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Chicago for Couples: Explorations in the Windy City

Last Updated on January 5, 2020 by Jody Halsted

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.

Chicago for Couples

Recently I had a business trip to Chicago for a tourism event. The airfare was crazy expensive for the direct 1 hour flight, 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.

Amtrak to Chicago

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.

Roomy seats on Amtrak to Chicgo. Photo by Jody Halsted, Halsted Enterprises, Inc.
Not as quick as flying- but much more comfortable!

The 7 hour ride was only slightly longer than driving ourselves and we arrived relaxed, work for the day completed, and ready to see Chicago- without the kids!

View of Chicago as Amtrak train arrives. Photo by Jody Halsted, Halsted Enterprises, Inc.
Riverfront view as Amtrak arrives in Chicago.

Chicago Explorations for Couples

Thanks to CityPASS we didn’t have to search for activities to keep us occupied. This handy booklet includes VIP or Express entry to 5 of Chicago’s top 7 attractions.

CityPASS Chicago Photo by Jody Halsted, Halsted Enterprises, Inc.
See Chicago’s top destinations with CityPASS

Day 1

While the attractions we visited 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 Doug’s 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.

Willis Tower- The Ledge- 103 floors straight down. Photo by Jody Halsted, Halsted Enterprises, Inc.
Doesn’t look like 103 floors to the bottom, does it?

It’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 Chicago’s 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.

Buttercrust Chicago Deep Dish Pizza at Lou Malnati's. Photo by Jody Halsted, Halsted Enterprises, Inc.
Buttercrust Chicago Deep Dish Pizza at Lou Malnati’s.

While my husband opted for a hearty red wine with dinner, I enjoyed my beverage as dessert.

Behold: the Tiramisu Martini.

Tiramisu Martini at Lou Malnati's. Photo by Jody Halsted, Halsted Enterprises, Inc.
Dessert in a glass

Day 2

The next morning 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.

perfect spring day in Chicago. Photo by Jody Halsted, Halsted Enterprises, Inc.
A perfect lakefront day in Chicago for couples!

For the sake of time we opted for a cab ride to begin our day’s explorations at Chicago’s Museum Campus, 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.

Not using a CityPass?
Read the Things I Wish I Had Known Before Visiting the Field Museum

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!

Beluga Whales at Shedd Aquarium. Photo by Jody Halsted, Halsted Enterprises, Inc.
Beluga whales greet visitors at Shedd Aquarium

Our walk through Grant Park was leisurely, with detours to look more closely at interesting architecture and the (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.

Arms and Armour at Art Institute of Chicago. Photo by Jody Halsted, Halsted Enterprises, Inc.
History and art at the Art Institute of Chicago

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 Bean’ as we passed through the park, heading back toward the Chicago River and our hotel on Michigan Avenue.

selfie at the Bean in Millennium Park, Chicago. Photo by Jody Halsted, Halsted Enterprises, Inc.
Obligatory ‘Bean’ selfie

This evening I had an event to attend, which left Doug to work in peace. When you are self-employed 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 (in the former John Hancock building), 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.

Chicago at Night from 360 Chicago . Photo by Jody Halsted, Halsted Enterprises, Inc.
Chicago at night from the 94th floor

While we didn’t try TILT, which actually leans out over Michigan Avenue, we did enjoy a drink at the Architect’s Corner Bar.

Chicago CityPASS

Day 3

Thankfully Chicago had given us that 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.

Raised Drawbridge in Downtown Chicago. Photo by Jody Halsted, Halsted Enterprises, Inc.
Raised drawbridge and Chicago architecture

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 had fascinating stories shared by our on-board docent.

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 hall’ with 14 different kitchens, the options were nearly overwhelming!

Options at FoodLife at Watertower place. Photo by Jody Halsted, Halsted Enterprises, Inc.
Just a few of the options available at Foodlife at Watertower Place

Meals are ordered at each kitchen and added to your individual ‘reCharge’ card. The card is scanned, and payment taken, as you leave. Both the quality and quantity of the food was impressive.

Soon enough we were at historic Union Station awaiting our train and a return to family life, this couples getaway complete- but a resolve to include more couple’s travel firmly in place.

Find Your Perfect Getaway in the Windy City
in one of these Chicago Neighborhoods

Great Hotels in Chicago for Couples

When you visit Chicago without kids you can splurge on great hotel rooms!

Try an Executive Club Level room at the Westin Michigan Avenue. The rate includes wifi (a necessity for us), continental breakfast, and evening hors d’oeuvres, which make the extra fee nominal.

Executive Club Level room at Westin Michigan Avenue

Though our room had no view, the king size bed was comfortable, and the inclusion of a couch with stacking tables made a terrific second work station for me.

Read Reviews for Westin Michigan Avenue on Trip Advisor

Just a couple doors down, the Hilton Chicago/ Magnificent Miles Suites are simply wonderful.

The 1 bedroom executive suite is similar in size to the Executive Club room at the Westin, but split into a living area and a sleeping area, it has a more spacious feel.

1 bedroom Executive Suite at Hilton Chicago. Photo by Jody Halsted, Halsted Enterprises, Inc.
1 bedroom Executive Suite at Hilton Chicago

Add Executive Lounge Access for evening hors d’oeuvres, premium breakfast, and beverages throughout the day.

Read reviews for Hilton Chicago on Trip Advisor

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Travel tips for a couples getaway in Chicago

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