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Traveling in 2020 : Chicago 1.0

Traveling this year has not been what any of us travel lovers envisioned. We've cancelled trips, had trips cancel on us, lost deposits, we've missed planned milestones, and so much more. The first part of this year we cancelled or called off five trips and, for awhile, we thought this 4th of July trip would be 6th on the chopping block. After lots of deliberation, fact checking, and confidence in our ability to travel safely, we kept the trip. I'm so glad we did.

I first visited Chicago with my sweet Dad when we attended the annual NRA (National Restaurant Association) show - we made it a tradition and 2020 was the first year in almost 5 years we didn't make it. On that first visit, I fell in love. I'd traveled overseas, been to NYC, but nothing compared to Chicago. The people, the views, the food, the vibe - the laidback city feel. When I met B and found out he had a similar love of Chi town - well, it was meant to be. I often get comments and "advice" about how dangerous Chicago is and why would I love it. This makes me so sad - these comments are usually from people who have never visited and only read news stories highlighting crime or from people who haven't ventured very far from their airport or hotel.

Every major city has flaws, has crime, has places you probably shouldn't go as a visitor or at certain times. To let those things rule your travel experiences is to snuff out a world of culture and magic. Don't let fear run your life, my friend. Each day is a gift.

Now... to the new way to travel!


For our direct flight from McGhee Tyson Airport (Knoxville) to Midway International Airport (Chicago), we flew Allegiant. Allegiant announced last year they would be offering direct flights to CHI in 2020 so that has been something we have looked forward to since we visit Chicago often. Compare almost $300 for one round trip ticket flying AA/Delta/United into O'Hare to $75 one round trip flying Allegiant into Midway. I found Midway is actually a lot easier to get in and out of + it is closer to downtown than O'Hare.

Allegiant did an excellent job in separating passengers and making sure everyone was wearing a mask and handing out free, sealed masks to all passengers. Each group had a row to themselves - so for two of us, we had two seats together and the third seat was empty. If passengers were traveling alone, they were the only ones in their row.

The flight crew did their best to ask everyone not to crowd each other in the aisles but that was not taken to heart by most passengers. I booked our flights early to ensure we had seats at the front of the plane and could be the last ones on (they board from the back up) and the first ones off. It is a nominal fee to upgrade your seating and, to me, worth it in this current climate if you choose to fly. Beverages and snacks were served, for a charge.


Public transit (especially the CTA) is my favorite way to travel in large cities, hands down. However, much to B's dismay (totally kidding - he hates public trans) we decided to skip it this time. It would have been several times in enclosed spaces with several people and we felt it was smarter this trip to hit pause. We did take a handful of Lyfts and that felt comfortable - drivers and riders are required to wear masks and also encouraged to roll windows down for fresh ventilation.

Chicago is a very friendly walking city so we walked pretty much everywhere - 5-7 miles a day and it was great. We got to see the city the best way possible while getting some sunshine and fresh air.


We stayed at the Kimpton Monaco right off Michigan Avenue. For the price point, you are centrally located within walking distance of many things and the CTA is right across the street. Nothing was majorly different staying in the hotel aside from there was no housekeeping. Some places will provide housekeeping services upon request, but they shared they were not allowed to enter the rooms. However, they were more than happy to bring up necessities like extra towels. The room was very clean and the bed was super comfortable - the decor is very colorful with some fun art and a little throwback to old glamour. There is a lot of city noise, but that's one of the reasons I love Chicago.


If you plan to travel this year, my biggest tip is: MAKE RESERVATIONS. If you want brunch, make a reservation. After dinner drinks? Make a reservation. If you do not have a reservation, your chances of dining where you want may be slim. Making reservations also allows you to pick your preferred seating, like outdoor patios, which are often booked. Many establishments are closing early - unless you see they have updated their hours on their website or social media, call ahead and double check.

Something else to get used to is most restaurants/bars are moving to digital menus so it's a good idea to download a free QR code reader to scan at the table, or better yet, look up the menu online. Some restaurants are charging a small percentage fee (4% or less) to help mitigate the billions of dollars lost in the restaurant industry. Lastly, tip generously - I suggest 20-30% and more, where you can. If you are able to travel during this season, think about those who have potentially been without work for months and are struggling to regain footing.


Again, plan ahead. Make sure the places you want to visit are open, find out what their requirements are, etc. As with dining, make reservations everywhere.

Choose activities that allow you to keep distance and are, preferably, outdoors. In Chicago, the Riverwalk is only open for active (exercise) use from 5am-10am - after that, it switches to passive use for dining, drinks, etc. I made the mistake of seeing this but not really seeing it so I tried to go for a run at 10:30am and the gate was locked. Similarly, B and I made plans to have a nightcap on the riverfront one evening and did not make reservations. The website said 11pm, but in all actuality they closed down at 9pm, some even 8pm due to limited business.


In Chicago, masks are mandatory in public areas. If you enter a store/restaurant/bar, you must have on your mask during the entirety of your experience. If you are dining/drinking, obviously you can take it off while seated but if you are moving about in common areas, going to the restroom, exiting you will need to put it back on.

For outside use, I would say it's about 50/50 - half of the people outside walking/exercising have it on, half don't. Some wear it in more dense areas walking in the street, some don't. The nice thing about being outside is you can distance yourself (for the most part) depending on where you are. For the workout class I attended on Saturday morning, masks were mandatory for the entire time and we were spaced out in the room for plenty of distance and space. I knew this going in so I knew what to expect and I felt safe doing so.

In summary

All in all, the best plan is to overplan - at least the things you really want to do on your trip. Call ahead if you need. Your travel experience will go much smoother if you are prepared. Also, go with the flow - things are changing every day so prepare to have to make last minute changes or possible cancellations. The City of Chicago, like many others, cancelled their annual fireworks show at Navy Pier. Sure, it was disappointing, especially going over the holiday, but we had so much fun doing many other activities and making memories in one of our favorite places.

Lastly, be kind. There is so much hate and judgment and negativity in this world. Support and love each other, even when you don't always see eye-to-eye. Life is incredibly short and not one of us is guaranteed a second. Live your life with joy and abandonment - don't cave to fear and mistruths, but instead be vigilant and smart.

I can't wait to share Part 2 with you later this week to talk about some of the yummy food we had and the activities that made this trip so special!


patty lauren


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