Flights for Two Overnight Trips to Boston and Baltimore from Chicago

October 2023. I made two overnight trips to Boston and Baltimore to run some errands. This post would be about the flights back and forth.

Oct 8-9 Boston

Ticketing

I learned that I needed to make this trip only a week in advance, while I was road tripping through Colorado. There’s not much flexibility with regards to timing (it must take place over the first weekend of October), and somehow flights into and out of Boston were very expensive over that particular weekend. Since I was personally paying for all these trips, given my schedule and hotel availabilities, I decided to fly to Boston on Sunday morning, and back to Chicago on Monday.

For flights to Chicago, United had a (basic economy) itinerary with transfer in Newark at 103USD, that would get me to Boston at 1pm. The flight to Newark departed at 7am, meaning I had to drag myself out of bed early in the morning. I had the option of redeeming 7500 Turkish Airlines miles for the same flight to Boston, with the Chicago to Newark leg departing earlier at 6am. Of course, I opted for more sleep.

For my flights back, I came across a set of Spirit Airlines flights that depart Boston at 1pm, with a short connection in Charlotte and land in Chicago at 5pm. Somehow, this itinerary only showed up in online OTA’s. To purchase it on Spirit’s own website, one had to search “multi-city” then manually enter both legs. At 168USD, this was still cheaper than other “one-way” itineraries. (The other airlines wanted ~300USD between the two cities.) The connection time in Charlotte was short but valid, and thus protected since they were on one ticket. I felt that Spirit Airlines wanted to make money on luggage, and by treating the two flights separately it could theoretically charge for luggage twice. Since I only stayed for one night in Boston, I didn’t need additional luggage.

United Airlines UA659 from Chicago O’Hare to Newark

Unfortunately, despite getting out of bed one time, I spent slightly longer on breakfast on the morning of Oct 8, that I missed a blue line train to O’Hare airport by a few seconds. The next train 15 minutes later was delayed by an additional 5 minutes compared to schedule. So by the time I reached the airport, it’s only an hour before my flight’s scheduled departure.
Luckily, this time there was literally no line for security at United’s Terminal 1. So by the time I reached the gate (in the satellite concourse C, just like every other time I flew United out of Chicago), boarding was halfway done.

United Airlines 659
Chicago O’Hare, IL (ORD) – Newark, NJ (EWR)
Boeing 757-200 (N29129)
Seat 23A
Scheduled Departure – 7:10am
Actual Departure – 7:28am
Scheduled Arrival – 10:23am
Actual Arrival – 10:02am
1 hour and 34 minutes

Here’s a video of the takeoff:

By the way, this was my first time flying Boeing’s 757-200. Sitting over its wing, it’s not hard to appreciate its enormity (compared to 737 for my next leg).

Click here to display photos from the flight from Chicago to Newark.

United Airlines B752 (N29129)
My plane to Newark.

Distant Hudson River
Governor Mario M. Cuomo Bridge with its distinctive shape across the river.

Skyscrapers of Midtown Manhattan

Skyline of New York City

Skyline of New York City

It’s a cloudy day over the Great Lakes and Pennsylvania, so there’s not much to show along the way. It’s a southbound landing into Newark airport, so I was given a tour of the Manhattan skyline before touchdown.

Here’s a video of the landing:

United Airlines UA721 from Newark to Boston

Probably due to United shifting some operations to Newark’s new terminal A, United’s old terminal C now felt pretty empty. I spent some time working on my laptop before my flight to Boston.

United Airlines 721
Newark, NJ (EWR) – Boston, MA (BOS)
Boeing 737-Max9 (N17529)
Seat 25A
Scheduled Departure – 11:52am
Actual Departure – 11:54am
Scheduled Arrival – 1:08pm
Actual Arrival – 12:37pm
45 minutes

Here’s a video of the takeoff:

Click here to display photos from the flight from Newark to Boston.

Providence

Distant Boston Harbor

Distant Boston Harbor

It’s a short hop so there’s not much to talk about. Here’s a video of the landing:

Spirit Airlines NK1166 from Boston to Charlotte

Fast forward to my flights back to Chicago on Oct 9.

