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.


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:


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!

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

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Great TR, a glimpse at better times to come!
And an AA flight that wasn’t delayed!

I saw Kaminski Park from the sears tower

Great report. Chicago is one of my favorite places. Next time check out the architectural boat tour by navy pier


So interesting! I love these posts!


Thanks dan!
I’m taking my kids for the day tomorrow from MCO to EWR on UA, just to be back in the air and use my DoorDash credit (No kosher options in NE Florida), so it’s great to know what to expect.

Good Vibes

Great TR.


Great review of the restaurants Elan, ehm… I mean Dan.


I had the exact opposite experience last week united was very strict about their masks and even came over to my daughter to make her pull it over her nose and on american they made one announcement at the beginning of the flight and during the course of the flight a number of passengers had their masks on their chins and there was no enforcement so it probably depends on the flight crew.
I also flew chicago Cleveland in american first class and every seat was taken. They will sell every seat if they can,they just happened not to in your case. Coach was half empty on that flight and they announced that anybody that wants to can change seats for social distancing purposes.originally the back half was full and not the front half but after that announcement slot of people moved up to the front half.
Alaska airways in my experience was very into their social distancing.besides keeping all middle seats open they also proactively changed people’s seats to give as many people as possible their own row of seats.

My experience

I flew with AA from JFK to Miami last week and the flight crew was very makpid that I pull the mask up over my nose as well. They even made numerous announcements throughout the flight stating as such. On my return flight from Miami to Newark NJ (as to avoid the mandatory quarantine had I landed in JFK), also with AA, they made a cursory announcement over the pa system and that was it. It was much more relaxed. I had my mask covering my mouth but not my nose, as well as many other passengers and they didn’t say anything. When we arrived at EWR from Miami, no one asked us for our address or phone numbers. No one stopped us as we got off the plane. B”H, the aitza of landing in NJ and then driving back to Brooklyn, really worked.

Stick to Southwest

I flew from LAX to ORD this past Wednesday night (08/12) on United. The plane was 95% full and the man sitting next to me refused to wear a mask. The United flight attendants asked him once to put one on (which he did not) and then left him alone for the next 3.5 hours. Very disappointed in how United is responding to COVID-19. Stick to Southwest.


great to read a write up about travel. Am I seeing right in the last picture, bourbon? Is that all they had, or did you switch? If you did, then please give a write-up on how that went…


Dan, having a negative antibody test does not prove you didn’t have covid19. Many who have had the virus have tested negative for antibodies and there is a theory that their bodies store memory of how to fight the virus and have immunity in another way.
(-According to the the local doctors in my area, one of the first and hardest hit in NY).


Read this with an amused smile on my face. One, because I live in Chicago and I guess sometimes just don’t realize all the “good stuff” we have here because, well, we pretty much always have it. Two, I fly pretty much every week of the year and flew all throughout COVID, parts 1 (March, when the airlines had no idea what hit them… or what was coming), 2 (April, when they started to realize the deep mess they were facing but still not sure exactly what to do) and 3-5 (the last few months as they started cutting flights, then adding flights, plus all the rules, enforcements-or lack of, etc, etc), so for me this has been more of a “movie worthy” experience than anything else. However, to see a veteran travel guru like you getting butterflies over flying again…. well, that was PRICELESS!

Welcome back to the Friendly Skies, we missed you up here!


Speaking of the Go Everywhere Pass, has that been extended to 2021, like all individual passes purchases in 2020?


As a Chicagoan, I learned that I need to try the desserts at Shallots and Evita’s

I flew to NYC last week for $70 r/t and stayed at a deserted Marriot Marquis in Times Square. Pretty eery.

American on the outbound was very lax with covid stuff. United on the return was pretty tough. Boarded by seat numbers.

Deal Guy

Now that you’ve flown, are you still doing the backyard minyan, or are you back to shul?


Nice to see a trip report again. Thanks.
Pretty incredible that for Dan, a CLE-ORD trip is ‘epic’. Surely a sign of the times. Hopefully things get back to normal sooner than later and the RTW trips can be up and running again.


This is great. As someone in Chicago I think you hit up more of these restaurants in 1 day than I would in a year!


Now I know why bar symon was out of kind bars
This past Friday and where they all went


How stupid can you be to think that flying in the continental US would make you safer from coronavirus than flying in Asia? How can you of all people not know that all of these flights are connected and someone who flew Cathay literally 3 hours ago could be on your Southwest flight ?


nice job! Good to hear of travels and travel experiences now. the food looks good and the segways look fun. I’m also in the “have antibodies will travel” category but haven’t ventured out yet. Also of the “it’s not how far you go or where, but how well you go and when.” view. Good Going!


“and returning at 8:20pm.” you meant 11:20pm


Love the TR Dan!!

I have been flying the last few weeks for work and I was actually in CLE the other week. If you take the (ridiculously long) shuttle to the car rental center and pass on the far side of Terminal D there are around 25-30 United planes parked there back to back.. I wonder if anyone ever considered putting the car rental center back where it was instead of the empty terminal.. interestingly enough United flights have been quite full (75% +-) recently..

Darius Rucker

what is Dan’s definition of a steak “cooked to perfection”

CLE Rocks

Dan. Spirit has cheap direct flights from CLE to MYR. I just went with my wife and had a blast at the Marriott Resort & Spa at Grand Dunes. Also, there pita planet which is tasty and delivers to hotel via GrubHub.


Dan, do u recall what Segway tour company you used? I’m looking to do that tomorrow and seems like they’re all $65+. Thanks.