Trip Notes, Back To The Skies: Flying To Chicago On American And United During The COVID-19 Pandemic

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COVID-19 came crashing onto US shores in mid-March with a vengeance. Since then I spent 155 days on the ground through August 2nd.

To a normal human being, that may seem fairly pedestrian, but for those of us blessed with 2 scoops of wanderlust, it felt like an eternity.

I’d snap the streak on August 3rd.

This meme sure seemed apt:

I looked back at my travels since I started blogging here when I turned 20 in November 2004 and couldn’t find a similar stretch of time when I was on terra firma.

Back in February I flew to NYC with Adam Levine, a friend from Cleveland. That was before COVID-19 entered our lexicon or even Italy’s, but it was already making its silent spread and odds are that we both caught the virus on that trip. Oddly enough our family members and friends did not get sick and our wives tested negative for antibodies, which firms up the super-spreader theory for me.

For several months we stayed home as much as possible. The virus never spun out of control in Cleveland as it has some other locations, but it has seen a steady spread. In late May my wife gave birth to our 4th child and perhaps that experience is worth a trip report on its own. After that, we started to venture out with precautions and we did enroll our oldest in camp this summer after doing a risk/reward analysis.

By August, the time seemed ripe for me to get back on a plane. Enough time had passed for us to have data points that made it seem highly unlikely that I would get COVID-19 for a 2nd time, at least anytime in the near future. So I asked Adam, a fellow foodie, if he wanted to fly to Chicago, and he was onboard. Our wives only wanted to know which novel virus we would come back with this time. 😉

Luckily, Ohio managed to stay off Chicago’s quarantine list.

Before the pandemic, American and United flew well over a dozen daily flights between Cleveland and Chicago. Once upon a time, United even flew a daily 747 on the route! Those schedules have been slashed, but tickets are dirt cheap.

I had butterflies in my stomach the night before the flight and had a hard time falling asleep, I was finally going back to the skies and the adrenaline was kicking in. I get a dopamine hit just booking a flight, even if the odds of actually taking it are small…gotta’ love free mileage redeposits!

We were originally supposed to go at 8:30am and return at 10:30pm, but due to flight cancellations we wound up going at 7:20am and returning at 8:20pm.

I hate spending extra time at airports, so I left my house at 6:15am, parked the car at 6:40am, and was going through CLEAR by 6:45am.

CLEAR was fully touchless, thanks to the iris scanner option. They also gave out free 2 ounce bottles of hand sanitizer:

At 6:55am we stopped off at Bar Symon, where I was able to get up to $56 of items for free thanks to Priority Pass. But it was too early to drink and I wasn’t about to shlep a 12 pack of beers through Chicago. Much to the consternation of the cashier, we just got some water and KIND bars, she really wanted us to max out the $56 in spending 😀

Adam was itching to get onboard, but when I saw all of the United planes parked at concourse D, I just had to take a few pictures.

“They’re planes Dan, what are you doing?”

“That concourse has been shuttered for over 6 years, there’s a fascinating history of the concourse and seeing planes…”

“OK, Dan. Do your thing and let’s make the flight”

Cleveland Hopkins Airport is 95 years old and is home to the first ATC tower, the first 2 level terminal design for departures and arrivals, and the first airport to connect a rail system directly to downtown.

Concourse D opened in 1999, built by Continental to expand their Cleveland hub operation. It replaced the rental car facility, which was moved so far offsite that it would make Tel Aviv’s Ben Gurion airport blush.

United merged with Continental and killed the Cleveland hub on 6/5/14. But they were still on the hook for the $1,112,482 monthly rent that Continental agreed to pay for Concourse D through 2027.

I flew my final Concourse D flight on 5/28/14 from Kansas City to Cleveland on a Q400 prop:

Cleveland’s now mothballed Concourse D hasn’t been accessible to passengers since June 2014:

I always liked the paper airplanes on display in the connector tunnel to Concourse D:

For the past 6 years the concourse has been deserted, but thanks to COVID-19, United planes were lined up at the concourse once again:

OK fine, let’s go catch our flight.

The United Club was closed due to COVID-19 and the airport was eerily empty. Signs reminded passengers that they must be masked at all times, unless they were eating or drinking.