It turned out that Chase’s Sapphire Lounge was just above the gates used by Spirit Airlines. (I guessed the typical passenger of Spirit Airlines wouldn’t be a good match for Chase’s supposedly premium lounge, but this could likely be the only location available for Chase to open a lounge in Boston airport.)
A short review (for this visit) was that Chase’s Sapphire Lounge in Boston had fancy decor, the food offerings was on par with the better part of “The Club”, but not as good as Capital One at DFW, or even Turkish at IAD in my opinion.

I watched the inbound aircraft pulled into the gate from the lounge. Since it arrived with some delay, I stayed in the lounge slightly longer and “guessed” the boarding time before making my way to the gate.

Spirit Airlines 1166
Boston, MA (BOS) – Charlotte, NC (CLT)
Airbus A320 (N642NK)
Seat 8F
Scheduled Departure – 12:48pm
Actual Departure – 1:28pm
Scheduled Arrival – 3:18pm
Actual Arrival – 3:24pm
1 hour and 54 minutes

Here’s a video of the takeoff:

Click here to display photos from the flight from Boston to Charlotte.

Spirit Airlines A320 (N642NK)
My plane to Charlotte.

Spirit Airline Planes at Boston Airport
Taken from Chase’s Sapphire Lounge.

Downtown Boston

Boston Harbor

Clouds over North Carolina

Lake Norman

Charlotte Skyline from Airport
Lots of American Airlines planes for its fortress hub.

The flight path from Boston to Charlotte was right over Baltimore and Washington DC that afternoon, but clouds were thick over these two cities.

While we were landing on Charlotte’s runway 18C, I spotted another Boeing 737-900 from United performing parallel landing on runway 18R. Despite being relatively far away, it’s still an interesting sight. Here’s a video of the landing:

It turned out that the same plane (N642NK) would continue to serve my onward flight to Chicago (I knew this by checking FlightRadar24 in advance). Despite we arriving in Charlotte with some delay, I figured I should still have time to check out “The Club” lounge during the plane’s turnaround, which was a short walk from Charlotte’s concourse A.
It turned out that late afternoon was a busy time at this lounge, which enacted a “waiting list” that I was told was “about an hour long”. With that, I headed back to the gate.

Spirit Airlines NK1175 from Charlotte to Chicago O’Hare

Spirit Airlines 1175
Charlotte, NC (CLT) – Chicago O’Hare, IL (ORD)
Airbus A320 (N642NK)
Seat 9A
Scheduled Departure – 4:08pm
Actual Departure – 4:58pm
Scheduled Arrival – 5:13pm
Actual Arrival – 5:28pm
1 hour and 30 minutes

Here’s a video of the takeoff:

Click here to display photos overlooking Chicago Skyline.

Downtown Chicago

Downtown Chicago

Overflying Chicago Coastline

Downtown Chicago

This flight wasn’t very noteworthy, except for the spectacular view of Chicago’s skyline glowing under the twilight sun as we approached O’Hare airport (slideshow above). It’s as if the entire city was engulfed by the mystic color blue, from the skies above to the lake below.
And here’s a video of the landing:

Oct 17-18 Baltimore

Ticketing

Unlike a week ago to Boston, this time, I had much more flexibility for my trip to Baltimore, in particular, it could take place in the middle of the week, when fares were lower. That’s when I came across Frontier Airlines offering flights between Chicago and Baltimore for 78 dollars roundtrip (of which only 29 dollars were fare and carrier charges, the remaining 49 dollars were government taxes). It felt to me that Frontier Airlines knew they couldn’t fill their planes given it’s the middle of the week and off peak, so they just decided to sell flights as cheaply as possible to have some marginal income, with the hope of making more money on bags and seats. (Unfortunately for them, I didn’t need those extra.)
Another sign for the weak demand, for the planes I flew on, I found Frontier Airlines scheduled flights sparsely, with typical turnaround times larger than 1 hour. This was in contrast to my impression of ULCC (plus Southwest), that tried to squeeze as many flights as possible into a plane’s schedule for a day. This sure helped with on time performance, which I appreciated.

