A Silver Anniversary Surprise: Celebrating In The Heart Of Chicago
How a spontaneous city break created unforgettable memories for two Scots abroad
My wife, Fiona, and I began dating in late 1996, and although we’re both Scottish, we chose to get married in Las Vegas, Nevada, back in 2000. Now, after nearly 29 years together and 25 years married, I wanted to find a special way to celebrate our silver wedding anniversary and show just how much our relationship means to me. I decided that a short city break, using our HGV Max membership, would be the perfect surprise.
We use our membership for our main two-week family vacation each year, taking advantage of the many options Hilton Grand Vacations provides. However, this trip was something different; it was a short getaway. Because our adult daughter requires around-the-clock care due to her disability, I made arrangements with my wonderful in-laws so I could focus on planning the surprise. The next step was choosing our destination. Las Vegas initially came to mind, but since we spent a week there celebrating Fiona’s 50th birthday in 2022, I decided against it.
Although Fiona and I have been together for nearly three decades, we rarely find ourselves watching TV shows side by side. The exception is live football (soccer); we'll sit together for a match, but not much else. However, for the past 13 years, we’ve always watched NBC’s “Chicago Fire” together. While the show is centered on the fictional Firehouse 51, some scenes are filmed at the real Engine 18 Firehouse. And since Fiona has often said that we have to visit Chicago one day, I knew the Chicago anniversary destination was meant to be.
I reserved a 4-night stay at the Chicago Magnificent Mile, a Hilton Grand Vacations Club where we enjoyed a spacious Studio Suite with a king-size bed. I also booked two 4-day Go City passes, giving us access to all the major tourist attractions and public transportation throughout the city.
Thursday: The airline spoiled the surprise of our romantic silver wedding trip by emailing my wife about a schedule change. We woke up at 3:00 a.m. Scotland time and caught our 6:00 a.m. flight to London Heathrow Airport, then headed across the Atlantic. After 19 hours, we finally cleared U.S. Immigration and Customs.
Check-in was quick and welcoming, and we wasted no time dropping our bags off in the Suite, which had views of the rooftop pool and terrace. We immediately set out to explore and quickly realized everything we could possibly need was nearby: a convenience store, coffee, donuts, sandwiches, bars, restaurants and a pharmacy. Since we had pre-booked a sunset visit to Willis Tower with our Go City passes, we took a stroll along the riverwalk. The views from the Skydeck were breathtaking. Afterward, we used our Go City passes for public transport back to the comfort of our king-size bed, where we happily crashed for the night.
Friday: We headed out for a leisurely walk to the John Hancock Center. After grabbing breakfast on the way, we kicked off our first full day in the Windy City. Amusingly, it wasn’t windy at all. The clear, sunny sky offered incredible photo opportunities. Afterwards, we strolled to Navy Pier, stopped back at our Suite and enjoyed more all-inclusive Go City pass activities including an architectural river cruise.
The impact of European migration on the development of U.S. cities, starting in the early 1800s, is unmistakable to a Scot like me who has extensively explored Europe. Each nationality seemed determined to outdo the others in architectural design, resulting in a vibrant and diverse cityscape. We ended a fantastic day with deep pan pizza at Lou Malnati’s Pizzeria, thanks to a Hilton Grand Vacations discount coupon from our check-in pack. We then enjoyed a relaxing stroll around Millennium Park before heading back to our Suite.
Saturday: We enjoyed another Lake Michigan cruise, this time in a power boat that felt straight out of “Miami Vice.” We also got to experience Flyover Chicago and were thrilled to see the city from a bird’s-eye view. Because of our shared love of football (soccer), we spent the afternoon at Timothy O’Toole’s Pub, diagonally across from the resort and watched the Champions League Final. After, we took another walk and hopped on the famous Loop Train for a ride around the city.
Sunday: Our 25th wedding anniversary! We kicked it off with a relaxing hop-on, hop-off BigBus Chicago sightseeing bus. We stopped at iconic spots like Soldier Field and the Adler Planetarium and visited the real Firehouse 18, receiving an all-access tour from the Chicago Fire Department firefighters, who were genuinely surprised that we’d traveled all the way from Scotland just to see their station. To wrap up the day, we enjoyed a wonderful anniversary dinner at MingHin Cuisine, just across the street from the resort.
Monday: Check-out day. We took one last stroll around the neighborhood and picked up a few souvenirs before heading to O’Hare. Thanks to the Go City passes, we rode the subway for free, which brought us directly to the terminal for our flight home. It was an exhausting but unforgettable trip to celebrate 25 years of marriage.
Read “Whose Idea Was This? The Hilarious Art Of Planning Group Travel” to learn about one Member’s memorable milestone birthday getaway.
Key Takeaways
- Meaningful Celebrations: Choosing a city break can provide a fresh and significant way to mark special milestones or anniversaries.
- Membership Advantages: Hilton Grand Vacations memberships offer flexibility and value, making it easier to plan short getaways filled with memorable experiences, including sightseeing and local dining.
- Coordinating Family Needs: Working with family or trusted caregivers to manage responsibilities at home allows travelers to fully enjoy their trips and focus on making the most of their time away.
- Streamlined Exploration: Sightseeing passes, like the Go City Pass, provide convenient access to major attractions and public transportation, maximizing both time and value during a trip.
- Creating Lasting Memories: Combining stunning views, historic tours, special meals and local culture ensures that each trip is filled with unforgettable moments and meaningful experiences.
FAQs
Q: What attractions are included with the Go City Pass in Chicago?
A: The Go City Pass provides admission to many of Chicago’s top attractions, including the Willis Tower Skydeck, John Hancock Center and Navy Pier. It also covers public transportation, offering excellent value for sightseeing in the city.
Q: How can families manage travel and care arrangements when planning a trip?
A: Families can coordinate with supportive relatives or trusted caregivers to ensure all Members’ needs are met during travel. This allows travelers to focus on enjoying their time together, especially during special occasions.
Q: What dining experiences should visitors try in Chicago?
A: Visitors to Chicago can savor local specialties like deep pan pizza at renowned pizzerias, celebrate with diverse cuisine at popular restaurants and enjoy neighborhood favorites like classic pubs.
Q: What tips can help couples plan a successful milestone anniversary trip?
A: Couples are encouraged to select destinations with personal significance, utilize travel memberships like HGV Max for added comfort and value and plan activities that both partners will enjoy.
