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Weekend Trip to Chicago

A post about things happening on the sidelines of my 2024 annual college reunion: flights, Chicago river tour, and the city’s various observation decks and museums.

Chicago was the last major US city where we still had a resident host who could accommodate our annual college reunion, so it naturally became the venue. We chose a weekend in late June, when most of us would be free.

American Airlines Flight 299 from Boston to Chicago O’Hare

After wrapping up a day’s work, I felt parts of the airport (shuttle bus and security line) seemed to be following an unhurried pace that was uncharacteristic for a Friday evening. This was my first time flying out of Boston Logan since moving to the area a few months earlier, and for some reason my laptop refused to connect to the airport WiFi. More curiously, after I asked ChatGPT to draft a complaint letter about the problem, the WiFi worked on my laptop during every subsequent visit to the airport.

As for the flight itself, the weather over Boston and much of Massachusetts was less than ideal that afternoon. The inbound aircraft had to make a long detour over northern New Hampshire and was therefore somewhat delayed. I was halfway on the upgrade list and no upgrade seemed to have cleared at the gate.

American Airlines 299
Boston, MA (BOS) – Chicago O’Hare, IL (ORD)
Boeing B737-800 (N947NN)
Seat 9A
Scheduled Departure – 7:30pm
Actual Departure – 8:30pm
Scheduled Arrival – 9:26pm
Actual Arrival – 9:41pm
2 hours and 11 minutes
Here’s GPS tracking:

There was a light drizzle as we prepared to depart Boston. Interestingly, while most departures that evening were using Runway 09 out over the water, we somehow slipped in between a widebody and a regional jet and took off from Runway 4R, which was being used mostly for arrivals that evening (evident in the obvious throttle our captain engaged while getting onto the runway). That made for an especially interesting traffic pattern, since under similar winds Boston would more typically use Runway 4L for landings.
Here’s a video of the takeoff:

Portions of this video, after 2:48, was sped up 2x.

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Planes in Line for Takeoff

Diamond Creek Marshes

Clouds and Sunset Glow

Erie, Pennsylvania

Lansing, Michigan

The flight itself was otherwise unremarkable. After landing in Chicago, I met up with a few friends and we hailed a rideshare downtown. It was already past 10 pm, yet there was still a modest traffic jam on the expressway.

Boat Tour of Chicago River

The first item on our weekend itinerary was a river tour of Chicago: a boat ride along the stretches of the Chicago River lined with skyscrapers, with a guide pointing out and explaining the notable buildings along the way. Having watched more than my fair share of tour boats on the Chicago River, I was finally getting the chance to step aboard one myself.
Here’s the GPS tracking of the boat tour:

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Buildings along Chicago River

Buildings along Chicago River

Buildings along Chicago River

Buildings along Chicago River

Bridges over Chicago River

Chicago & Northwestern Railway Bridge

River Cottages
By architect Harry Weese.

Control House of Chicago & Northwestern Railway Bridge

Buildings along Chicago River

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Wrigley Building
Spanish colonial revival design, first major office building north of the Chicago River.

Marina City Building
Iconic corncob-shaped towers

150 North Riverside Building
Designed so that the upper office floors cantilever out from the central core.

River Point Building

Fulton House
Former cold storage warehouse converted to a residential building.

Chicago & Northwestern Railway Bridge

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Civic Opera Building

Mask Sculpture on Civil Opera Building
Matching the opera theme.

Old Chicago Post Office
A building built over a highway.

River City Apartments
Liked a scaled down version of “Marina City” earlier.

Apartment Buildings along Chicago River

Geese

South Branch of Chicago River

Buildings along Chicago River

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110 North Wacker Tower
The tree-like support structure creating a wide promenade.

Chicago Board of Trade Building
With Statue of Ceres, the Roman goddess of agriculture on top.

Buildings along Chicago River

Willis Tower

Willis Tower
With its glass-floor observation decks.

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Buildings along Chicago River

Projection Lights
Used to put on the nightly light show on the facade of Reid Murdoch Building.

Buildings along Chicago River

Buildings along Chicago River

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Tribune Tower
Gothic revival style.

NBC Tower
Bears a high degree of similarity to its headquarter in Rockefeller Plaza in New York City.

St. Regis Chicago
Tallest building ever designed by a female architect.

Lake Point Tower

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Buildings along Lake Michigan Waterfront

Buildings along Lake Michigan Waterfront

Buildings along Lake Michigan Waterfront

Cycle Boat

Where the power supposedly come from those people paddling. I wouldn’t get on one without a backup power source. (Also, it was a hot day.)

Trump Tower over Chicago River

A brief impression of the Chicago River boat tour: because the river is quite narrow, much narrower than the waterways around Manhattan, the only other river tour in the US lined with skyscrapers, the buildings felt close, immediate, and almost tangible. There was also an appealing mix of architectural styles, though some of the newer buildings were little more than unremarkable glass boxes. The boat moved at a pace only slightly faster than a walk, which made the ride especially pleasant and, in many ways, far more enjoyable than walking along the river itself, especially on a hot day like this. Overall, it was a very nice experience.

