Roundtrip Flight between Washington Reagan and Chicago Midway with Southwest Airlines

March 2022, I flew to Chicago for some conference, as the first business trip I took in over 2 years from COVID.

Downtown Chicago

After almost two years of COVID restrictions, things were getting back to normal and I attended an in-person conference in Chicago in March 2022. Since my employer reimbursed the southwest credit that I got back in 2020, I was confined to fly Southwest, which happened to be providing a decent number of flights between the three airports of Washington DC and Chicago Midway.

Flight WN2026 from Washington Reagan to Chicago Midway

After 11 previous departures from Washington Reagan National Airport, this was the first time I would be departing from the 9-gate terminal A, which was connected to the rest of the airport and the metro station via a long indoor passage. There was a small exhibition area (p1-2 below) that would to some degree, make the walk less boring.
There were worker shortages across all sorts of jobs in the United States in early 2022, and Southwest’s deficiencies were in full display as I arrived at its checkin area with ridiculously long lines (p3), luckily there’s no wait at the nearby bag drop counter, nor was the security checkpoint.

Gallery

Along the walkway connecting Terminal A to the more modern Terminal B/C where metro station was located.
Gallery

Along the walkway connecting Terminal A to the more modern Terminal B/C where metro station was located.
Lines at Southwest Counter

The lines before the full service counter were unacceptably long, yet there weren’t any lines at the nearby “bag drop” counter. It’s very puzzling that so many people would require “full service”.
Terminal A Interior

Not a very spacious terminal, seating was very limited. This bar at the center of the terminal was the only dining facility.
Southwest B737 (N236WN)

Arrived at the gate slightly delayed, because, as expected, the previous plane couldn’t depart on time.
Refueling

After everyone was properly boarded, this fuel truck arrived and topped up the fuel tanks. It seemed weird as refueling should have happened long ago, instead of keeping passengers waiting. Maybe a change in routing would require additional fuel, or maybe this was another sign of Southwest’s operational woes.

Southwest called itself a “low-cost airline” despite it being the most generous when it comes to change policies and baggage fees. However, it shared some unwelcoming traits with the other ULCC’s in the United States (namely Frontier and Spirit), that it pushed unrealistically short turnaround schedules at airports with the minimal number of leased gates. As a result, any operational hiccup would cascade through its schedule, as the previous plane at the gate, WN647 to St Louis (N7725A), departed 30 minutes late. Because of that, my plane to Chicago (N236WN) had to wait at the ramp. And from my limited experience flying Southwest, that’s regrettably not unexpected.
Then I scouted around, Reagan Airport’s terminal A was a roundhouse with 9 gates that’s not too spacious. A shortage of janitors meant trash was very visible all around. Adding to that, there was certainly a shortage of charging ports around.
When it’s finally boarding time, the gate agents announced a full flight to Chicago (so as to encourage people to gate check bags), it ended up with a few empty seats, and I wasn’t a fan of lies.
Then I got onboard to find the seatback storage wasn’t properly cleaned, adding to the day’s dismay.

Southwest Airlines 2026
Washington Reagan (DCA) – Chicago Midway, IL (MDW)
Boeing B737-700 (N236WN)
Scheduled Departure – 2:00pm
Actual Departure – 2:32pm
Scheduled Arrival – 3:05pm
Actual Arrival – 3:15pm
1 hour and 43 minutes
Here’s GPS tracking:

And here’s a video of the takeoff:

After a snowstorm a few days ago, weather was great around Washington DC, so I got a tour of northern Virginia’s suburbs and mountains through the departure. While snow had mostly melted in Washington DC, slightly to the west Dulles Airport was much covered in snow.

Looking back at Reagan Airport
Dulles Airport
Shenandoah River

Appalachian Trail passed through the mountains in the right, separating Virginia from West Virginia.
Winchester, Virginia
Great North Mountain
Tuscarora Trail passed through these mountains, again separating Virginia from West Virginia.

Then we were onto the plains of Ohio.

Allegheny Plateau
Alum Creek
Just outside Columbus, Ohio.
Delaware, Ohio
Just outside Columbus, Ohio.
Lima, Ohio
Van Wert, Ohio
South Bend and Elkhart, Indiana
LaPorte, Indiana
Shores of Lake Michigan
Port of Burns Harbor

In addition to being a port, it’s also housed a steel factory. Yet from above, it looked pretty deserted.

We were to land on runway 22L, that meant during approach we flew just south of I55/Stevenson Expressway at a relatively low elevation. I was sitting on the right side of the plane and treated with vantage views of Chicago’s skyline.

Chicago Waterfront
Downtown Chicago
Downtown Chicago
Downtown Chicago
Downtown Chicago

And here’s a video recording of the landing:

Finally, Southwest’s ground crew at Chicago Midway brought some redemption, as I got my checked bag approximately 18 minutes after our arrival at the gate. Compared with its peers, that’s certainly a great time given the labor shortage in 2022.

Flight WN946 from Chicago Midway to Washington Reagan

Fast forward to the return trip, it’s a rainy afternoon as I arrived at Chicago Midway Airport. This time, the checkin area felt great, but there was some wait at the security checkpoint.

Checkin Area
With Southwest’s commanding presence in Chicago Midway.
Art
Gate A4

My plane would be boarding from this semi-circular building which was located at the far end of the terminal.

This time, I forgot to check in 24 hours before departure. I did it in T-22 hours and ended up seated at the last row of the plane (but not in a middle seat).
It’s one of the last flights of the day, and judging by the fact that we were only late by half an hour, it’s almost a miracle on Southwest’s scheduling.

Southwest Airlines 946
Chicago Midway, IL (MDW) – Washington Reagan (DCA)
Boeing B737-700 (N946WN)
Scheduled Departure – 7:15pm
Actual Departure – 7:57pm
Scheduled Arrival – 9:55pm
Actual Arrival – 10:20pm
1 hour and 23 minutes
Here’s GPS tracking:

It rained throughout the day in Chicago, and the weather system created some bumps between Lake Michigan and South Bend.
The clouds didn’t clear until we were over Morgantown, WV.

Morgantown, West Virginia
Morgantown, West Virginia
Flying past Dulles Airport
Reston, Virginia
Developed areas along Dulles Greenway.
John F. Kennedy Center for the Performing Arts
Washington Monument

After flying past Dulles Airport, we made a turn north and started River Visual Approach. I had flown that approach for a few times and the excitement certainly wore off, so I should conclude this post with the following video:

4 minutes, 2160p30fps, 4Mbps/125MB for H265, 4.5Mbps/124MB for H264.
END