Anniversary Getaway for Year 33: A Time to Enjoy, Remember, and Dream

We celebrated 33 years with an anniversary getaway to the Windy City. Chicago offered plenty of together-time, brought back memories of past visits, and inspired dreams for the future. Read on to discover ways to spark romance in your own marriage!

Last year, my parents celebrated their 64th wedding anniversary together, here on earth. Today, on what would have been their 65th, they are together in heaven. It’s made me ponder the importance of anniversaries and of marking the years with gratitude. We may not all be lucky enough to make it to 64 years. Whether we hit ten years, the silver 25, the ordinary 33, or the golden 50, our next anniversary together is never guaranteed. And so we celebrate while we can.

Anniversary Getaway to Chicago.

Tom and I tied the knot on April 16, 1988, and 33 years later, we’re still holding tight. Over the years, we’ve celebrated our special day in many ways. Some years it’s simple–with roses, small gifts, and a nice dinner out. Other years, we go big, with a weekend getaway. And a few times, we’ve gone really big, with a trip to Greece (year 17), a cruise to the Caribbean (year 20), and a fling in Zihuatanejo, Mexico (year 30).

The benefits of an anniversary getaway:

Enjoy the Moment: Whether you go big or small, it’s good to step away from the everyday household demands and just be in the moment together. Putting the screens away and just being present can help you reconnect and ignite the flame that burned so brightly on your wedding day. Saying “thanks” to God for another year of life together reminds us of the precious gift we’ve been given.
Recall the Memories: Not only is your anniversary a chance to be in the present moment with your spouse, but it also allows the opportunity to reflect on the past. Remembering past times, whether good or bad, reminds you of all you’ve been through already.
Imagine the Tomorrows: Our anniversary is often a time we spend dreaming together of the future. We speak aloud the hopes and wishes we have for ourselves, our marriage, and our family.

One of my favorite anniversary getaways was our 25th, when we went to a bed and breakfast in Saugatuck, Michigan. I remember going out for dinner to a little restaurant that used butcher paper for tablecloths and left crayons on the table for customers to get creative with. One of us had the bright idea to draw little pictures or symbols of some of the memories of our first 25 years. As one person drew, the other would guess the memory. We drew highlights and things we were thankful for, but also difficult times through which we had come together.

Then we changed it up. “How about we draw some dreams we have for our future?” We continued on. Drawing. Guessing. Talking. Laughing. My only regret is that we didn’t think to take our paper tablecloth home with us. I can’t remember now any of the things we drew on it then. But the memory of our time together, reflecting on the past and dreaming of the future, will last.

An Anniversary Getaway to Chicago

So how did we celebrate 33 years this past weekend, amidst a pandemic and threats of racial riots? We planned a Chicago anniversary getaway! The city is within a couple of hours, so we’ve been there countless times and know our way around. On the other hand, it’s a far cry from the peaceful woods we typically inhabit, so a big city getaway is always exciting, even during a pandemic.

Future-focused.

On this anniversary getaway, we started with some future dreams. We plan to remodel our kitchen at the end of the summer and would like to replace some of our appliances. My sister had told me about a huge appliance store on the north side of the city. It turned out to be all she had said (a huge selection of floor models to look at) and more (we enjoyed their lovely aquarium filled with tropical fish!).

After a nice anniversary dinner at one of my Chicago favorites–the Cheesecake Factory, we headed downtown to find our hotel and parking garage. A little travel tip: when heading into any big city, use a parking app (our favorite is “ParkWhiz”) to book your parking garage ahead of time. You can search for garages near your destination, find the best price, and book and pay for your spot ahead of time. Just make sure you read the reviews, so you don’t end up in the crazy situation like we did a couple of years ago. We laughed as we remembered our past harrowing experience wandering two stories below in the belly of the Chicago.

Our parking garage on Dearborn Street was super easy and a stone’s throw to our hotel. We stayed at the Cambria in the theater district. The hotel was clean with a modern, metropolitan vibe. Even though all of the theaters appeared to be closed due to COVID, there was still plenty of activity in the streets nine stories below that interrupted our sleep. Sirens and traffic noises are not what we’re used to back home in our peaceful woods. Thankfully, we could sleep in with no big plans the next day.

After a leisurely morning, we emerged into the bustling streets. We were only a few blocks away from Millenium Park, so we did what we do on nearly every trip to the city– we checked out “the Bean.”

I don’t know how many times I’ve been to the Bean (officially “Cloud Gate”), but this time was a unique experience. Due to the pandemic, there were barriers preventing people from actually going up to the structure. Seeing this work of art, unencumbered by the crowds of people that usually surround it, was eerily cool. I snapped several pictures, knowing I may never see it this way again. I guess there are some perks to visiting the city during a pandemic.

We strolled up and down Michigan Avenue, noticed a few stores boarded up in case of riots, and were grateful that all was peaceful during our visit. We grabbed lunch at Labriola (very yummy pizza!) before leaving the downtown area. With another look to our future, we wanted to hit a cycling shop north of the city as Tom is considering a new set of wheels before the summer biking season starts. We drove north, admiring the Chicago skyline to the east.

An eye to the past.

As with other anniversary getaways, this one brought back past memories, specifically of our many trips to Chicago. Since we live close, we’ve visited many times as we were growing up, after we got married, and as we raised our kids. In our many visits, we often fell into the rut of doing the same things and seeing the same sights. We would take in a well-known museum or see a show. Walk up and down Michigan Avenue. Visit the Bean. And find some deep-dish pizza.

However, since becoming empty nesters we’ve gotten out of our rut and have explored new sights. After dropping our youngest off for her first year of college, we took the Chicago Architectural boat tour. It was an amazing new view of the city we thought we knew so well. Then there was the time we took our bikes with us and rode the Lakefront Trail. Again, we saw a unique side of the city as we pedaled along the Lake Michigan shore. On another visit (after the parking fiasco), we visited the American Writers’ Museum and loved it.

In the moment, in Chicago.

This year, besides the shopping we had planned to do in the suburbs, we really had no plan. We weren’t sure if sites and stores would be open downtown and weren’t really feeling comfortable spending time indoors around crowds anyway. After our first night downtown, we decided to find a hotel in the suburbs for the second night, saving us the extra cost of parking and hoping for a more peaceful night’s rest.

I found a room at the Renaissance Hotel in Northbrook and noticed it was just five minutes from the Chicago Botanic Garden. This was another new-to-us Chicago attraction and we decided it would be the perfect end to our pandemic anniversary getaway. The Renaissance Hotel was also very modern and comfortable like the Cambria. On the upside, it was quieter but we weren’t impressed with the cleanliness. Oh well…you win some, you lose some.

On Sunday, after joining our church for online worship from the comfort of our hotel room, we drove over to the Chicago Botanic Garden. Being outside, walking through nature’s beauty, and enjoying the fresh air, was perfect for our pandemic pleasure-seeking. The gardens were lovely with spring blooms everywhere. And now we have another spot to add to our “Things We’ve Seen in Chicago” list.

We had a lovely anniversary getaway in the Windy City. Remembering past visits. Imagining future possibilities. But mostly, just being there, sharing the present moment, in gratitude for another year of life together.

If you’d like more information about any of the Chicago destinations above, please leave a comment/question below.

I’d also love to hear your ideas and experiences for anniversary getaways and things to do!

Anniversary Getaway for Empty Nesters: Three Ways to Celebrate Another Year