Chicago à deux: Explorations in the Windy City

As my daughters get older and find their own interests, activities, and life outside my orbit, I’ve been trying to focus more on my relationship with my husband. Too often it is easy to let life roll along, day in and day out, a kiss goodbye in the morning, a brief chat over dinner, but nothing that really brings us together sans kids. Recently I had a business trip to Chicago for a Tourism Ireland event. But airfare was crazy expensive for the direct one-hour flight (too bad I didn’t know about this hack). So I opted to take the train. But the train has its own drawbacks- namely a less than 50% on-time performance. Which meant traveling in a day early to guarantee I wouldn’t miss the event. As Doug had just finished a large project for a client and would be able to work remotely for a few days, I convinced him to join me on the excursion to explore Chicago à deux.

Riding the Rails

Chicago Bound the girls were still nestled in their beds when Doug and I left our house in the suburbs of Des Moines to catch the California Zephyr in southern Iowa. As I watched the Amtrak app the train would vacillate between on-time and delays that stretched to 45 minutes. Not too bad, considering some of the horror stories I had heard. Once on the train and seated in the very comfortable and roomy upper coach seat I may have vowed to include more train travel in my future. Reclining with the foot rest raised and the seat back lowered I settled in for a bit of reading as Doug, ever diligent, opened his tray table, set up his laptop, and connected to a few conference calls. The seven-hour ride was only slightly longer than driving ourselves and we arrived relaxed, any work for the day completed, and ready to see Chicago – without the kids!

Explorations in the Windy City (thanks to CityPASS) we didn’t have to search for activities to keep up occupied. This handy booklet includes VIP or Express entry to 5 of Chicago’s top 7 attractions. And while the attractions looked very similar to those we would visit with kids, our time at them was anything but. We began with an evening visit to Skydeck Chicago, atop Willis Tower. I may have held tightly to Doug͛s hand as the elevator rocketed us to the 103rd floor. Once there we were able to leisurely take in the 360° views before lining up for our turn on The Ledge- glass boxes that extend out from the building. It’s s a bit more terrifying that you may think! After tackling that feat of bravery- no small thing when you’ve a fear of heights- we set out to find Chicago͛s most popular meal: Deep Dish Pizza. The doorman at our hotel recommended Lou Malnati’s Pizzaria. Opinions on Chicago Deep Dish are strong, but, as a person who prefers a thin, cracker-type crust, I really liked the deep dish Buttercrust. It held up well against the heavy load of meats, cheese, and sauce, without becoming soft. While my husband opted for a hearty red wine with dinner, I enjoyed my beverage as dessert. Behold: the Tiramisu Martini.

Day two delivered a picture-perfect Midwestern day. Clear azure skies met the cyan hued water of Lake Michigan, inviting us to spend more time outdoors than in. For the sake of time we opted for a cab ride to begin our day’s explorations at the Field Museum, though, if given a second chance, I would have chosen to hire one of the Divvy Bikes. With stations all along the riverfront, this would have been a wonderful ride. We took our time today, wandering through a tattoo exhibit at the Field Museum before enjoying the antics of Beluga Whales and penguins at the Shedd Aquarium. With no children in tow we could leave without seeing absolutely everything- a welcome reprieve in these notoriously busy spots! Our walk through Grant Park was leisurely, with detours to look more closely at interesting architecture and the still empty Buckingham Fountain, before returning to the pathways closer to the lake.

Of all the sites we visited we spent the most time at the Art Institute of Chicago. Spread through four buildings there is truly something for everyone here. The majority of our visit was spent in the galleries of Medieval and Renaissance Art, as well as the Arms and Armor collection. Days would be necessary to explore everything on offer here, so we settled for a few galleries and a light snack in one of the cafes before venturing out again. A beautiful day in Chicago brings everyone out- even if it is midweek. Millennium Park, home to the famous Cloud Gate sculpture was thrumming with activity. We snapped a quick selfie with ͚the Bean͛ as we passed through the park, heading back toward the Chicago River and our hotel on Michigan Avenue. This evening I had an event to attend, which left Doug to work in peace. As a self-employed IT contractor there is always work to be done and a few hours apart was a nice break.

We enjoyed the last attraction in our CityPASS booklet, 360 Chicago (the John Hancock Observatory), at 10pm. The elevator to the 94th floor is said to travel 20 miles per hour, and the views were, in my opinion, better than from the Willis Tower. While we didn’t try TILT, which actually leans out over Michigan Avenue, we did enjoy a drink at the Architect’s Corner Bar. Thankfully Chicago had given us a perfect day because our final day in the city was chilly and wet. So, of course, we took a river cruise! The Chicago Architecture Foundation river cruise aboard First Lady Cruises is really the best way to view and learn about Chicago’s interesting buildings. Elaborate Historic Revival and Art Deco buildings from the first part of the 20th century were more interesting to my eye than the Modern and Post Modern buildings of the later part of the century, but all were interesting when our onboard docent shared the little-known stories behind them. Walking back to the hotel to grab our suitcases we debated on where to eat. Knowing time was short we opted for Foodlife in Water Tower Place. An ͚urban hall͛ with 14 different kitchens the options were nearly overwhelming! Meals are ordered at each kitchen and added to your individual ͚reCharge͛ card. Both the quality and quantity of the food was impressive.

Jody Halsted is a Midwest based freelance writer for outlets like, Holiday Inn, GoRVing, and Minitime. Passionate about all things Irish, Jody publishes Ireland Family Vacations, where families can find exceptional advice for a magical Ireland vacation, as well as travel planning services and Ireland itineraries. Read more of Jody’s work at Jody would like to thank CityPASS and the Chicago Architecture Foundation for hosting some of her Chicago activities.

9 Comments on "Chicago à deux: Explorations in the Windy City"

  1. awesome place and you shared amazing things about that place. its really enjoyable and stunning photos you shared.

  2. It looks that it is an amazing place to visit and have lots of fun, thanks for sharing this post with awesome photographs.

  3. Chicago is really a nice place to explore its every nook and corner, and these photographs are really awesome, thanks for sharing this post.

  4. I loved the last photograph most, very nicely taken and foremost a well-written post, thanks for sharing this post.

  5. This is a very fabulous blog. Really I like very much. This is so wonderful and nice pictures all. Thank you so much.

  6. What a perfect way to spend a day in Chicago … deep dish pizza, a chrome bean, and one of the most amazing skylines in America? Sign me up!

  7. Nice story. it is an amazing place to visit

  8. very nicely taken and foremost a well-written post, thanks for sharing this post.

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