Midwest, Play, Things to Do in Chicago
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Chicago Staycation Ideas: Be a Tourist in Your City

River Boat Cruise
Man and woman wearing masks while on Chicago tour

Along with the rest of the world, we’ve made significant adjustments and cancellations to plans this year. However, even with our big ideas and travel being off the table, we realize that there’s no need to cancel 2020!

So, we shifted focus to quick road trips close to home, being tourists in our beautiful city, and staycations! Adapting has resulted in much-needed refreshment and escapes from the craziness.

Multiple conversations within the family have centered around balancing activities outside of the home with remaining cautious during the pandemic. So we decided that patio dining and outdoor recreation will make up most of our entertainment for the foreseeable future. Fortunately, Chicago offers plenty of both!

Skyscrapers in Chicago on walking tour
Vista Towers

Playing tourists in our city is nothing new. However, my appreciation for everything the city has to offer is more significant than ever!

Chicago presents endless options for designing a staycation. More importantly, businesses have stepped up to the plate implementing procedures for public safety, so we felt confident venturing out.

Where to Stay in Chicago

Crown Fountain at Millennium Park Chicago Tour
Crown Fountain at Millennium Park

Now is an excellent time for planning a Chicago staycation as many hotels have great deals happening. Choose Chicago compiled a list of comfortable accommodations open and ready to host, eliminating the need for lots of research. Our hotel located next to Millenium Park made it easy to get to the destinations on our itinerary.

If you prefer an Airbnb check out this list of the top 12 Airbnbs in Chicago!

Saturday Itinerary

Chicago Architecture Center

We began our Saturday exploring the Chicago Architecture Center, a nonprofit cultural organization whose mission is to inspire people to discover why design matters.

Miniature building exhibit on display at Chicago Architecture Center Tour

There are two levels of exhibits focusing on Chicago’s diverse neighborhoods, housing types, leading architects, future projects, and includes the largest scale model of the city. It was a great prelude to our afternoon walking tour.

Must See Chicago Walking Tour

After exploring the center, we assembled for the Chicago Architectural Foundation’s Must-See Chicago Walking Tour, a fast-paced 90-minute stroll featuring some of Chicago’s most famous buildings, including the Wrigley Building, the Art Institute of Chicago, Willis (Sears tower forever to Chicagoans), and the Chicago Theatre.

Art Deco Style Skycraper on walking Chicago tour
Carbide & Carbon Building: Art Deco Architectural Style

One of my favorite activities is admiring architecture while walking downtown. This tour heightened my appreciation for the magnificent architecture in the city. We learned how to identify various architectural styles, and I’ve been strolling around being a know-it-all ever since, lol! There are so many things hidden in plain sight around Chicago. The buildings that I pass every day I now see differently. I realized that I don’t stop and look up enough, and I’ve missed out on so many details. Dave and I loved the content of this tour!

Man and woman standing in front of theatre marquee during Chicago Architecture tour
The Chicago Theartre

The group max was 6 individuals and required masks for the duration. Our guide was also alert to ensuring everyone kept a social distance. The Chicago Architecture Center offers over 50 different walking tours! Wear comfortable shoes for this activity.

Dinner at Virtue in Hyde Park

We headed to Hyde Park for dinner at Virtue Saturday evening. It was our first visit to the Southern American restaurant from Chef Erick Williams. Both Dave and I felt the cuisine was outstanding. We indulged in mac n cheese, fried green tomatoes, shrimp with grits, cauliflower steak, gumbo, and key lime pie. I don’t regret one calorie, I’ve already created a list of our friends and family to bring back!

Also noteworthy was the warm and hospitable service; overall excellent dining experience!


Absolutely Chicago Segway Tour

I’ve low-key wanted to do a Segway tour for years but never followed through, so I was looking forward to this tour. It did not disappoint! I smiled and laughed throughout and commented several times to Dave how much fun I was having. Absorbing the scenic beauty of Chicago on Segway was a real treat!

Tour guide explaining Buckingham Fountain during Chicago tour

We did Absolutely Chicago Segway Tours’ newest adventure ‘The Chicago Insider,’ which covers the good, the bad, the ugly, and totally weird stories of Chicago.

The 2-hour fun fest incorporated a variety of scenes and interesting facts about the city. Tour Guide Jen was loads of fun and kept us engaged throughout! I’d do this again in a heartbeat. Absolutely Chicago Segway Tours offers several different tour themes. An absolute MUST!

Architecture River Tour

Our weekend of tours continued with the Chicago Architecture Foundation River Cruise aboard Chicago’s First Lady Cruises. This 90-minute cruise is Chicago’s number 1 tour, according to TripAdvisor. It lived up to accolades. There’s nothing like gazing up at Chicago’s legendary architecture while floating in between the buildings. It was magical!

Woman standing on boat with cityscape backdrop on Chicago tour
Chicago Architecture Foundation River Cruise

The docents from the Chicago Architecture Foundation are passionate about architecture, making all of the difference with their tours. The Chicago River Tour should be on everyone’s bucket list! It was the perfect way to cap off our weekend!

I briefly wondered if three tours during the weekend would become monotonous. However, it was far from it. Each offered a varied perspective and insight. Dave and I couldn’t decide which was our favorite as we appreciated something from each experience! I feel you can’t go wrong with either and would even recommend all three in a weekend as we did.

Woman holding cocktail smiling at camera during Chicago Staycation

In Conclusion

Our staycation weekend was much needed and a reminder of why we fell in love with Chicago. Restarting activities outside of our home after the phase reopenings had me a bit nervous initially, so I’m grateful for the health and safety measures businesses put into place. We felt comfortable all weekend. There’s plenty to do around Chicago while remaining precautious and social distancing.

Hopefully, you’ll be inspired to take advantage of this time to be a tourist in your city and plan a staycation!

My weekend staycation itinerary was hosted by Choose Chicago, however, all opinions are my own.

Chicago Skyscrapers on Chicago Segway Tour


  1. You just gave me some new ideas for a future trip to Chicago! I love that city.

    • Flo says

      Great! It’s a gorgeous city with so much to offer!

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