Museum Campus

After lunch, we planned to explore Museum Campus, starting with the Shedd Aquarium and then moving on to the Field Museum (both part of the City Pass). Since I wasn’t a fan of caged animals, I shall skip the aquarium part. The Field Museum, however, offered a fascinating collection of fossils.

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Giant Dinasour Fossil

Head of Giant Dinasour Fossil

Model of Clouded Leopard
Looking pretty tired/lazy in this pose.

Marine Life Fossil

Dinasour Fossil

Dinasour Fossil

Dinasour Fossil

Dinasour Fossil

Edaphosaurus Fossil

After the museums closed, some of us took a leisurely stroll along the Grant Park waterfront toward a restaurant on the Chicago River, where we had reserved dinner. The walk part came with nice views of the city’s skyline.

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Chicago Skyline from Museum Campus

Adler Planetarium Building

Shedd Aquarium Building

Field Museum Facade

As darkness fell, we watched the river at the restaurant glow beneath the streetlights.

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Chicago River at Dusk

Chicago River at Dusk

Chicago River at Night

Chicago River at Night

Hancock Building / 360 Chicago

After dinner, we realized we still had time for the not-so-long trek to the Hancock Building and a visit to the 360 Chicago Observation Deck (also part of City Pass). Unfortunately, it was too late for its “TILT” experience. (Honestly, I didn’t think it would be thrilling anyways, and the darkness only took away its thrill/appeal.)

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Chicago at Night

Chicago at Night

Chicago at Night

Fireworks over Navy Pier

Western Chicago

Willis Tower / Chicago Skydeck

The next morning, the itinerary for those of us that managed to get up was Chicago Skydeck, the city’s other prominent observation deck (also part of City Pass). This time, we saw Chicago’s skyscrapers in daylight—a fitting complement to the night views from the evening before.
Fun fact: Willis Tower was the highest “point” in the state of Illinois, if one included artificial structure in the tally.

Click here to display photos from Willis Tower Observation Deck.

Skyscrapers of Chicago

Skyscrapers of Chicago

Hancock Tower

Jay Pritzker Pavilion and Maggie Daley Park

Distant Evanston

Northwestern Suburb of Chicago

Click here to display photos from Willis Tower Observation Deck.

Southern Chicago

Highways and Railyards to South Chicago

LaSalle Street Train Station

Museum Campus

University of Illinois Chicago and Its Sports Fields

Rooftop Garden of Old Chicago Post Office Building

Ceres Statue on top of Chicago Board of Trade Building

After our visit to Willis Tower, we had lunch and then spent a few hours at an arcade/bowling venue. As it happened, I was rather good at bowling—certainly better than most of my peers.

Southwest Airlines Flight 2594 from Chicago Midway to Boston

Southwest was offering quite competitive fares out of Chicago Midway this Sunday evening, so many of us ended up flying home from there. After dinner, we split into two cars and made our way from the restaurant to the airport.

Unfortunately, Midway was fairly chaotic that evening. To begin with, the security line was ridiculously long; it took me 21 minutes to clear, likely the longest security wait I had experienced for the year. Once airside, the terminal was just as crowded, and even finding an empty seat proved somewhat difficult.

My flight to Boston was the latest departure among my friends that night, so I had ample time to catch up with them at the airport before eventually heading to my gate. Unfortunately, the flight was severely delayed because the inbound aircraft (N8890Q) had been held on the ground for a long time in Portland, Maine, which the crew attributed to “nasty weather”. When I pointed out that United Flight 3624 from Portland, Maine to Washington Dulles had departed on time at around the same hour, the crew merely shrugged and replied, “It’s Washington.” As Chicago Midway was, to some extent, a Southwest hub, I was a little surprised that Southwest was unable to find a replacement aircraft and crew.

Even so, once the plane arrived at Midway, the turnaround was remarkably quick, to the point that I suspected corners had been cut when it came to cleaning, when I found trash on the floor beside my seat.

Southwest Airlines 2594
Chicago Midway, IL (MDW) – Boston, MA (BOS)
Boeing B737-Max8 (N8890Q)
Seat 19A
Scheduled Departure – 9:15pm
Actual Departure – 11:37pm
Scheduled Arrival – 12:30am + 1
Actual Arrival – 2:16am + 1
1 hour and 39 minutes
Here’s GPS tracking:

Since the flight was heavily delayed, I spent its entirety trying to catch some rest. However, even after we landed in Boston, we were held on the ground for another 10 minutes while Southwest pushed back another aircraft (N8619F) to clear a gate. That plane had arrived more than an hour earlier and was scheduled for a repositioning flight to Baltimore, so I couldn’t understand why they hadn’t taken care of it sooner. In the end, the weekend trip to Chicago came to a somewhat unhappy close.

END