Frontier Airlines F91153 from Chicago O’Hare to Orlando

When searching for flights, I found Frontier operated an earlier departure from Chicago Midway to Orlando that allowed me to take an earlier flight to Baltimore. It’s also priced as 39 dollars (one-way), but it had a shorter connection in Orlando, and allowed me to arrive in Baltimore early in the afternoon, with more time for my errands. Unfortunately, I hesitated for a few hours, and that flight was gone.
So instead, I had to make it to O’Hare’s terminal 5 (which wasn’t that straightforward since I took the subway). But at least unlike a week ago, I didn’t have to wake up early. There’s no line for security at O’Hare’s terminal 5 this time.

I had the option to check out Swissport’s lounge with my PPS membership, which was the only PPS lounge in Chicago O’Hare. Given its horrible reviews online, I figured I should do my part to help it go out of business and remove such disgrace from Chicago O’Hare, so I headed straight to the gate area.

Some other thoughts: I knew as O’Hare’s only international terminal, its terminal 5 was recently expanded. At the same time, it also had some new tenants (Delta, Frontier, Southwest) that ran predominantly domestic operations. It sort of defied the purpose of T5’s expansion as to increase international capacity. On a separate note, since afternoon-evening were peak times for international flights, maybe my visit in the morning wasn’t representative.

Apart from its linear shape that required a long walk, I found WiFi was weak at the gate area, and only a small portion of the benches had power outlets. So I guessed the only upside was that it wasn’t crowded in the terminal.

Frontier Airlines 1153
Chicago O’Hare, IL (ORD) – Orlando, FL (MCO)
Airbus A320neo (N383FR)
Seat 30A
Scheduled Departure – 10:09am
Actual Departure – 10:34am
Scheduled Arrival – 2:16pm
Actual Arrival – 1:43pm
2 hours and 9 minutes

Of the four legs that I flew with Frontier Airlines, this was the most crowded flight with only a few seats open. Nonetheless, I had an empty middle seat next to me.
Despite the inbound aircraft arriving early and boarding on time, we waited almost 20 minutes for takeoff. (It could be that the use of crosswind runway 22L reduced overall capacity at O’Hare.) The higher cloud ceiling meant I got clear views of Chicago’s skyline and Lake Michigan behind it. Here’s a video of the takeoff:

Click here to display photos from the flight from Chicago to Orlando.

Frontier Airlines A320neo (N383FR)
My plane to Orlando.

Planes in Line for Takeoff
Felt to me like the morning rush of O’Hare. We waited for almost 20 minutes before takeoff.

Distant Downtown Chicago

Overlooking Chicago Midway Airport

Southern Shore of Lake Michigan

Fast forward to arrival in Orlando, it’s a cloudless day (typical for Florida sunshine), offering views of the lake-dotted central Floridan landscape, and the sprawling metropolis that we flew past.

Click here to display photos from the flight from Chicago to Orlando.

Northern Suburb of Orlando

Orlando Executive Airport

Downtown Orlando

Eastern Suburb of Orlando

Overlooking Orlando Airport

Lakes to the South of Orlando

The final approach into Orlando was a little bit bumpy. Here’s a video of the landing:

Aided by tailwind, Frontier’s conservative estimation of ground delay at Chicago O’Hare, or a combination of both, we arrived in Orlando almost half an hour early (despite the takeoff was almost half an hour late). That meant my connecting flight to Baltimore was almost 4 hours later. I planned to check out “The Club” lounge, but with its three-hour admission rule, I first stayed in the atrium, which also dubbed as a food court (as a result of which, the chairs were not very clean).

Then a brief review of “The Club” at Orlando. I visited it briefly during breakfast hours last September. Back then I felt it’s one of the better “The Club” lounges. This time in the afternoon, it had a decent food selection (I was very into the beef egg rolls), it was packed but not crowded, and apart from one power outlet that didn’t work, it sure stood out among other “The Club” lounges in the states.