Without any large carry-ons I was in no rush to get to the gate until boarding was over, and sure enough we walked onto the plane at 7:05 and the doors were closed a couple minutes later.

I was upgraded to first class, but there was no first class experience to be had on this flight. No drinks or snacks were offered besides for this bag at our seats with some pretzels, water, and a sanitizing wipe.

Social distancing?

Ha! This is United. First class was fully booked.

Everyone was masked and was reminded to remain masked, but when someone sneezed they got a whole bunch of people staring at them.

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After spending a record 155 days on the ground and winning my battle against #COVID19, #ItsTimeToFly Empty airport sure feels weird, but like a fish out of water, I had to get back to the skies!

A post shared by DansDeals (@dansdeals) on Aug 3, 2020 at 4:07am PDT

United Clubs are only open at their hub airports, and we stopped at the Club in Chicago to use the restrooms.

The breakfast consisted of applesauce squeezies and yogurt:

If I’m not traveling then I’m probably on my computer. That meant 155 days of being immersed in the latest depressing news and politics, which was taking its toll. I was excited to get away from it all, even if it was just a refreshing day trip.

We took an Uber to Bond Coffee Collective, a great boutique cholov yisroel coffee shop in West Rogers Park.

When I was last here with my wife Mimi last year, also on a day trip, this place was packed. This time we were the only customers there and we ate outside.

The avocado toast ($8.99), topped with a mango jicama cilantro slaw, is excellent:

Top it off with a butter croissant ($2.49) and a spicy cinnamon mocha ($4.49), yum!

Last year I got the Hummus and Roasted Veggies Toast ($8.99), which was very good:

Mimi had gotten the Bond Breakfast Sandwich ($5.99) last year, which she still raves about to this day:

My Aunt Tova, who runs @MadeJewLaugh, lives around the corner from Bond, so I walked over to say hello and of course, drop off some of the best kosher donuts around:

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Happy national donut day! It may be the nostalgia, but I have never had better donuts than the ones from Unger's Bakery in Cleveland. My two personal favorites are the “cinnamon” – laced with gooey cinnamon and drenched in the perfect sticky white icing. And the “custard”- full of custard and covered in chocolate. There is no skimping on the custard here. Let. Me. Tell. You. The apple fritters are also amazing, but sadly not always available. Tell us where you get your favorite donuts and your favorite flavor (or flavors, cuz let's be real, no one eats just one #donut :)) #nationaldonutday -JJ

A post shared by DansDeals (@dansdeals) on Jun 7, 2019 at 9:40am PDT

My investment in Go Everywhere 2020 passes didn’t turn out so well this year (now there’s an understatement!), but I checked what attractions were open in Chicago. Not much, but they did have 360 Chicago available in the John Hancock Building, so we hopped into an Uber to head there.

In normal times there’s a long line to go up to 360 Chicago, but these weren’t normal times. We scanned our Go Everywhere passes and were taken to a sketchy looking service elevator as the regular elevators were not in service.

At the top we pretty much had the place to ourselves. The views were great.

Willis Tower, formally known as Sears Tower, is the black building on the right that has its peak in the clouds. Its’ Skydeck was also on the Go Everywhere pass, but it was closed on weekdays due to COVID-19.

Chicago’s Navy Pier normally has amusement ride attractions and fireworks, but not this year:

360 Chicago offers an upsell to a Tilt attraction for $8 ($7 with a Go Everywhere Pass) that tilts you 30 degrees down to the street as you hold on for dear life.

Once you’re up here, it’s certainly worth the adrenaline rush to try it out. They don’t allow you to take pictures inside when its in operation, so you’ll have to settle with someone waiting outside the attraction to take a picture unless you want to cough up $30 for their picture.

We walked around the John Hancock Building for a bit before heading to Shallot’s for lunch, where we ate outside:

It’s been a while since I’ve gone to Milt’s and that has always been my go-to place for lunch in Chicago, but they were closed for lunch due to COVID-19.

Adam ordered a margarita, while I had the Godfather. Both were strong drinks, so I was happy not to be driving!

