Pre-Flight
After four great days in the Pacific Northwest, it was time to head to back east, but I wasn’t headed home right away. I had decided to give my relatives in Wisconsin a visit, and since options for getting directly from Portland to Madison were limited, I decided to fly into ORD and take CoachUSA’s Van Galder bus service up to Madison. I’ll get more into that later.
I generally found United's website and booking to be smooth and easy to use, but this flight had a bit of a hiccup to start. I was originally not able to select an economy seat when booking (even though I wasn't in basic economy), but after checking each day leading up to the flight, I found a window seat, which would allow me to sleep easier on the redeye. However, when trying to check in on the morning of the flight at about 6:00, I got a message that "Check-in has been restricted to the gate. Airport check-in is required." I was worried that this meant that the flight was oversold and I was too late checking in to have a seat on the plane, but at about noon, I was able to check in and keep my seat. What a strange check-in experience. Anyway, I rested a bit easier that afternoon knowing I was all squared away.
At the Airport

My parents dropped me off at around 9:25, about 2 hours before boarding. I was hoping I would have a decent amount of time to check out PDX's new terminal, but the security queue had other plans. The line was fairly long with lots of eastbound passengers and there were four officers deputized to check IDs, but there were only two scanners open while several other officers were roving around doing nothing. There also seemed to be way more officers in the PreCheck queue than they actually needed so maybe they could have opened another scanner for the rest of us. I ended up being waved through the standard metal detector, but both my backpack and suitcase got flagged by the machine, as did an unusually large number of bags. The officer ended up swabbing the baseball I bring along with me to relieve the plantar fasciitis I get in my foot, and when the swab came back clear and the officer bounced it up and down a sufficient number of times to see that it wasn't a threat, he let me proceed. If you're flying a redeye out of PDX, pack your patience and arrive at least 2 1/2 hours early.

As a result of the very long security queue, most of the establishments post-security had already closed. Maybe next time I'll have more time to check them out. We didn't have a large dinner at my aunt's house before the flight so I was somewhat hungry, but all that was open was the convenience store and Hopworks Brewery, and a $19 plate of nachos didn't seem very appealing, so I just had a Nature Valley granola bar that was in my backpack and watched the weekend's Josh Cahill, Noel Philips, Simply Aviation & Patrick Shea videos on my iPad at my gate. UA has a bank of redeye departures at this time of the night and the EWR flight was departing from the gate right next to mine (which someone we had seen that weekend at the memorial was on). My plane had arrived on time from ORD and all signs were pointing towards an on-time departure for us. The same could not be said about the flight to IAD at the gate next to ours, as there was a gate change and the herd of passengers all got up at once and headed down the hall, reminiscent of that scene in "Airplane!". I decided to check my suitcase at the gate so that I could put my backpack in the overhead bins, and have the space under my seat for my legs to try and get some sleep on the plane. Boarding began right on time, and once I got on I threw the backpack in the overhead bin and only kept my earplugs with me.


The Tillamook children’s play area in terminal E, right across from the Tillamook outpost

My 737-800 that had just arrived from ORD

I got to board before Group 3 as I had checked my carry-on at the gate

This 737 MAX 9 was IAH-bound

Cabin shot after the “boarding complete”
The Flight
Once I sat down, the flight attendants were working very hard to get everyone seated so that we could get out on time, as they announced that over 100 people had connecting flights. When I booked this flight, it was set to be on the 737 MAX 8, but it seemed like there was an equipment swap to the 25-year-old 737-800 (maybe that had something to do with why I couldn't check in immediately?). UA has really been moving quickly on updating the cabins on their older aircraft, and this was complete with seatback IFE screens and much sleeker seats, and the first class seats were also the latest design. There would be no IFE for me on this flight, however, as I was planning on getting to sleep immediately after takeoff. The safety video was played and we made it out to the runway after a very quick taxi, and took off only about 5 minutes late. On my last redeye flight (SEA-IAD on DL), I had a neck pillow with me and I took a melatonin before the flight, but I had neither of those with me for this flight as I couldn't fit the former in my luggage and just forgot to bring the latter, so I shut my screen off and tried to get a bit of shuteye.

I'm pretty sure I dozed off somewhere over Idaho and woke up over southeastern South Dakota, and when I woke up there was about an hour and 15 minutes left in the flight, so I didn't actually get a ton of sleep. The crew did come through with some water a couple times, which was appreciated but I was quite hungry as we didn't have the largest dinner ever at my aunt's house about eight hours before. I figured that I wasn't going to get much more sleep, so I just looked out the window as Iowa passed by below, and we were about to arrive almost half an hour ahead of schedule. Right around Rockford, we made a turn to get aligned with the O'Hare runway from the west, and it was a straight shot in as we touched down at 5:27 AM. It took about 10 minutes to taxi to the gate, and we actually would end up parking at the G-gates in Terminal 2 due to construction on the runway/taxiway–not UA's typical territory, but they told us that our bags would come out at Terminal 1, so we would have a bit of a walk.

Waterloo and Cedar Falls, Iowa down below

Beloit, WI

The Wood Dale, IL Metra stop and a train waiting to bring commuters into Chicago

Parked next to this NK A321 which had arrived the night before from RSW and was returning there in a couple hours
Post-flight
After making the walk through the maze of corridors between Terminals 1 & 2, my bag was waiting on the carousel for me and I made my way to the L into downtown Chicago for a couple hours before catching my bus up to Madison. The L station at O'Hare is underground and is reachable through a tunnel which is very dark and stuffy, and if you're arriving or departing from terminals 1/2/3, you can just take an escalator down from arrivals to get there. I hopped onto one waiting on the platform and it got me into town in about an hour for breakfast and a walk along Lakeshore Drive before continuing on to Madison.

The very cramped Terminal 2, no wonder this puer mostly houses the low-cost airlines

The connector between Terminals 1 & 2

Nothing like cruising by the Chicago traffic on the train!

You can take public transit from the airport right to the shores of Lake Michigan
The last part of this trip would be on the Van Galder CoachUSA service from downtown Chicago up to Madison, WI. It's about $40 to ride the whole route, and in downtown Chicago it picks up on W Jackson Blvd, across the street from Union Station. You can buy your single-use ticket online and ride anytime–no reservations for a specific date/time are needed. It goes to O'Hare (the multimodal facility on the way out of town, and it stops at each terminal on the way into town), Rockford and South Beloit in Illinois, and then Janesville and two stops in Madison in Wisconsin, with the latter one being on Lake St on the University of Wisconsin campus. Be warned though, the legroom on this bus is worse than almost all the airlines, and at 6'3" it was very tight for me. Luckily, I dozed off anyway between Chicago and Rockford and I had no seatmate from Rockford onwards. We arrived into Madison bang on time, and my uncle was waiting for me right across the street when the bus pulled in.


My final destination, Madison, WI with Lak