Testing the Waters: A Quick Trip to Chicago

The past 16 months have been some of the longest and darkest. While Covid-19 spread across the world, the safest and most responsible thing to do was to stay in my 5 mile little bubble where the highlight of my month/week might be a simple trip to the grocery store, hoping that I would be able to secure everything on my list. Sadly, even today, this seems to be a hard thing to do due to the continuing and on going shortages for certain goods. I mean you know it’s bad when people started purchasing the gluten free items due to shortages.

To help ease back into the easy of traveling, I decided I need to visit somewhere that met the following criteria:

  1. Safely open for business, i.e. followed the recommended CDC guidelines due to needing to take into account other individuals risks.
  2. A location that was easily accessible by car and ideally within 4 hours drive.
  3. A location that was close to restaurants that offered GF carryout or access to a grocery store
  4. A location that offered accommodations and activities that were open.
  5. A location that wasn’t going to break the bank and had the potential to use a variety of travel certificates.

After looking at a handful of options, Chicago fit the bill.





View from a WOW suite at the W-Lakeshore

Due to ongoing Covid restrictions, reduced travel, and reduced staff, my go to hotels were not available for booking. Sadly, once the hotels began opening up, the rates were much higher than my existing booking. As a result, I ended up staying at the W- Chicago Lake Shore with a nice upgrade to a WOW suite thanks to a Suite Night Award that allowed me to sit back and watch the Saturday night fireworks over Nay Pier.

The location end up working out based on the activities that I had planned for my short visit; however, I wouldn’t necessarily go out of my way to stay there again for the following reasons:

  1. W’s are hit and miss on the vibe, and in most cases, I don’t fit in with it
  2. For whatever reason, there are some hotels, that have these weird obsession with using a ridiculous number of mirrors in the design/decor
  3. Price, it can run high if you don’t get a low season rate or have points/certificates to burn
  4. . While the furniture appeared new, the bathroom (i.e.  grout/paint) and and one off added details (strips of the something that was once a wall feature had just fallen off/burnt out lights in a fixture) just seemed tired and neglected. Small and petty, but for what you are paying, it’s the little details that seemed off.





Immersive Van Gogh Exhibit

Located at the Lighthouse ArtSpace at the Germania Club, this exhibit was on my must do list during my visit.  Having visited the Borderless Labs exhibit in Tokyo, my expectations were set high, and sadly, they weren’t meet.

The space was setup with socially distanced circles/ a handful of benches to sit on with the exhibit having two large rooms, a balcony overlook, and two smaller rooms. Representations of Van Gogh’s work (Mangeurs de pommes de terre (The Potato Eaters, 1885), the Nuit étoilée (Starry Night, 1889), Les Tournesols (Sunflowers, 1888), and more), would be displayed on the walls of the rooms that had an accompanied musical sound track. This display would be the same in all rooms and continuously loop every 40 minutes.

For the price of the ticket and overall experience, it was a once and done experience.  If you’re one whose looking for content for your social media, this would be right up your alley.

Shoreline Sightseeing Skyline Lake Tour

Thanks to a gorgeous sunny day, I ended up finding my way to a packed Navy Pier and a last minute ticket to a Skyling Lake Tour.

The tour itself set me back ~$27 after taxes; but it offered 40 minutes cruising on an open aired boat listening to a tapped recording while overlooking the Skyline.

If you’re more interested in Chicago Architecture, Shoreline offers an excellent 75 minute tour. If you plan to do this tour, I would recommend pre-booking a ticket around sunset.



During my visit, restaurants were still under capacity and other Covid safety restrictions, so I primarily ended up eating at the same two places because I was able to order in person and take my food back to the hotel and enjoy watching the sunset.

While many restaurants have implemented ordering through Apps, online portals, walk up kiosks, one of the biggest things that is overlooked it being able to callout, request for modifications,  or request extra per cautions for allergies. For this reason, if you have an allergy, you will most likely have to make additional effort to make sure your order is safe as possible.

+  Chipotle – This chain is my go to when seeking out a relatively safe cheap meal. Due to restrictions on their app, I recommend going in person to place your order if you have a gluten allergy.

+Lyfe Kitchen – Once again, this is a chain. Their App and even their in store ordering kiosk had no where you could denote that you had a gluten allergy, so you would need to place your order and quickly grab the attention of one of the employees to explain your allergy and request for them to chain their gloves to avoid potential cross contamination from gluten.



  • Make sure you are aware of any local/state health rules
  • Even before Covid, if there was a museum that you really wanted to visit, you need to make sure to get tickets ahead of time.
  • If you plan on parking a car downtown, use parking apps, such as SpotHero to find and book parking ahead of time. This will save you the frustration of possibly struggling to find a spot due to a busy holiday weekend with a full hotel garage, and who knows, you might even get a cheaper rate!



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Whether it be for work, fun, or just every day normal life, I always seem to be on the go. While living life out of a suitcase, I try to make the most out of my business trips and explore wherever I happen to be. From sampling the local cuisine, to getting lost and finding places I never might have found. I continue to check off and add to my ever growing bucket lists. While not on the road, I like to try to catch up and explore all that Indy has to offer.

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