I ordered rice crackers topped with salmon ($16), which are always out of this world, with the perfect crunch, spice, and balance of flavors:

I also had a spicy vegetable tempura ($15), which was very good:

Adam ordered Rumaki ($23), which were excellent:

And he ordered a signature black prime filet with blackened garlic ($60), which was cooked to perfection and bursting with flavor:

For dessert, nothing compares with their incredible Strawberry Shortcake ($16), easily the best version of the dish that I’ve ever tried:

Looking over the rest of the pass activities on my Go Everywhere Pass that were actually open, there were options for a boat tour or an escape room. I’ve yet to be on an exciting boat tour and while I do absolutely love escape rooms, we wanted to do something outdoors as the weather was perfect.

I’ve gone on a Segway tour in Chicago on a DDF DO, but that was 7 years ago, so that seemed like a decent way to spend a few hours. Segways tours that I’ve done in Amsterdam and Paris were the highlights of those trips.

There are tons of Segway operators in Chicago, and many of them have specials for just $45 or so for a 2 or 3 hour tour due to the pandemic.

Originally they told us that nobody else had signed up for the tour, but in the end a local family of 7 signed up as well.

We toured around Chicago’s massive Grant Park, but the space was mostly deserted.

Fountains were emptied so that they wouldn’t attract crowds:

Here is the same fountain on a 2013 Segway tour on a DDF DO:

We moved at a good clip, which was fun as we sped around museums:

Learned about putting ocean water on a train from Florida to fill the aquarium:

Soldier Field:

And some time outs for pictures:

The Skyline is picturesque from the park:

All in all, it’s a great way to spend a few hours outdoors.

Mimi was pregnant when we went to Chicago for a day trip last year, so we couldn’t do Segways. Instead we checked out the impressive kosher section at Jewel in West Rogers Park, reflected at the bean in Millennium Park, and enjoyed some quiet time at the Waldorf Astoria spa:

And then we were off to dinner at Evita Argentinean Steakhouse.

One of my favorite meals of all time was at (now defunct) Asian Restaurant in Buenos Aires. Argentines sure know their meats!

Does Evita hold up to those standards?

Seating is only available indoors. I went here as well with Mimi on our day trip last year and the place was jammed.

Not so much this time:

I started off with a ginger beer, which was excellent.

Mimi and I skipped lunch last year, so we were able to try out some appetizers before dinner. This time Adam and I skipped the apps and went right for the entrees.

Heavenly onion rings ($11), were available last year, but were not on the menu this time around. Too bad, as these were insane!

We also ordered very good Empanadas ($18) last year:

One of the stars of the show was the “small” rack of ribs ($65). These are tender and delicious! They’re brought to the table as a large rack of ribs for 2, but I was able to order them as a single portion both times. It also comes with side dishes included, and the yucca fries were phenomenal in the chimichurri sauce!

Last year we also got the dry aged Bondiola ($85), which was a bit too marbled for our taste:

But this year Adam got the Churrasco Argentino ($58), a 14 ounce butterfly steak which was incredible with the chimichurri sauce:

And no Argentinean cuisine can be had without churros ($14). Evita makes an awesome hot cinnamon bowl with ice cream inside:

We left Evita at 7:20pm, an hour before our flight to Cleveland and were at O’ Hare by 7:47pm. There was no line at Pre-Check, so there was even time to go to the Admiral’s Club, which I have access to by being a free authorized user on someone else’s AA Executive card. However despite the AA app showing the club was open until 8:30pm, it was closed when we got there.

The flight was mostly full in coach, but I was upgraded to first class and there was nobody else in my row.

Announcements about keeping your mask on were made continuously throughout the flight and flight attendants walked up and down the aisle to police it much stronger than on United.

American actually asked what I wanted to drink, rather than having to proactively ask on United.

Normally there would be a snack basket, but that was not available due to COVID-19.

It was an epic day trip and it felt good to make it back into the skies and escaping for a day, even if it meant traveling with more precautions. I’m not ready to travel with my family yet, but I can’t wait for things to go back to normal!

We were back home by 11:20pm, stuffed and exhausted, but thrilled that we went. Adam said that it was an epic trip, but where are we going next?

Good question!