? When I rushed to return home before taking care of them, I had to balance that workload with unpacking, household stuff, and the everyday work tasks that constantly knocked on my office door.
Handling it from my hotel ended up being more efficient in several ways—the details were fresh, I wasn’t exhausted from the madness of O’Hare, a 5-hour flight, and passing through Canada Customs and, of course, no distractions! I recall enjoying room service and a mid-day nap. It was almost as good as a trip to the spa. Any guilt from taking the extra days vanished. This was the new way. Whenever someone expresses reservations on taking an extra day, I tell them: “Self-care isn’t selfish, and it benefits more than just you.”
Moving Downtown: Actually Seeing the City
The next time I went to Chicago was an opportunity to take it to the next level. What if I stayed downtown for a couple days? I could arrive a couple days early and commute to my meetings from downtown on the last day. It was a radical thought. Going from a 10-minute walk to a 1+ hour drive or a 90-minute train ride? Taking a whole day or two off to explore? Splurging on dinner at a 3-Michelin star restaurant (because I loved food, so why not)? Looking back, this trip felt like quite the adventure, and it’s not like I hadn’t been traveling internationally for years. But something about it was different.
This time, I was traveling with my sister, and one of us had the crazy idea to stay on a boat. In a marina. In the winter. Okay, maybe it wasn’t quite the dead of winter, but it was definitely cold. The boat was cozy and charming, but it was also made of wood, so we turned off the space heater every time we left and huddled in blankets when we got back until the cabin warmed up.
Taking a work call from the boat.
We walked from the marina to the Field Museum, found new restaurants by wandering the streets and following our noses, and stumbled upon an oysters-and-jazz joint down a set of stairs. We ate at Alinea, considered one of the best restaurants in the world at the time. It was a magical experience, somehow made even better by sharing a burger afterward. On our meeting day, we took the train to Rosemont, just like locals. I’d finally visited Chicago, and it was a trip I’d never forget.
Heading Home Rested
These little changes, made over time, started to ease the effort of travel and turn work trips into something I could enjoy again. My flights home became a chance to breathe and enjoy an in-flight movie instead of madly catching up on emails or reviewing my show notes. I was making memories and exploring what made a place unique (one of the side benefits I used to enjoy about my work but that had disappeared as I got more & more busy). I began to plan my flights around a late hotel checkout and a rush-hour-free arrival. And, most importantly, I arrived home rested and ready to kick ass.
Why It Became An Annual Ritual
It didn’t take long for this to become an annual trip that I really started to look forward to. Each time, I discovered a new way to make it even better, sometimes adding on a show, finding a hot new restaurant, or picking a new neighborhood to explore. My annual trip to Chicago became the highlight of my year: a chance to get curious, creative, and rested. I still frequented my favorite Mexican restaurant (the fabulous Maria’s in Rosemont) and started inviting others to join me on my extra days. This regular work trip went from something that was blending together in my memories as a never-ending cycle of ‘always the same’, to a source of wonderful shared experiences and treasured moments.
Small Things That Add Up
As usual, it’s the little things that end up making all the difference:
Choose your hotel for comfort and quiet. Read reviews with those in mind, and call ahead to ask about construction or large group bookings that could slow down breakfast service or add nighttime noise.
Request a room with a real desk, and ask about early check-in or late checkout to make your arrival and departure easier.
Schedule flights to avoid rush hour instead of arriving just in time for a meeting. It removes stress before and during the trip.
Make a few reservations, then leave room for exploring. It’s the right balance of structure and freedom.
Plan a morning for follow-ups and phone calls before you leave work behind and enjoy the city.
Switch hotels for your personal days to make a clear line between work and personal time.
Check for shows, fairs, or other local events that are scheduled for before, during, or after the trip dates to incorporate some sort of current or cultural activity.
Working With Me
This is just a small part of what I incorporate into every trip I plan, whether it’s for myself, a loved one, or a business client. From getting to know what truly matters to understanding what would delight, a first conversation with me feels more like a coffee between two friends or a call with your long-time executive assistant. From there, I put together a trip brief that outlines the timeline and relevant details, along with initial ideas and prompts for how to take your trip to the next level.
My goal is to handle all of the coordination before and during the trip so you can show up and be present for what really matters, whether that’s nailing your meeting or wowing your partner. For a regular trip to the same destination, I make it my mission to turn each trip into its own unique memory in a way that matters most to you—just like I would for myself.
Do you have a regular work trip that’s starting to feel like a tired old rerun, or travel that has you arriving home more stressed and exhausted than when you left? Give yourself a little extra love by adding just one extra day to your trip, and get clear on what that extra day needs to do for you.
Hint: Pick just one thing.
If you need a little extra help, shoot me a message. I’d be happy to brainstorm with you.
