Duo Travel

Chancing it in Chicago

My last plane trip of 2020 was to visit my boyfriend in Chicago from March 13-17. It will most likely be my last plane trip of the year and boy was it a strange experience. The airports were far less crowded than usual, many shops were closed and overall, people were being more mindful of hygiene by using hand sanitizer and cleaning seats off with cleaning wipes.

This weekend visit was to be chock-full of St. Patrick’s day celebrations, but the rise of COVID-19 had other plans. Prior to traveling there, I was aware of the potential pandemic, but I remained skeptical. It was not until my weekend in Chicago that I had a sudden change of heart.

The usually booming and energetic city was deserted. I have been to Chicago nearly a dozen times and have never seen this city come close to resembling a Ghost Town. It was eerie and caused me to reassess the situation. There was no traffic on the roadways and there were no crowds in the city. Many people canceled their travel plans and locals were minimizing their time in the city as well. The Patty’s day festivities, such as dying the river green, were cancelled. Luckily the travel changes allowed me to book a splurge hotel at a reasonable price.

Chicago Athletic Association

Due to the pandemic, our stay at the Chicago Athletic Association was quite reasonable. The hotel offered decreased room prices, so I decided this trip was the perfect time to stay at the CAA, which normally would be priced as a splurge. It was worth every penny and I can see why the rates are usually high.

Further into the post I will write about the amenities, but let me say that there was no better place in the city to be stuck inside during a pandemic, because the hotel has a lot of entertainment.

From the rooftop of our hotel we could see that the Cloud Gate, better known as the bean, was blocked off to prevent any gatherings. We only saw a few couples here and there wandering around the perimeter of the bean. Otherwise, the popular attraction stood in solitude.

Pandemic Memory

We had an apocalyptic experience one day when Zan was driving us to a local restaurant. While waiting at a red light, the man in front of us started honking his horn at the car in front. He yelled out the window, “RUN THE RED LIGHT, THE WORLD IS ENDING.” When the light turned green, he whipped around the front car and took off like a bat out of hell running red lights through several intersections up ahead. Fortunately, there were no accidents, the roads were that empty.

Chicago Athletic Association Amenities

At this point, early in the trip I was taking the pandemic very seriously. We took our time exploring the hotel, which had a grandiose staircase. Another enjoyment was Fairgrounds Coffee & Tea on the first floor where we had our morning fix of caffeine and some afternoon sweet treats.

The Chicago Athletic Association had a few bars, one of which sported a game room with board games, pool, and shuffle board. I beat Zan at checkers 3 out of 5 times and he beat me at pool (barely), despite an unbelievable trick where I pocketed 2 balls at the same time! We had some delicious drinks and fried pickles during our game day too.

We also used the hotel’s enormous basketball court to shoot some hoops. We played a game of horse, but being that Zan is a skilled basketball player, I was smashed. It was great exercise and the hotel amenities were the best entertainment we could want.

Foodie Adventures

Our other prominent activity outside of hotel games was food, which we often ordered to-go and ate back at the CAA.

Day 1 we had the butter crust pizza from Lou Malnati’s, a place I must eat at every time I’m in Chicago! They have delicious Chicago style deep dish pizza!

Another local must, in my opinion, is to eat an Italian beef sandwich or two.

He took me to a place I’ve never been, a local hole-in-the-wall, a mom and pop treasure called Bombacigno’s to order some absolutely delicious Italian Beef sandwiches. A good foodie knows that the best restaurants usually are not touristy, but rather local treasures.

One exception to the touristy restaurant “rule” is Portillo’s, a very popular Italian beef spot I frequent. I’ve been almost every time I venture to Chicago and have never had a lackluster food experience. Portillo’s has a lot of seating and a large parking lot, which is big news in a city that seems to thrive on paid parking. I recommend getting the Italian beef sandwich with a side of cheese fries. It is wildly unhealthy and satisfying.

Additionally, we ate delicious breakfast burrito bowls from Burrito Beach; and satisfying nachos from the Broken English Taco Pub–home of the vibrant mural pictured.

Finally, we drank some indulgent adult beverages and one of my favorites was the Milkshake Martini from Rudy’s Bar and Grille. While there, we also saw 3 guys attempt to complete Rudy’s Famous Challenger Burger consisting of 5.5 pounds of food to consume within 30 minutes. They failed.

We were lucky to have this trip and remain healthy. We weren’t sure when we would see each other again, since air travel no longer seemed like a good idea. The great news is that he has made the road trip to see me twice so far, which has made staying at home a little easier on me. I wish you all health and happiness!

xo Rae xo