Frontier Airlines F91242 from Orlando to Baltimore

Frontier Airlines 1242
Orlando, FL (MCO) – Baltimore, MD (BWI)
Airbus A321neo (N604FR)
Seat 32F
Scheduled Departure – 5:43pm
Actual Departure – 5:52pm
Scheduled Arrival – 8:02pm
Actual Arrival – 7:36pm
1 hour and 42 minutes

This was my second time departing Orlando. Like the previous time, it was from runway 17L/35R. I felt this runway could use some intersection departure (instead of having to taxi all the way to its end), it’s 10000ft/3048m long after all.
Here’s a video of the takeoff:

Once airborne, darkness and clouds both arrived as we entered the Carolina’s, followed by an uneventful flight.

Click here to display photos from the flight from Orlando to Baltimore.

Overlooking Orlando Sanford Airport

Daytona
With its iconic motor raceway.

St. Augustine, Florida

Overlooking Fort Pulaski

Clouds with Sunset Glow

Frontier Airlines F91573 from Baltimore to Atlanta

Fast forward to the next day. I finished my errands early and made it to the airport at 1:15pm, more than 2 hours before my flight’s departure. With that, I checked out “The Club” at Baltimore. This was a small-size lounge but not as crowded.

Frontier Airlines 1573
Baltimore, MD (BWI) – Atlanta, GA (ATL)
Airbus A321neo (N606FR)
Scheduled Departure – 3:47pm
Actual Departure – 3:49pm
Scheduled Arrival – 5:51pm
Actual Arrival – 5:17pm
1 hour and 28 minutes

The flight to Atlanta was only about half-full, that flight attendants had to re-seat people for weight and balance purposes. In the latter part of the flight, I caught some sights of the southern part of Blue Ridge Mountains.

Click here to display photos from the flight from Baltimore to Atlanta.

Boarding Flight to Atlanta

Asheville, NC

Blue Ridge Mountains
Near Beech Gap.

Lake Lanier

Lake Lanier

Distant Downtown Atlanta

Distant Downtown Atlanta

And here’s a video of the landing:

We landed more than half an hour early, but was held for 15 minutes for a gate to become available. A sign of Atlanta as the world’s busiest airport.

After that, I had a 4-hour connection for my flight to Chicago. So I headed for the international concourse F and hoped to check out “The Club” lounge. This was a busy lounge, outside which there was a line to get on its “waiting list”.

It turned out that the “waiting list” was pretty short (~10 min), and once inside “The Club”, about 1/3 of the seats were unoccupied. On the flip side, the food and beverage offerings were, at best, mediocre. They were unappetizing enough that later, I returned to concourse E to grab some McDonald’s.
The only remarkable part of the lounge was probably its “business center”. From its name, I envisioned it would feature computers and printers, but instead, a few recliner seats. The seats were so comfortable that I felt asleep on them (so long for the “business” part).

Frontier Airlines F91356 from Atlanta to Chicago Midway

Once at the boarding gate, the few Frontier agents were busy meddling with their boarding pass scanner that seemed for a moment was broken. This resulted in some delay (frankly, of the four Frontier legs, this was the one I really hoped to be on time).

Frontier Airlines 1356
Atlanta, GA (ATL) – Chicago Midway, IL (MDW)
Airbus A320neo (N335FR)
Seat 28F
Scheduled Departure – 9:46pm
Actual Departure – 10:46pm
Scheduled Arrival – 10:22pm
Actual Arrival – 10:46pm
1 hour and 24 minutes

Click here to display photos of Chicago skyline at night.

Approaching Chicago

Overlooking Chicago at Night

Overlooking Chicago at Night

The flight itself wasn’t remarkable, until it ended with a spectacular neon show of Chicago’s skyline. Just like a week ago, but this time I flew into Chicago Midway where the approach path was closer to downtown Chicago. Minutes later, we landed into a rainy Chicago night.
END

Flights for Two Overnight Trips to Boston and Baltimore from Chicago by Huang's Site is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.